v.26 Feast, Famine, and the Mindf*ck of Creative Entrepreneurship: The Emotional Cost of Working for Yourself
Welcome to Life, Created—a new [old school] blog for modern times. This twice-a-week(ish) dispatch is a space for us to dig deeper, recognize microjoys and build community beyond the mindless scroll.
Lately, I’ve been having the same conversation with friends—over coffee, cocktails, mid-afternoon walks when we probably should be working (but also, should we?). It’s the contradiction that so many creatives live with.
We set out to build creative, non-traditional lives—choosing what we create, how we work, and rejecting structures that never fit us. And yet, we still expect our careers to follow traditional rules. We crave freedom, but we also want the security of a steady paycheck. We want to work on our own terms, but we feel guilty when we’re not hustling. We tell ourselves we’re building something different, and then, when our income fluctuates, or when we realize that we’ve only worked four hours that week (but still earned plenty), we panic. Should I be working harder? Should I have a “real” job? Is it too indulgent that I take a Pilates class at 10 a.m. on a Tuesday when I should be working?
Deep down, we’ve internalized a set of expectations that were never meant for us. And unlearning them —ain’t easy.
A creative life isn’t just for musicians or people with paint-stained hands and tortured souls (hi, painter friends, I see you and I love you). It’s also for writers, chefs, tattoo artists, yoga teachers, small business owners, speakers, filmmakers, florists, entrepreneurs, therapists, herbalists, and healers... It’s anyone taking unconventional routes, creating work that doesn’t fit neatly into a corporate structure.
And the thing is, a creative life isn’t defined by the what—it’s defined by the how.
Traditional careers follow a linear trajectory: internship, entry-level, middle management, senior leadership, retirement—and a gold watch, if you’re lucky. Stability. A clear next step. A path you don’t have to carve yourself. (Side note: do companies still give out gold watches? Are they actually genuine gold? Sorry, I digress. )
But creatives? We are making it up as we go. No ladder. No step-by-step guide. Just choices. One project leads to another. One connection sparks something unexpected. One opportunity shifts everything.
It’s thrilling. But it’s also exhausting. Because while there’s deep joy in carving out a path on your own terms, there’s also deep uncertainty. And this, folks, is where the psychological fuckery kicks in.
Creative entrepreneurs live in a constant state of mental whiplash. One minute, we’re riding high—getting paid $50K (or $500 or $5 million #manifesting) for a project, booking work consistently, feeling like an absolute star. The next? Silence. Crickets. A slow month where we make $50 (or hell, $0) and suddenly start questioning everything. In that moment, it doesn’t matter how much money we’ve earned or success we’ve had—it feels like this could be it. We’re done. Washed up. I see it constantly. Regardless of our perceived successes, we think about this often. Building a creative business is not for the faint of heart and it isn’t just about money. But. And. Money does matter. The need for a stable paycheck is real. But so is freedom, creativity, joy, impact, and space to breathe.
I know because I live this every. single. day.
I can have a particularly incredible month—speaking gigs, consulting, book stuff—all hitting at once. I might earn more in that month than I used to make in an entire year at my first job. And then the next month? Nothing. It’s like the universe side-eyes me and says, “You thought you had this shit figured out, didn’t you?” And suddenly, I doubt everything. Not because I’m not doing well, but because I’ve been conditioned to believe that success means consistency. That stability looks like an equal amount of money in and out of my bank account every month.
But here’s what I’ve learned: creative success isn’t consistent—it’s cumulative. It builds. It fluctuates. It expands in unexpected ways.
I remind myself daily that just because I don’t earn money on a Tuesday doesn’t mean I’m not making a living. My work doesn’t function like a traditional job, and my income doesn’t either. I earn between $10,000–$20,000 for a single talk, depending on the audience and scale. So no, I don’t need to work 40 hours a week to hit the same numbers as someone who does. (Quick note, because I know people will get caught up on these numbers: 1. Yes, I realize the privilege I have in charging my rates and no, I will not apologize for this— I’ve earned it. 2. Not every speaker charges this—some charge much less, some command much more. I could speak more often if I charged less; I just don’t want to. Pricing depends on many factors, and that’s a whole other conversation. 3. Yes, I know talking about real numbers might feel tacky to some and shocking to others but that’s not my problem, is it? Transparency is incredibly helpful—especially for women.) Now that my TED talk is over, let’s move on.
