Fail Until You Don't

by Bobby Bones

Clock Icon 72 minute read


Fight, Grind, Repeat or . . .

Your Motivational Guide to Being Less Terrible at Life

When I decided to write another book (even though I didn’t know if I had another chapter in me, let alone a whole new book in me), I wanted to write about how to face your fears. I figured I’d describe a lot of the fears I’ve felt in my life and how I faced them all—like the superhero that I am. But, to be honest, that would be a load of crap. And my fans are quick to smell the BS. (It’s weird to call my people “fans.” When I think of “fans,” I picture a Green Bay Packers diehard with face paint and no shirt fighting the elements in subzero temperatures. My people aren’t fanatical about me. They understand me—or at least can stomach me for relatively large amounts of time. That’s all I really need. And I appreciate that.)

So instead of hitting you with a fake face-your-fears-it’s-amazing read, I’m going to tell you the story of when I faced my biggest fear. And I’m writing this just a few hours after it actually happened. Basically, this is the book version of an NFL instant replay. Except not so instant, because you’re reading it months after it happened, because these books take forever to get published.

Rest assured, the details are still fresh in my brain as I sit here in the Little Rock airport, a familiar and comfortable setting. I’m surrounded by nice folks decked out in Arkansas Razorbacks hats and T-shirts. About ten people have already stopped to tell me that they listen to my show. I appreciate when anyone stops me to say they tune in to the morning show I’ve been doing in some shape or form for nearly twenty years. (Man, I’m getting old. I know I started radio at seventeen, but twenty years? So, my career is as old as some of the girls I’ve considered dating. I mean, I know twenty is too young for me. They can’t even get into a casino. But I’ll start taking rejections at age twenty-five or so.)

Although my morning show is nationally syndicated, it’s always cool when someone from where you grew up says they listen. It’s especially sweet in Arkansas, my first home (with Austin and Nashville coming in second and third). Despite all that good stuff, my cage is a little rattled right now. Mostly because of that fear I just mentioned. (You know, the one we discussed before debating openly if I’d still date a college sophomore. To reiterate, I don’t think I would.)

Before I reveal the mysterious fear, a little backstory.

You know all about this if you read my memmmmwarrrrrr (a.k.a. memoir), Bare Bones by Bobby Bones (that’s me); or have listened to my radio show, where I talk a lot about myself; or have stood anywhere within twenty feet of me in the last hundred months. But just in case you don’t fit into any of those categories, here’s a quick version—I don’t know my biological father. I mean, I know who he is, like his name and where he comes from. It’s the same place I came from. (Not the same vagina. That would make him my “brother-dad,” and I’d have a reality show on TLC right about now.) But that’s about it.

This stranger, otherwise known as my dad, left my mom and me around the time that my memories started being formed. So I have only fleeting impressions of him sort of being there, but no full-on memories. No ball playing. No whuppins. No “you’ll eventually get girls to like you,” or “you can’t date that many girls at once.” (Amy, my cohost and moral compass, set me straight on that one.)

So, yeah. I don’t know my dad. He’s never been a part of my life. It’s sad. So sad that I decided to turn it into a joke for my stand-up act. Here it is:


I was on Facebook yesterday looking at the tab of People You May Know and my biological father popped up. (Long pause for effect.) I didn’t.

I’d now like to do an impression of my biological father . . . (Then I walk offstage.)

(In my mind, that joke was a real hit, even though it just confused the audience. But I love it. I love creating any sort of emotion. I love to make people confused and question if they are supposed to laugh. I love to make people feel, which often means taking them out of their comfort zone.)

Jokes aside, when it comes to not having a dad, I’ve been sad, angry, resentful, apathetic (having repressed all the previous feelings), and then sad again. That’s a cycle I’ve repeated for about the last thirty years of my life. And, as I was thinking of the scariest things I’ve ever done—you know, for a relatable and engaging anecdote to open my new book—I felt like it would be hypocritical not to describe my biggest fear. And that is . . . meeting the person I’ve turned into the ultimate villain in my mind. My dad.

I let my anger and fear keep me from ever reaching out. I thought I was punishing him for not being around when I was a kid. In reality, though, I was punishing myself. It wasn’t until I started thinking of the central ideas of what I wanted this book to be about that I felt I finally had to take that polar plunge. (That’s the stupid group of people who jump into the water in winter because they say it’s so invigorating. But most of the time, I think they just end up with pneumonia.) Although I might have been subconsciously looking for any reason, I decided to reach out to my dad after all these years because I didn’t want to feel like a hypocrite when I wrote about all the positive results that come from facing fear.

The adventure started with a text to my cousin Mary asking if she had his number. She did. Crap! Now I had to reach out. Again, if I wanted to lecture you about chasing your biggest fear, you would come back at me about why I hadn’t done mine. So I was in it to win it. Or, as they say on the streets, “I was in it because I was writing a book about failure and didn’t want the whole thing to be a farce.” Yeah, that’s street lingo.

“Hey. It’s Bobby Estell,” I texted, thinking if I just wrote “Bobby” he probably wouldn’t know who it was. (I nearly texted, “It’s your long-lost son Bobby.” But I wasn’t sure he would get the sarcasm.)

“I’m going to be in town,” I continued, “and wanted to know if we can meet up.”

Then I waited for a text back.

One hour—nothing.

Two hours—nothing.

I assumed he wasn’t like me, the guy who keeps his phone in his hand the entire day, but it was still nerve-racking to not get a text back after a few hours. I had really put myself out there by sending that message. The least I would expect was an answer, even if it was “No.”

I was traveling that day, so I didn’t have a lot to do except stare at my phone, which made time drag by even slower and my anxiety ramp up even more. I began to think he wasn’t going to text me back at all. Rejected again.

Finally, about four hours and twenty-three minutes later (but who’s counting?), I got: “That sounds good. Let me know.”

What did that mean? “Sounds good”? And “let me know”? AND why did he take four hours to get back to me? Was he on a job site, getting an MRI, trapped in a well? Or did it actually sound not good to him . . . I don’t know what I was expecting. “WOWOWOWOWOW!!! Glad to hear from you. I’ve been meaning to text you for the last 30 years but I couldn’t find your number.


But still.

Over the next few days, I distanced myself from my nagging doubts. If there were an Olympic sport in compartmentalizing emotions, I’d take down Muhammad Ali or Michael Phelps as being the greatest of all time. Right then, I separated myself from it. Bam! Much like doing the Tide Pod Challenge, I acted like I didn’t want to go through with it, but secretly I wanted to see what all the fuss was about (both meeting my dad and eating Tide Pods). (By the way, WTF are people thinking eating those small packets of washing detergent? And by people, I mean adults who are smart enough to put videos on YouTube. There’s no reason we need to do PSAs for twenty-three-year-old Internet attention whores who choose to eat soap. For moms with babies, I get it. “Hey, new moms! Watch out that little Katie doesn’t eat those packets that look a lot like candy . . .” But for adults to learn on the news: “Don’t eat detergent, because you can die.” They already know that! To report on the obvious is to do nothing but compel fools to continue eating the clothes-cleaning poison. That’s right: I blame you, Today show!!! Sorry. I’m just dealing with a lot of Tide Pod stories right now. Onward.)

The trip to see my father became just a date on the calendar. I booked my flight from Austin to Little Rock and carried on with my life. Nothing to see here. (Imagine me whistling after I say, “Nothing to see here,” like they always do on television from the fifties. Yeah, that was me playing it cool.)

It wasn’t until I was on the flight to Little Rock that it thumped me in the ear: I was going to meet the man who helped bring me into this world, then disappeared over thirty years ago, and for all that time hid in plain sight. He lived no more than a few miles from me for a lot of the time I was growing up, but for that story you’ll have to read my first book.

One of my favorite creatures is the butterfly. (It’s not my absolute favorite. That would be dogs, with koalas coming in a close second. I got to hold a koala in Australia, and he didn’t bite or take a crap on me, so I was pretty pumped. After that, the koala shot up the favorites list very fast.) I say I love butterflies because I love that feeling of butterflies in your stomach that you get when you’re nervous. We don’t have a lot of times in our lives when we get to be genuinely nervous about a potentially positive outcome. Being nervous is uncommon; it’s uncomfortable; it’s stressful. That’s why it’s awesome. Being nervous is how I feel alive. To me, it’s a rush. A mental bungee jump.

On the plane to meet my dad, though, I wasn’t nervous. At least not in the awesome way. I was overwhelmed with thoughts about where this whole thing would lead. I wondered if my father was suspicious of my motives. I’m the one who has yelled on the radio and written in a book that I was pissed about his sudden departure all those years ago. And yet here I was initiating contact by texting him out of the blue. What could he be imagining—that I wanted to beat him up? Or be best friends? Did I need a kidney?

I was trying to get into his head more than I was worried about what was going on in my own. This was no doubt an intellectual defense mechanism, because I knew that a few layers down, I was petrified.

As soon as my flight landed in Arkansas, I texted him that we should meet for lunch the following day at a BBQ restaurant I had found online and chosen for its convenient location. I had initially thought about meeting in a park or just on a bench somewhere, but then reconsidered. That was just too weird. If someone who I hadn’t seen in years told me to meet him at a park in the middle of the day, I’d instantly assume it was because he wanted to jump me for money . . . maybe to buy that new kidney I was talking about.

The next day, at exactly noon, I drove into the parking lot of the BBQ joint and—bam—there he was, sitting inside his truck. I knew it was him because I had seen him in a couple of pictures over the years. And I also could just tell. He looked like me more than anyone else I’d ever met. Or should I say, I looked like him.

Now, I had purposely showed up right on time in order to avoid this situation. I hoped he’d be early and inside waiting on me. Not the opposite. This was now turning into a first-date-with-a-hot-chick experience. Except instead of a hot chick, insert “the man who abandoned me thirty years ago.”

