The Side-Hustle Suffocation

A 20-year retrospective on the urge to scale everything.

“You are allowed to enjoy something without turning it into a second job.”

I paused upon the words, then read them again. Haley Rose‘s message stood out like a gut punch from someone tired of our bullshit, yet caring enough to know it’s for our own good. Maybe if we were forced to stop and catch our breath, we could remember how nice it once was to not treat everything as potential ‘content’. I’m as guilty of this as anyone.

But 20 years ago, I wouldn’t have questioned it.

I was debating which friends to feature in my Top 8 on MySpace, reposting lists of favourite bands or recent concerts, and writing Family Guy quotes on Facebook Walls. The all-consuming idea of achieving “financial freedom” was still decades away, and turning my beer pong party tricks into a crowd-funded revenue stream never felt like an option.

10 years ago was the start of the decline.

I closed the pages on my comedy-philosophy blog to invest more energy into ‘Design Twitter’ as a means of making myself known. I tried to turn home brewing with my dad into a short-lived brand dedicated to tips, tricks, and craft beer news aggregation. Social media claimed hours a day in search of a lucky payoff.

5 years ago further entrenched the suffering.

My wife would spend nights alone on the couch while I tediously tended to every waveform on my Everyday Experiences podcast. She’d go to bed frustrated. I’d go to bed wondering what else I could work on. How else would we achieve our dream life? By continuing to do well in our 9-to-5s, and enjoying the things we could already afford? No way! That’s no strategy for jet-setting success! If co-producing comedy shows or co-hosting design meetups couldn’t bring home more bacon, I must just be missing the mark.

1 year ago had me convinced that what I was missing was scale.

So, I ramped up video production and bought all the gear. I launched the Formula Fast Track online course for getting the millions of new Drive To Survive fans up to speed with Formula 1, and again waited for the paycheque to roll in. I didn’t expect for it to nearly turn me off F1 completely. I was no longer watching its tech talks to satiate my interests in innovative engineering, I was voraciously consuming every car update in search for a new angle to sell it.

The quickest way to kill a hobby is to make it about money.

Apologies to everyone along the way that I had tried to convince otherwise—I’m glad you hadn’t listened to me (but please hear me out about this haha).

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This was originally posted on my website gwilsonswork.com as the home for all my works.