Pick Three

by Randi Zuckerberg

Clock Icon 90 minute read

Introduction

This year I made an oath to myself to stop feeling guilty about everything. Guilty about not being perfect all the time (or ever, really), guilty for not having the most exemplary wardrobe or flawless body, guilty for eating too much gluten or drinking too much coffee, guilty for making investments or taking career risks that don’t pan out, guilty for not responding to every e-mail, guilty for not being the perfect mom, wife, or friend. (I’m exhausted just writing about all this unnecessary guilt.)

When I dug deep and thought about why I’ve wasted so much of my short, precious time on earth apologizing for things, I realized that it stems from an intense pressure to have it all, do it all, and be it all at the same time. You can’t be everything to everyone, whether you’re a student, a parent, a boss, an employee, a spouse, an athlete, an artist, a friend in need, an entrepreneur, or a multihyphenate. We’re told to be great at everything in order to achieve some lofty and unrealistic level of balance across all areas of our lives.

I’m here to burst that bubble. I think the idea of being well balanced is about as off-kilter as a born-and-bred Scotsman dancing the Irish jig (get it, off kilt-er?). I believe that striving to be well balanced is a lousy setup for one of three things: failure, unreasonable expectations, or worse, MEDIOCRITY! Shudder.

The people you love, the passions you have, and the things you want to accomplish shouldn’t be limited by how well you can balance everything because, let’s face it, you can’t achieve anything of importance or significance by striving to HAVE IT ALL in a twenty-four-hour period. Talk about stress!

Speaking of having it all, even though I do subscribe to the “more-is-more” philosophy of life, I’m sorry, but “all” is not necessarily better. Have you ever gone to one of those twenty-four-hour all-you-can-eat Vegas buffets? Ten servings later, at 3 A.M., did you still feel that “having it all” was a good life decision?

Whatever it is you want to excel at—whether it’s your career, your family, your fitness level, a personal passion, a specific project, your social life, anything!—you have to prioritize it by putting it at the top of your to-do list. Over and over and over and over and over again.

Well balanced? Ha! I have a different theory to success.

Living Lopsided

The idea of being well lopsided first came into my life when I was applying to college. I was an ambitious, motivated go-getter at the highly competitive Horace Mann High School in Riverdale, New York. Like every other New York prep school student, I thought that the pinnacle of life was getting into Harvard University. Can somebody say PRESSURE!?

The problem was, I wasn’t the typical person you think of when you think Harvard. I’d been held back a year in two subjects. I didn’t have perfect SAT scores. I wasn’t student body president. I hadn’t started a nonprofit or interned for some fancy company. I had zero connections or legacy. Instead, I was a theater nerd. Watch out, Ivy League, here I come—with jazz hands!

Growing up I spent every waking moment singing or being involved in the theater, any way I could. Summers were dedicated to touring with a semiprofessional opera company. I performed in multiple shows a year. I created my own independent study where I attended the dress rehearsals of operas at Lincoln Center and wrote term papers based on those works. I took AP music theory instead of calculus. I dropped science my senior year of high school so I could focus more on music. My dream was to perform on Broadway, and if I couldn’t perform on Broadway, to help run Broadway.

As much as my family supported me and my personal life plans, I’m not really sure anybody believed I’d ever get into Fair Harvard. My mom said she hung her head in embarrassment as Mr. Singer, my high school guidance counselor, asked her which college was my top choice and she had to reveal what she thought was the most implausible choice of all: Harvard. As if I could actually be accepted. But, encouraging my dreams, my mom took me to tour the campus, where, of course, I fell in love with the school. From the gorgeous colonial buildings to the traditions and history, I wanted it BAD.

We met with an admissions officer who said something that sticks with me all these years later (well, not that many years, geez!). Her words became the foundation for this book: “Randi,” said the admissions officer, “Harvard looks for two kinds of people. One, those who are well balanced, and two, those who are well lopsided. The well-balanced students serve as the backbone of the class, but it’s the well-lopsided students who make the class incredibly interesting.”

Oh my gosh, that’s me! I remember thinking. I’m one of the lopsided ones! Fast-forward nine months and there I was, receiving a thick Harvard-embossed envelope stuffed with my acceptance letter to the class of 2003! My first encounter with the world of well-lopsidedness was a win! I decided there and then to make it more than just my motto to live life lopsided, but also to pass on the wisdom and knowledge this strategy has afforded me as well.

From the moment I sat in that admissions office as an overeager, starry-eyed high school junior, I decided to follow my passions, to be one of the interesting ones, and to dive into things the best way possible—living the lopsided dream.

As I moved on from higher learning to the real world, I knew I needed something to help ground my many tasks in a way that an app just couldn’t do. I had a bevy of outside interests, I was working a high-pressure job, and my husband and I were on our way to having a family. Stress was weighing me down. Right when I thought I’d have to bow to the pressure and give up a few of my favorite things, like staying fit or seeing live theater all the time, I remembered the admissions officer’s description of being “well lopsided” and an idea hatched.

I don’t have to give up anything! I thought. Maybe instead of being balanced, I should turn this whole thing on its head and focus on being unbalanced! Instead of trying to do everything every single day, what if I look at the major buckets of my life (work, sleep, family, fitness, friends) and PICK THREE to focus on each day? That way, I can do those three things WELL and I can pick a different three tomorrow. Over time I’ll be well rested, fit, successful, and cultured—all with kids in tow! And thus, from a Harvard admissions meeting, where I wasn’t even expected to get in, Pick Three was born.

I’M SURE I’M NOT THE ONLY ONE WHO’S HAD THAT ONE STRESSFUL moment that truly weighs you down. We’re all carrying the weight of the world on our shoulders. In fact, if I took a good hard look at the things you accomplish each week, I’d probably be asking you to autograph this book for me! When you think of all the things we attempt to balance, it can feel completely overwhelming.

Here’s a rough list of things I would have to do every day in order to have it all:

  • Raise two boys to be good men who work hard and treat women with respect
  • Spend meaningful time with my husband
  • Run my business well and keep everyone happy (not easy in New York!)
  • Write a book (aka this book)
  • Prep and host my weekly SiriusXM radio show
  • Eat healthy (except during Pumpkin Spice Latte season, but liquids don’t count as food, right?)
  • Plan my travel for the forty-plus speeches and lectures I do each year
  • Coordinate childcare for when I am on the road
  • Feel guilty about traveling and not being with my children
  • Maintain our home (except that I sort of live at the airport . . .)
  • Keep in touch with family (sorry for not calling, Mom! What time zone is it again?)
  • Fulfill board of directors and advisory board obligations
  • See sixty-plus Broadway and Off-Broadway shows a year for Tony Awards and Chita Rivera Awards voting
  • Post to social media accounts
  • Check other people’s social media accounts (and consequently decide their lives are so much better than mine)
  • Respond to an avalanche of e-mails and messages (why does that little number on my inbox never go down?!?!)
  • Tell myself, “Randi, you should really respond to that e-mail,” while knowing full well that as soon as a few more e-mails come in above it, it will vanish from my mind forever

Oh! I can’t forget my aspirational goals:

  • See my friends. Ever.
  • Stay in shape (ha!)
  • Sleep (capital HA!)
  • Shower (Don’t judge.)

Well, that was exhausting. Maybe I should just crawl back into bed and call it a day.

What if I reframed that overwhelming list from Things to Do Today to Things to Do This Year? Or over three years? Or ten! This way, I could choose a few things to do each day and do those few things really, really well, completely focused on the tasks I choose and not so much on EVERYTHING ALL AT ONCE. (caps lock underline UGH!)

Even with so much on my plate, I consider myself to be one of the extremely lucky ones. I have a wonderful, loving partner in my husband, Brent, who takes on a huge amount of parenting and household work. I have an incredible team at Zuckerberg Media who make sure everything runs smoothly. And I work with amazing partners at Jim Henson Productions, Universal Kids, CAA, HarperCollins, and SiriusXM. I have the monetary resources to hire trustworthy childcare. And I have loving, supportive friends and family. Plus, as one friend said recently, “You’re only as happy as your least happy child,” and both of my kids are healthy and happy, thank God.

The truth is, most of the time we’re all thinking about how happy or unhappy we are. Are we happier playing with the kids at home? Happier running away to the gym for an hour? Or happier sitting at work finalizing the last paragraph of that report? Happiness is something we naturally strive for in life. But with the stress of finding balance, it’s no wonder we’re all so darn unhappy.

The 2007 World Happiness Report had the United States ranked third-happiest among the thirty-five countries in the Organization for Economic Co-operation and Development. But before you start celebrating, less than ten years later, in 2016, the U.S. dropped to nineteenth out of thirty-five. Reasons for this drop include declining social support and increased government corruption (no comment).1

To further the unhappiness, all you have to do is spend one second on your favorite social media platform, and suddenly you’re bombarded with images of everyone else’s perfect lives, their fancy vacations, their intellectual book clubs, leaving you feeling that everyone else has got it down WAY better than you. You start to think that maybe you’re not the #ninja you thought you were five minutes ago. Of course, deep down we know that everyone is just putting on a show online, broadcasting only the very best, glossiest parts of their lives—but we still can’t help but feel a bit inadequate. Sound familiar?

In 2016, the Pitt’s Center for Research in Media surveyed 1,787 young adults nationwide about their use of eleven popular social media platforms (Instagram, Facebook, etc.). The people who reported using the most platforms (seven to eleven) had more than three times the risk of depression and anxiety than people who used the fewest (zero to two platforms). Maintaining a regular presence across many sites (aka social media multitasking) led to poorer attention, cognition, and mood.2

Along with that, a Royal Society for Public Health study reports that social media brought out anxiety, fear of missing out (FOMO), bullying, high levels of depression, and low levels of sleep quality among teens.3 And to top it all off, a 2017 You.gov poll found that 26 percent of Americans say receiving a negative comment on social media has ruined their day.4 Even worse—it might not even be a human who left the bad comment! With messaging bots on the rise, it could be a robot that winds up making or breaking your day.

FOMO, depression, social media comparisons—you get it, and I’m right there with you. But you’re not here for all this doom and gloom. As I’m writing this book I’m in a place where I feel truly, deeply happy—take that, U.S. happiness rate! In many ways, I already have it all. All the #Blessed hashtags combined.

But it wasn’t always this way, nor is it always this way. Things go differently than planned. Emergencies—big and little—pop up at the most unexpected and inconvenient times. In true neurotic Jewish mom form, I always worry that the better things are, the sooner the other stiletto will drop. I fear that glass half full is going to spill any minute.

We all have different situations and challenges. Some of us raise children as single parents or work multiple, grueling jobs to achieve financial independence. Many maneuver through the difficult hands life has dealt. In other words, many of you are IRL #SUPERHEROES. Not from the pages of DC Comics, but in reality, you’re making the world turn for those you love and care about, no matter the cost.

Whatever situation we find ourselves in, there is one common denominator: we all feel incredible pressure to balance everything we need, have, and want, and to get it perfectly right—or else.

But what if we didn’t have that pressure weighing on our shoulders all the time? What if it were okay to pick a few things to focus on each day? What if it were all right to give yourself permission to be well lopsided instead of well balanced? And what if I showed you a way that focusing on just a few things at a time could actually make you happier in the long run (as long as you eventually choose everything on your to-do list at some point)? Would you sign up? Well, get your cursive skills ready (my what?), because I’m going to show you how it’s done!

Work. Sleep. Family. Fitness. Friends. Pick Three.

When people hear that I’m on the road for work roughly one hundred days a year, their most common response is one of horror. “Don’t you miss your children?” Of course I miss my children! I’m not a monster. But I also love what I do. There’s nothing I enjoy more than meeting fellow entrepreneurs, students, and dreamers creating and innovating new ideas from around the world. The feeling I get when I travel for work, sharing stories, making new friendships, and inspiring others is my bona fide Happy Place. But if I were focused on being well balanced all the time, I wouldn’t be on the road nearly as much as I am.

Providing for my family is extremely important to me and contributes to my own sense of purpose and meaning. So sure, I’d probably be, like, a 3 percent better mom if I were traveling less—but I’d also be a lot less happy. I have tremendous passion and enormous pride in my work. If I dialed that back, I’d be dialing back what’s at the very core of my identity and sense of self. To satisfy the imbalance of what makes us happiest, we have to make trade-offs in different areas of our lives.

My kids know how much I adore them. I’ve carved out a life for myself that allows me to do the work I love, then come home and give quality, undivided attention to the people I care about. I know a group of fantastic moms from my sons’ school who look out for my boys and send messages and photos to keep me in the loop of what’s happening while I’m away. Do I beat myself up that I’m gone so much? Absolutely. I’m in Round 4,245,003 of my own personal title fight. But I feel like I’ve got guilt up against the ropes, because I’ve made a commitment to stop feeling bad about not having the ideal work-life balance, because it’s impossible! Now I know that it’s only when I give myself permission to be lopsided toward work on some days and lopsided toward my family on other days that I actually do the best job at both.