I turned off the gray Jeep Cherokee I had rented, got out, and walked directly into the restaurant. I didn’t want to walk inside with him.

Who opens the door for who? Pass on that situation.

The awkward talk and walk, side by side? Pass on that, too.

The BBQ place was the kind where you order from a counter, get a number, seat yourself, and wait for your food. I was looking up at the menu above the counter when he walked in and stood right behind me. He was wearing a blue work uniform. Blue on blue, and extremely white tennis shoes. Let me commend his white shoes, by the way, because I know those were probably work shoes, and they were as clean as could be. I got a pair of white Yeezys and before I could get them out of the box, somehow they looked like they had been in a charcoal bath. White shoes are THAT hard to keep clean. So I respected that. He also had on a camouflage ball cap on top of his long hair.

With my dad too close to ignore and continue ordering, I turned to him. “Hey, man. Good to see you,” I said, reaching out my hand to shake his and thinking, Please don’t try to hug me.

He didn’t. He shook my hand and said it was good to see me as well. We had a brief, uncomfortable conversation about what to eat. (Luckily, I already knew what I wanted. I know what I want to eat before I get to a restaurant almost every time I go to one. I prepare for the menu as if it were a driving test. Although I don’t have to cheat with menus like I do with driving tests. I’ve never NOT cheated the eyesight part of the driving test. You see, I can’t see. I have one eye that simply doesn’t work. My right eye only sees light and fuzzy shapes. And when I look into that machine with said eye, I see nothing but a bright yellow stain mocking my inadequacy. If you google the right things, you can memorize that current test. I shall say no more for fear of having my driver’s license revoked, but, yes, I’m always trying to game the system.) Then I put in our order and sat in the back of the restaurant.

He was smaller than me. I liked that, because if things got ugly I knew I could take him to beatdown town, except for the small fact that I’ve never actually punched anyone. Still, I liked that I was bigger. My brain started to draw complex maps of the unknown terrain ahead.

What do I say first?

Did I really use the phrase “beatdown town”?

I’m such a loser.

I decided to go with thanking him for taking off work to meet me as an opener. Then I asked the most important question first. I mean, sitting in front of me was someone who was supposed to be the most important man in my life and I hadn’t seen him in thirty years. Now was my chance to find out what I wanted to know more than anything else. So I just went for it. I asked it. Straight up.

“Will you pull your hat back?” I asked. “Do you still have all your hair?” He let out a nervous chuckle and pulled his hat back.

“I’ve still got it all,” he said.

He wasn’t bald! Or even losing his hair! As a matter of fact, he has lots and lots of it. He basically looks like everyone from Lynyrd Skynyrd. That was awesome, and I was grateful. He may not have bought school supplies, taught me how to shave, or awkwardly told me it was “normal for men to play with themselves,” but he did give me good hair genes. And before you tell me, “Hair is all on your mom’s side,” that’s BS. It’s been proven 123,413,232 times that it can come from either or both. I have a lot of friends who are just as bald as their dad. So, hair. Check!

The food came. I noticed his hand was shaking when he took a bite of his sandwich—and that was pretty much the only bite he took. However nervous I felt on the plane yesterday or even in the parking lot a few minutes earlier, it was clear my dad was way more nervous. There was something about seeing how rattled he was that settled me down. When crazy situations arise, most of us fall into roles. Mine was the calm one. He hardly touched his food, but I was devouring mine. As I went through an entire rack of ribs, I had them bring me an extra plate for the bones and more paper towels.

We talked about what he does now (he works with my cousin Josh, who runs a roofing company) and about how he had been sober for a while.

“I’d really like to drink,” I said, “but it doesn’t seem to be a good spot for any of us with our genetics.” He agreed and urged me to stay away from it since I’ve gone this long without touching the stuff.

He talked a lot about his horses. “I get back to my land whenever I can to make sure they are fed and taken care of,” he said with obvious pride. I was happy to hear that.

I wanted to talk about jail. See, a lot of my family has been to jail and I wanted to know why. He told me he had only done a “few rounds” for dumb stuff, and for very small amounts of time. We talked about my cousin Derrick, who made the national news a couple of years earlier for escaping prison.

“I couldn’t believe that it was on Good Morning America,” I said. “The cops were calling asking if I knew anything.”

He said the same thing happened to him. I think they showed up at the house of pretty much every Estell to see if Derrick was there. By the way, google “Derrick Estell prison escape.” That’s my first cousin!

I don’t remember my dad asking me any questions. Part of me thinks that he listens to the show and reads things like this book, so he has a good idea of what’s happening with me. Part of me thinks he was just too freaked out. Either way I was okay, because being in his physical presence was enough.

For once in my life, I just wanted to sit across from my dad and have a conversation, even if it was about nothing. And for forty-five minutes, over lunch, I did. Sure, he’ll never be my “dad” in the way most people use the word, but by not reaching out to him because I was scared of rejection I wasn’t giving either one of us a chance to change the story. As a defense mechanism, I had turned him into the Joker or Bane, a supervillain out to destroy my life. By avoiding him, I had made him into something much larger than he actually was—someone who has screwed up a lot, someone who is extremely flawed, someone just like me.

The End.

Except . . . not really. That was the perfect ending for this section: dramatic and heart-wrenching, with a hint of self-reflection. But I don’t go down like that.

Can I first say how awkward it was for me to write the word “dad” in reference to the man I had lunch with? I just got tired of writing “biological father” in every paragraph. I wouldn’t call him “dad” to anyone, except for the fact that I’m a lazy writer. I also won’t call Kid Rock “Bob.” (His real name is Robert Ritchie, and his friends call him Bob.) I’ve spent some time with Kid Rock recently through work, and everyone keeps telling me to call him “Bob.” Even Kid Rock says, “Call me Bob.” Won’t do it. I nod and say, “You got it, Kid Rock!” He will always be freaking Kid Rock. And I’m a huge dork.

The real end of the story with my—gulp—“dad” is a lot less dramatic. We’ve exchanged a few texts since that lunch, and I plan to reach out next time I’m home. I never thought we were going to turn into Andy Griffith and his son, Opie. The greatest outcome from that lunch is that I will no longer NOT go home because he is around. This fairy-tale ending is still growing its wings. Hopefully nobody dies!

What I hope you take away from this is that sometimes we assign completely false narratives to stories because they make life easier to understand. I did. I imagined my real dad lying in bed at night, laughing like a maniac about how he had wronged his son. Totally false. He didn’t like it any more than I did. But it was easier for me to believe that over the truth, because it allowed me to make him the bad guy. The truth is that he is just flawed. I am also flawed, and I hope people can understand and forgive me like I have my dad.


By now, you’re probably wondering how this depressing story about a deadbeat dad and his neurotic son is going to lead to self-improvement, right?

I’ll be honest. At first, I wasn’t sure I wanted to write this book. I’m not a guy who looks for signs in the universe to tell him things. I believe that if you search hard enough for the answer you already know, you will find it. As human beings, we generally follow an instinct but still chase affirmation from something bigger than us to tell us that instinct is right. But I’m not a normal human being, and I’m not going to do that. I don’t believe in luck. I don’t believe in destiny. Instead, I believe that our lives are powered by countless microdecisions. Some dude found a million-dollar lottery ticket on the sidewalk walking to work one day. What if he hadn’t gone to work? What if he hadn’t chosen that sidewalk? What if he hadn’t looked down at the ground? All of these are factors that we assign to luck. But I believe every single thing that happens to us, good or bad, is affected by decisions we make.

The title of this book should be a tip-off that this isn’t going to be some think-positive-thoughts-to-success kind of program. I always come to things from an underdog’s point of view, and who am I to offer any kind of “program,” anyway? My preferred place to start is the bottom, where, as they say, you have nowhere to go but up. And when you start from the bottom and succeed, you also have a theme song. Cue Drake’s “Started from the Bottom.”

The point of the lunch-with-my-dad story isn’t even that I had faced my biggest fear. For years and years, I had thought about meeting him, even at times obsessed over it, but I never, ever made a single attempt. As those years kept ticking by, the act of trying just got bigger and harder—and so I had to turn my dad into a villain to explain my inaction.

By giving the act of meeting my dad one legitimate, full-hearted try, I knew that no matter what happened, I wouldn’t fail. At least not in the long run.

In my book (both literally and figuratively), failing isn’t bad. Oftentimes, people won’t try things because they’re afraid to fail, but my philosophy in life is all about winning by losing. That might sound like a foreign concept, because the general rule is that if people are good at something, they win. But really, from all I’ve learned, the biggest winners are also the biggest losers. And I definitely put myself in the biggest loser category. Not to be confused with the TV show The Biggest Loser. The only episodes I’ve seen are the ones where the contestants bust through the paper of their old selves and poof, they are one hundred pounds lighter. That show makes losing a hundred pounds look pretty easy, even though obviously it isn’t. I’d like to equate the finale of The Biggest Loser with your life. Most people will just see you bust through the paper in whatever transformation you’ve made and think, “Ah, that was so easy for you.” But they don’t know you’ve been grinding on a treadmill for hours when the cameras were off. They don’t know you’ve been getting yelled at by Jillian Michaels for licking the plastic wrapping on a cookie a few too many times. They don’t know! But I do know, because I’m someone who has failed so often that eventually I learned something useful to break the cycle. And I plan to give you the information to turn heartbreak and failure into inspiration.

I developed the strategies I lay out in this book (including embracing failure) out of necessity. I had a dysfunctional upbringing that lacked any of the resources—financial or cultural—that people typically need to succeed. And yet, I had big dreams for myself. I wanted to do more than follow the example of my parents and peers in my small, poor, dying Arkansas town. I wanted to beat my very bad odds. When you’re trying to beat bad odds, you have to do more than what’s expected (like going to college and working hard). A lot more. And you have to be your own champion.

