Hustle Harder, Hustle Smarter - chapter 1

Chapter 1

Finding Fearlessness

I wouldn’t give a tinker’s damn for a man who isn’t sometimes afraid. Fear’s the spice that makes it interesting to go ahead.
—DANIEL BOONE

A few years ago I hired a French guy named Corentin Villemeur to run my website. When he wasn’t working for me, one of Corentin’s hobbies was to take selfies in spectacular settings—standing precariously on the edge of a cliff or sitting on the roof of a high-rise with his legs dangling over the sides.
When he’d show those pics to the guys in my office, they would shake their heads and laugh, saying, “Only a white guy would do that.” To them it was like skydiving or trying to pet wild animals. An unnecessary risk that only someone who had never experienced real danger would take.
I saw it differently.
I saw an opportunity for freedom.
So one day I took Corentin up to the roof of my old offices in Times Square to take some pictures of my own. But instead of just dangling my legs over the side, I decided to up the ante.
On the roof was a water tower, a wooden, barrel-like structure rising several stories above us. Without any hesitation, I climbed up its rickety ladder and took a seat on its edge. I must have been forty stories up in the air. Below me, the people on the streets looked like ants at a picnic. If I slipped, it would have been a long trip down to the sidewalk.
The stakes (and me) were very high, but I didn’t experience any fear. Instead, I took in the spectacular view. The New York Times Building towered over me to my left, and the Hudson River sparkled behind me. I felt incredibly alive. Seeing my hometown from a bird’s-eye view filled me with the same ambition I’d felt as a younger man. New York City was literally at my feet. The city of dreams. And I was going to keep hustlin’ my hardest to realize every one of them!
I leaned back and Corentin snapped a spectacular shot for IG. When I got back down to my office, I posted it with this caption:
I live on the edge. I’m only free because I’m not afraid. Everything I was afraid of already happened to me.
A lot of people loved the post. “That’s real,” one wrote, with another adding, “Man, what a powerful word.” But not everyone appreciated it. About a week after posting the pic, I received a letter from my insurance company explaining that if I knowingly risked my life like that again, they would immediately cancel my policy.
The insurance company shouldn’t have been surprised, though. If there’s one trait that has defined me since an early age, it’s fearlessness.
A lot of people probably think I was born fearless.
I might project that energy, but it’s not true.
I was scared of the dark as a child. Just like I was definitely terrified of being killed when I was on the street, or petrified of failing when I started rapping. I’ve experienced anxiety and angst of all kinds.
The difference is I refuse to allow myself to grow comfortable in those fears. Comfort, I’ve learned, is a dream killer. It saps our ambition. Blinds our vision. Promotes complacency.
The number one thing most people are comfortable with is fear. Not that most of them would admit it. Ask someone if they’re living in a constant state of fear and they’ll probably say, “Of course not.” That’s just pride talking, though. Fear dominates most people’s lives. Fear of loss. Fear of failure. Fear of the unknown. Fear of loneliness.
I don’t think there’s anything shameful about experiencing fear. A little bit of paranoia is actually extremely helpful. There are a lot of real dangers out there. A lot of people with bad intentions. Being aware of those possibilities makes it easier to avoid them.
What you cannot do is become complacent with any of those fears. If you fear loss, you can’t spend your life avoiding intimacy and love (something I’ve struggled with). If you fear failure, you can’t stop taking risks. If you fear the unknown, you can’t stop trying new experiences. “It is not death that a man should fear,” said the Roman emperor and philosopher Marcus Aurelius, “but he should fear never beginning to live.”
I can trace the root of my own sense of fearlessness back to one specific event: the death of my mother. That’s a special kind of fear, one that’s hard to describe. More than getting shot nine times, losing my mother was the most significant thing that ever happened to me. Even in middle age, I can still feel her loss.
But through her death, my mother managed to give me a rare gift: the seed of fearlessness.
It would take a lot of time for that trait to fully blossom in me. I would, unfortunately, have to experience a lot more difficult and dangerous moments until it became second nature.
In this chapter, I’m going to share some of the experiences and situations that helped encourage that sense of gutsiness in me. That allowed me to accept that what lives on the other side of fear isn’t danger, or even death, but freedom.
