Man at His Best

What Do You Wish You Knew Then That You Know Now?

Esquire US resident Old Guys™ have some life lessons for their younger selves.

BY Luke O'Neil and Dave Holmes | Aug 7, 2017 | Money & Career

Image from iStock

In the past couple weeks we've covered how old is too old to still be out at the club, and what is the actual best age to be, both of which required looking back and reflecting with the added perspective of experience. So it seemed appropriate that this week we ask, knowing what we know now that we're wise and accomplished, what do we wish we knew when we were wobble-legged fawns?


THE DEBATE


Luke:
It's a question that comes at a fitting time for me, as I've just gotten back from an annual trip to Maine with a group of college friends. (By sheer coincidence, you and I are both Holy Cross grads Dave, which places us somewhere between Clarence Thomas and Bill Simmons and the kid who puked a full plate of pancakes in my dorm shower on the spectrum of noteworthy graduates.)

As I do every year, I can't help but think when I see my old friends, now scattered around the country, how little has changed. Aside from the fact that they all have about 15 kids each—it was a Catholic school after all—and respectable careers as doctors and professors and such. I'm still sort of the weird outlier with my comparatively care-free life of going out and doing all the other shit that the arrested development identity of working in media affords you. It's a role that was always pretty cool when we were younger, but may end up being less so if the business continues the way it seems to be going. I sometimes think if I were to go back to the guy I was when I first met this group of friends, sulking in my dorm room playing mopey Elliott Smith covers on the acoustic, that I would do what my parents did, in the words of Jeffrey Lebowski (a movie we watched a few times back then), and get a job, sir. A real job. But maybe it's just a matter of the grass is always greener.

Something I always think about when it comes to these sorts of topics: Is life long, or is life short?

Dave:
Both, and this is the first thing I wish I knew when I was younger. Life is long, in that you will not get what you want right away, and you will have to keep trying over the course of many years. When you are young, you will almost always be forced to watch someone else—maybe someone you cannot stand—get what you want. You'll see them land the dream job, the perfect partner, even a very good apartment, and it will frustrate and anger you. I compared my career to other people's when I was younger, and drove myself crazy with rage and envy when mine didn't measure up. But success in life comes in waves, generally three to five years in length. When you're at it for a few decades, you will see people ride one of those waves for a while, then get cocky or lazy, then lose it and have to struggle to get it back. I've seen people have hot streaks, immediately let it go to their heads, and then watched them sink right back to where they started. Success is not permanent, and neither is failure. Don't compare your path to anyone else's. Just keep your head down, do the work, and keep your mind on the bigger picture.

That being said, life is also terrifyingly short, and it moves faster the older you get. When you're a kid, adults say "time flies," and you pretend to agree with them, but inside you're like: "I've been in fourth grade forever. What are you talking about?" When you're 10, a year is a tenth of your life. When you're 23, it's a twenty-third. And so on. You hit a temporal patch of ice in your thirties where life really picks up speed, and there's not a damn thing you can do about it. So when you're young, and life moves relatively slowly, savor those endless days. Linger over dinner tables with friends. Stay all day on a blanket in the park with the Sunday paper. Wring it out, every drop. I was in a big old hurry to grow up when I was younger, and now I'd do just about anything to slow the time.

How about you, Luke? What wisdom has come to you with age and the growth of your majestic, Russian-novelist beard?

"LINGER OVER DINNER TABLES WITH FRIENDS. STAY ALL DAY ON A BLANKET IN THE PARK WITH THE SUNDAY PAPER. WRING IT OUT, EVERY DROP." - DAVE

Luke:
My beard is actually the source of all my power, so thank you.

Maybe that concept, about the manner in which we perceive the passage of time, relates to our attempt to find the best age last week. Perhaps there's a sweet spot where a year actually feels properly like a year? Where the measure of time is, for once, an honest reflection of itself? I suspect that there comes an age when things slow down again, when you're retired and don't have much to do, and an afternoon feels like a luxurious unfurling of opportunity before you anew.

The stuff you say about careers feels true to me, although it's something I have to question a lot, particularly with the shit stew state of online media. I have younger people messaging me often asking for advice on how to break into it, or how to land such and such a job. I always do my best to respond, although I've got a few I've been backed up on lately. (Sorry!) My instinct is to say, do not rush, it will come. Write, and read, and write, and read, and do whatever you have to do to pay your rent, and if writing, music, or whatever other career it is with a high barrier for entry remains the only thing you can envision yourself doing, eventually it will be the thing you do. From the perspective of the younger person that probably sounds like shitty advice. No one wants to be told they'll find their dream job five years from now, because they have to do something in the intervening days and weeks and months.