None of that’s easy, which is why I came up with these strategies to help me along. But let me say, they weren’t right the first or second or ninety-third time I implemented them. And they continue to be partially wrong even today. I have figured out that you never completely figure it out. If that makes me sound like the Aristotle of Arkansas, so be it. Everything in life is a moving target. I set absolute goals (e.g., I’d like for my show to be heard in one hundred cities or to make my next romantic relationship last for more than eight whole days), but regardless of the result, I learn from it and keep going. Too many people in my life just blow in the wind and change what they want as the weather picks up. I’m basically Jim Cantore from the Weather Channel; I stand out in the hurricane and take it on to see what happens on the other side.

Take, for instance, this Category 3 hurricane that blew in just today, conveniently, as my deadline arrived to commit to writing this next piece of literary genius. My latest inspiration in the winning-by-losing game came just two hours ago in the form of being rejected yet again for a television show. If you haven’t read my first book (Bare Bones by Bobby Bones, in case you already forgot), I should give some more backstory. That book started with me auditioning for a TV show. And ended many months later with me landing the part (yay!) but the network ultimately not picking up the show (boo!). And lots of life stories, both happy and sad in the middle . . .

Here we are. Again. I got a no on another TV show. But at least you didn’t have to wait through an entire book to find out the ending. And it motivated me to start this book right.

(For your visual consideration: I’m sitting at a red desk, wearing a pair of blue shorts and a fake vintage AC/DC T-shirt—even though, for the most part, I think fake vintage shirts are so cornball. The problem I have with fake vintage shirts is that people wear them to look way cooler than they really are. Someone with real style or passion for a vintage band or piece of clothing would have many options to find a legitimate, authentic band shirt: eBay, thrift shops, Etsy. But nah, instead we find it at the mall or Target, buy it, and Wikipedia JUST enough about the band or album in case anyone asks us about it. My light blue AC/DC shirt that I’m wearing right now says 1974 JAILBREAK. I wasn’t even born in 1974. I admit to being a cornball, but I would like to establish a new rule about wearing music T-shirts to simply look cool. If you are wearing an artist on your shirt, and you don’t know at least five of the artist’s songs when someone asks, you owe a five-dollar donation to the charity of that person’s choice. With this rule now in place, either people will learn more about Merle Haggard or puppies will get fed! Either way, it’s a win.)

So back to my latest rejection, which arrived in an e-mail, notifying me that a show I was executive producing had been turned down by a major network. This was one that I felt pretty sure was going to work (and I’m a very pessimistic person). It was about a couple of people in the country music world and their family life. Nothing earth-shattering, but we weren’t trying to be groundbreaking here. The finished product was warm, funny, and not puke-inducingly fake. In reality-show terms, that’s the best you can hope for. The network’s test audiences gave it great reviews. And even so—bam!—nope.

My response could have been to curl up into a ball and binge-watch The Walking Dead, but I have a general rule: the bigger the disappointment, the harder I keep trying. A wise man once said, “Instead of crying, I keep on trying.” And that wise man is me, because I just made that up. I think. Quote me on that unless you see it in a meme somewhere where Billy Graham or Gandhi said it. Otherwise, yeah. I just made that up.

I’m not going to give up or let this setback stop me from getting lots of TV shows on the air (and right now “lots” means one). So here I am, hours after being told NO to yet another TV show, taking a few notes on what I’ve learned this time around, and bouncing back with the knowledge that if I keep trying and getting better at making television, something will actually work—and I’ll Win by Losing.

Now, I can imagine you may not be very inspired by this kind of advice from a guy like me. I’m no longer broke, I have radio’s biggest country music morning show, wrote a bestselling book, and front a band that has also had a number-one record and song—and here I am patting myself on the back for recovering after not also getting a TV show. But if you knew where I came from, you might understand the power of my mindset and see how it has helped to get me to where I am today. Like many other people, I grew up with so much adversity and negativity, it would have been easy to get overwhelmed and give in. But by turning negatives into positives, losing into a journey to winning, I have been able to overcome the odds that were against me and change them into motivation for my success. It’s that mentality I hope to pass on in this book to others who are struggling.

I was raised in the small town of Mountain Pine, Arkansas (population seven hundred—and that’s optimistic). Typical of a company mill town after the mill shuts down, it’s an impoverished place. When I was growing up there, money wasn’t a thing people missed, because no one had any of it. If you give a sixteen-year-old a BMW, take it away from him, and replace it with a Kia, he’s probably going to be upset. We didn’t even know BMWs existed. It was the same with options in life. Hardly anyone left Mountain Pine to pursue his or her own dreams. We didn’t even know BIG dreams were allowed to happen. The folks who I grew up with weren’t mad about that; we just knew our place. And we knew it because we saw it every day all around us. No one told us we were stuck. But no one told us we weren’t, either. Suffice it to say, my hometown was not conducive for a kid’s dreams of creating his own media empire.

Yet, even within this poor community, I always felt that I was coming from a disadvantage. My mom, who struggled her entire life with alcohol and drug addiction, had a hard time holding down a job and often left me in the care of my grandmother for long stretches. For years I resented the fact that I was a food-stamps kid, a head-lice student, a connoisseur of the finest welfare checks. I hated it. I blamed everyone around me, and I loathed other kids with the flimsiest of safety nets, because I had none. I never saw this uncertainty for the strength it gave me.

It wasn’t until much later that I realized the dividends all those years of suffering and struggling have paid. Starting from zero meant I had nothing to lose. Most important, though, having no options kept me focused in a way that would have been impossible otherwise. There was no plan B for me. I didn’t have the luxury of a fallback career. My only choice was to keep plugging away even as I failed. And failed. And failed.

But I didn’t just fail; I also kept notes. And learned from my mistakes. And kept my head in the game. As my stepdad used to say to me when I was in my teens, “You can’t catch a fish if your hook isn’t in the water.” I kept my freaking hook in the water. All the time. Even until this day. My hook is never coming out of the water.

John Mayer once told me that he figured out the world was “bendable” when he was around nineteen years old. Although I had never used his fascinating term for the experience he was describing, I knew exactly what he was talking about. I didn’t discover I could move around in the world freely until my early twenties.

Around the time I graduated from college, I realized that it wasn’t just me who felt insecure and at times defeated; most people didn’t know what they were doing, either. They were also figuring it out as they went—and that’s nothing to be ashamed of. If I just showed confidence in a direction I had chosen (false confidence or not), that was good enough. I didn’t need to have any special knowledge or power to give something I wanted to try a shot. I just needed to do it—and there’s a lot of freedom in that line of thinking.

I believe with all my heart that if you want something bad enough, with the right life choices and work ethic, you can get it. (Unless it’s physically impossible to attain, so don’t hit me with “I want to dunk a basketball but I’m an overweight five foot three.” It’s not going to happen for you, dude.)


I didn’t come from the toughest background of all time. I understand that I had privileges others didn’t. I met a guy a couple of months ago who had been homeless all the way through high school. Still, he graduated, went on to college, and even earned an advanced degree. So, when I say the privileged have it easier, we are all a little more privileged than somebody else. It doesn’t just go one way.

The reason I talk about where I come from is because I come from the same type of background that a lot of America comes from: small town; week-to-week paycheck; some sort of not-so-pleasant family situation that may or may not include a lot of illegal substances. You may be a rich kid who had a terrible family situation. We all have our baggage. I’m not the only one. Mine’s bad. Others have worse. Who is capable of judging on that kind of scale? I used to build seawalls (one of the many jobs I’ve done—you’ll read more about those later), and the worst part of that was carrying large white buckets of wet concrete up a hill. They’d bruise your legs, hurt your hands, and there was always another waiting for you at the bottom of the hill. We all have our different buckets of concrete.

I know there are a lot of people out there who can relate to me. And it’s for folks who don’t have anyone to say, “Not only do I know where you come from, but you can do this,” that I’m writing this book.

When you are coming from less (and there’s a lot of us), you have to give more to get equal to the rest of the world. It’s not fair. But the fact that we have to fight our way to the top makes us so much stronger when we eventually get there. How counterintuitive is that? When we start from worse, it can make us better! But it’s a real advantage if we use it the right way.


If we take a look at some of the most successful people in our culture, you’d be surprised how often they failed. I could give you a million examples, because I’ve studied this. But here are just a few striking ones:


Walt Disney was one of the most creative and innovative minds of the twentieth century. He created freakin’ Mickey Mouse! He dreamed up Disney World! He produced over six hundred animated movies! No way he ever sucked! Right? Wrong.

  • He was fired from a local newspaper because he lacked creativity. (Can you believe that someone thought this dude lacked creativity? That’s like me getting fired because I don’t have enough Bs in my name.)
  • His first business went bankrupt.
  • He was told his little mouse was a terrible idea because it would terrify women.
  • More than three hundred people turned down investing in his crazy theme park about that same terrifying mouse.

But Walt believed, and now there’s probably not a person on the globe who doesn’t know the name Disney. Because he kept on, that “terrible idea” turned into a global multibillion-dollar corporation of parks and resorts; broadcast, cable, and radio stations; a killer movie studio; toys; apps; clothing. . . . And I think his head is still frozen somewhere, regardless of what anyone says. (Okay, so maybe not all of Walt’s ideas were winners, but you get the point.)