When I look back at the past twenty years of my life, all my proudest, most rewarding, greatest moments—the moments I will hopefully live to tell my great-grandchildren about—all happened when I allowed myself to be lopsided. Had I chosen to be well balanced I wouldn’t be where I am today—where I’m HAPPY to be today. Thank heavens for living at a sloped angle!

For me, half the fun of being lopsided is being able to throw myself headfirst into things that excite me. Whether it’s work, sleep, family, fitness, or friends, I can’t ever know exactly what’s going to happen, but when I’m armed with equal parts passion and data, I always know I’ll be glad I tried. Living life loudly and lopsidedly on your own terms, without guilt, without caring what other people think or say, without allowing yourself to be frozen from a fear of failing, is where the fun really begins.

There are so many ways to be a well-lopsided person. Some are conscious choices. Some are forced due to situations beyond your control. Some accommodate the interests of loved ones. Some are decisions about what NOT to make a priority rather than what to focus on. All of these choices are just as valid and wonderful and appreciated as the next. There is no right or wrong way to be lopsided, as long as you aren’t so lopsided that it affects your health and happiness, or hurts the people who love you—although sometimes that’s exactly what happens (we’ll discuss this later on).

In this book I’m going to share interviews I conducted with some of the most well-lopsided people I know. Like Arianna Huffington, who, after suffering a health wake-up call of her own, shifted her entire focus to the importance of sleep awareness for professionals. Or Dr. Adam Griesemer, who often works forty-hour-plus shifts as a pediatric organ transplant surgeon. I spoke with Melinda Arons, who left a lucrative role at Facebook to go all-in on Hillary Clinton’s presidential campaign. I chatted with Rebecca Soffer, who lost both her parents in a short time and channeled her pain into helping others who are grieving after the death of a loved one. I talked to Brad Takei, who decided to make it his life’s purpose to help his husband, George Takei, succeed in all he does. And I sat down with Reshma Saujani, who realized that losing two political elections was key to understanding her life’s purpose.

I’m going to share stories of others who became lopsided in different ways—some by choice, some by situation. I’m going to arm you with all my tips, tricks, and life hacks to becoming your absolute best, well-lopsided self. At the back of this book is a workbook for you to track your own Pick Three progress and help hold yourself accountable.

Your journey in how to better prioritize, focus, and, yes, surrender, started the minute you opened this book. I applaud you for choosing an alternative path to happiness. See? You’re doing great at this lopsided thing already!

Pick Three is my motto, my creed, my personal life force, and I’m honored to share it with you.

Screw balance. Let’s be interesting! Let’s be different!

1

What Is Pick Three?

Let’s Get Lopsided!

“There is no such thing as a work-life balance. Everything worth fighting for unbalances your life.”

—ALAIN DE BOTTON

The first time I actually said “Pick Three” out loud was in a moment of frustration. It was approximately the one hundredth time I was part of a conference panel where I’d been asked by the moderator, “Randi, you’re a mom AND you have a career. How do you balance it all?” Of course, nobody would ever ask the men on the panel that question. Like it’s some ancient secret that the exact same skill set that makes someone a great parent (organization, prioritization, long-term planning, patience, creativity) also makes someone just as great an employee or entrepreneur (shocker!).

Most of the time when I’d get that same inquiry (that is, every time I’m on a panel), I’d grit my teeth, force a smile, and say something trite about how I try to balance it all. Except for one day when I just couldn’t muster up the strength to BS through it anymore. After the unsuspecting moderator asked how I balance it all, I shook my head and said, “I don’t.

“In order to set myself up for success, I know I can only realistically do three things well every day. So, every day when I wake up, I think to myself: Work. Sleep. Family. Friends. Fitness. Pick Three. I can pick a different three tomorrow, and a different three the following day. But today, I can only pick three. As long as I wind up picking everything over the long run, then I’m balancing my imbalance. It’s solving the great entrepreneur’s dilemma.”

And almost immediately I was quoted in business publications around the world. Pick Three had gone viral.

I later realized that the dilemma doesn’t just apply to entrepreneurs—it applies to EVERYONE. No matter what you do for a living, where you live, or what your responsibilities are, nobody can have it all without a little bit of sacrifice, focus, and energy. Over time I stopped calling it “the Entrepreneur’s Dilemma” and renamed it as Pick Three. Not only is it more inclusive, it’s instructional.

The five main categories in your life might be slightly different than mine, but for the purposes of this book—and the forthcoming exercises—let’s assume that my five categories work for you as well.

Work, Sleep, Family, Fitness, Friends: The Breakdown

Projects where you contribute time and, in return, derive value, which could be in the form of money, passion, meaning, a sense of contribution to something greater, or a stepping-stone to a long-term goal. Value could result from a traditional job, a passion project, a class or coursework at school, an internship, a charitable initiative, etc. You are creating output for some sort of input.

That pesky thing that eats up 30 percent of your day (if you’re lucky!).

This could be the family you were born into, the family you create, the family you choose. This doesn’t have to mean your biological family, either. Maybe your church is your family. Maybe you have a “modern” family, or a nontraditional family. However you define family in your life, this is the category for prioritizing it.

While the term fitness conjures up images of dumbbells and sweat, to me, this category reflects a broader goal of self-care and health: physical fitness, mental fitness, emotional well-being, mindfulness, stress management, and healthy eating.

This is my personal catch-all for things that are fun. When you think about friends, you typically think about the closest people in your life. But this is where I also think about side hobbies and outside interests—the people and activities that bring pleasure outside of work and family.

Now that we have our five categories down, it’s time for the fun part.

Pick Three

Now is the time for ruthless prioritization. So, sorry, you don’t get to pick all five. Not today. Not any day. If you want to be great at what you do, Pick Three and only three. And don’t waste one minute feeling guilty or bad about the two you didn’t pick. Because you’ll get another chance to pick them tomorrow. Or the day after. Or next month—it will happen.

Because every single day you get to pick a new three of these categories to focus on, you can pick the same three as the day before, or switch gears and pick a different three. It’s YOUR CHOICE. Maybe you have a weekday Pick Three and a weekend Pick Three. Maybe you have a summer Pick Three and a winter Pick Three. Maybe it changes every day. Regardless, Pick Three enables you to have the best in terms of short-term focus and long-term balance.

I can hear you now: “Randi, I can totally pick all five! I can exercise with my friends and call my mom on the way to work! Fitness, Friends, and Family, done! Two to go!”

While I have no doubt that every once in a while, for a day or two, you can manage to hit all five of these, it’s really not sustainable in the long run. If you try to accomplish all five things WELL (keyword: well), you’re headed for complete and utter burnout. You’re not going to grand-slam all five at a high-functioning level. Sure, it’s humanly possible to touch upon your family, your friends, your work, your sleep, and your fitness every day. But doing all five things—even just for a day—means you’re probably not doing any of them with any real depth.

We’ve been taught that imbalance is a dirty word, but I think it’s actually the key to success and happiness. The Pick Three lifestyle can help you nail life (and keep your sanity) by being well lopsided. When you focus solely on the trio you choose each day, prioritizing becomes totally manageable and you give yourself the permission to do those three things with the kind of excellence that will propel you further than weeks of half-assed focus. Over time, as you pick a different three every day, it evens out into—abracadabra!—BALANCE!! Okay, so it’s not magic, but how great would it be to reach the end of the day and know that you not only accomplished all three things you set out to do, but you did a fantastic job at each of them, too?!

Norwegians have known this for years. According to the World Happiness Report (yes, that thing again), Norway has jumped from fourth place in 2016 to first place in 2017, followed by Denmark and Iceland.

Why Nordic countries, you ask? Isn’t it freezing there? Heck, yeah, it is, but weather plays little into happiness. What those three countries have in common are high values in six key variables: income (work), high life expectancy (fitness), family values (yup), freedom (sleep), trust (friends), and generosity (all of the above).

The Pick Three Method

THERE ARE A FEW BASIC RULES TO REMEMBER WHEN FOLLOWING THE PICK THREE METHOD:

  1. YOU ONLY GET THREE. While it’s incredibly tempting to try for more (we’re an increasingly multitasking culture, after all), remember that we’re going for quality over quantity here. Work. Sleep. Family. Friends. Fitness. Pick Three.
  2. BUT HAVE NO FEAR, YOU CAN PICK A DIFFERENT THREE TOMORROW! No need for buyer’s remorse. The beauty of Pick Three is that when you wake up, it’s a brand-new day and a brand-new opportunity for you to pick a different three categories to focus on.
  3. NO GUILT! Keep reminding yourself that you can’t do everything well all the time. Give yourself permission to be great at the three things you’ve picked and try not to waste one precious second feeling guilty about the things you didn’t pick. If that’s not possible, blame me. After all, I’m the one who told you that you could only pick three things!
  4. BE GREAT! There’s no point to Pick Three if you’re not going to go all in on the three things you’ve picked to focus on. So pick your three and do as amazing a job as you possibly can.
  5. TRACK YOUR CHOICES. Like any system that holds you accountable, Pick Three works best if you jot down your choices each day and refer back to make sure you are roughly picking all five categories the same amount over the course of time. Whether you want to track it on paper, on your phone, or in our Pick Three app, logging your three daily choices will give you a sense of the broader overall picture of your life—and where you may need to shift a bit more effort.

A Slice from My Own Pick Three Pie

Take a look at my sample week from my own Pick Three journal and think about how you might want to pick and schedule your Pick Three.

Monday, September 4:

To Do: Family. Sleep. Fitness.

Today is Labor Day, which means no one will be shocked, angry, or disappointed if they don’t get a response from me. My kids haven’t started the school year yet, and my in-laws are in town. I pick Family so I can spend quality time with my kids, husband, and visiting relatives; Sleep since my wonderful, gorgeous, looking-younger-every-day in-laws have volunteered to get up early with the kids (hello, sleeping in!!), and Fitness because my husband and I are going to go on a jog around the park (after sleeping in, that is!).

Ta-da! Pick Three complete!

Tuesday, September 5:

To Do: Work. Friends. Family.

I start off the morning with an early-morning television appearance discussing new back-to-school apps and gadgets. I always love hosting segments, but to get TV-ready means I won’t be picking Sleep, since I have to wake up at the crack of dawn. My good friend Erica joins me in the studio and we catch up over coffee afterward. Friend time: Check! After that, I head to the office, where I have tons of work to catch up on. That’s Work times two! I make it home in time to kiss my boys, help my six-year-old son prep for his first day of school, and catch up with my husband when he gets home from work.

Ta-da: Pick Three crushed!

Wednesday, September 6:

To Do: Family. Work. Fitness.

At 7 A.M., I put my six-year-old on the bus for his very first day of first grade. Which means Sleep is out (but I wouldn’t miss this for anything). On Wednesdays, I spend the day at SiriusXM, hosting my radio show Dot Complicated with Randi Zuckerberg, on Channel 111 Business Radio (shameless plug), so I head straight to the studio to prep for the show, greet my guests, and go on air. Later that evening, I’m heading on a flight to Boston for a work event, so I come home after my radio show ends in order to pack, get in a quick workout (120 burpees! Eek!), and spend some quality time with my boys (playing Pokémon Go), before heading to the airport.

Ta-da: Pick Three next level!

Thursday, September 7:

To Do: Work. Family. Sleep.

I wake up super early in Boston to get ready for a big day ahead (where are my in-laws now?). I’m giving a keynote speech to more than a thousand business professionals and entrepreneurs about disruptive tech, social media, and leadership in the digital age, and I need to wake up early to prepare. The speech goes fantastically well (phew), and I follow it up by signing copies of my first book, Dot Complicated (another shameless plug!). Then it’s off to the airport to head home. I am absolutely exhausted when I get home, but it’s just in time to take my sons out for our promised dinner date. Afterward I tuck them into bed and collapse into my own.

Ta-da: Pick Thrzzzzzzz . . .

Friday, September 8:

To Do: Work. Friends. Family.

YUUUGE day of work. Whenever I’m on a business trip, there’s always a double-plus pile to do when I return, and today is no different. I have SIX hours of back-to-back meetings. But it’s Friday, so no matter what, if I’m in town I always make sure to be home in time for Shabbat dinner with my family. Shabbat in our home is really special. We light candles, we say a prayer of gratitude, and we each go around the table recounting the many things we’ve been thankful for during the week. We do a special “yum yum” blessing, too, because on Shabbat, we get to eat dessert before dinner! Talk about something to look forward to! (Note to self: Why is there no dessert option for Pick Three?) Once the boys are in bed and our babysitter arrives, my husband and I go to an Off-Broadway show and meet up with some old friends. When the show finishes, we all know we should go home and get some sleep, but we go out to a jazz bar to have a nightcap instead. It’s 1 A.M. already?! Good thing I didn’t pick Sleep.

Ta-da: Pick Three complete!

Saturday, September 9:

To Do: Family. Fitness. Work.

It’s another gorgeous day in NYC, so we use one of our favorite life hacks to get in a longer run with our sons in tow: Scooters! Even if we have to occasionally pull the boys uphill, it’s a double Fitness/Family Pick Three bonus! We decide we’ve earned a delicious brunch (with the rest of the unofficial religious zealots of NYC, aka Brunchtarians) before I’m off to work finishing deadlines on this book. I head inside for the rest of the day to enjoy the beautiful warming glow of my computer screen.

