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…

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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.