I want to show you that fearlessness is a strength you can develop, too. A muscle you can build, hopefully without having to experience the trauma that made mine so jacked. You don’t have to lose your mother, or survive getting shot nine times, to develop the belief that you can survive anything that happens to you. That the only thing you can’t overcome is never taking risks in the first place.
DON’T BE AFRAID TO GET HIT

Team sports weren’t my thing as a kid. Didn’t matter what we were playing—football, basketball, or baseball—if we lost, I’d always be quick to point out whose fault it was. “Yo, we got blown because you can’t guard your fuckin’ man!” I might tell a teammate who got burned on defense in basketball. “He kept bustin’ your ass. We lost because of you, bro!”
It wasn’t that I was trying to evade responsibility. If I made a bad play or couldn’t guard my man, I’d be the first to admit it. It was more that I didn’t like having my success ride on someone else’s ability or inability to perform. It’s a feeling I haven’t been able to shake to this day. I always say that if I were ever going to bet on a horse at the track, then let it be me, goddammit. Because I know I’m going to run as hard as I can.
I was smart enough to accept I wasn’t emotionally suited for team sports. I needed a sport where if I lost, it was my fault alone. Individual sports like golf and tennis weren’t sports anyone I knew played. (I only lived about twenty minutes from where the US Open is played in Flushing, but it might just as well have been in another state.) And in my hood, you usually only find yourself running if someone was chasing you.
There was, however, a Police Athletic League boxing gym near me, run by a local fighter named Allah Understanding. He was from the nearby Baisley Projects and came up in the days when having a strong knuckle game was something people respected, aspired to, and feared. I training with Allah when I was around twelve years old, and I knew almost right away that boxing was the right fit for me.
One day I was hanging out at the gym when a street dude named Black Justice stopped by, accompanied by one of his boys. Blackie, as we called him, was one of the most respected dealers in Baisley, a top lieutenant for the Supreme Team, the biggest drug crew in Queens at the time. His boy was essentially his muscle, a constant presence to make sure a rival would have to think twice before trying him. They were probably only eighteen or nineteen years old themselves, but already their reputations were well known around the neighborhood. The kind of young guns you didn’t want any problem with.
The gym got quiet as we all watched Blackie and his boy walk around. Then, without a word, Blackie’s boy stopped in front of one of the heavy bags and started laying into it.
Bam-bam, bam-bam-bam.
As the youngest kid in the space, common sense would dictate I keep my mouth shut and just observe. But, maybe because I was the youngest, I felt a little bolder and my big mouth got the better of me. As soon as the guy was finished on the bags, I called out to him.
“Hey man, you look good hitting that bag,” I said, loud enough for everyone in the gym to hear. “But that bag doesn’t hit back.”
Blackie whipped around. “What you say, young boy? You talkin’ to me?”
“Naw, you a big nigga,” I quickly replied. “I’m talking to him,” I said, nodding toward his man.
Most guys in their position might have whooped my ass—or worse—on the spot. But these guys took my shit-talking in stride (Blackie had a generous spirit, free of the greed that infected a lot of his peers). Instead of taking offense, they both respected my outsize courage.
“Yeah, I like this kid,” Blackie said, gesturing to me. “We gonna have some champions come out of here, because these little niggas crazy.”
That recognition alone would’ve made my whole day. Instead, Blackie did us one better. “This gym could use some work if we gonna get the most out of these fighters,” he announced, looking around at the shabby setting. “What kind of stuff do y’all need? Write it all down.”
Two weeks later the gym was completely refurnished. Blackie had gotten us boxing shoes, trunks, new ropes, punching bags, and a new set of weights to replace our old rusty set that probably hadn’t been updated since the sixties. From then on, Blackie took care of us. Whatever we needed, he got us. Although it was technically the Parks and Recreation Department’s building, after that it was Blackie’s gym.
I hadn’t opened my big mouth just to get it fed, but that’s what ended up happening. It was an important lesson for me to learn. You need to bend fear into moments of action at every opportunity, because the fearless not only recognize but also often reward one of their own.