Ta-da: Pick Three slaughtered.

Sunday, September 10:

To Do: Sleep. Family. Friends.

Sunday = Funday! My husband offers to get up early with the boys, so I get to sleep in. Woot! On Sunday evenings, we grill outside, so we have some friends and their kids over to join. I’m heading out for another business trip tomorrow, so I call it an early night so I can hit the ground running tomorrow.

Ta-da: Pick Three, mic drop.

How Did I Do? Let’s Tally Up the Results:

WORK: 5

SLEEP: 3

FAMILY: 7

FRIENDS: 3

FITNESS: 3

I’m glad I was so lopsided in favor of my family this week, because I’ll be heading out on a four-day business trip next week, which means I’ll really only get to spend time with my children and husband the next weekend. My coming week will be very lopsided in the direction of work, so when I return I could stand to prioritize sleep, friends, and fitness a bit more—especially since I won’t be able to do that much of any of those while I’m away on business. Overall I don’t have heavy guilt or pressure weighing me down, so I feel pretty great about my choices. I’m able to close the chapter on the past week feeling successful, complete, and, most of all, happy.

By using the Pick Three mantra, I’m able to eliminate any self-condemnation or shame I might have from a generic, all-over-the-place to-do list. I promise, you will feel the same. Pick Three leaves you better able to focus, prioritize, and carry out actions in the areas you choose. And at the end of the week you’ll be able to take a mental snapshot of where you spent most of your time and energy, where being the most lopsided served you, and take stock of anything you’d like to change or adjust in the coming days.

If you know that you’re going to be incredibly lopsided in certain categories in future days or weeks, try to choose the other categories now, before life gets too out of whack and you end up sleeping all day long or working until you can’t see straight. There’s well lopsided and then there’s Help! I’ve fallen and I can’t get up lopsided, and we don’t want to go there.

To get an idea of how Pick Three works, I wanted to lay out a few examples of others living by the Pick Three mantra, proof that it works the best when you make intentional choices every single day.

Emmy

Emmy is basically most of us before taking on the Pick Three lifestyle. She tries to be too balanced by picking everything and ultimately spreads herself too thin. She picks three things a day but often tries to squeeze in a fourth as well. After a week she feels stressed out, run down, and exhausted. Here’s a slice from her Pick Three journal:

“Monday: Work, Family, Fitness. Oh, and Sleep! I overslept my alarm and went to a later spin class than usual. I rushed out there and was making good time, but then there was a ton of traffic so I was super late to work, which meant I had to stay later than I had planned, which meant tonight’s special family dinner was not-so-special takeout. They forgot to put in my son’s burrito, so I ended up having to drive back to the restaurant. When I got home the kids were starving and cranky, so I let them spend the evening watching TV while I caught up on e-mails. Maybe tomorrow will be better.”

Can you tell what went wrong with Emmy’s day? That’s right, she picked four—Fitness, Work, Family, and Sleep—and consequently everything went awry. Had she stuck with three choices for the day, she wouldn’t have been late to work, she would have enjoyed her spin class, and she would’ve been home earlier to spend quality time with her family like she’d hoped. Instead, her multitasking kept her from accomplishing any of her goals.

Steve

Steve is the person who’s a bit TOO lopsided. He overprioritizes work so much that he often focuses on only two choices from his Pick Three—which leads to unhealthy consequences. Here’s a look at Steve’s Pick Three journey.

“Thursday: Work, Sleep, Friends. I have a huge work project coming up, so I’ve chosen Work as one of my Pick Three every single day for the past two weeks. Maybe tonight I’ll try to get to bed at 1 A.M. and sleep in until 6:45 instead of 6:30 tomorrow. Probably not, though—I’m so stressed, I can never fall or stay asleep. I told Tyrone I’d meet up with him for drinks later, but this project has me chained to the computer. I’ve been eating my takeout lunches and dinners in front of my screen since last Saturday. I feel like I’ve put on ten pounds! When this project finishes I’m going to pick Fitness every day! I hate how I feel.”

Right off the bat we can tell how overworked Steve is. He’s tired, irritable, making bad food choices, and suffering the consequences. He’s really only chosen Work to focus on, skipping out on his friend and sleeping less than five hours a night, if that. A lack of rest and stress plus unhealthy eating has left Steve depleted. He wants to choose Fitness, but is not making the time for it. Now he’s feeling the effects of being too lopsided in one direction. Steve needs to summon his willpower to focus on his own health outside of work, otherwise things will quickly go from bad to worse.

James

James is like the Pick Three Goldilocks—he’s got his well-lopsidedness down just right. Here’s a day in the life of James:

“Sunday: Sleep, Fitness, Friends. One more day of the weekend left! I sleep in until ten, feeling reenergized. I take a twenty-five-mile ride with my bike group and catch up with a few riders over brunch at the end. After the long day, I shower and read, taking my time doing both. In the evening I enjoy a quiet evening with Netflix and a glass of wine, preparing myself for a busy week ahead. I know I’ll be choosing Work every day this week, so I’m glad I had such a long ride today, as Fitness will have to fall by the wayside until Saturday. Until then, I’ll make sure to get plenty of rest to keep the stress at bay.”

James has got Pick Three down! He knows he’s going to choose Work for a few days, so he factors the loss of Fitness into his current schedule, giving himself permission to be lopsided for a short amount of time. He knows how important choosing Sleep is to his stress levels, so he makes it a priority, while combining Friends and Fitness to ensure both goals are complete. Well done, James! He’s a Pick Three superstar!

YOU CAN SEE HOW PICK THREE WORKS (AND DOESN’T WORK) FOR such a wide variety of people. Some people have flexible jobs and can truly pick a different three things every day. Some may find it easier to have a regular routine during the week and then a different Pick Three on the weekends. It’s hard to get the perfect mix, but with practice and your very own journal, you can crush it at picking three and finding happiness through lopsidedness.

Pick Three Workshopping

Ask yourself:

Which Pick Three have you chosen today? How about yesterday? Tomorrow?

Which Pick Three would you like to be focusing on instead of what you are currently focused on?

Which Pick Three were you focused on when you had your proudest accomplishments?

Is there any category you’ve neglected (or sacrificed) too much? If so, do you constantly feel guilty and beat yourself up?

Does this sound familiar? If only I had more money, or more time, then I’d be able to focus on my dreams. How can you put that aside and start working toward them today?

Has there been a day where you were so lopsided you were barely even able to pick two?

Journal your answers to discover how, why, and where your lopsidedness is leaning.

We will have moments when we’re able to choose what we want to be lopsided in. Other times our decisions will be made for us by events outside of our control: age, career stage, financial independence, geography, cultural and religious influences, health, education, family pressures—these all play a role.

In many of the books I’ve read that tout the perfect work-life balance, the author often seems to set their reader up for failure by assuming everyone enjoys the same level of privilege as they do. I’m not going to assume that. I know some people are born lucky; they get to pick their passion with the wind at their back. They have loving, supportive families and the means and resources to pursue their dreams, all while living in good mental and physical health. For others, the day-to-day battle is more of a struggle than an achievement. Just keeping our heads above water deserves its own medal. Sometimes we have to reduce the quest for balance to a simple hashtag on Instagram—which, honestly, feels good enough sometimes. But it doesn’t have to be. We can be better!

That’s why it’s not enough to just throw out five categories, tell you to pick three of them, and call it a day. I also want to address the types of situations and circumstances that could lead to your lopsidedness, and how to ensure you put yourself on a path most destined for happiness—no matter which road takes you there.

With That, Please Meet My Pick Three Friends:

THE PASSIONISTA: The person who chooses what they want to be lopsided in for themselves. They are currently in a healthy place where they have the support of a loving family, friends, or community to help make their decision.

THE ELIMINATOR: Sometimes, knowing what NOT to do can help you choose what to pick. Some people have a better sense of what they don’t want to focus on, rather than what they do, and they wind up being lopsided more by process of elimination than anything else.

THE SUPERHERO: A person who never actually wanted to be lopsided but, due to unforeseen circumstances (e.g., current events, illness, finances), they were suddenly forced to live life askew.

THE RENOVATOR: Someone who started off as the Passionista but hit a serious roadblock. They’ve had to rebuild and pivot to reach their goal.

THE MONETIZER: This person capitalizes on one of our basic human needs for Work, Sleep, Family, Fitness, and Friends. Through their products or services, they help us reach our goal that much quicker and achieve more in that area than was originally thought possible.

THE EXPERT: The go-to person who knows a boatload more than I do about why Work, Sleep, Family, Fitness, and Friends are so important in our life.

Which one are you?

I’m sure you can relate to aspects of many of these personas (like when you read the astrology for an Aries but you’re a Capricorn, yet the horoscope still makes sense). On any given day your Pick Three might feel very different. But remember, there is no right or wrong way to be lopsided. Whether it’s by choice or by circumstance, Pick Three enables you to get through any challenge life throws your way, through carefully chosen focus.

Speaking of challenge, living lopsided does require sacrifice—but the good kind! You have to surrender the notion that you’ll be able to accomplish everything, every day. You have to be willing to say, “Bye-bye, gym, not today” or “I’m taking that trip without my family” or “Guess I’ll have to survive on four hours of sleep tonight” or “Not answering e-mail today.” It’s simply not possible to pick Work, Sleep, Family, Fitness, and Friends all at the same time AND to do them well.

It can be difficult feeling like you’re giving something up or accepting the fact that you’re a mere mortal. But I swear that once you start focusing, prioritizing, and picking three—once you give yourself permission to be well lopsided rather than well balanced—I know you’ll find yourself happier, more fulfilled, and way more successful at the things you choose. It’s completely changed my life, and I couldn’t be more excited for Pick Three to change yours!

2

The Big Five

Work. Sleep. Family.
Fitness. Friends.
#GoTime

“The typical office worker spends forty to sixty hours per week at their desk—that’s a lot of time! It’s so important to find a job that fits your life.”

MARYJO FITZGERALD,

ECONOMIC COMMUNICATIONS MANAGER OF GLASSDOOR

I’m not going to lie: sitting down to write this chapter felt a bit like going to therapy. If I had to pinpoint the one problem area of my own Pick Three, it’s that I always want to pick Work. If I’m not crazy busy working on something, or circling the globe for speaking engagements, I somehow find a way to invent new projects. I actively have to tell myself to pick Work less and focus on the other areas of my life a bit more. Especially as a mom, I feel pretty guilty saying that out loud.

What drives people like me to constantly seek out intense work environments? Why do some of us choose to repeatedly be so lopsided toward our careers? Certainly there are many people out there for whom work is just a paycheck. Some people derive meaning from relationships and activities outside of their careers. So why do some of us put so much meaning on what we do professionally, making our work such a critical part of our identity? And what happens when we dial it back? What effect would it have if we stopped picking Work altogether? And what happens when we shift our priorities, or when life hits us with something that forces us to pick Work a little bit more or a little bit less? Getting to the core of these questions is critical to understanding the role that work plays in each of our individual Pick Three goals—and, truth be told, for my own sanity as well.

I’ve always felt that the key to success is hard work. There’s simply no shortcut in life to putting in the hours, hunkering down, and working your butt off. Whenever I see someone else being successful and I wish it were me, it simply makes me hungrier, and I work even harder.

But this isn’t a recent development. Ever since I can remember, I’ve been a hard worker. From the day I could say the word Harvard, I wanted to go there. Which meant working and studying all throughout middle school and high school. My parents provided a wonderful, comfortable upbringing, and they paid for my education so I never had crippling student loan debt. Yet I always had a little nagging voice in the back of my head saying, Randi, you can’t depend on anyone else in this life. Work hard. Earn things for yourself. Make your own money.

Whether it was helping my dad in his dental office after I finished my homework, caddying at the local bridge club, or babysitting my younger siblings and their friends for five dollars an hour (there’s monetary value in being the oldest of four children), I never turned down an opportunity to work.

And it wasn’t enough for me to just work. I wanted my money to work, too. I didn’t have much to my name, so I enlisted my dad to help me understand the stock market so I could start investing. I ultimately chose three stocks: McDonald’s (because it was delicious and I liked to go there on special occasions), American Express (because my parents had a card and used it to buy me cool things) and, only because it had a cool name, I chose this new stock called “Google.” Guess which one did the best?

Throughout high school, I worked as a restaurant hostess at the Central Square Café in Westchester, New York. I tutored local students (once I was accepted to Harvard I was able to triple my prices!), and I got promoted to head caddy at the bridge club, which meant, in addition to a bump in salary, I now got to manage other caddies. Hello, upper management!

In college, when everyone else was backpacking through Europe, I was working, often taking on two or three internships at the same time, all while continuing my private tutoring business. I even turned down an opportunity to perform at the world-famous Edinburgh Fringe Festival in order to take on a summer job. I’ll admit that one was a tough decision.

