the anxiety you're rewarded with for being a girlboss

Ever since I was a little girl, I knew I didn’t want to work for a middle-aged white man who tells me how much money I will make and when I can schedule my dentist appointments. Growing up in a home that was the definition of a textbook family on the outside (emphasis on outside) and being preached the traditional way of doing life for as long as I can remember, I knew that once I entered adulthood, I wanted to rebel against every rule my parents ever tried to teach me.

While my parents worked stable corporate jobs, I dreamed of being my own boss—leading a small team of hipsters who supported my mission to change the world, writing dinners with the girls off as business expenses, having a golden credit card with access to airport lounges, and flying out to Cape Town to run marketing ads that were too creative for the mainstream public to fully understand.

Now that I’m my own boss, I do none of these things and silently envy my parents for the abundance of stability in their lives. At least sometimes. I love being my own boss, but unfortunately, I also hate it. On the not-so-bright side, I also hate being an employee, because I only like getting told what to do en la cama. So yes, being a business owner has been humbling, to say the least, because I realized that: a) I can’t write off dinners with the girls as a business expense, and b) if I don’t work all the time until the business runs itself, I’ll have to live with financial anxiety until my death—which reminds me that I also don’t have a retirement plan in place.

Monks and shamans I’ve talked to have been telling me that the secret to life is to always feel like you have enough, no matter how little you actually have. But I have a really hard time believing that when my problems suddenly turn existential. Although from the outside it looks like I accomplish pretty epic things—like having people pay me for my writing (weird!!) and getting approached by media outlets to feature my life story (even weirder!!)—I can’t fully acknowledge my success, because I’m always mentally preparing for the next big tax payment or losing a paid subscriber (please don’t ever do this to me).

Actually, I do the exact opposite of what those wise men have been telling me. I keep telling myself that once I have more systems in place, an assistant, or at least a steadier income than I have now, I’ll finally see myself as a successful entrepreneur. But to be honest, I don’t think I’ll ever notice this milestone, because by then, I’ll be busy stressing about bigger problems.

So my question is: am I doing it all wrong, or does being a girlboss suck? The freedom this lifestyle promised me did a flip and is now strangling me to my silver MacBook Pro, working overtime on a Friday night. Fun, right? From my table in the upper-left corner, I watch families passing by, little kids smiling at me, and couples holding hands. I often find myself envying their brains, which must know what it’s like to just be in the moment—without a constant trending tiktok audio penetrating their brain or the urge to turn every minor life event into a Substack essay.

It’s annoyingly ironic, because the more I work for myself, the more I want to work for someone else. But also, I don’t. I find myself envying their simple lives, even though I’ve been wanting to live a fergalicious life for as long as I can remember. Maybe it’s my frontal lobe developing, and I’m starting to realize that a simple life—where I work a normal 9-to-5 and gossip with my colleagues about their husbands’ affairs over a cold instant coffee—is actually where it’s at. Or maybe I just want what I can’t have. Either way, I hope all you 9-to-5 babes are appreciating your paid vacation days, because honestly, that’s the most amazing shit ever.

I think it’s also ironic that, although I can work on my own schedule, my social life was thriving the most when my free time was in the hands of a middle-aged white man. Back then, socializing didn’t feel like a reward I get to do after I’ve done enough work, but a natural part of my week. It’s funny how having less control over my time made me more present for the people in my life. Now, with the so-called freedom of being my own boss, my social life feels like an afterthought, something I’ll “get to” once I’ve ticked off enough items from my to-do list (spoiler: that never happens). The irony of it all doesn’t escape me—this lifestyle I worked so hard for has me chained to a wooden table in a hipster café, while the one I swore I’d escape gave me an actual life outside of work.

Maybe that’s the cruel joke of it all. When you work a 9-to-5, you fantasize about freedom. But when you finally have it, you realize freedom is just a different kind of grind, blurring the boundaries between work and life so much that you find yourself hiding in the bathroom of a club to reply to an email. Sometimes I wonder if I’d be happier going back, letting someone else handle the deadlines, the tax filings, and the endless decisions. But then again, would I be able to handle someone else calling the shots again? Probably not. I guess this is just part of the trade-off.

Oh, and don’t even get me started on my nonexistent dating life. At this stage of my life, where 24 hours a day feels like it will never be enough to tackle my never-ending to-do list, having my time wasted by a man could literally mean bankruptcy. So for now, I’m stuck in this weird limbo of wanting connection but terrified of what it might cost me, both emotionally and financially. And until I figure it out, I guess I’ll keep pouring my energy into the one relationship that’s guaranteed to stick around: making my paid subscribers insanely proud.