I entered Allah’s gym as a chunky twelve-year-old, the 150 pounds I was carrying making me seem older than I was. You ever heard the expression “punching above your weight”? Well, in that gym I had to punch above my weight and age from my first day. There were no other kids my age in the program, so Allah Understanding had me fight whoever was in my weight class, which usually meant opponents four to five years older than me. That might not seem like a big deal, but there’s a massive difference between a twelve-year-old and a seventeen-year-old. Those seventeen-year-olds were basically men, whereas I was still waiting on my balls to drop. I might have been in the same weight class, but I lacked their strength and maturity. It was intimidating as hell to step into the ring with those guys.
I never gave in to that fear—mostly because Allah Understanding refused to let me. One of the best things he and the other coaches did was refuse to coddle me. If an older boy hit me in the face while we were sparring, they didn’t stop the proceedings and ask if I was okay. They were going to teach me to keep fighting no matter how scared or hurt I was.
The lesson I learned from those ass whippings would be twofold.
First off, I learned that I could survive them. Yes, getting hit in the face wasn’t pleasant. It would leave you disoriented. It would hurt. It might leave your eyes watering. But those blows didn’t kill me. Hell, they didn’t even knock me out. Once I realized I could absorb them and then keep moving forward, most of the fear I had felt evaporated.
Second, and I’m forever indebted to Allah Understanding for teaching me this, I learned that if I didn’t like getting hit, then I needed to do something about it. “Keep your fucking hands up!” he’d yell if I let down my guard and my opponent tagged me. If my opponent started laying into me with body shots after trapping me in a corner, Allah would holler, “Get back into the center of the ring!” Punishment, Allah Understanding taught me, wasn’t something I had to accept. I could always do something about it.
They knew I was outsized and often overmatched, but they refused to coddle me. You ever see a kid fall down and scrape his knee? How he reacts largely depends on the parent’s reaction. If the parent runs over and worriedly asks, “Oh baby, are you okay?,” the kid is probably going to cry. But if the parent assesses the situation, figures the kid is fine, and doesn’t ask if he’s okay, the kid is just going to brush his knee off and get back to whatever game he was playing. That’s the kind of parent Allah Understanding was to me. He taught me to brush off being hit and get back to what I was doing.
He wasn’t being heartless—he was trying to condition me to brush off the inevitable blows life was going to rain down on me and keep moving forward to where I was trying to go, instead of where I was being pushed.
Once I learned not to be afraid of getting hit, I became a much better boxer. Instead of constantly staying on my heels, worried about what my opponent was going to do to me, I brought the fight to my opponent. I learned how to dictate the terms of the confrontation. If I lost, it wasn’t because I’d been backed into a corner and beaten down. It would be because I’d gone for what I wanted and had simply come up against someone with more skill.
It’s been a long time since I’ve gotten popped in the face inside the ring, but I’ve tried to keep that attitude in everything I do. I refuse to be afraid to take a punch. I know the blows are going to come, and some of them are going to stagger me, but I’ll be able to take them.
A lot of y’all are like the kid who fell off his scooter and waited for his mommy to come over and say, “Baby, are you all right?” Not me. When I fall off, I’m not waiting for a sympathetic word or someone to check in on me. I’m getting right back on my feet and continuing my journey.
I’ve accepted that the punches are going to come in life, and some of them are going to land. But I’m always going to survive and keep fighting for the things I want. That has to be your attitude, too.
FACING FEAR HEAD-ON

As I’ve said, my mother’s death is what forced me to build up my immunity to fear. Learning how to get punched in the face only increased my insensitivity. For a while, it seemed like fear might be an emotion I’d never have to deal with again.
It wasn’t to be the case, though. Getting shot definitely reawakened that sensation in me.
First and foremost, in the weeks that followed the incident, I found myself very afraid of the people who’d shot me. I knew that they were still out there, not very far away and eager to finish the job they’d started.
In addition to the emotional anxiety, the physical pain of getting shot also reacquainted me with fear. Not in the moment I got hit—the adrenaline stops you from feeling too much of that—but in the months that would follow.
Once the adrenaline wears off and the doctor tells you that you’re going to make it, you start to acutely feel the effects of bullets ripping through muscles and pulverizing bone. I felt pain everywhere—where lead went through my thumb or through my cheek. For months it was like I had headaches throughout my body: a relentless and deep throbbing I didn’t know you could feel in your leg or your hand.
