When Your Side Hustle Feels More Real Than Your Job

Money or meaning? It’s my turn to go through it.

Recently, one of my boxing students recorded a small-group fight class I was teaching. I watched it back and saw myself joyous, completely in my element. There was no polish—just a raw glimpse into a moment where I was fully present, instructing and coaching with an ease I don’t often feel elsewhere.

It was a jarring contrast to the person I am at work. At my office job, I sit through a maze of “All Hands,” “Town Halls,” and Comm reviews. Sure, I get my work done. But there’s a difference between being effective and being fulfilled. One is pure execution; the other feels like real purpose.

And so at 35, I’m caught between two worlds: one that gives me security but leaves me restless and searching for more; another that fills me with meaning but remains, at this time, a cool side gig. I know it’s the cliche of cliches: the disillusioned office worker wondering if his hobby is his true calling. Is this my midlife crisis? Is it my turn to realize what you work so hard for doesn’t always turn out to be what you truly want?

Growing Pains

Rewind to 2017. I had no money, no job, and was stressing like hell every month to make rent in New York City. I remember sitting in cafes for hours, throwing job application after application into a digital void. I was scraping by, taking any freelance gig that would pay anything at all.

I caught my first tiny break coming up with creative ideas for a BlackRock marketing deck—a four-day gig that paid $40 per hour. After that, nothing. Then more nothing for two months. But slowly, very slowly, I was able to take on more projects, built up my portfolio, and in 2018 used it to land a role at Facebook. Two years later, I moved to TikTok. I had finally made it. This was the version of success I had envisioned, proof that all the struggle had been worth it.

I know I should be grateful. In this economy, with so much job uncertainty, it’s a privilege to be in a good role. Even writing this piece feels arrogant—a “woe is me” lament from someone in a fortunate position. I’m hesitant to vocalize any of this because I worry it comes off as entitled whining from someone who doesn’t appreciate what they have. 

But at the same time, is it wrong to acknowledge when something no longer fits? Is it selfish to admit that what once felt like a dream now feels Sisyphean? I don’t take what I have for granted, but I also can’t ignore the feeling that I could be doing something else. Advertising and branding strategies, corporate storytelling, product positioning—I became good at it, but honestly, who cares? I spent years refining messages that drive “business outcomes.” But my own personal outcome is that it’s a road to nowhere meaningful.

The Ring as a Reprieve

I took my first boxing class in 2017 through ClassPass. By 2019, I was training consistently. By 2022, I had my first fight. Now, I coach.

When I’m at the gym, I feel engaged in a way I never do at work. There’s no corporate artifice, no empty performance. There’s just the immediacy of effort, the satisfaction of seeing students improve, the clarity of a punch landing exactly where it should. Unlike the corporate world, boxing doesn’t pretend to be more than what it is. There’s no inflating results, no Zoom meeting doublespeak. You either put in the work or you don’t, and either way it’s going to show.

And yet, even here, doubt lingers. My coaching peers are current and former pros, Olympians, and lifelong fighters. I’m just a tech marketer. I didn’t grow up here. I came from the suburbs, where fights were to be avoided, not studied. There’s an inherent impostor syndrome in stepping into a space where others have spent their whole lives.

But I have to remind myself that skill isn’t dictated by childhood origins. I’m a good boxer and a good coach. While the doubt may always be there, so is the proof: I’m tested and I know I’ve earned my place.

Getting Ahead of the Fork

So money or meaning? If boxing is what I love, why not make the leap? Tech provides stability, and leaving that behind seems insane. More than that, I wonder if boxing, when transformed into full-time work, would lose its meaning. What if it becomes just another job, stripped of the passion that makes it fulfilling?

There’s also the fear of staying too long in a tech industry that may not need me much longer. AI is changing everything. What once required human creativity is now being automated—ad copy, campaign strategies, idea generation. In real time I can see the industry shifting, streamlining and outsourcing tasks that once required whole teams. The writing’s on the wall and these days it’s all authored by ChatGPT.

The dilemma isn’t just about passion versus stability—it’s about control. Do I cling to a job where my skills may soon be obsolete, or do I pivot preemptively, betting on something that feels more real? If the floor beneath me is already shifting, am I making a mistake by waiting for it to collapse?

For now, I straddle both worlds. I put my head down at work. I also coach boxing with more urgency, knowing I may need to make a substantive choice sometime in the next year.

I understand I should feel lucky. After all the struggle to get here, after clawing my way into an industry that once felt impossible to break into, I should feel nothing but gratitude. I do feel that. And yet, I also know that success isn’t just about reaching a destination. It’s about whether, once you’re there, you actually want to stay.

I tell myself there’s still time, that clarity will come. But deep down, I suspect the restlessness won’t go away. I probably already know the answer. The question is whether I have it in me to follow through.