Given all of this, I still spiral over an empty inbox. Because that’s how deeply ingrained this whole “busy = successful” lie is.
One of the biggest mindfucks of working for yourself is constantly wondering if you’re doing enough. I don’t work 40 hours a week or 12 months a year. I never want to again. And yet, even knowing that, there are days when I feel guilty. Like, if I can go to yoga on a Wednesday morning, am I really “working hard enough”? If I take a long lunch with a friend just because I feel like it, does that mean I’m slacking? If I worked more, would I earn more? And wouldn’t earning “more” be better? This line of thinking is absurd. But that’s how deeply ingrained the traditional work model is.
For so long, we were taught that time = value. That the more hours we put in, the more worthy we are. But that’s not how most creative work functions. The most creative people I know (myself included) don’t work eight-hour days. We (try to) work smart. We charge a premium for our expertise. We rest when we need to. We work in bursts of intensity and give ideas space to percolate. And yet, because society worships productivity, there’s still that nagging feeling that if we’re not constantly hustling, we’re somehow less than.
So how do we unlearn this? We have to completely reframe what work means to us. If we’re going to do this creative thing for the long haul without losing our shit, we have to shift the way we think about all of it.
A few things I remind myself daily (because, yes, I need the reminder):
My income will fluctuate. That doesn’t mean I’m failing—it means I’m running a business. Some months are big, some are small, but over time (hopefully) it balances out.
Working less doesn’t mean I’m lazy. If I’m producing high-quality work and getting paid well for it, the goal isn’t to work more just to prove something. The goal is to work well.
I need to know what enough looks like for me—literally, I need to know the real dollar amount. Not for my neighbors, my cousin, or my friends. If I’ve already hit the number that supports my life, savings, and goals— I don’t have to live in a constant more, more, more mentality.
My version of success is mine alone. Maybe I don’t want to scale a business, manage a team or buy a 7-bedroom house in the suburbs. Maybe I just want to make enough to live well, travel and actually enjoy my life. And that’s more than valid.
I don’t need permission to structure my life in a way that works for me. If I want to take Tuesdays off, I will. If I want a nap at 2 p.m., I’ll take it. (I’m not generally a napper but I like the idea of naps.)
I have to build a financial system that supports my reality. Save aggressively when things are good so I can breathe when things slow down. I have to build several income streams. Learn how to manage money so I don’t feel like I’m free-falling every time work slows down.
The bottom line? We didn’t choose a traditional life, so why are we still measuring ourselves by traditional standards? We walked away from the well-worn path for a reason—we wanted something different. More freedom, more creativity, more meaning. We chose this life because we refused to be bound by someone else’s rules, timelines, or definitions of success. So why do we keep comparing ourselves to a system we were never meant to fit into?
The real measure of success isn’t just making money—it’s making a life. One that feels expansive. One that honors our work and our wellbeing. One where, years from now, we get to look back and know—with absolute certainty—that we lived with passion, we bet on ourselves and our loved ones, and we built something that would not have existed without us. And really, isn’t that what makes all of this worthwhile?
P.S. Per usual, if this resonated with you- PLEASE repost, comment, share and spread the word. 🩷
P.P.S. No advice, creative or otherwise, works for everyone. I fully recognize that privilege, access, and circumstance shape opportunity in ways that can't be ignored. Take what resonates, leave what doesn’t—here’s no one-size-fits-all path for being a creative entrepreneur.
This picture just popped up on my Iphone: Over the holidays, we sometimes go to my brothers’ place for dinner (two of my brothers live together, which is a sitcom in itself). This past year, Ira asked that they set aside two eggs for him so he could make the stuffing when he got there. Simple request, right? We get there, open the fridge, and see a carton of eggs—plus two eggs, separately placed, literally labeled in Sharpie with Ira’s name. Have I mentioned that my brothers are 50+? Also, let’s not even talk about the Sharpie poisoning that I’m sure we all got from this. But. And. Alas. It was so ridiculous, so childish, and somehow exactly what we needed. A microjoy, indeed.
That’s all for today. Thanks for reading Life, Created.
With love, wisdom [and small mercies] from Montclair. xx
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