Why is it so hard to accept that your job and career can be two different things?

And what is a career, really?

One of the reasons it’s felt hard to commit to a creative career is the sense that my success feels truly out of my control. For me, it’s not about winning awards or becoming a millionaire, but having access to more opportunities so that, ultimately, you can unlock your potential and eventually support yourself from it.

Yet most successful creatives argue for the opposite. Elizabeth Gilbert (a controversial queen, I know) explicitly encourages young artists not to quit their day jobs because making a career as an artist is impossible, a stance that other artists have since criticized for discouraging people from dreaming (which I’m not sure I agree with, but that’s a separate conversation).

She speaketh

But I’m a pragmatic person, and pragmatically speaking, Gilbert is right. If you look at any creative industries, simple laws of economics will tell you that there’s more supply than demand, which inherently means that the chance of supporting yourself is slim. And yes, maybe, if you work at it over a long enough time horizon, it might work out. But what if it doesn’t?

I recently had a conversation with my screenwriting teacher/mentor, who used to work full-time as a TV writer until the recent TV contraction, and now has a day job in advertising. I spoke to him about this contradiction—that, despite having a day job and making projects, I still felt lost because progress in my career feels so inextricably tied to things outside my control. He understood where I was coming from, having made a similar journey in his career. He told me the wisest thing that I could do was not tie my livelihood and sense of fulfillment to this career, treating it as a permanent side hustle.

While his advice makes total sense to my pragmatic side, a part of me believes that truly accepting that means I’ve failed. That I’ve given up and become complacent, accepting that just doing the thing is enough. After all, aren’t the successful people the ones who get to do this full-time, because they’re talented and resilient enough to make it?

When I examine this challenge further, I realize that the real issue is my desire for predictable momentum and growth. I miss the days of tech when there was a ladder laid out for me, and progress felt predictable: it was clear what I needed to do at the next level. It was also externally visible: more money, fancy title. I thought I was one of those people who didn’t care… but maybe there’s a part of me that does care, because these things reinforce the belief that I am good.

I’ve always had a soft spot for beautiful lattes in beautiful cups… so maybe I am a little materialist after all.

This desire for momentum and progress powers my discipline and work ethic, yet it’s also my Achilles’ Heel when it comes to embracing a creative career. I constantly doubt whether I can make it because I don’t have the same level of predictable progress as I did in tech. It’s a vicious cycle: the lack of progress reduces my confidence and sense of self-worth, which in turn lowers my motivation and the quality of my work. It’s also, frankly, not great for my mental health.

I don’t know how to change this belief. My sense is that experience is our greatest teacher, so maybe I’ll need to achieve some level of the success I desire before I realize that it’s not the answer. Or maybe through therapy, I’ll accept that this discomfort will always be there, but how I navigate and process the discomfort will improve over time. Or perhaps by searching for other ways to feel fulfilled and stable, I’ll naturally put less pressure on my creative career, and learn to accept the progress for what it is rather than what I want it to be.

Whatever the thing (or combination of things), I hope that one day, I can accept, and perhaps even celebrate, the permanent side hustle of my creative career.

Thanks for reading!

If you like this post, consider sharing it with a friend.

Better yet, tell me what I should write next!

And if you haven’t subscribed already… now’s your chance! I publish essays on navigating the next phase of my career as a former product manager, unwinding my relationship to my achievement, taking sabbaticals, and more!