Whenever you read articles or books that talk about the cofounder of Apple, they always bring up that he, like Bill Gates, dropped out of college—and still became one of the most successful people in the universe. But that was just one of his “failures.” The man, who basically created the way we talk to each other now through technologies like the iPhone and iPad, had a whole bunch of massive product failures with that company he started in his garage. Even after he became a success, he was fired as an executive from the company he created! People took many things away from the famous biography of him by Walter Isaacson—that he was controlling, that he had a big ego—but what I saw was a guy who people considered nuts and who wouldn’t give up when it came to his vision. I hope to be considered as crazy one day.


Writers, like actors, are famous for getting rejected. It goes with the territory. But the bestselling horror writer took rejection to a whole other level. “By the time I was fourteen the nail in my wall would no longer support the weight of the rejection slips impaled upon it,” he wrote in On Writing: A Memoir of the Craft. “I replaced the nail with a spike and went on writing.” Still, when his first book, Carrie, was rejected by thirty publishers, even he got discouraged. You can’t blame him for throwing the manuscript in the trash, which is what he did. Luckily for him, his wife fished it out and encouraged him to give it one last shot. I guess the thirty-first time was the charm, because it was accepted and became a runaway bestseller. Since then he’s sold more than 350 million copies of his books worldwide, many of which have been made into movies that scare the crap out of kids everywhere. And by kids, I also mean adult men in their thirties who wear dark-rimmed glasses.


Let’s talk about him for a minute. We know him as pretty much the first great American solo artist. But when he went to the Grand Ole Opry, they basically said, “Dude, don’t come back. You can’t sing.” Then they advised him to go back to being a gravedigger, which is what he had been doing to make money. He couldn’t even get into an a cappella group—and nobody likes a cappella. Except Pentatonix. Pentatonix! You’re cool.

“Ode to Failure,” My Poem-ish Thing from My Tedx Talk in Nashville

Even Disney got fired

The opposite of winning . . .

Now we love that cartoon couple

Mickey Mouse and Minnie.

Honest Abe failed at business

How much lower can you get?

He dusted it off, got up again

Became our sixteenth president.

Do you know how many Jobs . . .

Steve was fired from?

Now we’re all swiping Apples

So much it hurts our thumbs.

Oprah was let go as a reporter

At the age of twenty-three.

Oprah Winfrey in the daytime

Highest-paid host on TV.

The Beatles were turned down

By some record label jerk.

You tell McCartney or Lennon

That his music wouldn’t work?

And I don’t stand here before you

As the picture of success.

I just got real good at losing

And held out longer than the rest.

The pattern is real; the people who make it are the ones who don’t quit. They are borderline crazy about what they are trying to achieve. They fail. But they don’t quit.

That’s been true in my life as well. Out of thirty radio jobs I applied to in my career, I only got three of them. And thirty is a low estimate. Those are the ones I can remember not getting. Still, one in ten—that’s a lot of freakin’ rejection. Sometimes a formal rejection was the best thing that could have happened. Want to feel like you really suck? Send a full package—your résumé, tapes, the full thing—and hear nothing back. Not even crickets to keep me company. That happened to me more times than I was told no.

I wanted a job so badly that one time I placed a tape of my radio show, my résumé, and my picture in a pizza box. Then I put on some khakis and a button-up shirt to deliver the pizza box to the station myself. I figured if the program director thought it was pizza, he would open it and take note of my ability to go the extra mile creatively. I walked into the station and the program director was in the reception area! Jackpot! “This is for Peter Cottontail,” I announced. (Not his real name, duh.) Freaking Peter Cottontail opened the box, excitedly looked inside, and then mumbled, “This isn’t even pizza. This is an f-ing demo tape.” That was right before he threw it into the garbage. Needless to say, I moonwalked out of that place and did the ol’ “nothing to see here” whistling trick until I got far away!

Do I enjoy bombing out? No, of course not. But I’ve learned far more from my failures than I have from my successes. It’s almost a feather-in-the-cap-type thing when you mess up and can figure out what went wrong, because then hopefully you won’t make the same mistake again. The next time, I sent a pizza with the demo tape. I still didn’t get the job, though. It’s like the baby that touches the stove. Most babies don’t give that stove a second grab. I try not to give boneheaded moves a second grab. And rarely a third. (If you keep making the same mistake over and over, it’s time to call a shrink—because there’s some hidden cog in your brain that’s sabotaging your best intentions, and you gotta work that crap out. See: every relationship I’ve ever been in.)

University of Alabama head football coach Nick Saban once said, “I don’t want to waste a failure.” That struck me. Every failure is some kind of opportunity in disguise. In fact, I’m only writing this book because I failed at pitching a children’s book.

True story. I went from publisher’s office to publisher’s office, selling my idea for a kids’ book. Except no one was buying. Finally someone (my wonderful publisher) decided that I should do a kids’ book “later” (still waiting) and begin my career as an author with a motivational memoir instead.

I was petrified to write that thing, and, frankly, at first I didn’t think it was very good. I wasn’t sure if my stories were relatable, inspirational, or at all entertaining to anyone. Particularly smart folks like you, who read real-life books!

Smash cut to my first book making the New York Times bestseller list. And it never would have happened if I hadn’t failed at writing a children’s book. It’s unbelievable looking back at the turn of events that led to Bare Bones and all the awesome people I met during the process. Turns out readers not only sympathized but mostly empathized with my stories. My whole perspective on my own life story changed because I failed.

Fail. Learn. Repeat. Fail. Learn. Repeat. Keep failing, until you don’t.

Don’t believe me? I get it. I’m just a radio dork/barely decent comedian/mediocre musician. Why would you take my word for it? I am about to get all smart on you and reference something pretty amazing. How about a Stanford professor and one of the world’s leading researchers in the area of motivation, who has spent her life studying the secret to success? After decades of researching how people achieve, psychology professor Carol Dweck discovered a simple but revolutionary concept she calls “mindset.” Basically, she breaks mindset into two different types—fixed and growth. Those who have a fixed mindset think that their ability and intelligence are fixed and that talent is the biggest predictor of success. If you have a growth mindset, on the other hand, you believe you can improve any of your natural skills through “dedication and hard work.” As the good professor writes: “Brains and talent don’t bring success. . . . They can stand in the way of it.”

That’s really something coming from a lady who’s taught at Harvard, which is ground zero for brains! But I get what she is saying. Knowing you can improve is a highly undervalued form of intelligence. Some of the smartest people I knew in high school and college have struggled. But the folks who always worked their faces off are all doing fine. There is no genius in effort. There is no genius in fortitude. I’ve found that the most successful self-made people are those who are great at chasing an idea hard, screwing it up, learning from it, and getting right back into the chase. It’s about keeping up the hustle. I love the hustle.

Dweck is a huge fan of effort, arguing that you can always improve no matter where you are starting from, and that mindset “creates a love of learning and a resilience essential for great accomplishment. Virtually all great people have had these qualities.” In her book Mindset: The New Psychology of Success, she shares how her research began with a desire to figure out how people deal with failure. She created a study where kids were presented with puzzles that got increasingly harder. Some kids simply gave up, while others embraced the challenge and got psyched on the struggle so they could get better at doing puzzles. “I always thought you coped with failure or you didn’t,” she wrote. “I never thought anyone loved failure. Were these alien children or were they on to something?”

It seems those kids were on to something and so was Dweck, whose theory has had wide-ranging implications for the fields of business, sports, and education. “Failure is information,” Dweck later told Forbes. “We label it failure, but it’s more like, ‘This didn’t work, and I’m a problem solver, so I’ll try something else.’”

That gives us failures some real hope! As long as we can find the resilience to bounce back from defeat and the consciousness to learn from it, we can achieve “success.” According to people who study this stuff, a lot of it depends on your attitude toward whatever you find hard. If you think that you’re a loser because you didn’t get math, the girl, or the job, you’re probably going to have an even harder time making a go of it next time. If there’s a next time. But if you can flip the idea of rejection on its head and turn it into a chance to improve your algebra or your pickup lines, then you aren’t stuck at the bottom of the heap but at the beginning of a long, optimistic hike up the mountain.

If failure is information, according to Dweck, I got a huge data dump on me during my network TV debut, when I was tasked with interviewing Jason Aldean on an awards show.

The plan was for the chart-topping singer and me to talk for a solid two minutes, which is an eternity for live TV/radio/anything. Look in your mirror and just try to talk for two minutes straight. Then come back to reading this, and you’ll have a lot more empathy for this story.

With microphone in hand and a ton of questions and witty comments in my head, I waited backstage with Jason for our cue. Moments before we were set to take the stage, a producer yelled, “We have fifteen seconds! Not two minutes.” Fifteen seconds! That is hardly enough time to say “Jason Aldean.” This was no longer an interview but an intro. Before I could process the information, the producer had counted me down and I was onstage. Away I went, and by “away I went,” I mean I screamed like a parrot. If I could write how my intro sounded, it would go something like this: “Jason Aldeaaaan is neeext, babyyy, woooooooosadfsldkfaljsdflsd.” And then the camera shut off, someone grabbed my mic, and I was led to my seat.

You can always tell when you don’t do a good job, because no one wants to talk to you afterward. Sometimes people will talk to you—but not about the presentation you just gave in the office or your performance in a community theater production but about something totally random. While I walked back to my seat, a friend said, “Man, your jacket looked great on camera.” He might as well have said, “You sucked, and I need something else to compliment you on because otherwise I’m gonna feel really awkward.”

No one would have blamed me if I chose to ignore the whole embarrassing moment where I choked on national TV. Instead, when I was back on the radio Monday, I played my parrot imitation over and over. Everyone laughed, which is always the aim of my morning show, but I was doing something for myself. By repeatedly exposing my screw-ups, no matter how painful, I minimize my chance of repeating them. I can promise you I’ll never sound like a wounded chicken on national TV again.


I don’t want you thinking I’m the only one who fails big time. That’s why I asked some of today’s top talents in sports, entertainment, and media to share their biggest failures.