I didn’t even take any time between college and entering the workforce! I had dreams of hanging out with friends, traveling, enjoying New York City. But no. A long weekend was what I got. I graduated from Harvard on a Thursday and began working in New York at Ogilvy & Mather the following Monday. At Ogilvy, I regularly worked twelve-hour-plus days, but never thought twice about it because all my friends across every industry I knew of were doing the same. When you’re in your early twenties, you’re still very much in the “building” phase of your career, and if you have ambitious career goals, being lopsided toward Work is more of an expectation than a choice.

Back then I still had the energy to go out with my friends until all hours of the night—every night. We were living in the city that never sleeps and wanted to take full advantage of it. When I first began dating my husband, we were both twenty-two, and I remember having the philosophy that if we came home before 4 A.M., it was officially a “lame” evening. Somewhere along the years, that was revised to 2 A.M. Then midnight. Now, when we’re lying in bed at 10 P.M., we often remind ourselves of that too-cool time limit and laugh.

I thought I was working hard living in New York City, but you haven’t seen anything about what being work-lopsided looks like until you’ve worked at an early-stage tech start-up! Moving out to Silicon Valley to work at Facebook in 2005 redefined what intense work meant for me.

Back then Facebook was only a few dozen employees in a small office above a Chinese restaurant. Everyone did everything. If you didn’t know how to do something, you figured it out and did it anyway. At a start-up, the pace, the hours, the atmosphere are all so intense. Your work becomes your life. There is no separation. No balance. Colleagues become your best friends, your family, your everything. It all melds together. Which means you’re pretty much working all the time, which is a huge reason start-ups are often dominated by young people without families of their own yet. You essentially have to pick Work as all three of your Pick Three just to survive.

Stay with me and try not to be too shocked when I tell you what we did for fun: we worked MORE. Every few months, we’d hold a hackathon for the employees. Everyone would be invited to pull an all-nighter at the office and work on a project for twelve straight hours (what sort of invite is that!?). The catch—or the fun part, rather—was that the project you worked on couldn’t be at all related to your day job. You couldn’t sit in a corner and get your work e-mail down to inbox zero. You couldn’t work on a presentation for an upcoming meeting. This was twelve straight hours of passion project completion, anything new and creative. If you were still standing at seven the next morning, you got to present your idea to everyone in the company, followed by a pancake breakfast.

I know what you’re thinking, and you’re right. Our idea of a break from working was to work on other things?? Yes, this is why start-up entrepreneurs are crazy! It’s in our DNA to work, work, work, and never rest. How often is Elon Musk coming up with some new way to get to the moon, speed across the country, never pay for gas? The Boring Company? Elon Musk is anything but boring! Relaxing for even one moment gives your competitors the chance to catch up, which can mean the end of your business. So yes, we worked for work. And, we also worked for fun. I don’t want to scare you, but if you’re reading this book, thinking of starting your own company, and don’t have this worker mentality, you might want to think twice. Work to entrepreneurs is fun, and our Facebook hackathons were fun incarnate.

I don’t want to brag or anything, but I have two hackathon projects that I’m particularly proud of. The first was an employee eighties cover band called Feedbomb. Made up of current and former Facebook employees, Feedbomb played at company parties, charity events, you name it. Our motto was: We play for free, and you get what you pay for. We may not have been the world’s greatest rock band, but we had a lot of heart (and we played Heart songs as well!).

My second hackathon idea, and the one I’m most proud of, wound up being rolled out to two BILLION people. In fact, it’s probably on your phone right now. You may have even used it! It’s called Facebook Live.

I was (and still am) super passionate about the intersection between digital content and digital media. Back in 2010, when we weren’t watching Game of Thrones on demand from our laptops, when Netflix and Amazon weren’t spending billions of dollars on original, beautifully produced series, I spent a lot of time wondering if there could be a world in which television networks could live inside of Facebook. I started envisioning a place where anyone, not just giant TV conglomerates, could speak directly to their audience whenever they wanted to using Facebook as their medium of delivery. Since nothing like this existed, I went directly to some of the big networks I had led successful partnerships with previously—companies like CNN and ABC News—but since the concept was so new, I had trouble explaining my vision in a way that they could buy into, so I got turned down. Everywhere. But I didn’t give up on the vision, I just had to do it myself. So at the very next hackathon, I created “Facebook Live with Randi Zuckerberg.”

It was a flop. Only two people watched my first broadcast: Karen and Edward Zuckerberg. My parents.

I was so dejected, I didn’t even stay up the full twelve hours to present my vision to the company. I gave up, went home, and went to bed.

But somewhere something struck a chord, because only a few weeks later I got a phone call from pop star Katy Perry’s manager saying that Katy wanted to use my Facebook Live show to launch her world tour. As I was about to downplay my creation—“Sorry, but it’s not a real television show, it was just a little project I hacked together”—I stopped myself and asked, Randi, what would your male colleagues do? They’d want to meet Katy Perry. They would MAKE. IT. WORK.

And so, I made it work. Katy Perry was the first official Facebook Live broadcast in January 2011. Millions of people tuned in. Her world tour sold out in minutes. From that point on, Facebook Live became a bona fide media outlet. Everyone wanted to take part. We had celebrities, politicians, athletes, world leaders—you name it—flocking to Facebook HQ to partake in Facebook Live.

Then, in April 2011, I got a call from the White House (who gets to say that other than Olivia Pope?!) because President Obama wanted to use Facebook Live to speak at a town hall with America. In fact, he loved the platform so much, the White House began doing a weekly Facebook Live video on important information and updates happening around the nation.

A few months later, I was nominated for an Emmy Award for Facebook Live, but lost to Anderson Cooper, reporting live from a ditch in Haiti. (You win this time, Cooper.) The most exciting event of all was when Facebook launched a Facebook Live button to every single person on Facebook (more than two billion people). This, from a tiny idea that I hacked together using my free time, soon became a pivotal part of Facebook. Even though I’m no longer with the company, every time I see an ad for Facebook Live in Times Square, or watch someone speaking directly to their followers and friends, I feel proud to have invented something so ubiquitously used by billions around the world. Without ever intending to, I left my own legacy on a company that has another, far more famous Zuckerberg at the helm.

So that’s where it became pretty meta, I guess. My extracurricular work, which was supposed to be a fun break from my actual work, turned into so much work that I had to make a decision between focusing on my actual job, my side hustle job, or doing both and having no life. At a start-up, there’s only one correct answer to this question: NO LIFE.

Well balanced wasn’t even in my vocabulary during those years. When you’re given the opportunity to work on something so massively successful, which also has such a tremendous impact on every industry and event, you don’t think about balance. My work was my life. I worked around the clock for seven straight years. I traveled to over twenty countries per year for work. The weekend before I gave birth to my first son, I stayed up for three straight days, prepping for President Obama’s Facebook Live broadcast at our office.

I loved being at Facebook. But I started to realize that when you work at a start-up you didn’t start up yourself, you’re lopsided toward somebody else’s vision (even if it’s family). Great leaders are excellent at getting thousands of people to see their vision so passionately that those people become lopsided in their leader’s vision, too. But I couldn’t shake my personal passions and dreams of what I wanted to be lopsided in. It wasn’t someone else’s vision that was driving me.

Now that I think back on it, this is the main reason the performing arts kept sneaking their way into all my work projects. First, the arts just hung out on the periphery, like Feedbomb, my eighties cover band. When I think about why I created Facebook Live, a big part was my own personal desire to produce and create a new channel for the arts.

I tried really, really, really hard to suppress the artistic part of me. In Silicon Valley you’re supposed to be 100 percent focused on your start-up. If you aren’t, you’re looked at as a faux-preneur—a person who wants to lead but just doesn’t have what it takes to do so. And personal passions and hobbies are considered the absolute worst distracting, frivolous, self-indulgent, not-what-it-takes qualities to have. Magnify those qualities tenfold if you’re a woman, and a hundredfold if you have the last name Zuckerberg (hi!). There was (and still is) a serious case of Tall Poppy Syndrome in tech. The more ideas you have that create value and build your own personal brand, the more attention you draw to yourself. Draw attention to yourself, and eventually you’re going to get chopped down to size.5

This was happening to me. The more I put myself out there, the more shade I got. Blog posts mocking “Mark Zuckerberg’s sister who sings” flooded the interwebs. I had mentors give me advice to “be less interesting” if I wanted to succeed as a leader in the tech world, especially as a woman.

But I didn’t want to be less interesting! Had I really worked this hard just to be invisible? To not reap any of the payoff of putting in all that time? To me, this is where so many companies get it wrong. They think that their employees work hard only for money, so if they just throw money at their workforce, those employees will continue to keep their heads down and be just as motivated. Until they aren’t. Because we are human beings. We don’t all work hard just for money. We work hard for all sorts of reasons: recognition, pride, acceptance, feeling like part of something bigger, a few seconds of fame or notoriety, strong work ethics, etc.

All of which are exactly why I left Silicon Valley for good when my number-one bucket list life dream presented itself to me: the chance to star on Broadway in Rock of Ages.

I spent my entire elementary school, middle school, high school, and college years performing wherever and however I could. I was sure I was going to be a huge star! But life got in the way, and soon there I was, in my early thirties, working in tech, living in the California suburbs with my husband and our two-year-old son. I assumed my dream had long passed me by.

But that’s the funny thing about dreams. Sometimes they come back and find you when you least expect it. One day, out of the blue, I got a phone call from Scott Prisand, one of the producers of Rock of Ages. They were looking for something “new and fresh” for the show and wanted to bring in a guest star—a tech personality. (OMG. Was this the moment I’d been waiting for all my life? Followed by . . . Oh no! What if he asks for my brother’s contact info!? I’ll die!) You can imagine my relief and exhilaration when Scott said several people had recommended ME. His offer was a leading role in a Broadway show!!

The only catch? I’d just found out that same morning, mere hours earlier, that I was pregnant with our second child.

It was a beautiful February California day (okay, every day in California is a beautiful day). Scott asked me if I’d be available in a few months, maybe May or June, to take the role. I quickly calculated when my belly would start showing. Two plus six then carry the one . . .

“How about this Monday?” I suggested.

After a short discussion with my husband, many tears of joy, and some consultation with my doctor, I was off to New York City a few days later—while my husband and toddler son stayed behind in California. Once I arrived in New York, I had a total of eight rehearsals before I made my Broadway debut in the role of Regina Koontz in Rock of Ages—exactly three weeks after receiving that phone call. It’s hard to put into words what that experience was like, so I’ll just say that it was one of the most incredible moments of my life. But not everyone agreed with my decision.

Several mentors advised me not to sing on Broadway, that I would never be taken seriously in business again if I left Silicon Valley to don a sparkly leotard and belt out “We’re Not Gonna Take It.” You know what I thought? I DON’T BUY IT. What was the point of continuously picking Work in my Pick Three if it only meant that I would have to keep picking it for the rest of my life at the expense of everything else? Hadn’t I been so lopsided in Work so that when the time came to focus on something else, I had built up enough credibility, stockpiled enough Work Pick Threes? I was certain that at the end of my life I wouldn’t be thinking, Wow, I wish I hadn’t sung on Broadway so I could try to please people who were never going to be pleased by me anyway. That’s how, after a decade of being incredibly lopsided toward other people’s dreams and visions, I decided to focus on my own.

A study by the Association of Independent Professionals and the Self Employed (IPSE) found that 86 percent of nine hundred freelancers said they were “better off in terms of job satisfaction and similarly happier in life overall than being an employee doing something similar.”6 When I left Facebook, I started my own company, Zuckerberg Media, and immediately began consulting, speaking, and working for myself. Suddenly I could be lopsided however and whenever I wanted. It was liberating, exciting, and oh so freeing.

That said, I am NOT telling everyone who’s unhappy at their job to quit. I know not everybody would have made the choice I made, but it was the right choice for ME. I wanted to start a family. I wanted to build my own company. Being lopsided can help you find your happiness, but everyone’s version of being happy looks completely different, depending on where you are in your life. Your happiness may or may not be telling your boss to take your job and file it. (Though I do think more women should go start their own businesses!)

I know my story, but in no way do I claim to be an expert on Work, so I enlisted the help of a true Work Expert, MaryJo Fitzgerald—the corporate affairs and economic communications manager of one of the fastest growing job sites, Glassdoor—to weigh in. MaryJo told me there wasn’t anything wrong with me for being a workaholic, but she encouraged me to redefine it as being “career oriented.” However, that certainly doesn’t mean focusing solely on your work and nothing else. “While there’s nothing wrong with being career oriented,” she said, “keeping balance in all aspects of your life is important!” She agreed with my theory of being well lopsided and not trying to have it all, at least not at the same time. “Allow yourself leeway when your focus needs to be on work, and when it needs to be on other aspects of your life.”

In fact, she told me I was nowhere near alone in my career-oriented tendencies. According to a Glassdoor survey that MaryJo shared with me, Americans only take about half of their earned paid time off.7 I was part of that statistic. One year, I had literally earned a free weeklong luxury cruise as part of a work project—and I never took it! I couldn’t find one single week in the calendar year to take that damn vacation. Now, I’m kicking myself. What a fool! But in the moment, work seemed so important, with so many people depending on me, that I felt like I just couldn’t step away.

