You’ll Never Really Feel Like You’ve ‘Made It’ (And Why That’s A Good Thing)

Ryan Holiday

A fourth grader lines up obediently to return to class after recess. Looking around, surrounded by boys and girls the same age and the same size, he sees out of the corner of his eye a group of other kids who seem different.

They are older. Bigger. More confident. They make their way leisurely to their own line, not nearly as rushed by the thought of seeing their teacher. Their clothes look better. They have clearer cliques, roles within those cliques. They seem like they are having more fun too. They are cooler. So much cooler. These kids: Sixth graders.

The kid thinks to himself: In two years, I’ll be a sixth grader. Soon, I’ll be just like them.

Maybe you remember thinking this in fourth grade. Or you had your version of it as a freshman in high school. Or college. Or maybe you remember some moment in your childhood where it occurred to you that your parents were a certain age, and that one day you would be that same age. Or maybe for you it was with your career or with earning a certain amount of money. You had this vision of arriving at some special, better point in the future.

Whatever the analogous situation, you know now a truth that the fourth grader in line is still two years away from learning for the first time: You’ll never be just like them. You never end up feeling like a sixth grader. You never actually “arrive.”

I remember when I started in my first job in Hollywood, I worked for a powerful talent executive. He made a lot of money, had phone calls with interesting people and did cool work that I admired. He also had this dream schedule. I remember he thought it was a waste of time to be in the office or attend pointless meetings, so he was always making up excuses to work from home or do what he wanted—and he was so good, they let him get away with it. I remember thinking: Man, this guy is living the dream.

There was this sense to me at the time that he must have felt very powerful to have all that. And I just assumed that, of course, everything about his lifestyle was conscious and deliberate. More than anything else, I think that’s what I wanted. Not the perks per se, but whatever feelings went along with them: Confidence. Appreciation. Enjoyment.

It was only many years later that I would realize, having built up my own career and had my own successes, that I had long ago objectively worked out my own version of the schedule and lifestyle that I had once admired. I did what I wanted. I had a cool life. I even had my fair share of younger employees who looked at me a certain way.

And yet, not only did I not feel those things I thought I’d suddenly feel, I really hadn’t even noticed that I’d arrived in the vicinity.

In the wonderful new novel, The World is a Narrow Bridge, by Aaron Thier, the characters go on a roadtrip across the country. It’s full of all sorts of beautiful observations about history and life, but the best is the one he makes as the characters are driving through St. Louis and crossing over the Mississippi river. This is where they literally enter the American West, with all its grandeur and significance. And yet, everything seems the same. The same trees, the same scenery, the same air. “It’s the old story,” Thier writes, “You wait for the big moment, and what you get is gradual transition.”

Most of us who work very hard, or drive ourselves to do things—even if it is not our primary motivation—have this idea that when we get it, everything will be different. We’ll feel more whole. We’ll be satisfied. We’ll feel the way we made up in our heads that the people who first inspired us obviously felt.

And when we get it? That’s where the awkward truth comes in: You really don’t feel anything different. You’re still you. Except now you’re you with a million dollars or a gold medal or a hot spouse or an office on the top of the building. And what you missed on your journey to get these things was your own gradual transformation. Your evolution.

One of my favorite questions that Brian Koppelman asks on his podcast, The Moment, is whether the actors and artists and producers and comedians he interviews feel like made guys. That’s a mafia term that Brian uses to describe the kind of Hollywood person—man or woman—who has done enough, or done something so brilliant, that they are guaranteed a career. In one episode, he talks to a well-known director and asks, if he saw a group of other famous directors at the commissary on the Sony lot, whether he would feel comfortable walking up and sitting at the table with them. The director says, no, probably not. But you’re a made guy, Brian says, of course you deserve to sit at that table.

But that’s the crazy part. Very few people ever feel like that. Even when they objectively deserve to.

I bet Aaron Thier could speak to this notion, how it felt to publish one novel, then a second, then a third. Eventually you feel like a writer, right? Like you’ve done it, are doing it? Nope.

This is probably why on a certain level, we admire—if only sideways—incredibly egotistical people like Kanye West or Donald Trump or Joni Mitchell. We suspect that there must be something great about that comfortable bubble of confidence. They must never have these doubts I am having. They have the power, the appreciation, the enjoyment. They must really feel like they’ve arrived, like they’ve made it and deserve what they have—and have since the beginning. Of course, that’s not true either. It’s just more of the same wishful thinking. In fact, my suspicion is that these people actually feel worse. They’re the fourth grader who was beaten down, literally and figuratively, by their schoolmates and their parents and life itself. The outsized public persona—all the remarks and the craziness and the ego—it’s just a way of distracting from what they feel even acutely than the rest of us in moments when they are alone.

Isn’t this all imposter syndrome in various forms? You might think so, but I don’t. Imposter syndrome is the scared feeling that you’re a fake and that other people will catch on. That’s not the feeling I feel. That’s not what you felt your senior year, wondering why it wasn’t quite as great as you naively assumed it would be as a freshman.

No, this is more like chasing the horizon. You can never quite get there. It always seems a little bit further away.

In a way, it’s a curse. Some people see it that way. It angers them: The thing they want so badly will never be fully theirs to grasp. They whip themselves, they neglect life in the present as they plan the next thing, the thing that will finally, magically, permanently solve all their problems.

What they miss is the journey. That’s the blessing.

That sense that the director doesn’t quite belong at that table with the other directors? That’s what keeps pushing him to make great movies. It’s what gets a fourth grader through the difficulties of the fifth grade. It’s what keeps the road trip interesting.

Most of all, it’s what keeps us looking forward in life—towards what comes next, towards better days and better things.

We might never “arrive” but the transition is not so bad either.

Like to Read? I’ve created a list of 15 books you’ve never heard of that will alter your worldview and help you excel at your career. Get the secret book list here! TC mark

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