First up is one of my best friends, Andy Roddick. He also happened to be one of the top tennis players in the world before he retired in 2012. He’s an athlete with heart, having established the Andy Roddick Foundation, which since 2001 has raised more than ten million dollars to provide education and sports-based mentoring to low-income youth. Whether on the court or advocating for kids, Andy is a true fighter. As Tennis magazine described Andy: “He kept working, kept searching for new ways to win, kept listening to new voices and kept himself near the top of the game.”

“My biggest failure is not winning Wimbledon. I lost to Roger Federer in three finals and, for better or worse, that defeat defines me to most of the public. I have been the number-one-ranked tennis player in the world; won the U.S. Open; finished in the Top 10 of ATP’s rankings for nine straight years—but the only thing people want to talk about at Starbucks is ‘that match with Roger.’ While I still have moments where I feel sick to my stomach when I think of how close I was to beating the greatest ever in a Wimbledon final, that match completely changed my relationship with tennis fans—for the better. Viewing me through a different lens, they began to always pull for me, say hello, or tell me where they were for ‘that match.’ I went from a temperamental, polarizing, arrogant, sometimes misunderstood (by my own doing) figure, to simply . . . Andy. Press was easier. Public practices were more fun. I was now flawed and relatable. My biggest failure created thousands of these mini moments, simple interactions that meant so much to me. I don’t know if I would have appreciated that kind of human attention if I had won that match. I might have taken self-absorption to another level. Who knows? I love where I’m at now—and I wouldn’t be here if I hadn’t lost at Wimbledon.”


Life is weird. Or maybe, better put, frustrating. Or how about this? Unfair. A hundred right decisions might not make you a success, but one really bad decision can ruin you.

I was at the gym today and a guy there started talking to me about his brother, who had crashed into a tree because he was driving drunk. Now he’s in the hospital on a ventilator. Doctors aren’t sure he’s going to make it. The guy was naturally upset because of his brother’s condition, but he was also surprised that his brother had been drinking and driving. He had never known him to drink that much, let alone get into a car drunk. The only thing he could be thankful for was that his brother didn’t hit anyone else.

I don’t drink, never have. My parents’ own struggles with booze have scared me straight. But I could still relate to the scenario. That one decision to drink and get behind the wheel, which may change the course of his life forever—if he lives—probably all came down to a single moment of at best, not thinking clearly, and at worst, making a stupid choice.

Drinking and driving and almost dying is a morbid example of how with just one bad decision you can lose everything.

So I want to make a very clear distinction between failure and screwing up. Failure is when you’re working toward a positive goal and you either have a setback or have to start from square one. Screwing up is when you’re not thinking or when you’re making excuses for why something’s okay when you know it really isn’t. This has nothing to do with risk. Sometimes you have to take risks. I’ve taken many, but they’ve all been calculated. There’s a big difference between calculated risk and risky behavior. Risk is what billionaire hedge fund managers assess before making a stock trade. Risky behavior is what teenagers do in the back of parked cars.

Rewards are much harder to come by than consequences. It’s not a fair fight. But “fair” is just a fairy tale anyway. Don’t let that be your excuse to throw it all away with one stupid choice. Keep fighting and you’ll get there (in one piece).


I’m fully aware that it’s way easier to type these words than to actually do what they spell out. When you get divorced or let go from your job, it feels like crap. In those moments, it’s hard to find a positive takeaway.

I do a lot of speaking, especially at schools. Whenever I do, the kids ask some version of the question “How do I become successful?”

It’s such a big idea that it’s almost meaningless. Except that it’s the most meaningful question in the world. They’re asking me what we all want to know: Am I going to do something with my life? Am I going to matter? Am I going to be all right? I wish I had an answer that made life easier, because if I did I’d use it for myself.

I’m still working on and learning about myself all the time. I think about my revelation after recently meeting my dad. As we were walking out of the BBQ place, I thanked him again for taking off from work and meeting with me.

“You’re welcome,” he said, turning to look me in the eye. “It was weird having a day off.”

“You don’t take many days off?” I asked.

“Hardly ever. I end up thinking about sad sh** too much.”

In that moment, I saw a mirror of myself and realized that the man I had turned into a supervillain was just a flawed and vulnerable person like me—and like most of us.

Unless you are a sociopath or a Tim Tebow, basically we are all the same: normal freaking humans. When I put myself in my dad’s position (he was sixteen and in a bad place when he had me), I had more compassion for who he was and the decisions he had made in his life.

There are no easy answers, and that’s kind of the point. I want people to feel better about the struggle. So when those kids in the auditorium ask me how to be successful, I ask them the same thing that I’ll ask you in this book.

Can you fight, grind, and repeat?

Fight. Grind. Repeat. This isn’t just something I use in my speeches at schools. I say it over and over again on the radio. I say it to myself. I have these words written on the wall at home; on many of my workout shirts; and on my chair at work (thanks, Garth). I even have them tattooed on my scrotum. (Okay, that last one’s a lie. I’m not that tough.)

Because this phrase is such a huge part of my identity, people often ask me how I came up with it. Here’s what I can tell you: it wasn’t something I gave a lot of thought. Once I get past stage one of thinking, I start to overthink. That’s when things get murky, and I usually land in trouble. “Fight, grind, repeat” was born one day after I’d worked fifty-three days in a row doing radio shows, comedy sets, shows with my band, and a few TV appearances.

I was exhausted to the depths of my soul (and I’m someone who has to wake up every morning at 3 A.M. for work, so that’s saying something). To get through the last few days of this grueling stretch I needed something to hang on to, something to say. I needed a reminder of why I was doing all of this. There’s nothing like a half-empty theater where the few people who are there aren’t laughing at your jokes to make you want to call it quits for good. (Especially if you’re running on three hours of sleep a night.)

Fight. Grind. Repeat. Those three simple words were enough to shift my psychological state from defeat to, if not victory, at least the will to stay in the game.

Fight: Because every day is a fight. In some form or other. It could be a fight from within to push yourself to a new limit, or it could be against one of the many people in this world who want to tell you no.

Grind: The thing is, when a fight starts out, there’s a lot of adrenaline. But that’s quickly drained and what you’re left with is technique and stamina. This is the everyday stuff that’s not cool or interesting or all that brave. It’s waking up at 3 A.M. so that you’re never late (if you’re me) or sitting down to fill out those college applications. The little details of working toward what will most likely be failure (at least for a while)—that’s the Grind. This is where it gets hard.

Repeat: Now take the Fight, the Grind, the failure—and then do it all again. And again. And again. The Repeat is truly the only way to separate yourself from the pack, and where it gets really hard. It’s also where you’ll find true success.

I’m going to tell you lots of stories about my being really crappy at things until I wasn’t anymore. To add some variety, I’m also going to share stories about cool and influential people such as Charles Esten and Walker Hayes who were told they weren’t so hot, either. Hopefully, we’ll all learn something. If not, at least you’ll get a chuckle out of my ability to muck things up.

Ready? Let’s do this.

Welcome to my somewhat motivational, somewhat humorous, but very reasonably priced book, Fail Until You Don’t. And if you’re listening to the audiobook, thanks for buying it! With my last book, I thought the audiobook was just part of the deal, meaning I’d have to read many hours as part of my contract. NOPE! They paid me extra to read it. Bonus!! Here’s to a positive attitude, and hopefully another audiobook.


There isn’t anything earth-shattering about the three words “Fight, Grind, Repeat.” They are just the ones that work for me. Like a mantra, I say them out loud at times when I’m just not feeling “it,” or when that alarm goes off and I didn’t get to sleep until midnight the night before. I’ll say them before a single eye opens. I believe in them.

If they work for you, too, go for it and use them. But maybe you just aren’t feeling them. If not, find three different words that work for you.

Take out your smartphone, computer, pad and paper—whatever is easiest for you to put ideas down. Brainstorm a bunch of words for each category. Maybe less negative words work for you (like “Dream, Hard Work, Revision”). Or maybe you go for humor (“Crap, Crappier, Crappiest”).

The actual words don’t matter; it’s the concepts behind them. Whatever words stick in your head and stay in your heart are the ones you should use to know that you’ll be bad at stuff when you first start out and that that shouldn’t stop you from pursuing your dreams. In other words, it’s okay to suck—just don’t give up.

Just a warning: this book is going to seem really negative at times. And at times it’s going to be quite inspirational. I struggle with that balance even in life. And you could argue with me about every single point in this book. Because in the end, we are all wrong, all the time. See how negative that sounds? Get ready for a master class in Bobby’s life theory.

Part 1

What Is the Fight?

I exercise a lot. I try to do it for at least an hour, five or six days a week. And I hate exercising. It’s the worst. There’s not a moment of working out where I think, Oh, this is just fine. Nope. Torture. Every minute. For me, it’s like waking up at three o’clock in the morning—something I’ve done for the last fourteen years, thanks to the fact that I run a national morning radio show. I hate waking up way before the crack of dawn, too, but I do it because otherwise I wouldn’t get to keep my radio show. So, the long-term payoff is way nicer than the momentary pain. It’s the same with working out. The feeling of muscle exhaustion and mental victory when I’m done is so much better than the pain I went through to get there. (Plus, working out is how I maintain my girlish figure.)

But because I exercise a lot—and hate it—I’m always on the lookout for new workouts. I’ve tried everything from jogging to lifting to spending all my money on those Billy Blanks DVDs. Yes, I was once an avid Tae Bo disciple (which, I may add, made me quite popular with the middle-aged moms I worked out with at the gym in my apartment complex). I’ll do something a ton, get bored, and then move on.