MaryJo agrees with present-day Randi (and all of you) that yes, I was a fool. Okay, so maybe those weren’t her words exactly, but she did say that taking a vacation is key to productivity. “Making time to put aside work and check out is important, and American workers aren’t doing it enough . . . or at all,” MaryJo says. “We are more productive when we have had time to step away—truly vacate—from our jobs.” Maybe it’s time to move to Fiji o’clock.

Working too hard without a break leads to all of us being far less effective in our jobs. MaryJo says the physical, mental, and emotional effects of overworking are terribly detrimental to the quality of our output. “If you’re working ten, twelve, fourteen or more hours per day, you’re no longer going to be effective at work. Our brains need time to rest so we can continue to be creative, strategic, and thoughtful. Find ways to be more efficient rather than simply burning the midnight oil. More hours spent working does not necessarily mean that you are a better worker. Quality over quantity.”

Um, MaryJo, can you please tell that to my children? They’re the most demanding bosses around!

The honest truth is that we all make our own choices. Which is wonderful. The amount that I pick Work in my Pick Three might feel way too lopsided for you. Stepping out of the workforce and not picking Work in Pick Three might feel like a saving grace for some but a horrible punishment for others. MaryJo says, “The idea of work-life balance is a very personal one, and reflecting on what your line is—when you may become unbalanced—is key. Know your limits and stick to them.” I couldn’t agree more. We all get to choose our own Pick Three.

Understanding yourself, your lifestyle, and the demands on your time and attention can help you as you navigate the role of Work in your own Pick Three.

The Work Passionista

A person who chooses to be lopsided toward work makes a choice for themselves, not out of necessity or circumstance, and generally feels that they have the support of their friends, family, and/or community in making work a priority.

“One of my big frustrations about the way the media portrays single ’career’ women is that we’re all these crazy ambition monsters who chose not to get married and have a family. My least favorite meme is: ‘She woke up at forty and realized she had forgotten to have a family!’ Nobody hits forty and thinks, Oh my God, I forgot to have a baby.”

—MELINDA ARONS, FORMER DIRECTOR OF BROADCAST MEDIA FOR HILLARY FOR AMERICA

After starring in Rock of Ages I was invited to be a correspondent for the Tony Awards, which meant interviewing stars and performers backstage—five months pregnant. I decided to go “in-tech-nito” to better distract attention from my belly, so I walked the red carpet wearing my Google Glass (the precursor to augmented reality glasses that had its fifteen minutes of fame—the Tony Awards happened at roughly minute 14:46 of that time frame). I was in my element. Theater plus tech plus Tonys, oh my!

In the Venn diagram of people who work in tech, people who are backstage at the Tony Awards, and Work Passionistas like myself, there are two people: myself and Melinda Arons. Melinda was overseeing creative video integration at my work alma mater, “The Book.” That year she was responsible for getting Tony winners to post their thanks to fans on their Facebook pages. We bonded over being fellow theater/Facebook lovers, and from then on I was a Melinda Arons #fangirl.

Melinda Arons isn’t a household name yet (just you wait!), which is precisely what drew me to speaking to her as a Work Passionista. Sure, we hear the stories of the same few dozen high-achieving famous names in business over and over again, but there are millions of us who love working hard, who are passionate about our careers, who make sacrifices in our lives in order to be career oriented. Most of us never get the same kind of notoriety, which, in a way, gives us more freedom to choose the Pick Three we want, because the world isn’t watching our every move.

I could immediately relate to Melinda. She has always been drawn to high-pressure jobs, but she doesn’t think she’s super intense herself. She simply wants to be attached to things that are the best and hates to be associated with anything in which she hasn’t given her all. Even in Melinda’s personal life, she agonizes over which restaurant to go to, which vacation to take—she strives for perfection in everything she does.

Some might call this Type A; she calls it maximizing. Why waste the opportunity to have a good meal eating something average, especially if you can avoid it? She carries this philosophy into her professional career, thriving where the action is, surrounded by other high-performing people at the top of their game.

Melinda started her career at Nightline, where she played a pivotal role in revitalizing the show. From there, she went to work at Facebook, joining the company at the time of a high-growth sprint, post-IPO. All was going upward until a few years later, when Melinda left that high-profile job at Facebook in order to take a not-so-high-profile senior role on Hillary Clinton’s 2016 presidential campaign.

Not many people would have had the guts to leave a big job like Melinda’s. She described to me the lightning-speed time line in which she received the phone call from the Clinton campaign and was given five days to make the decision to pack her bags. In that time frame, you don’t really have the luxury of weighing the pros and cons, you have to go with your gut. Melinda had always defined herself by her job titles, by the high-profile companies she worked for. She certainly was not the kind of person to make an irrational, spontaneous decision about anything—not which restaurant she was eating at and certainly not her career! Yet here she found herself making a risky, career-defining decision, with no time for data or lengthy conversations or weighing the pros and cons. A huge opportunity had presented itself, and in that situation a Work Passionista knows what has to be done.

(Melinda is the only person I know who’d leave an intense, demanding job at a tech company to work an even more intense, demanding job on a presidential campaign.)

Melinda took a huge gamble giving up the kind of job people work their whole lives to get, and all because she knew she couldn’t watch such a monumental presidential campaign pass by without getting involved. She wouldn’t have done it if it had been anyone else running for president. Melinda told me in our conversation that she would have gladly stuffed envelopes on that campaign and felt proud to do it. “The 2016 presidential election was a battle for the soul of the country,” she told me. She felt that she couldn’t wake up on Election Day and look herself in the mirror without knowing that she had given her all, worked for the outcome she wanted with the same focus and intensity as she had always approached her work.

But everything has a trade-off. Melinda acknowledges that she had to make some big sacrifices to be so focused on work. Which begs the question that every Work Passionista has to ask themselves at some point: Is it worth it?

(Especially considering her candidate didn’t win.) (Written with a heavy sigh.)

For Work Passionistas, often our biggest strength and biggest weakness are the same thing. Our intense drive and motivation to succeed propels us to incredible heights in our careers, yet can also blind us to some of the other aspects of our lives that we might be ignoring.

The question Is it worth it? is one that we all ask ourselves, at many different points in our lives. And it’s certainly a question that anyone who makes a drastic career jump must ask themselves (as both Melinda and I had done, jumping from Facebook to politics and Broadway, respectively). For Melinda, the answer is a resounding yes. It was worth it in spades. Even though the election didn’t have the outcome she had hoped for, she was proud of herself for taking a huge risk and diving into the unknown headfirst. “I finally felt like I had broken free from having my self-worth associated with big-name companies.”

But anytime you’re that lopsided in one thing, you have to look at the full picture, and for Melinda, an intense focus on her career coupled with the fact that she was living in big cities where “men really do not have to ‘settle down’ in a timely manner, if ever,” turned into an all-too-familiar-for-many vicious cycle. “You’re working crazy hard, and you haven’t met the right person yet. But then, because you haven’t met the right person yet, you work even harder to fill the void.” Melinda told me stories of how she truly felt for the struggles of working moms but, at the same time, why did nobody ever ask her about balance? Why was work-life balance only a question for people with children? Why was she always the one expected to work late hours because she didn’t have a soccer game to run home to? Didn’t people appreciate that she also wanted to go out and have a life, so that one day she could also feel that same mommy guilt to rush home to a soccer game?

Melinda felt constant anxiety over the fact that her Pick Three was being decided for her—not by her—by people who had chosen their own priorities. Which compounded her mixed feelings of wanting to pick Family, just not sure if it was in the cards for her. “I want to have children,” she said. “I just really don’t want to do it alone.”

Now Melinda is taking a break in her career, for the first time ever. After the extreme intensity of the campaign and the disappointing conclusion, she felt she needed some time to reflect. Not for long, I’m sure. Work Passionistas never do last long out of their native habitat of the workforce. In fact, by the time you’re reading this, she’s likely leapt right back into a high-pressure, intense work environment. But the year off has already done wonders for her. When I spoke to her, she looked refreshed, energized, and relaxed. She told me that for the first time in her life, Work wasn’t in her Pick Three. She was focusing on Friends, Sleep, and Family. “I know that sounds strange to hear from a woman my age without children, but one of the things I am most proud of is my relationship with my family.”

She also acknowledged that her age had something to do with her ability to take that break. She felt like all the hard work she had logged in her twenties and thirties, the years of intense commitment and long hours, had given her the credibility and the reputation to be able to take some time off without judgment. It also boosted confidence in her ability to jump right back into being a Work Passionista when she was good and ready. She told me that if she were in her twenties she wouldn’t have felt like she could take this time off and, quite frankly, she said, “I wouldn’t have deserved it.”

If you can relate to being the Work Passionista, that’s fantastic! It’s wonderful to value your career and make it a focal point of your life and identity. On the positive side, you’re likely destined for career greatness! Just remember that any time you’re consistently and repeatedly lopsided in one area of your life, it means that you only have Pick Two left, so it’s important to make sure you’re shuffling through Work, Sleep, Family, Fitness, and Friends, in as equal a way as possible. For Work Passionistas, it’s really easy to burn out if you bite off more than you can chew—especially if Work is the meat, potatoes, salad, and dessert of your meal. If you can, try to take at least one day each week where you don’t choose Work at all.

On the complete other side of the spectrum, there’s the viewpoint of people who live an incredibly rich and meaningful life without ever prioritizing Work—people who focus and Pick Three by choosing what not to do, becoming lopsided by process of elimination, removing Work as a category they ever have to choose.

Take Your Work Game to the Next Level (Without Burning Out)

If you’re a Work Passionista and you want to take your job to the next level in a way that doesn’t necessarily mean putting more hours in at the office, here are a few great tips:

BE A THOUGHT LEADER. If you want to be known as an expert in your field, you have to create content that helps other people. Luckily, there are so many easy ways to set up your own blog, or author posts on popular social media sites. Weighing in on current events in your industry, writing thought pieces, or sharing your own tips can be a great way to go from superstar employee to bona fide expert in your field, without taking up tons of extra time. (I know you’re busy, Passionistas!) I recommend posting something at least once or twice a month.

LEARN HOW TO BE A GREAT PRESENTER. You can be the greatest employee in the world, but if you don’t know how to present your ideas in an effective, compelling way, you’ll find that you eventually hit a ceiling in your career. I’ve seen way too many excellent entrepreneurs whose presentation skills hinder their ability to raise funding and recruit awesome candidates. Working with a presentation coach, joining a public speaking group, or even taking an improv class can make the difference between getting your startup funded, pitching and getting a new client, getting your idea green lit, or landing that next big raise or promotion.

GET COMFORTABLE DELEGATING. One thing about Work Passionistas: we love to do it all. But you’re never going to level up in your career if you don’t start offloading smaller tasks that allow you to focus on the bigger strategic ones. There are several tools in the marketplace that allow you to hire a virtual assistant to help you with basic tasks, freeing you up to take on more challenging assignments. Perform a cost/benefit analysis for tasks like housekeeping and cooking. Would the hours you saved from those tasks be worth outsourcing?

JUST SAY “NO.” This one seems a bit counterintuitive (won’t people be impressed if you take on more work?), but learning what to say “no” to is even more important than saying “yes.” Of course certain people are more difficult to say “no” to (i.e., your boss), but the higher you climb in your career, the more distracting things will get dangled in front of you. Lots of people want you to spend time helping them with their goals. Keep your eyes on the prize and stay ruthlessly focused on your goals. The better you do for you, the more you’ll be able to help others.

BECOME AN E-MAIL NINJA. I know you probably have a ton of e-mails to get through. Not to mention texts, posts, and all the other messages cluttering your gadgets. Train yourself to keep your e-mail communication as short as possible. If you have the type of schedule that allows it, train yourself to answer e-mail in batches, opening your e-mail only a few times a day, instead of a constant stream of disruption all day long. It goes without saying that anything remotely emotional or sensitive should always be done via phone, video chat, or in person.

The Work Eliminator

A person who makes a conscious choice NOT to focus on Work, by retiring, taking time off, staying home as a caregiver, etc. This person may or may not know what they want to be lopsided in. Regardless, they know that Work isn’t it and that they don’t want to be defined by a job or career.

“It was less judgmental than it was today. Many more women stayed at home. The ones I became good friends with, we had all given up successful careers. We were all-in on our family. I felt for the moms who tried to do both. Someone would have a court case and a child was throwing up and it just tore them to pieces.”

—KAREN ZUCKERBERG,
PSYCHIATRIST AND MOTHER OF FOUR

There are many reasons people become Work Eliminators. Some people feel like they have a calling in an area outside of Work. Some people find themselves in a financial or life situation where they have to stay at home as a caregiver. Some people have worked hard for many years and are now enjoying the fruits of retirement. Some people have a spouse who is a Work Passionista, which affords them the opportunity to direct their energy toward home.

Whatever the reason, most people don’t want to pick Work every single day of their lives. And that’s a good thing. But there’s a difference between simply taking a short career break and being a long-term Work Eliminator, and I really wanted to understand what drives people to become the latter.