Every time I had to go to physical therapy and put weight on my leg, or break through the scar tissue in my thumb, it hurt like hell. I realized I was scared of having to go through that process again. Maybe even more so than dying.
But as my rehab continued, I also came to understand another important truth: I wasn’t comfortable being scared. That might sound like an obvious thing to say, but I think it’s actually what makes me unique. Most people are extremely comfortable with their fears. Afraid of flying? Stay off of planes. Afraid of sharks? Don’t go snorkeling on your Caribbean vacation. Afraid of failure? Well, then don’t even try. A lot of people live their entire lives that way.
Not me. I hated being scared. I hated looking over my shoulder. I couldn’t stand the idea of staying off the block till things cooled down. To me, hiding would have almost been worse than getting shot.
In some ways, the physical pain I endured was my friend. It pushed me further than most people are willing to go. Trust me, when you get hurt that bad, there’s a shift. You want to approach the problem instead of run from it. Which is exactly what I did.
After several weeks in rehab, I went back to my grandmother’s house in Queens. Literally back to the scene of the crime. That in itself was a big step for me psychologically. The easy—hell, the sensible—thing would have been to move far away. A place where no one except my closest friends would know how to find me. It didn’t even have to be far in terms of mileage. I could have moved to the Bronx or Staten Island, and it would have been like going to another country. I was determined not to give in an inch to my fear. I was going to go back to where I wanted to be, which was my grandmother’s house.
When I left rehab, the doctors told me to start jogging to build up stamina and strength in my injured legs. I was committed to their plan, but almost immediately I hit an obstacle. One morning I took a peek out my grandma’s window and saw someone I didn’t recognize in front of her house. To me, he was trying too hard to look inconspicuous and blend in. I was admittedly in a very paranoid state, so it could have been nothing. But paranoia sharpens your senses the way an antelope’s acute sense of smell can identify a lion from hundreds of yards away. Maybe I was sensing my own predator.
I canceled the jog I had planned for the day. And the next day, too, after I saw the same guy lurking on the street again. By this point I was experiencing a lot of confusion. Were my heightened senses tipping me off to unseen danger? Or was I imagining menace that wasn’t really there? I couldn’t tell. All I knew for sure was that fear was starting to consume me.
I decided that if I stayed in that house and didn’t follow my rehab plan, then I had already lost. When fear interrupts your routine, or makes you rethink it in any way, it’s gotten its hooks deep in you and will hold you back forever. “Cowards die many times before their deaths,” wrote Shakespeare. “The valiant never taste of death but once.” I wasn’t trying to go out like a coward.
The best way to get past a fear that’s holding you back is first to acknowledge it and then come up with a plan to get past it. So that’s what I did. First, I accepted that I was afraid. Then I gathered my most trusted friends in my grandmother’s living room and explained that I was going to need them to go jogging with me the next morning. “No doubt,” everyone said. “We’ll be back tomorrow.” When the next morning rolled around, however, only one of them actually showed up: my guy Halim. I don’t think the rest of them were scared of any potential drama—they’d proved themselves in that realm too many times already. I think they were more afraid of the idea of having to do some cardio in the morning. That wasn’t something they were comfortable with.
I decided to head out with just Halim, even though he wasn’t the ideal candidate: he was in even worse shape than I was. More important, I had serious doubts about how he might react if a threat did present itself. In a crew full of dudes just looking for any excuse to let one fly, Halim’s nature was to look for a way to avoid confrontation.
As for Halim, since he was out of shape, I gave him a bike so he could keep pace alongside me. As for my second concern, I opted to take matters into my own hands, literally.
I found a small pistol, put it in my good hand, and then wrapped it with medical bandages. Everyone knew me as a boxer, so to the casual eye, it just looked like I’d busted my hand in the ring. I used so many bandages that the gun disappeared into my “cast” almost completely, with only the barrel peeking out. I told Halim to pedal alongside me and keep an eye out for anyone who looked like they wanted to jump out of the bushes and take a shot at me. All he had to do was sound the alarm, and I’d take it from there.