Bored was the state I was in when, several months ago, I noticed a boxing gym near where I live in Nashville. I didn’t know anyone at the gym or anything about it, but I decided to give it a go. (Trained as I am in the Blanks method of martial arts on steroids, my hands are lethal weapons. Okay, not really, but I figured the gym would probably just be a lot of moms toning their arms and taking out their frustrations in the ring. It was my kind of place.) I called the number in the window one weekend and said, “Hey, I want to come in and box.”

What I didn’t realize when I made an appointment was that I had booked a one-on-one session with a boxing coach. I thought I was signing up for a group class with the ladies. Instead I met a former trainer of pro boxers and other professional athletes, who looked like he could be one himself. Boxing was the hardest physical activity I’d ever done. And I was immediately hooked. (Although, don’t get me wrong; I still much prefer after I’m done boxing to before I’ve started my boxing workout.) I immediately booked three sessions, then nine, then twenty. Ever since I walked into that gym, I’ve been boxing so much that I’m now considering opening a gym of my own. (If you know anything about me, you know I’m a person of extremes.)

You’re probably wondering what makes boxing so great, particularly for a guy who isn’t fond of physical exertion and only brags about going to beatdown town. Simply put, boxing is a challenge, and I like to be challenged. Whether it’s performing onstage, interviewing famous musicians, or exercising, I actually enjoy the uncomfortable feeling when something is unfamiliar and hard enough to make me consider quitting. And boxing, if nothing else, is really hard. It’s by far the most grueling exercise I’ve ever done. And I’ve done them all. I did an Olympic-distance triathlon, cheated during a marathon, got into the cult of CrossFit, considered myself a recreational bodybuilder, stretched it out in yoga. Well, that’s not ALL of them, but it’s a lot. And boxing is the most mentally and physically taxing of them all. Before I got into the ring, I thought the sport was just about who can punch the other person in the face the most. Now I understand it’s about muscular strength, cardiovascular endurance, agility, strategy, and pain tolerance.

I’m not a boxer. I’m not even pretending to be one. Come on, I’m skinny and wear glasses. I’m never going to get in the ring and try to fight another human in any kind of real way. When I talk about training, I’m not paying money for someone to punch me in the face fifty times. The goal isn’t to front that I’m something I’m not—or lose any teeth. (I saved a long time to pay for these teeth, which were once terrible due to the fact that when I was a kid growing up poor in Arkansas, the dentist was as foreign a concept as the queen of England. Since earning a decent paycheck, I’ve become very well acquainted with the field of dentistry. My new teeth are amazing, and I have no shame whatsoever about telling you that they are bought and paid for. Shout-out to Dr. Cutbirth. That was not a paid shout-out, by the way. Although maybe I can get some sort of rebate by throwing his name in here.)

Back to boxing . . . The kind of boxing I do means I won’t lose my teeth, but I can still take some pretty nasty blows that result in big old bruises. In order to avoid getting hurt in the ring, even in the mildest of training sessions (the ones that are over an hour of nonstop cardio, with added weights and core work thrown in, and barely time to get a drink of water or towel off your eyeballs covered in sweat), you have to work not only on your conditioning and footwork but also on how best to position your body to minimize the impact of your opponent’s punches.

Because, just like in life, you are going to get hit in the ring. So you need to plant your body at the right angle so you are only grazed instead of absorbing a full shot to the nose.

How do you put yourself in the best position to succeed?

That’s not just my boxing coach talking. That is the perfect metaphor for the Fight. It begins with setting up the right foundation so you can feel your strongest.

I’m constantly working on my footwork and rhythm when I’m in the ring, which isn’t all that different from how I think about my regular life. Whether it’s being on time for work or how I talk to people in meetings, these are the disciplined, small actions that become the sum total of my behavior. Each step counts, even if they are easily forgotten or dismissed for a million different reasons.

Maintaining your stamina and confidence is that much harder when you get punched in the side of the head. No one wants to get into a fight and be outmaneuvered. But it happens. When hits are coming at you quickly, how do you regain your composure and find the spot where you can take a punch and turn it back over again? Like Mike Tyson said, “Everyone has a plan until they get punched in the mouth.”

Whether it’s boxing, work, or love, my plan is always to plan to get punched in the mouth. In my life, when my radio show has bad ratings, a theater full of people don’t laugh at a joke, or another relationship falls apart, it feels like I’m getting punched in the face. During those times, I deflect the shot as much as I can, learn from it, and use that knowledge to my advantage. That, for me, is the Fight.


Fighting is usually thought of as a bad thing. When you’re a kid, your parents and teachers tell you not to fight and get mad at you if you do. As an adult, there are the folks for whom everything is a fight. You know, the guy who honks his horn as soon as the light turns green, then speeds up alongside your car to make sure you fully understand how much he doesn’t appreciate your driving skills right before he cuts in front of you. Or the person who sends back every dish at every restaurant, blaming the poor waiter or waitress for never getting it right. Constantly battling the entire world because you have some deeper issue you’re not facing is no way to live. That’s exhausting for you and everyone you come in contact with—and it’s not the kind of fighting I’m talking about.

My kind of Fight isn’t about negativity. It is about survival. It is in my DNA.

It all goes back to that small, poor kid who grew up in a small, poor town just trying to keep his head above water. Fighting might have been part of my nature from birth, but it was also how I nurtured myself into something better than what I was born into. Socioeconomically, I had to work extra hard to catch up to my peers. I had jobs before anyone else my age. I’m not bragging that I was some kind of business genius. I didn’t create a state-of-the-art lemonade stand or invent the gluten-free Bitcoin. I was just out raking leaves as soon as school was over until it got dark. No, I was never the one with the brilliant idea; I was just the one out doing anything I could for a dollar.

Money wasn’t the only area of struggle. Physically, I also had to do more just to meet the average. Athletically, I was never the fastest runner. Never had the best hands. Nor could I hit the ball the farthest. Heck, I only have one working eyeball. (My right eye only sees light. It’s never been able to perceive color or any real definition, so my brain doesn’t even try. I wore a patch as a kid to try to fix it, but no dice. Hence my life of cheating on those driving tests we talked about earlier.) I made up for my lack of visual depth perception and puny frame by putting in hours of training. I would get to practice first, or beg to get in the field house to work out even when we didn’t have practice. The effort paid off; I was drafted third overall by the Chicago Cubs in the 1999 baseball draft. HA! Kidding! But I was an all-conference first baseman and named to the all-district tournament team as well as defensive player of the year. And don’t get me started on my football accolades (mostly because there aren’t very many).

I’ve always felt like I had to work harder in life—and despite all that’s gone right, I still feel that way. I’m constantly fighting to improve.

Every day is a fight to get ahead. There are the internal fights with myself: to prepare for the best show possible; to land jokes funnier for my stand-up act; to write better songs for my band. There are also my constant fights with the rest of the world: with others who want to take my job, to beat me in the ratings, or generally to see me fail.

My battles are not only self-interested. I also fight for causes I am passionate about: St. Jude Children’s Research Hospital, which treats kids with cancer and other life-threatening diseases; the Andy Roddick Foundation, launched by my good friend, which gives children from disadvantaged backgrounds awesome after-school experiences; and Austin Pets Alive, a no-kill animal shelter that does amazing work in Central Texas. I might not be the most articulate defender of these organizations, but I’ll be the loudest, screaming on the radio, from the stage, in interviews, or in the pages of my books.

Enthusiasm is my way of combating the fact that I’m never the most talented, smartest, or anything-est person in the room—or profession, while we’re at it. (I was just recently inducted into the National Radio Hall of Fame at age thirty-seven, making me the youngest member in the organization’s history, and I started my speech with those exact words, “I’m not the . . . est person at anything.” I didn’t say a word, just est. Now that I think about it, I don’t know if it made sense to anyone but me.)

My mediocrity has only become more obvious as I’ve gained a little bit of fame and entered arenas where everyone and their uncle are endowed with incredible gifts.

Take awesome artist Walker Hayes, who for my band The Raging Idiots cowrote with me and produced the song “Namaste,” which was the number-one comedy song for weeks on the Billboard chart. Working with him in the studio, I couldn’t keep up with how his brain processed music. It was like listening to someone speak a language I didn’t know existed.

I didn’t get defensive or freaked out when all I could do was sit like a dummy by Walker’s side as he worked his magic. I’m able to enjoy myself in moments like that, because I’ve had a lot of practice. I’m used to being out of my depth, which happens all the time. It’s a natural by-product of constantly trying to get better.

I was definitely out of my league when I did podcasts with John Mayer and the songwriter and record producer Busbee. These two guys went on about philosophy and art in a way that made it clear they were on a totally different plane than me intellectually. Although I pride myself on having learned a lot about music and culture from my surroundings, moments like when John described the sounds, tones, and overall recording of “Gravity” blew my mind. Where I just heard a good song, he heard the micro details that come from having a hypertrained and talented ear. As confused as I might have been, I was just happy to hear experts talk in a way they would only talk to other experts. It was as if someone got to an advanced level of Super Mario Bros. and then handed me the controller. I wasn’t good enough at the video game to get there myself, but to experience what the super pro gamers feel like was really freaking cool.


This talented singer-songwriter is the dictionary definition of a fighter. After his two debut singles didn’t do what his record company hoped they would, he was dropped by his label. Meanwhile his wife, Laney, was pregnant with their fifth child! The music business doesn’t care how many mouths you have to feed. If you don’t hit the charts high, that’s it, game over. So Walker took a job doing the graveyard shift at Costco. His hours—4 A.M. to 10 A.M.—meant he could still pursue his dreams during regular business hours. While he struggled with paying the mortgage, he also struggled with alcoholism. Eventually, not only did he get sober but he also used the struggle as inspiration for one of the songs (“Beer in the Fridge”) that got him signed to a new label and named one of Rolling Stone’s 2017 “10 New Country Artists You Need to Know.”