But there's a contradictory bit of advice I often give as well, which I would've done well to hear when I was first starting out: If no one is currently paying you to do the thing you want to do, do it anyway and get a head start. I spent too much time when I was coming out of college waiting for the right publications to grant me entry into The August World Of Letters, instead of starting my own thing. And back then there was plenty of open space in which one could start something! I could've registered, like, Toilet.com and sold it for $10 billion, next thing I'd own a basketball team and be considered a serious presidential contender.

If I had to distill the point though, it would be something like: No one is coming for you. No one is going to discover you. You have to come for yourself. (Also good sex life advice coincidentally.)

Was there something you wanted to do after college that you didn't, and you regret it?

Dave:
I regret everything I did in college and for the first five years after. I was an idiot. I carried with me a very Midwestern, very Catholic view of work: that it is a thing to be endured. To be taken seriously as an adult, I thought, one must put on a tie and do a thing one does not enjoy. It is fine to have interests and hobbies, but it is foolish—dubious, even—to attempt to make a life out of them. What respectable job could a person get himself with a passion for the written word and an encyclopedic knowledge of popular culture?

Luke:
And you thought that at a time when people could still make a handsome living in this business!

Dave:
God, what a dummy I was. And bear in mind: I got out of college in 1994. I was present for the Big Bang that created the internet universe. I didn't pursue creative jobs within that brand-new field for the simple reason that I wouldn't have been able to explain them to my family. I did the practical thing, and I sucked at it, and it took me a few years to snap out of that mindset and try to cut my own path.

Luke:
Wait, I feel like we're sort of accidentally encouraging millennials to ...be more millennially?

Dave:
For some people, the more practical path is the right one. But if that isn't you, you're not defective. There's just something more out there for you, and you'll have to spend your days pushing yourself forward to the place you should be. And then keep pushing. I still am, and I'm comfortable with that. I don't want to be the next anyone, I want to be the first me. It's only been within the last 10 years that I've even understood that that's a possibility. Take bigger swings younger, I guess is what I'm saying.

Luke:
We're gonna get kicked out of the old folks home at this rate.

"NO ONE IS COMING FOR YOU. NO ONE IS GOING TO DISCOVER YOU. YOU HAVE TO COME FOR YOURSELF." - LUKE

Dave:
I also stayed away from some exciting opportunities because of my ego. I was terrified to fail, and I was even more afraid of looking silly. I missed out on being in the first improv class at Upright Citizens Brigade in New York, because I didn't want to have a bad improv scene in front of people. I didn't aggressively pitch shows during my time at MTV because I didn't want to see them do poorly. I didn't understand the value of failure, of vulnerability. To take a real chance in life, you have to risk looking like a fool. You have to do a show where there are more people on stage than in the audience. You have to tell jokes and hear silence. You have to be a guy in his thirties with a Tumblr. You have to be deeply uncool. I have failed on stage more times than I can count, and it's made me better in every way, and the people who failed onstage with me now have books next to mine in the bookstore, or shows on television, or their voices in your earbuds. I wish I'd known a little earlier that this was how it was going to turn out. I might have been bolder.

How about you? Has your ego stood in the way of progress?

Luke:
Yes and no. I spent a significant chunk of my twenties playing music, and there was nothing more spirit-crushing to me than playing in front of no one. I never found it to be character-building, like you said, but from everything you hear about musicians and comedians and other performers who make it, that's the thing that is always a through-line: You keep going even when you feel ridiculous and no one seems to care.

Writing, for one reason or another, always came more natural to me. I somehow managed to fight through the years of humiliation in that field, which is why I guess I'm a minorly-regionally-well-known internet writer now and not a minorly-regionally-well-known musician. Probably because the shame is more private and internal. You get rejected or ignored over and over by editors, and it fucking sucks, but you get up and try again the next day. No one but you gets to see that process though. With performance it's much more public and embarrassing.

I think one good bit of advice I could draw from that, however, is that no one in the world but you cares about or remembers your failure. The worst humiliation of your life is gone—even in today's Twitter world where we all document and keep on hand our enemies' resumes of indignity—because, really, no one cares about you that much. There's a good lesson: No one cares about you.

Dave:
Nobody cares! Let that truth set you free. Now go make fools of yourselves, kids.

From: Esquire US


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