There’s no one better I could have learned from about making the conscious decision to eliminate Work as one of their Pick Three, either for a period of time or for good, than the most badass, intelligent stay-at-home parent I know—my mom, Karen Zuckerberg.

My mother was on track to be an accomplished physician. She was valedictorian of her school, and, in true supermom form, despite having two children while in medical school and dealing with sexist comments left and right in a male-dominated field, she still graduated with flying colors. After graduation she went through several more years of residency, pulling multiple weekly all-nighters at the hospital—only to step away from all of it to become a full-time parent. After investing years of time and energy in her education and training, she realized that she didn’t want to pick Work, she wanted to stay at home and focus on her children. She knew that there would be people in her life who wouldn’t like that decision, or who would put pressure on her to finish what she had started, but she also knew that it was her life and she wanted to live without regretting her choices. Working late at the hospital when she had young children at home had left her with too many regrets.

I asked my mom why. Why would she do that? Why invest all that time, money, and sweat just to quit ten yards from the finish line? Did she ever wish she had stuck with her career? It was interesting to be sitting down with my mom discussing this because basically I was asking her, “Was it worth it to give up your career—for me?” I had never had such a candid conversation with my mother about her own goals and aspirations. And those include the trade-offs she had made to be such an involved parental figure.

She said that before having kids, she wouldn’t have been able to understand her line of thinking, either. She had no idea what it was going to be like being a parent until she was one. What she thought would be an easy decision—of course she would return to work—became quite painful and difficult. She found that she hated leaving her children with someone she didn’t really know. So when push came to shove, she stepped away from her career in order to stay at home.

There are real detrimental effects of mommy guilt. Guilt keeps us from truly focusing and feeling good about our successes and can cripple our forward momentum in our Pick Three progress. Maybe I’m not one to talk; I beat myself up with mommy guilt every time I take a business trip and miss our bedtime routine. This past Mother’s Day I wore a T-shirt that said WORLDS OKAYEST MOM, which is all too true. But the real truth is that being a good parent doesn’t necessarily mean choosing your family as your number-one priority every day of your life, it just means making sure you’re completely present and engaged when you are around.

All in all, it seems like my mother is quite happy with her decision. After all, I think we all turned out okay. But it was a bit difficult to hear her talk about feeling judged at cocktail parties, how people would talk to her for two seconds, hear that she was “just a mom,” and quickly walk away to go talk to someone else more “useful.” It seemed like she had many years in which her entire self-worth was completely wrapped up in her children and their accomplishments. When I asked if she had any regrets, she teared up a bit, talking about the life she always thought she would have, with her own private psychiatry practice, and told me, “Of course I do. But if I had to do it all over again, I wouldn’t change a thing.” Aw, thanks, Mom.

However, when I asked her what she would tell one of her own daughters if they told her they wanted to follow in her footsteps and be a stay-at-home mom like her, she told me she’d have to think about it. After a long pause, she said, “I’d be supportive of their decision, but I would strongly encourage them to have something of their own going on. Something they could fall back on if needed. A passion or interest that gives them an identity separate from just having children.”

She was also quick to recognize that many people do find that deeper passion and meaning in their family and that stepping away from work is absolutely the right decision for them. “The key is to find what you are passionate about. By having a passion in your life, you have a goal to work hard toward. It gives you meaning.” So if, like my own mother, your passion is for being there for your family, that’s a beautiful thing.

I was shocked (and a little guilty) to also hear my mom say that the hardest thing about being a stay-at-home mom is having your children grow up, move across the country with your grandkids, and never call or text. (Umm, who could she possibly be talking about?) Choking up a bit, she explained, “Motherhood is a job that, if you do really well, you’re no longer as needed.” I’d beg to differ. No matter where you go in life, no matter what you do, mom is always needed.

“Just looking at the adults my children have become, I’m so proud of every single one of them. I can’t believe how incredibly blessed I am,” my mom shared at the end of our interview. All I can say is that I am definitely the one who is blessed. I can only hope that my own sons feel the same way about me one day. Even though I am not a Work Eliminator, by the end of our discussion, I had a real understanding and connection for why so many people would make that choice. (Also, at the conclusion of our chat, I pulled out my phone to prove to her that I did in fact contact her at least every two days!)

But what if you were once a Work Eliminator and have now changed your mind and want to reenter the workforce? Of course, there are many situations where that makes sense. Children grow up. Financial and marital situations change. A chance to dust off that ol’ master’s degree is suddenly a welcome adventure.

According to a study published by the Harvard Business Review, 37 percent of qualified women leave their jobs for extended periods of time. Of those women, only 40 percent find full-time jobs again, 23 percent find part-time work, 7 percent are self-employed, and 30 percent don’t return to the workforce at all.8 More than three million women with college or advanced degrees are currently trying to find jobs, says Jennifer Gefsky, cofounder and CEO of Après, the staffing and recruiting company for women reentering the workforce.

I recently had Jennifer as a guest on my SiriusXM business radio show, where she gave advice to parents who had previously been Work Eliminators and now wanted to pick Work in their Pick Three once again. “Career gaps should be embraced,” she told my listeners. “Don’t run away from the résumé gap. We know it! It’s okay! Just own it.”

If anyone knows, it’s Jennifer. She left a huge job as the former deputy general counsel (and highest-ranking woman) in Major League Baseball, in order to stay at home. Reentering the workforce with gusto, Jennifer started her own company. She claims that businesses don’t put enough value on the school of life. “Life experience is huge! I have so much more to offer now than I did at thirty-five!”

Jennifer had some excellent tips for those who think they might take some time as a Work Eliminator. For instance, if you’re going to step out of the workforce and think there’s even a fraction of a chance you might want to go back and become lopsided toward Work again, it’s important to think about how you can still maintain your skills and keep a foot in the door. But Jennifer warns that certain skills and associations are more valuable than others. I was shocked to hear her say, “If you have PTA on your résumé, there’s a huge chance that résumé will go straight in the trash can. But if you put ‘I raised $100,000 for our local school,’ then that’s a transferable skill that is considered valuable in any business setting.”

When I had my second son, I decided to take some time off from work—three whole months, which felt downright luxurious, considering I had never taken so much as even a three-week vacation up until then. I know it should be standard, believe me, but that’s a whole different topic for a different book.

Voluntarily removing myself from my job for an extended time felt a bit foreign to a workaholic like me. Also, let’s remember I was working for myself by then as well, so taking time off means no clients, which means no income—exactly what Jennifer Gefsky of Après had gone through when she left MLB.

Jennifer says that when we make the decision to leave the workforce, we need to make the decision with our eyes wide open. Your current salary might not be enough to cover a full-time nanny, and therefore, you’re better off at home. But then we forget that salaries increase over time, plus all the other benefits like health care, 401(k)s, etc. You might not feel a difference with your salary today, right this second. But Jennifer urges, “The exponential loss of incoming money will make an impact”—and it might take years to realize it. So before you make the decision to be a Work Eliminator, it’s important to understand exactly what you’re up against.

Prior to my self-enforced maternity leave I’d been in discussions with SiriusXM about starting my own business talk show. They offered to set up recording equipment in my house so I could start during my leave. After some thought, I realized that this was the perfect way to keep my foot in the door while I was taking time to focus on the new baby.

Just one hour a week on the radio would allow me to stay up-to-date on the latest business news and trends, and maintain relevancy in my network. Thinking about little things you can do to keep the conversation going and maintain contacts will go a long way in the future, especially if you ever want to access those networks again. It might not be feasible for every single person to start their own radio show. (Although why not! There are more than a million podcasts in the iTunes store!) Jennifer suggests making it a priority to have at least one networking meeting or phone call on your calendar each week. And to think about keeping your toe in the water by starting a blog, becoming active with a nonprofit, or maintaining a regular professional LinkedIn account.

And let me speak to all the incredible men out there who are Work Eliminators and caregivers: advice relating to career gaps and how to reenter the workforce applies to everyone, not just women. A Pew Research Center report estimates that two million U.S. fathers with children aren’t working outside the home.9 Of these, 21 percent, or an estimated 420,000 men, say they are home to care for family. This percentage is a fourfold increase from 1989, when only 5 percent of men claimed full-time caregiving as their reason for not working outside the home. Men are definitely not absent from the stay-at-home-parent equation, and we salute your efforts!

If you can relate to being a Work Eliminator, either a temporary one like Jennifer or a permanent one like my mother, I take my hat off to you. The people in your life are very lucky to have you. The wonderful thing about eliminating work is that your relationships often pay off abundantly (my mother is one of my very best friends), resulting in lasting value that’s priceless.

I want to caution Eliminators—especially after speaking with both my mother and Jennifer—to make sure that your identity and self-worth do not get too tied up in other people. We can’t control what other people do or how appreciative they are, no matter how much love, time, and energy we put into those people. Both Jennifer and my mom echo the sentiment that for Work Eliminators, it’s crucial to have your own personal projects or hobbies and to try to dip at least one pinky toe in the water with professional contacts if you think there’s even the slightest possibility you might want to be lopsided toward Work in the future. As Jennifer puts it, “Know the price you’re paying for what you’re doing. Keep a foot in the door. Do something once a week to keep going.”

My mom, the quintessential New Yorker, put it a bit more bluntly. “If you don’t have something of your own going on, you won’t be interesting to people, and they won’t want to connect with you.” And, if and when you DO decide to go back to the workforce, don’t delay—just get started. Good things happen when you put yourself out there.

Keeping the Door Open

Many people take a break from their careers. Sometimes it’s a short break, sometimes an extended one. If you think there’s even the slightest chance you might want to return to work one day, here are a few ways to keep one foot in the door so that it’s much easier to reprioritize your career if you choose to do so.

READ. A LOT. Stay informed on current events and industry trends so you can have an intelligent conversation with people who could become valuable connections. If things you’re reading and learning about make you feel so inclined, play around with the idea of writing the occasional blog post or starting your own podcast on a topic of your interest and expertise.

MAINTAIN YOUR CONNECTIONS. Make sure you don’t lose touch with former employers and colleagues who might need to serve as a reference or make introductions for you one day. Make sure you at least lightly stay in touch with your professional network on social media, send holiday cards, and pick up the phone at least once or twice a year to say “hi.”

TAKE ON A VOLUNTEER POSITION. But do it strategically. Depending on what industry in which you want to stay connected, certain volunteer activities will be viewed as more transferable and applicable than others.

KEEP UP WITH TECH. Has the technology in your industry been changing? Make sure you stay up to date on changes, even if it means taking an occasional class or getting a tutor. The better you keep up, the less overwhelming it will be to try to reenter a career where all the tools of the trade have completely changed.

BECOME AN INTERN AGAIN. Don’t be afraid of unpaid, temporary, or part-time positions. Maybe you have children going away to camp for the summer? Maybe you have some extra time in the mornings? Maybe you’re able to work a few hours from home? Some companies have more formal “returnships”-intern programs for people coming back from a career break.

The Work Renovator

Someone who hits a roadblock that causes him/her to have to rebuild and refocus career plans.

“Failure can be a blessing. I don’t even realize the times when I do things that are seemingly brave. Losing the election was such a gift. I didn’t die, and I live a life that’s honest enough. It doesn’t mean there aren’t consequences, but I don’t feel duplicitous.”

—RESHMA SAUJANI, FOUNDER OF GIRLS WHO CODE

It can be difficult to reinvent yourself in your career. Sometimes no matter what you do, no matter how hard you try, you just keep hitting wall after wall after wall. After I left Facebook, I had moments of crippling insecurity when I worried no one would care about me if I was no longer tied to one of the hottest global companies in the world. Would I ever be anything except for somebody’s sister?

A few weeks ago, I was on CNBC discussing an exciting new project I was launching, something that has absolutely nothing to do with Facebook whatsoever. Yet the anchor introduced me by saying, “Mark Zuckerberg’s sister is here in the studio with us today.” So I replied, “Sorry, I haven’t legally changed my name to ‘Mark Zuckerberg’s sister’ yet, so please just call me Randi.” It’s taken me a few years of moving to a different coast and having several successes all on my own, but now I truly have the confidence to embrace my personal reinvention.

Most of us are somewhere in the process of reinventing ourselves. Perhaps that’s why you’re reading this book—to learn how to better restructure your career, rebrand your life, shift gears. The world is changing so quickly that people who dedicated their entire careers to one company now suddenly find themselves out of a job when their company goes under. People who chose what would normally be evergreen, “safe” jobs are now seeing that no position is truly safe in the tech era. The world is full of motivated, ambitious people who have been forced to become Work Renovators.

Take Reshma Saujani, the founder of Girls Who Code. I first met Reshma in 2010, when she was running for Congress. In fact, the first political campaign I ever donated to was Reshma’s! Even though she didn’t win that election—or her following run for New York City public advocate—Reshma’s passion for community leadership and change shone through, and I was proud to support a young woman running on such an ambitious platform.