“I draw strength from a bunch of stuff. The example I wanna set for my kids. The husband I wanna be to my wife. The son I wanna be for my parents. The singer-songwriter I wanna be for this town. The man I wanna be for myself. I have been given gifts, and it’s my responsibility to share them in order to leave this world better than I found it,” Walker says. “I feel like ‘life’ should be spelled F I G H T. Success and sobriety aren’t all they are cracked up to be. Success just makes me want more success, and even though I’m not getting messed up, I’m still pretty messed up. It’s always a fight.”

I’m never the guy who tries to be intimidating because of my skills or good looks (okay, stop laughing at that last one). I’m just the guy who shows up. If I have any talent at all, it is the willingness to fight. But I don’t know that I can even call it a talent, since I’ve worked on that, too.

I pride myself on not being the best. Never have been. Everything and anything I’m halfway decent at now, I really sucked at during some point in my life. Sometimes I continue to suck and still do it. Case in point: my radio career. I have a job where I make a great living talking—and I’m not even a good speaker! I speak in broken sentences. I speak too fast. My speech pattern is technically “bad.” (This is all according to serious professionals.) And yet I get paid (handsomely, I may add) to talk to millions of people every morning.

It might seem counterintuitive, but because I’m not naturally good at stuff, I have to make my presence bigger whenever I try something I want to do. I have to try harder and make the stakes higher when I put myself out there. Don’t believe me? How about this: I get paid to sing, and I can’t sing! My band, The Raging Idiots, is one of my coolest examples of what you can do when you engage in the Fight.

I started The Raging Idiots as a teenager with some friends in high school. Our band’s original name was the Concubines, but we were told to change it if we wanted to play at local churches and family-friendly events. (We were fine with that since we didn’t really know what “concubine” meant.) The first incarnation of the band fizzled after people actually saw us play and realized that we did indeed suck as much as people thought we would.

I brought The Raging Idiots back as an accompanying band to my stand-up act. “Bobby Bones and his hilarious band The Raging Idiots” wound up being me doing seven minutes of bad comedy and then, after grabbing a guitar, becoming a one-man, one-instrument band. The rest of the band was always “sick” or on tour with Lou Bega, who was at the height of his “Mambo No. 5” fame.

I reappropriated the name of my high school band whenever I wrote song parodies or spoofs that I played on my radio show with my producer, Eddie, on guitar and backing vocals. The audience reaction was good enough that I dreamed up a plan to make The Raging Idiots a legitimate band. Smash cut: four years later, we have a number-one comedy record, a number-one kids’ record, and a Top 5 country album. We’re playing main slots at major festivals. We’re headlining big theaters. We’re making millions for charity.

And did I mention I’m a C+ singer at best? By the way, that’s up from the D+ level I started at. I’ve not only worked hard to improve my singing, I also surround myself with awesome-r people. (Pro tip: this is a must. Drop the ego and put better people around you.)

So how did I turn my parody-playing group with a lousy front man into a band that sells out shows to thousands of people? The success of The Raging Idiots goes back to how we started by playing the kind of bars where people don’t need the music to be good to enjoy it. The audience (and I use that term “audience” generously) might not have cared if we were funny or in tune, but from the first Raging Idiots “concert” I was convinced I could market our group into something much bigger than it was. I might have been rocking out in the back room of a burrito joint, but I was captivated by the idea of creating an act worth seeing by convincing people it was worth seeing. I knew if I could get momentum going through excitement, our band would rise to the challenge by improving as we went along. The Raging Idiots was my version of a science experiment, with the added benefit of doing some good for good causes.

From the moment I committed to this concept, I wanted to figure out how I could make my band seem much cooler than it really was and get bigger as fast as possible. It wasn’t about money (at the time)—all of that was going to charity. Remember, I come from a family with serious addiction issues. While I might not drink or do drugs, I do have the same drive for wanting more and more. This drive can be used for good or for evil; I hope that I choose a good way more often than not.

Back to my rock ’n’ roll master plan. What I did was book these tiny rooms (fifty-person-maximum-capacity tiny), simply because I knew they’d sell out immediately. This wasn’t an exercise in ego boosting. I knew our sold-out shows had nothing to do with our talent and everything to do with the size of the room. It was a marketing ploy. If I brought home the message that we were selling out, it didn’t matter how small the venues—just that we were selling them out. I kept ratcheting up the size bit by bit. We graduated from one-hundred-capacity rooms to two hundred and so on, until today, when we’re playing two- to three-thousand-person venues.

Now that I’ve achieved my goal of growing the audience of The Raging Idiots, I have to live up to my original promise to myself of actually becoming a really good band. Because we kept selling out the festival and theater dates we booked, promoters kept giving us bigger and more prominent venues. The proof was in the ticket sales. The success of the radio show has helped with promotion and we’ve gotten better, but in my estimation, we’re still not as good as the huge stages that we play. So the new Fight is figuring out how to grow into our rooms.

The Fight—a quality I’ve been blessed with and nurtured into an amazing tool—is a way to level the playing field of life.

You may think I’m the unfunniest guy on earth and the worst musician. You may hate my radio show and my politics. You may think I’m stupid and stupid looking. But the one thing nobody can say about me is that I was born with an easy pass to life. When I started my career in a radio market so small it was unrated, it was a huge achievement for me. I knew no one and had no money. Every move I made was a risk. Some of my gambles failed. A lot didn’t. But no matter, for over a decade, I always showed up—for twelve-, fourteen-, eighteen-hour workdays.

Maybe you weren’t born on third base either. Or maybe you were, but, for whatever reason, you don’t feel like it. I’ve learned, as my life has evolved, that it is never not a struggle. I know people who have a hundred million dollars, and even for them, it’s never not a struggle. Sure, they have different issues than people who don’t know how they are going to make the mortgage payment month to month. But, believe me, everyone has stuff. The sooner you embrace this truth, the sooner you can leave behind the bitterness of what you don’t have and start trying to get what you want.

The Fight is a way to do something about your stuff. Whether it’s leveling the playing field or beating the competition, there is nothing better for overcoming hopelessness than digging in and getting to work.

Every day, everyone’s fighting to survive and be more—and it’s not negative. It’s not a fistfight because you’re angry. It’s not a punch in the face. It’s doing whatever is necessary, no matter the outcome. It’s a sharpening, a constant and wonderful struggle, much like my boxing classes, where if I don’t prove I want it enough, I’m not even allowed in the ring! According to my trainer, I have to work out at a level high enough for the privilege of getting into the ring for more punishment. Does that make sense? I have to show up, kill myself conditioning for forty-five minutes, and if I’ve worked hard enough, I’m permitted in the ring for the chance to vomit my guts out. If that sounds like a win to you, then you understand the Fight.


What words do you use to describe the Fight? Here are some of mine:











What Are You Fighting For?

If people keep saying no and you keep wanting it, that’s the definition of Fight-worthy.

A friend of mine—a successful executive—decided that since her two kids were off to college and out of the house, she finally had a little time to pursue something she had always wanted to do: painting. Not house painting, but the kind you put a lovely frame around.

This is a lady who I have no doubt could pretty much do whatever she set her mind to. Well, being a lover of the arts, she decided she wanted to paint pictures. So, she bought paintbrushes, paints, canvas, and an easel—and put the whole setup in the most beautiful sunroom you can imagine, with the most perfect lighting and all manner of artistic inspiration. She even hired an art teacher to come to her house once a week to give her some instruction.

Problem was she never painted. Ever.

When, at a business meeting in her office, I asked her how her painting was going, she answered in her typically blunt style. “I never do it,” she said.

Despite having vast resources at her disposal and talking about taking up the hobby for years and years, she explained that the paintbrushes and canvas just sat there untouched. She felt guilty every time she walked by them—so much so that what had once been her favorite room in the house had turned into a place she hated. After creeping around her extra room for a couple of months, she finally faced the simple fact that “if I really wanted to do it, I’d do it.”

She is absolutely right. Now, this example might seem kind of trivial, but it gets to the heart of a major stumbling block in fighting for what you want—and that’s figuring out what you want.

People tend to romanticize their goals. Whether it’s learning to paint or making a lot of money, at times we think we want things that down deep, we really don’t want. Goals can seem important because of our parents or sexy because of the people we follow on Instagram. Did you always want to be a dentist, or are you in dental school because that’s what your dad does? (I’m not talking to you, Dr. Cutbirth. I know dentistry is your calling, because you are a genius. Can I have that rebate now?) Do you really want that huge house with more dormers than Dracula’s castle? Or is it just that everyone in your town wants a McMansion of his own? (Those huge lawns are murder to maintain. I know because I’ve been fined at least thirty times by my homeowner association, and I’m never even home to enjoy my house.) It can be hard to separate yourself. Everyone gets sucked into false goals, me included.

My I-don’t-really-want-this goal was to play the piano. I didn’t expect to become Jerry Lee Lewis (I laugh out loud as I write that analogy because I could have used John Legend, Alicia Keys, or even Elton John, but nope, I immediately went with a guy from the days of black-and-white TV who also married his cousin), but I wanted to become decent enough to perform onstage. I tried. I took lessons and practiced . . . for a while. Soon, however, I was blowing off both. Everything new is challenging at the beginning, and as I said, I typically love a challenge. But with piano it was different. As soon as it got frustrating, I told myself, “I’m no good.” And I quit.

But I’m usually not put off by sucking at something. Sucking at something has never kept me from going after it, never when it’s a real priority. My actions—or lack of action—proved that piano wasn’t a true goal. Despite what I told myself, it turned out I didn’t really want to play like Jerry Lee or marry my cousin.

