When Do I Stop Aspiring?

Dave Gutteridge
From the Gutt
Published in
6 min readJan 31, 2022

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A dartboard with three darts that have all missed the bullseye.

“Maybe it’s time for me tot leave Japan,” my friend says. “I feel like maybe it’s now or never.”

He, like me, would like to be a standup comedian with more success than doing shows for the English speaking community here in Tokyo where we were having this conversation. He’s considering going to LA, one of the comedy Meccas, because there’s actual opportunity and reward there.

Of course, that’s only if you can navigate the significant challenges of succeeding in an environment like that. We both have friends who went to New York, LA, or London, and didn’t become any more successful as a comedian as a result. But, at least there’s the potential.

Where I’m living now, in Tokyo, no matter how funny I am in front of an audience, ultimately, the most I can really get out of it is the satisfaction of making a room full of people laugh. There are no agents in the crowd scouting to see if there’s someone they can use, there are no auditions being held looking for breakout talents, the community isn’t big enough to be an ecosystem that cultivates entrepreneurial entertainment projects. It is what it is, and no more.

I ask my friend, why now? Why is now being compared to never?

“I feel my body decaying,” he says both truthfully and ironically. “I mean, I feel like any later than this, I might be too old to go for it.”

He’s younger than me by just a little bit, so if anything, I feel the same decay, and maybe a little more.

The thing is, though, that I’ve felt that decay all my life.

“Decay” might be the wrong word. It’s something more like, “already late.” When I was twenty five it felt like I had already taken a few wrong turns at age twenty and maybe I had missed some key moments that were supposed to shape my life. I stumbled between a college, an art school and a film school, not knowing what the utility of any of it was. I didn’t really know what I wanted to do with my life, while so many friends around me seemed to be on a distinct path.

At thirty, I looked back at twenty five and lamented how I missed the boat then, too. At thirty five, I thought I had to recover from mistakes at thrity. Forty, same. And still now, same deal.

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Dave Gutteridge
From the Gutt

I don't post often because I think about what I write. Topics include ethics, relationships, and philosophy.