It would have been easy to get jaded after losing two elections in such a short period of time. I mean, a regular person can hit a brick wall and face public rejection only so many times before they give up, but, luckily, Reshma is not a regular person. She stuck with her decision to give back via public service and was able to reinvent herself in one of the most masterful pivots I have seen: as the founder of Girls Who Code, a nonprofit that teaches programming to young women in order to increase the number of women working in computer science. A true Work Renovator in every sense.

Reshma pivoted her career after her two-time defeat. She jokes that it wasn’t really even a choice. When I spoke with her she said that each time she lost a campaign, Girls Who Code got bigger, growing with every setback. Although her mission was always to launch GWC, her initial plan was for someone else to run the organization while she spent her own career working in public service. “But I guess that was never God’s plan, or anyone else’s plan,” Reshma admitted. “When I lost my public advocate race and got shut down on getting computer science into every classroom, I said, ‘F you. I’m going to do this on my own and build this massive movement.’ ” Where many would have backed down, Reshma instead reached even higher, using the pain from her failures to create something larger than anyone had expected.

Years later, Reshma says she can finally admit that losing the election was like a gift. While, of course, she was disappointed and had to reconcile that she might never have the life in politics she had always dreamed of, she still felt that at the end of the day she could hold her head high because she’d tried. She went for it. The vast majority of people would have been too scared to even step into the ring.

I speak to many successful people every week on my SiriusXM show, and most of these entrepreneurs have faced failure, rejection, and disappointment. It’s how you respond to that failure, how your inner Work Renovator starts rearranging the pieces, that truly defines you in that moment. Reshma’s experiences helped her redefine what success means to her, and that success now means running an incredible organization that creates opportunities for girls that wasn’t available before.

Recently Reshma became a mother, which added a whole list of joys—and challenges. Reshma and I joked about the mommy guilt we feel when we leave on business trips. She quoted Arianna Huffington, who said, “We take the baby out, and we put the guilt in.” Reshma told me a story about a time she decided to bring her son along to an event she was speaking at. Her nanny had a last-minute emergency and couldn’t watch Reshma’s son on the day of the event. “I’m about to go onstage and address all the governors of the country and my son starts having a fit,” she told me, describing a situation that would make pretty much any parent cringe with understanding. Kids always have such impeccable timing! “My team’s looking at me like, ‘Whoa.’ And of course in my mind I’m like, ‘Why do I do this to myself? I could’ve left him at home.’ I’m happier when I’m with him, but that often creates more chaos.”

All kidding aside, I truly appreciated Reshma’s parting wisdom to me about how she constantly asks herself how she can be better and how she constantly pushes herself outside her comfort zone to the edge of her ability. She’s found that as she’s gotten older, she rarely does things that make her comfortable, and that those moments where she’s testing her limits are truly what make her feel alive.

When to Break Up With a Client

Sometimes if you work for yourself or are a freelancer, being a Work Renovator means knowing when you have to move on from a difficult client. It may seem like a first-world problem to have to turn down business, but time and talent are things you should never be okay with someone else taking from you.

I was flown out to New Delhi for a tech conference a few years ago. I flew halfway around the world to give a thirty-minute keynote about the future of social media and its importance to Digital India—an initiative to advance the tech infrastructure to all Indian citizens by 2019. The conference sounded exciting and definitely within my wheelhouse. I was proud to be asked to be part of a panel that included the head of Google India, who was making sweeping digital advances in the country.

But once I got to India, it was a different story entirely. India is still a male-dominated country, and I heard from a few Indian women that they had “many, many, MANY glass ceilings to break there.” My speech was cut down from thirty minutes to six minutes because the man speaking before me went over his time. During our Digital India panel, I was the sole woman present and I was only asked ONE question: how I balanced having children and working (go figure), a question that made my eyes roll and that none of the male panelists were asked. So yes, I got paid for that trip, but did I feel good about earning that money? NO. I felt underutilized and embarrassed.

MORAL OF THE STORY: if you work for yourself, value yourself. Establish your rates. Find that number you can say without laughing . . . then add a little bit more. (I’m looking at you, ladies!) The more you set some ground rules and stick to them, the more others will value your time as well. And if a client isn’t working out, well, sometimes renovating means doing some spring cleaning.

Can’t we all relate to the Work Renovator? We have dreams of what we want to be when we grow up, what we’re going to do—then life happens. When you read about great entrepreneurs, you’ll often hear about the concept of “pivoting,” or being able to react quickly and swiftly to changes in the market in order to set your business on the right track, even if it means scrapping your original plans and doing something completely different. Well, human beings pivot, too. Very few of us are doing today what we thought we’d be doing when we were children. (I thought I was going to be a mermaid!) All of us hit roadblocks and obstacles.

Work Renovators like Reshma are resilient, they are bold, they know how to pick up the pieces of their professional life that work—and how to walk away from what isn’t working. Lots of people get stuck. It’s difficult to venture out into the uncomfortable, the unknown, but Renovators are resourceful. Had Reshma not experienced those defeats, she wouldn’t have been able to conquer them, achieving the success that brought about great change both for her career and for the world.

The Art of the Pivot

There’s no perfect time to make a career pivot. Sometimes it’s by choice, sometimes a wrench unexpectedly gets thrown into our employment plans. But if you wake up and realize your career is on the wrong track, then by all means do something about it! You’re not alone. Most of us, at one point or another, will make a career switch, change jobs within the same company, decide to freelance, or even start our own venture.

GET ADVICE FROM OTHERS, BUT YOUR THOUGHTS MATTER MOST. Lots of people will tell you the many things that could go wrong. It’s usually a mix of them being risk-averse because they love you (and change is scary) stirred in with some jealousy because they probably wish they could make a big change, too. If your heart tells you it’s time for a career pivot, don’t let other people’s fears dissuade you.

TAKE STOCK OF YOUR SKILL SET AND WHAT YOU LOVE DOING. Chances are good that once you pinpoint what you enjoy doing and what you’re good at, you’ll be able to find several industries that utilize those skills. Network with others in those industries or attend local meetups to figure out what skills you might need to catch up on.

UPDATE YOUR PROFILES. Make sure any website or social media account others can find via Google is updated often and refers to your projects and skill sets. Just because you’ve mentally begun the process of pivoting doesn’t mean that everyone else knows!

TIMING IS KEY. If you’re going to start talking about making changes publicly, make sure you’re ready to follow through. If people send you leads for new jobs, clients, or opportunities and you don’t follow up, you’ll find that people become less likely to want to help a second time around. Have a clear plan of action so you can act on leads that come in.

JUST DO IT. Honestly, sometimes the best thing to do for your life, for your soul, is to make big changes and go for it. Don’t drag it out. If you know you want to do something, then your heart and mind are already made up, you just need to take the leap. The worst thing that can happen is that it doesn’t work out and you find another job. There’s never been a better time to take risks. I’m excited for you!

The Work Superhero

A person who becomes lopsided toward Work in support of someone they love—a spouse, a dear friend, a family business, etc. No capes necessary.

“As the years have ticked by there’s something in our chemistry that is abnormal in the sense that we’re together 24/7. So many couples split up during the day. We never escape from each other. I don’t know if that’s good or bad. But it works for us.”

—BRAD TAKEI, BUSINESS MANAGER AND HUSBAND OF GEORGE TAKEI

Sometimes we become lopsided not for ourselves, but for the people we love. My husband is someone who truly embodies this. When I received that phone call to sing on Broadway, suddenly my husband turned into a single parent in California—and he supported my decision every step of the way.

For my final performance he flew to New York to see the show again (his sixth time, I believe). After the show he helped pack my things up for my return home. Even though I was ecstatic to return to my family, I cried the entire taxi ride to the airport. Like, ugly cried. The cabdriver had to turn up the volume on the radio, I was sobbing so hard. To this day I can’t hear John Legend’s “All of Me” without weeping.

By the time the plane touched down, my husband proposed that we consider moving back to New York City, permanently. Even though he didn’t know if he would have the same career options as in Silicon Valley, he told me I seemed lighter in my soul. “You love theater,” he said. “How can someone like you be happy living in suburban California? I’ll find a great company to work for. We’ll find a great school for the boys. Let’s do this.” So we did.

(For context on how über lucky I am, this is the same man who turned down his dream job in California to stay with me when I lived in New York after college. A few months after the job offer had passed, I decided to move to California to work with my brother at “The Facebook.” After a year of long distance, my husband moved out to California to join me. You can see why I married the guy!)

In the summer of 2015, we moved to New York City and never looked back. (Well, okay, maybe a few times in bitter-cold February, we may have questioned our decision.) Now I’m a voter for the Tony Awards and the Chita Rivera Awards. I’m happily required to see sixty shows a year. My husband—who couldn’t even name three musicals when we first started dating and could count the total number of theatrical shows he had seen on one finger, now spends most of his weekends seeing shows with me. He can name every Broadway show that’s come out in the past five years and has a knowledge of show tunes that could rival Kristin Chenoweth’s.

These same traits of my husband embody the Work Superhero—someone who is lopsided toward Work to support the career passions of the person they love deeply. Aside from my husband, there is nobody who embodies this role with more grace, passion, and enthusiasm than Brad Takei.

Most people know Brad’s famous husband, George Takei, and his groundbreaking role as Mr. Hikaru Sulu, the helmsman of the USS Enterprise in Star Trek. Brad and George have been married for nine years and together for thirty. Brad has endured the ups and downs of a Hollywood career, providing encouragement and guidance and, in many ways, changing his own identity to support his husband’s.

George and Brad met in the early eighties, when Brad was a full-time print journalist. When he met George, Brad was a recreational runner, something George was also passionate about. They met through LA Frontrunners, a gay and lesbian social running club. They ran around the Silver Lake reservoir and the rest was history. They kept their relationship a secret for eighteen years. In 2008, George and Brad legally married after being domestic partners for two decades.

Brad didn’t always work as George’s business manager. He valued his career as a journalist and loved his work. But little by little, their relationship started to shift from being life partners to becoming coworkers as well. Brad started to realize how detail oriented he was in comparison with George, who got lost in lofty artistic and intellectual concepts. “He’s always got these big ideas, but is he going to make that flight on time? As a journalist I’m detail oriented and do great bookkeeping. We became a good combination. So, from the nineties onward, we’ve been Team Takei. Taking the ups and downs of life and work.”

George is seventeen years older than Brad and has acted as a mentor, while George sees Brad as his reliable Rock of Gibraltar. “Every morning I always bring George a cup of hot green tea and the print edition of the New York Times when it’s available. We end our day, even if we’ve had any spats or conflicts, with a kiss before we go to sleep.”

George is the brand of Team Takei, so when Brad and George attend sci-fi conventions, George, one of four original Star Trek cast members still alive, is often the center of attention. “A couple of decades ago I was in the shadows, but George has made a point to share his life with people. Since we’re always together, he’s inclusive about me. Now people want my picture, too. I have just enough introvert in my personality to be fine with George being the center of attention. I’ve always been blessed, I’ve never felt jealous.”

Brad and George have a wonderful working relationship because they have a strong personal relationship. Brad feels that being together 24/7 is actually a relationship saver, because they can address everything in real time so they’re always on top of things. “The truth is, we had to make choices all along to get to where we are. The dirty secret of our personal and business life, the reason it works so well, is that we are both workaholics.” (I corrected him: they’re both Work Passionistas!)

George was already a household name when he and Brad met. In 1965, the creator of Star Trek, Gene Roddenberry, cast George as Hikaru Sulu, which suddenly provided George with a megaphone where millions of people were listening. He wanted to use that megaphone for something meaningful, so he began telling the story of the Japanese American internment camps he grew up in as a child in America. When Brad and George met later on, Brad understood that supporting George meant supporting George’s passions, so as part of #TeamTakei, Brad championed his husband’s decision to use his celebrity to speak out against inequality and the lesser-known horrors of American history. “If you don’t use the platform you’re given, you’re not helping. When forced into the position of doing the right thing, it can be both challenging and rewarding at times.”

Brad is happy being George’s middleman between Hollywood and the outside world. He provides George with everything from Kleenex to vitamins to green tea. “I think to myself, we’ve never had a marriage counselor or therapy in our life because I can forget about the petty stuff. George is an artist, so I let him have his space. Maturity is really helpful. I made my life commitment to George in my thirties. When it was time for George to settle down in his forties, it was a commitment. I don’t really understand divorce too much. I’m a child of divorce. And I couldn’t imagine separating from George. I made a commitment to this person. It’s not about me. It’s about us.”

The saddest part for George and Brad was that when they got together, LGBT people in America faced more obstacles than they do now. George was in his late forties, Brad in his early thirties, and they knew they would never have children together. “We were closeted gay men at the time, so it would have been unfair to the kids. . . . If you know George and me, what great parents we would’ve been. We have younger kids in our life we get to shower our affections on. George loves kids and would’ve been a great father. We don’t have the energy now, at eighty and sixty-three.”

If you can relate to Brad or my husband, and feel like you have changed your course or shifted your career to accommodate someone in your own life, then clearly you’re a Superhero! It’s a wonderful thing to be able to give so freely of yourself and apply your business skills in a way that benefits someone you love so dearly. In fact, you’re making me feel like I should probably go give my husband a big hug right about now, because it is impossible to accomplish anything in life without a strong support system—if you’re a Work Superhero, then that’s you!