Halim and I performed this routine every morning. I was committed to getting my strength and stamina back, and wasn’t going to let a threat—perceived or actual—get between me and my goals. Was I actually scared on any of those runs? At first I was, but I took comfort in knowing that each time I set out, I’d done all I could do to take the necessary precautions. I had both a lookout and protection, which was at least more than I had when I’d been shot.
It was an extension of what Allah Understanding had taught me: instead of being afraid of getting hit and just giving up, do the things that make you a difficult target. In the ring, that meant staying on my toes, moving constantly, and keeping my hands up. On the street, it meant jogging with a bodyguard and a pistol up my sleeve.
No one ended up challenging me, and I was able to get myself back into shape through those runs. But looking back, I can see that I didn’t have to be so aggressive in confronting my fears. I didn’t have to run through the same streets where I’d just been shot—I could have just as easily gone to a local gym, or even put a treadmill in my grandmother’s basement.
I was just so uncomfortable that anything less than jogging outside, in full view of the whole neighborhood, would have felt like a complete concession to fear. A concession I wasn’t willing to make.
Today, I’m a little less likely to be so aggressive in confronting things head-on. In fact, if I’m being completely honest, there are still some fears I’ve barely confronted at all.
THE ONE THING I’M STILL AFRAID OF

We can spend our entire lives—and many people do—trying to ignore something we’re actually carrying around with us every day. But you can’t hide from something you never put down.
To give you an example, when I look in the mirror and take an authentic assessment of where I’m at in life, the thing I’m most afraid of is family.
It’s a fear I haven’t wanted to admit, because I know for the vast majority of people, family brings incredible comfort. Security. A sense of well-being and connection.
I’ve never had that feeling. Family makes me uncomfortable as hell. It doesn’t make me feel safe. It makes me feel extremely vulnerable.
That’s probably not a surprise given my background. The number one fear every child experiences, no matter where they live or what their circumstance, is losing a parent. It’s built into our DNA. You don’t have to download that app onto your phone; it comes preinstalled. Psychologists say the fear of losing a parent is especially acute between the ages of four and eight. Every kid in that age range is going to start worrying when their parent is late coming back from the store, or goes away for a couple of days. Of course the parent always comes back, and in time the kid stops obsessing over the possibility that they won’t. Well, my mother never came back. So when every child’s worst fear actually came true for me, it made it very, very hard to open myself up to the type of love I had for my mother with anyone else.
As you’ve probably gathered, things didn’t get much easier once I went to my grandparents’ house. Their love was unquestionable, but the environment was chaotic even in the best of times. There was never enough money, attention, or stability. But there was plenty of drug and alcohol abuse. A lot of dysfunction. My grandparents’ house was not the ideal place to mourn my mother.
But they were the only family I had. I’ve never met my father. I don’t even know who the guy is. A lot of people who have grown up fatherless have a desire to reconnect when they’re older, but I’ve never felt that way. In fact, I’m glad he hasn’t come forward. The things he could have helped me with—the lessons he could have taught me—those moments have all passed. I don’t think there’s anything positive he could add to my life now.
Like many people do, at first I continued the cycle of dysfunction that began with my mother’s death. When my son Marquise was born, right around the time my rap career was blowing up, I thought I’d turned a corner. I remember telling an interviewer, “When my son came into my life, my priorities changed, because I wanted to have the relationship with him that I didn’t have with my father.”
That was my pure intention, but it’s not what happened. Instead, Marquise’s mother, Shaniqua, and I got caught up in an extremely dysfunctional relationship of our own. I’ll talk about some of my frustrations with Shaniqua and Marquise later in the book. But for now I’ll admit a lot of criticism I’ve received for how I’ve dealt with that situation has been justified.
I’m someone who’s incredibly honest and transparent, and the things I’ve said publicly about my older son are the same sorts of things a lot of parents who are stuck in bad relationships also think and feel. They just don’t articulate it. That doesn’t make it right, but it might make it a little bit more relatable.
If I have done one thing right when it comes to family, it’s that I’ve tried to break that cycle of dysfunction with my younger son, Sire. His mother and I aren’t together, but I’ve tried to be much more present in his life. He lives with his mom, so I go see him whenever I get the chance. We’ll hang out at the pool, play video games, and watch sports. The normal things fathers and sons do. Most important, there’s no tension when I see him. His mother and I are on the same page and do a great job coparenting. So when Sire sees me walk up for a hug, it’s nothing but love.
