Sometimes you do things and you think they’re kinda cool and great and interesting — like, “Wow, I can’t believe I’m doing this!” — but then you look back and realize you’ve already done those things and that they were cool and great and interesting when you did them five years ago.

Sometimes you want to grow, may have actually grown, and are in the processing of growing more — like, “Gee, look how much bigger, faster and stronger I am now!” — and want to engage in activities and work that represents, exhibits and displays that maturation.

But, for some reason — maybe it’s the industry you’re in, the people around you or your own inability to take the next steps — you’re kind of stuck in the same place. You don’t realize it at first, but then you do, and it’s kinda depressing.

I guess the upside is that you have to feel blessed to just be working at all, but at the same time, there is this sort of thinly-veiled wall you keep hitting where it’s like — “Is this all I’m ever going to do? There has to be more. I’m better than this.”

I think it was probably easier to gauge that growth years ago, when things were more static, and less susceptible to catastrophic levels of disruption.

Take music, for example. Fifteen years ago a person in some small town might have had big dreams just to make it to New York, Los Angeles or Nashville. There, they could immerse themselves in the scene, maybe work with a few people, possibly record a demo and if the demo was any good, maybe get a record deal.

After the record deal, they presumably would cut some songs for an album, pick a single, shoot a video, get it on TRL and hopefully sell some records. They’d tour and with any luck they’d develop a loyal fan base, play bigger and bigger venues, release more music and there would be, like, a progression there. The later music would be different, more challenging — maybe even less enjoyable — but through it all they’d feel like things were moving in a linear way.

Or, maybe they wouldn’t, and maybe this is just a fantasy in my head. I suppose that when it comes to music, if an artist hasn’t reached a certain level of success after a certain passage of time, the artist hangs up their professional shingles, gets a day job and becomes a grownup.

And, in the grand scheme of things, comparing things to music is stupid, because that shit is entertainment and not real life for most people. But it’s my life, so that’s all I really have to go on.

Still, I can’t help but feel like a lot of people are probably in situations where they are forced to punch way below their weight class. Sometimes it’s just the system at play, and the way a person is positioned within that system, that they can’t advance to GO and collect that $200 they deserve so badly.

I don’t have any answers here. Only questions. I’m trying to assess when the endless repetition of something is redundant to the point of being pointless. Again, you get into these modes where something is genuinely exciting, and it does feel vaguely new and somehow interesting, even though you’ve done it a thousand times and it’s not quite as challenging as you’d like it to be.

Does everything need to be a challenge? Maybe not. Maybe the key to being professionally happy is to know the median level of effort and expertise that is required to do something efficiently without being forced to kill yourself to make it happen.

Again, I don’t know. Something just feels too strange about going back to a place you’ve already been one too many times.

Written by

Wrote for the New York Times, New York Magazine, Esquire, Rolling Stone, Vice, Fader, Vibe, XXL, MTV News, many other places.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store