This entire book is about Pick Three, and you’ve pretty much beaten me at my own game because you’ve already accomplished a major life hack by picking two things at once, so congrats!

That said, it’s important, too, that your independent sense of identity stays strong and you keep at least one or two interests that are solely for yourself—whether that’s a fitness routine, a genre of music, or a book you’re reading. It’s very easy to allow your identity to get swallowed up by someone you love and support, especially when your career decisions all come back to that person you love. (Not that I know anything about being involved in a family business and starting to lose your own identity—Oh wait, I do.)

Brad Takei admitted his secret way of getting in some of his own Brad time: reality television! “I download reality TV shows on my iPhone—Housewives, Survivor—at night while [George] is reading Japanese novels that help him intellectually. He has no interest in reality TV. . . . He also loves going to see Shakespeare. For me it’s like watching paint dry.”

It took me a few years post-Facebook to feel like I was back on the path to having my own identity. Hopefully you make sure to keep a few interests and activities that are just for you, even if you find incredible meaning in helping someone else achieve their career dreams.

The Art of the Side Hustle

Actor/singer or writer/director—it used to be that only entertainers could add the slash in their career summary. But nowadays it’s becoming more common that people pay the bills with their nine-to-five job and fulfill their dreams from five to nine. It’s called side hustling, and it can actually become so lucrative that you can quit your day job to follow your passion.

Take Shark Tank’s Daymond John, who worked at Red Lobster for four years while trying to build his clothing brand FUBU, which is now worth millions. Or actor/physician Ken Jeong, of the Hangover franchise. Jeong was a licensed doctor, performing stand-up on the side, when he got cast in Judd Apatow’s Knocked Up, and his career soared up from there. Side hustling is not as simple as ignoring your day job and pinning all your hopes on one prospect. Just ask Hulk Hogan, whose Pastamania restaurant lasted less than a year in business.

Tina Yip is the cocreator of 5to9, a podcast for those looking to pave the way for their dreams while working a regular nine-to-five.

“Having a side hustle is a great way to explore your passions. It’s a blank canvas that is 100 percent you. No one is judging you, and you can do whatever you want with it! No matter how much you love your job, you’re making someone else’s dream happen. With your side project, you’re making your dreams happen at minimal cost. It’s where you can be 100 percent you. . . . The tough reality is that because of survival and economic needs, we’re forced to follow career paths and opportunities that value making money more than doing what we love. To make our careers closer to our passions, we need to be creative and find ways to integrate the two.”

Four Ways to Create Your Own Side Hustle:

  1. IDENTIFY THE PURPOSE AND ASK YOURSELF WHY: Whenever you have an idea about a project, ask yourself why you want to do it and how it serves a greater purpose in helping you be who you want to be. A lot of side projects lose steam because people simply go with their first instinct and realize soon after that they don’t really want to work on it. But by all means, if the purpose of your side hustle time is to experiment with as many things as possible that struck a chord with you, then go for it!
  2. STAY ACCOUNTABLE WITH A THIRTY-DAY OR ONE-HUNDRED-DAY PROJECT: This is a great way to structure your side hustles and keep yourself accountable.
  3. COMMIT BY SETTING SIDE HUSTLE MEETINGS AND BUDGETS: Treat your side hustle time like a real appointment. If you can make an appointment for your mani/pedi and show up, you can set aside side hustle time.
  4. TELL AS MANY PEOPLE AS POSSIBLE: Because you never know how much people are willing to help.

The Work Monetizer

Someone who creates a business around the fact that other people want to pick Work in their Pick Three. They help other people become lopsided toward Work—and make money in the process!

“My only regret is that I didn’t become an entrepreneur sooner in life. I could have left the corporate world years earlier. I wish I had done that, but I didn’t have the mind-set at the time. If you have that mind-set, go for it.”

—LEAH BUSQUE, FOUNDER OF TASKRABBIT

Some people dedicate their career to being an IRL fairy godmother, helping other people who want to work. Whether that’s being a recruiter, a career counselor, a coach, a mentor, or an angel investor, I knew I wanted to talk to someone who, when they choose Work for their Pick Three, are really choosing to help other people in their own choosing of Work.

Leah Busque is one such person. Leah is the founder of TaskRabbit, which helps users hire local, freelance labor to perform everyday tasks, like cleaning, moving, delivery, and handyman work. Her company was recently acquired by the IKEA Group, a company known for its particularly difficult-to-assemble furniture. In order to help people who have free time and want to use that time to work, Leah built TaskRabbit to help those who want to focus on their career find ways to outsource the more menial tasks of life.

She created the company when she realized that nothing like it existed to help with her own needs. Leah and her husband were on their way to meet out-of-town friends for dinner, but they were out of dog food. She knew there must be someone in her neighborhood they could hire to pick up a can of Alpo, and, as an engineer herself, she saw a gap in the market. Where was the mobile app that combined location awareness with task completion? A lightbulb went on, and Leah knew that her calling was to build a service that brought people together around helping out with tasks—providing real opportunity for people on both sides of supply and demand. She built and financed the idea for a year out of her own pocket, and then quit her job at IBM.

Leah first launched TaskRabbit as a moms’ organization—because, honestly, who needs more help outsourcing tasks than moms? The moms used the TaskRabbit taskers to outsource trips to Target, grocery stores, dry-cleaning pickups—you name it! Since the mom network is so strong, the word of mouth spread like wildfire. TaskRabbit was soon expanding beyond the initial few neighborhoods Leah had launched in, and she found herself recruiting taskers to service different neighborhoods around the nation. Leah has not only built a great tech platform, she created an entirely new marketplace.

Both supply and demand were strong. On the supply side, during the tough economic crisis in 2008, there was no shortage of people willing to make money on a flexible work schedule. Even retirees who wanted to stay active found a place at TaskRabbit, and professionals could work on nights and weekends to help make an extra buck.

On the demand side, moms, busy professionals, and those who were bedridden were all using TaskRabbit to ease the load of their day-to-day needs. One particular story that stands out for Leah is from a San Francisco mom who had a twenty-year-old son in Boston going through cancer treatment at Mass General.

Pick Two to Create One

Ted Eytan, M.D., is the medical director of the Kaiser Permanente Center for Total Health and vocal advocate of walking meetings. He’s a family medicine specialist with a focus on total health and diversity.

In 2008, Ted posted an essay called “The Art of the Walking Meeting” on his Web site.10 Ted says, “I was perusing through the excellent December 2007 issue of Health Power! Prevention News and happened on a review of this systematic analysis of the impacts of using pedometers to increase physical activity and improve health. . . . This caused me to think creatively about how to get steps in—and combining work and walking was an idea. I was hooked immediately. This is among the most contagious innovations I have ever experienced. So much so that even to this day every person I take on their first walking meeting pledges to do it again. What human would rather sit in a room and stare at someone else for a half-hour versus walk in their community?

“[I’ve experienced more] mental clarity and brain stimulation that comes from exercise. No ability to check your e-mail and tune out while you’re walking! And there’s scientific proof!

“Also, I found I had experienced the equivalent of two or three gym workouts from a day of walking meetings. Suddenly I craved them and even started looking for reasons to meet with people, if only to meet my fitness goals. To this day, I walk to and from work in Washington, D.C., two to three miles each way (different route every day), and I actually tweet about each one!”

Ted’s advice on how to start your own walking meeting trend at work? “Make no assumptions. Ask people first and use their curiosity as an opportunity to learn. The thing about sitting meetings in a room is that you need have no curiosity about the other person because that’s the default, lowest-common-denominator interaction. With walking, you’re going to go somewhere with someone, and that requires you get to know a little bit about them—can they physically do it? Do they want to do it? What types of walks do they like? Nature or urban? What memories might this bring up for them if they’ve been to a place before? How will they react to things they see on the street?

“I tell the story once of an executive who I asked to go on a walking meeting with me. When I arrived at her office, she said, ‘I brought running shoes to work today for my walk with you,’ and to me it was the kindest display of respect and support. I will never forget that. (And then I spent the next half-hour trying to keep up with her. I will never forget that, either.) So I guess that’s one meta-benefit—the relationships and special moments I’ve created with people that are unexpected and wonderful.”

“She couldn’t fly out to visit him as often as she wanted, so she went on our site, hired someone to visit him every single day, sit with him, bring him a meal, and call her every day to report on how he was doing. The tasker was another mom, and over time, the two women formed an incredible bond.” Leah is honored that her company helps people redefine who their neighbors are and who they rely on. She’s proud that her platform uses tech to bring people together.

If you identify as a Work Monetizer, it’s wonderful that you’re so passionate and driven by helping other people realize their professional goals. Congratulations on having such meaning and purpose! But, at the same time, it’s easy to get too lopsided as the Work Monetizer. You’re probably already a Work Passionista, and when you add onto it other people’s Work Passionista tendencies, it can be very easy for every conversation, every interaction, every moment to turn into work.

Make sure you’re taking time to be around people who aren’t just looking to you for something work related. Build time into your schedule that has nothing to do with your own career or finding careers for other people.

The Person Who Writes Summaries

Just kidding! Sort of . . .

I think most of us can see ourselves in a few of these categories. While I would overall refer to myself as the Work Passionista, I’ve also been the Work Renovator, like when I left Facebook to start my own business. Or the Work Eliminator, like when I put that same business on hold to follow my dream of performing on Broadway. Aside from establishing lopsidedness in life, the purpose of Pick Three is to look back and see which obstacles made us stronger and how future opportunities can be tackled head-on. We are wiring our brains for a successful outcome, regardless of what may get thrown our way.

Whether you’re a Passionista, an Eliminator, a Monetizer, a Renovator, a Superhero, an Expert, or some combination of several of those, there will be times in your life when you may be very lopsided toward your work. There will conversely be times in your life when family obligations or personal reasons require you to stop choosing Work and set your sights on a different trajectory.

Both Reshma Saujani and Melinda Arons were involved in political campaigns that had a different outcome than they had initially hoped. Melinda decided that after years and years of being all-in on her career and constantly picking Work, she was going to take a year off to focus on herself. Reshma channeled her energy into building a nonprofit organization to accomplish the goals of her political platform in a different way. My mother went from an intense career in medicine to deciding to be a stay-at-home mother, while Jennifer Gefsky went from a high-powered career in sports, to becoming a full-time caregiver, to launching her own start-up. Brad Takei shifted his career to support his husband, George, and Leah Busque built a business around empowering other people to pick Work.

Even in my own life, I’ve had moments of being all-in on my career, shifting my plans to work for a “family business,” stepping away to focus on personal dreams, and eventually jumping in even deeper by starting my own business. Every single one of those decisions has come with incredible benefits and equally difficult challenges.

I’m proud of the incredible companies I’ve worked for, and especially all the leaders I’ve had the opportunity to learn from, including that dude in the hoodie. I’ve consistently worked hard my entire life—hopefully that will never change. What has changed, though, is how I work, what I want to work on, and, most important, who I want to work for. Somewhere along the line, I got tired of creating value for other people.

When I started Zuckerberg Media, it started off as a marketing agency and production company. Through trial and a lot of error, I realized that creating my own intellectual property sparked a fire inside of me far stronger than being in client service. I was creating all of this IP as a side hustle, including my first book, Dot Complicated, which is now a radio show on SiriusXM, and my children’s book, Dot., which is now an award-winning television show aired around the world. Or Sue’s Tech Kitchen, my tech-themed family dining experience. Now Zuckerberg Media focuses almost exclusively on creating, growing, and licensing our own intellectual property. It’s hard to describe how amazing it is to watch something you fully created take on a life of its own.

Now, when I choose Work in my Pick Three it comes with a slight caveat of doing work that creates value for me. What does work do (or not do) for you? Take note of your answer and keep a log (like the one in the back of this book). How often do you choose Work for yourself? Ask yourself why you choose Work. Is it because you love it, you have to, you have a deadline—what is it that moves your career? Only YOU have the power to define what your job means to you. Once you understand how, when, and why you make the choices you make, you can better figure out if changes need to be made—and how quickly you need to make them.

We all have different paths, different goals, different opinions on the role of work in our lives. Remember, as long as you balance the trade-offs that come with any lopsided decision, everything will be A-OK.

As our Work Expert MaryJo Fitzgerald says, “I believe a work-life balance is attainable from a big-picture perspective, as the demands across areas of your life and work ebb and flow. You’re not going to feel perfectly balanced every day, but aim for a larger sense of balance in your week or month. Allow yourself leeway when your focus needs to be on work, and when it needs to be on other aspects of your life.”

This is the essence of Pick Three.

If life sees you lopsided toward Work, that’s awesome. Stop feeling guilty about the things you’re not choosing and give yourself permission to kick ass in your career. If you’re not choosing Work right now, you’re also doing great! Whatever you choose to be lopsided in, dedicate yourself fully and do it well.

All this work talk has me exhausted. Guess that’s our cue to talk about sleep!

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