It brings me a lot of happiness to know that I’m always going to be a big part of his life and be there to help him navigate the inevitable peaks and valleys. To make sure that Sire doesn’t have to make the same mistakes that I’ve made. That’s what I wanted for Marquise, but neither his mother nor I was emotionally mature enough to create that foundation for him. The truth is, I was scared of having a family. Maybe she was, too. Our son suffered for it. And now my relationship with Marquise is just a reflection of the negative energy between his mother and me.
My relationship with Marquise is the area in my life where I’ve got the most work to do. There have been times, even recently, when I’ve thought about writing that relationship off forever. I don’t want to do that, but sometimes when you’ve been hurt a lot—and you’ve done your share of the hurting, too—it feels best to walk away.
I came extremely close not long ago, after I unexpectedly bumped into Marquise at my jeweler’s store in Manhattan. I didn’t even know he was in the city at the time, so I was shocked to see him. I tried to start a conversation, but he immediately accused me of having him followed. I told him that was crazy, but things only went downhill from there.
The energy between us was terrible. Marquise even said, “What, am I supposed to be afraid of you?” That really messed my head up. This was my firstborn son, my own flesh and blood, and we couldn’t even speak to each other, let alone hug and laugh at an unexpected encounter. Finally, without a word, Marquise basically fled the store, leaving me dumbfounded.
A couple of my guys went down to the street to try to catch up with Marquise and say, “Why are you bugging? This is your father. Come and talk with him,” but Marquise had already disappeared. He didn’t want to be found. I couldn’t even follow them into the street—my mind was fuzzy and I couldn’t think straight. I had to take several minutes to compose myself.
There are very few times when I’m knocked completely off-kilter, but when they happen, they always involve family. Let me bump into a rapper who dissed me, or a CEO I’ve had a tense negotiation with, and I’m good. In fact, I’m great. Those moments don’t faze me—they’re what I live for. Only family seems to faze me.
It’s not just my relationship with Marquise, either. I don’t even like going home for holidays anymore because seeing my family makes me so tense. I’ll stop by my grandmother’s old house a day before Christmas to kick it with my grandfather. But I won’t come back on the actual holiday. Even if I bring only positive vibes into the house, someone is inevitably going to bring their negativity toward me. An aunt or a cousin will end up saying, “I’m tired of everyone kissing his ass because he’s 50 Cent. Shit, he ain’t that special.” Instead of a celebration, the entire night will be about what I did for one person but didn’t do for everyone else. That sort of energy makes me extremely uncomfortable.
I know my fear of family isn’t healthy, and I’m working on it. It may take years, but I’m committed to the process. So by the time I’m my grandfather’s age, I hope I’ll have a solid relationship with my children, and maybe their children, too.
RAISE YOUR HAND!

I know I have a reputation as a hothead, but in reality, no matter what private jet I’m flying on or corporate boardroom I’m seated in, I’m always relaxed. The person operating under the least amount of fear. I’m confident nothing that gets said, threatened, or promised in any of those conversations is going to hurt me. Sure, I’d like to seal that $30 million distribution deal or land the role of a lifetime. But I’m not afraid they might go away. Why would I be scared? I’ve already been through some of the scariest shit life has to offer.
So how do you harness the same sort of confidence I have? To keep cool where most people would be sweating through their shirts? It’s not rocket science. The only way to access that kind of confidence is by putting in the work. That’s it.
Have you truly dedicated yourself to learning everything that you can about your field? Do you give 100 percent every time you walk in the office, sit down in the classroom, or step onstage for an audition? If the answer is yes, what do you really have to be afraid of?
You’ve already done everything you can do. Now you just need to make sure the world recognizes it.
That can be a challenge, especially if you’re not someone who’s been raised from an early age to think that you belong in those meetings. If you’re not a white guy or didn’t get into the “right” prep school, you might have to go a little harder to get the credit you deserve. It shouldn’t be that way, but it’s what it is. For now.
You’re going to have to project the confidence that you belong, that you’ve got the answers, even if the people you’re talking to aren’t giving you the credit. All your hard work isn’t going to be worth shit if you’re not ready—no, determined—to share it with the world.