Unfortunately, we can only prioritize so much. It’s impossible to do eleven different things at once—at least not at a high level. That’s because time is limited. (Unless you’re stoned, or so I’m told. Still waiting to try that. If I ever do, which I probably won’t, I’ll definitely go the edible route. Do they make weed Werther’s Original? That’d be crazy.)

Figuring out what’s truly important to you (and not to your mother, first cousin, significant other, or dog) is the first step to the Fight. And it’s worth spending a little time up front on sorting through your true motivations and fantasies in order to keep you from wasting a whole lot of it later.



Do I really want this?

That’s not an easy question to answer. Painting and playing the piano can be seen as superficial examples. When my executive friend and I gave up on our “passion projects,” they had very little bearing on our lives. Some decisions—like getting married, having children, or pursuing a particular career—carry a ton of weight. But the questions you need to ask yourself are the same, whether you’re choosing to play tennis or quit your job.

For me, figuring out the career part of my life has always been straightforward. There has never not been a time in my life that I didn’t have a clear vision of my dream job. It has always been a national morning radio show and a TV talk show like my hero David Letterman. Every step I make—from comedy to music to writing—is a step in the direction of that goal. That doesn’t mean I’ve always gotten what I’ve wanted or even known how to get it, but I’ve always known what I want—and as I said, that’s the first step to this whole Fight thing.

My personal life? Well, that’s a whole other story. Despite all the wonderful women I’ve dated and all the therapy I’ve had, I still don’t know what I want. The way I grew up—with a mom whose addictions were so bad I was adopted by my grandmother—created conflicts that are hard to get over (yup, I’ve had a lot of therapy). In some ways, I recognize that my drive, when it comes to work, is a function of the fact that I can’t figure out how to get and give love like a normal person, so escaping into work is a defense mechanism at times.

I perform every day, whether it’s on a microphone or onstage. Why the maniacal need to sing, dance, act like a fool for others, all the time? When it comes down to it (I mean really down to it, like therapy down to it), I’m just looking for the love of others. We all are—in our own ways. Although no one has cornered the market on the proper way to find and reciprocate love, some people undoubtedly have healthier methods than others. I have a friend who is overly kind. Is that even a thing, you may be asking yourself? Yes. One hundred percent. He’s the guy who’s trying to buy everybody’s meal at every dinner, in a way that is so over the top that you don’t even want to go out with him. Or he’s late to his kid’s recital because he was at his friend’s kid’s recital. He’s so nice that he actually makes his own life worse. “You’re not doing good,” I’ve said in a frank talk with him. “You’re doing harm—to yourself.”

I think love is why everybody does everything. But you must figure out if your Fight is for what you love or what you’re doing for love. That’s an important distinction. As human beings, our A-number-one instinct is to find love, but that’s different than having a purpose and a plan. It’s not easy to completely untangle this (uh, that’s why therapy costs so much and takes so long). But you can ask yourself one important and clear question: Is my Fight good for me?

To find the true answer, nothing beats some deep-down soul-searching. (I’m talking to you, millennials—pick your head up from Instagram to finish this sentence . . . but only after you follow me @MrBobbyBones.) There is no substitute for reflecting on your actions and feelings—and how the two interact.


If you’re twentysomething and rolling your eyes right now, just know that I also rolled my eyes when I heard older people tell me the exact same thing about the importance of reflection and experience in finding your path. And now here I am repeating it. It’s the natural cycle of things.

But, fine, if you want a simple life hack, here you go:

If you keep being told no, and you continue to keep trying for it, that’s how you know that you really want what you think you want. Put another way, if someone saying no to you doesn’t make you want your goal any less, then you are following the right goal.

Even in an industry—show business—known for rejection, I’ve been turned down an absurd amount of times. I’d say twenty-five nos to one yes is an accurate average for me. Those stats are brutal. And yet, I’ve never thought about quitting.

It’s kind of like a Masochism Meter. When people repeatedly say no and I keep going, I think, “Okay, I must really want this. Otherwise, why would I put myself through so much abuse?” You can ask yourself the very same question.

You don’t need to have a Ph.D. to know if you’re going for something that’s “good” or “cool” but doesn’t feel right. If you’re pursuing what you want and you’re not getting any satisfaction (or even worse, you feel awful), you have to step back for a second. It won’t be comfortable to question your motivations, but it won’t kill you, either.

This process of deliberation is especially necessary when you’re heading into murky areas of your life. For me, as I said, that’s relationships. While I totally know my mind about business, with women my head isn’t always screwed on right. I’ve pursued girlfriends who were fun, pretty, smart, nice, and successful—but that doesn’t mean they were right for me (or me for them, as I’m sure they’d attest to). What’s perfect on paper isn’t what’s perfect in real life. That’s not only true for matters of the heart but for careers, friendships, even what you want to eat for lunch!

Unfortunately, to figure it out, you gotta go through a lot of making the wrong decisions for the wrong reasons. That’s the learning process of growing up. It’d be great if you’d known what you needed to do back before you needed to start doing it—but unless you have a time-traveling DeLorean (old reference that you youngsters won’t get; move along. From my contemporaries, let me get that fist bump. Shout-out, Michael J. Fox!), it ain’t gonna happen. Sometimes you have to go through a lot of relationships to find the right one or try a lot of jobs until you find what you are passionate about.


More than five years ago, my cohost Amy was on a mission trip to Haiti, where she visited an orphanage and fell in love with a little boy, whom she couldn’t stop thinking about when she returned home to Nashville. Amy and her husband—who were having trouble conceiving—returned to Port-au-Prince to meet the two-year-old boy again, whom they immediately decided to adopt, along with a five-year-old girl.

Well, they might have started the process immediately, but there’s nothing immediate about the process. Amy spent years doing paperwork, paying tens of thousands of dollars, completing lots of home visits, background checks, and other security reviews, and becoming their legal parent—and still she had trouble getting her kids home! It was heartbreaking for everyone. Her kids suffered, but so did Amy. There were times when she broke down, but there were many more when she should’ve broken down and she didn’t. Instead of getting depressed, Amy constantly corresponded with government agencies, cheered her kids up over FaceTime, and visited Haiti, where the show and our listeners have supported the children’s orphanage and also created a bakery that offers both food and jobs for lots of folks in need.

How Amy functioned every single day, refusing to give up no matter how frustrating things got, well, that’s a Fight. She never thought this process would take as long as it did; still, she wouldn’t stop fighting. “Even if it had taken ten years, we would never give up on them,” Amy said. “Two little humans were depending on us. When things seemed hopeless, I prayed for more faith in the process. How could we ever walk away and give up on something we had asked for?”

Amy relied on her husband, family, friends, and faith to get through the hard times. She also hung pictures of her kids as a constant reminder to never lose hope. “I had their sweet faces up in our hallway over a year before they actually got here,” she said, “because eventually this would be their home, too.”

Finally, roughly five years after she found the children, she was able to bring them home. “They are truly a gift, one that we had to work hard for but a gift nonetheless, and I thank Jesus for them every day,” Amy said. “Even though it’s like I was pregnant for sixty months instead of nine months, it all worked out.”


What do you want to NOT suck at? What are you willing to fail at so much that you embarrass yourself? What will you do anything for? Here are some questions and exercises to get you thinking about your Fight—and whether it’s really the right one for you. These are questions you can return to over and over whenever you’re having doubts.

If you’re still searching for your Fight:

  • What moments in the past have made you the happiest? They can be small or big ones—or even certain periods of time. Don’t overthink this, just see what comes to mind.
  • What was it about that time that made you happy? Is the essence of that time something you can re-create now? For example, if the happiest time in your life was summers working outdoors as a kid but now you have a desk job that’s killing you, maybe try volunteering at a local park or outdoor recreational area to see if you can recapture that feeling. Volunteering or a part-time job is a great way to make incremental change without upending your whole life.
  • What are you passionate about doing? Be honest. Even if it’s eating in restaurants, that might be a big clue to a job you’d be passionate about.
  • What percentage of your day/week/month do you spend devoted to your passions? Is that enough for you? If not, how could you increase it?
  • What areas of your life need a lot of work? Relationships with family members, dating, losing weight—those are classic ones. What specifically relates to you? How much control do you have over the situation, and what, if anything, could you do, no matter how difficult, to improve?

If you have a Fight but want to do a gut check on it:

  • When you think about doing the thing you’re fighting for, what do you feel? Does your stomach knot up? Or do you just want to put this book down and get back to it?
  • If you are a procrastinator or are scared to put yourself out there to achieve your dreams, what is holding you back? Is it fear of failure, or something less intuitive—fear of success?
  • Where do your dreams and goals come from? If they are yours, when did you first conjure them up? Does anyone else you know have the same Fight? If so, why?
  • If you succeed at your goal, where will it take you in five years? How about ten years? What’s the pinnacle of that path? Picture yourself there and see if you like it.


Chris Stapleton, who has written hit songs for everyone from Adele to Luke Bryan and has won multiple Grammy and CMA Awards as an artist, has been coming to my radio show since long before he became seriously famous. He’s not only a cool guy but someone I’ve developed a personal relationship with over the years.

“The day that my dad passed away, I was in South Carolina, taking my kids to the beach with their other grandparents. I got the call—my brother called. So I took a little walk, kinda soaked that in. You know, I had seen my dad two days prior. We had played a show near where he lived, and he had told me good-bye or whatever. I could have stayed over. I could have figured something out. But I used some lame excuse, like ‘I gotta get on the bus ’cause it’s leaving.’ That was a failure. I don’t have many regrets, but I do regret those two missed days. For some reason those two days magically mean more than all the other days I could have been there saying hello, or doing something with my dad. That was a failure as a son, I guess. You can’t get those things back, but you can learn to try not to let the professional outweigh the personal or steer it more than it should. That, for me, was the lesson.”

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