I’ll give you an example. A guy in the music industry who I’ve known for years hasn’t been able to translate his hard work and talent into the success he deserves. I won’t say his name because he’s a great dude and I don’t want to hurt his confidence. (See, I am maturing.)
He started as a street guy, but thanks to his charisma, intelligence, and work ethic, he was able to make real inroads in the music biz. He became close to several moguls, myself included, who really trusted his judgment and taste. He made good money and was respected in the industry, but he was never quite able to reach the mogul level himself. And I knew that frustrated him.
He’d ask me for advice, but I couldn’t honestly put my finger on what was holding him back. Then one day we went to a meeting with some big executives at a record label. Smooth guys in suits with good haircuts and nice leather shoes. Guys who were extremely self-assured.
They were confident, but they also didn’t really understand the project we were there to discuss. My guy did, though. Up and down. Back and forth. We’d spent hours talking about it, and he understood it both factually and instinctively. That’s why I brought him with me, because he could articulate what needed to be done better than I could.
I expected him to blow them away, but when those executives started asking questions and spitballing ideas, he just sat on his hands. Didn’t make a peep. You would have thought he was just a buddy of mine along for the ride, instead of what he was, which was the one true expert in the room.
At first I couldn’t understand what he was doing (or not doing). Then it dawned on me: He’s afraid. He’s scared to raise his hand because he doesn’t want to give the wrong answer. He’d put in the work, but in the presence of those executives’ self-assurance, he lost faith in himself.
And that meant the executives never noticed him. Never made a mental note that he was a guy to keep an eye on. Never offered him the platform he was looking for—and deserved.
Instead, he stayed stuck in place. It was a pretty good place, one that a lot of other folks would have liked to reach, but not where he aspired to. He was stuck at a level that wasn’t equal to his skill.
When the money in the music business started to dry up, he found himself in a very vulnerable spot. If he had made it to that mogul status, he would have been okay. He would already have put away his rainy-day money. Instead, the rain came and he got soaked. He was one of the first to lose their jobs. (It’s great to be a highly paid exec, but when things start to go south, those are the first people to get the ax. Sometimes it’s better to be a little underpaid.) Today, he tries to do consulting work, but he’s on the outside looking in, becoming an old man in a space that prioritizes youth.
Don’t make the same mistake. If you’ve put in the work, and know your shit, raise your damn hand! Every single time. There’s nothing worse than being someone who’s spent hours—even when you’re off the clock at home—studying your company’s reports, but when your boss asks for that information, you always let someone else provide it first.
That person probably hasn’t put in nearly the work that you have, but they’re also not afraid to be wrong. So when your boss looks at that person, she sees someone who is active. Who is participating. Who seems passionate. When she looks at you, she doesn’t know what to think. Maybe she doesn’t think anything at all.
It’s not fair, but that person with their hand always up is going to get promoted before you. They’re going to get an office before you. They’re going to leverage their promotion to a better-paying job at a competitor before you even get a raise. You were better trained, better prepared. But you didn’t let the world see that because you were scared. That fear is going to stop you from getting full value for your work. Don’t let it happen.
On the other side of this coin is the person who’s too quick to raise their hand. They’re doing it because they’re fearful that someone else is going to get props before they do. So even if they don’t know the answer, they’re going to say something anyway.
I knew a guy like that, too. We’d go into a meeting, and he’d be shouting out a solution before anyone had even identified the problem. He just wanted to be heard. Whenever he’d start doing that, I’d just shake my head and think, “Yo, what is wrong with you, bro?” It got to the point where I had to tell Chris Lighty, my manager at the time, not to bring this guy to any more meetings. It was unfortunate, because he was smart and talented. But he was doing too much. He was so fearful of someone else getting to shine that he ended up costing himself opportunities.
Being fearful can trip you up in so many ways, in both your professional and personal lives. That’s why it’s so critical that you identify the things you’re afraid of and put in the work to get past that fear. In your personal life, letting go of all that baggage will be such a relief. You won’t know how heavy the load you’ve been carrying around all these years has been until you finally put it down once and for all. The moment you do, you’re going to feel nothing but freedom.