Being self-employed is one of the most freeing and empowering choices I’ve ever made. I get to call myself Executive Director. I get to decide how my art, my music, and my voice move through the world. I answer to myself, not a boss.
But here’s the truth no glossy entrepreneur podcast tells you: freedom comes with a weight.
Compliance. Gatekeeping. Loneliness.
Every grant application, every LLC filing, every tax receipt is another hoop to jump through. And no matter how many pro bono workshops I sit in, or how many times I trek across Washington, California, or Texas to sit across from nonprofit lawyers and “free” support programs for artists, it often feels like only 10% of it is useful. The rest? Wasted hours. Running a hamster wheel in the dark.
⚖️ Compliance is Heavy
There’s the constant anxiety: Am I filing correctly? Am I logging expenses right? Is my LLC safe from audits? It’s like carrying a backpack full of bricks while trying to run a marathon of creativity.
You start realizing that “being your own boss” really means being your own HR, legal team, accountant, and compliance officer. And none of those roles are creative, freeing, or fun.
🚪 Gatekeeping Never Stops
Then there’s the gatekeeping. You think being your own boss will free you from it, but gatekeeping just takes new forms.
Funders who say they want to support marginalized artists, but really just want a slick narrative that fits their agenda.
Family members who run nonprofits, hold housing workshops, and have the resources — but don’t tell your mom, don’t tell you, because you’ve been cast as the scapegoat, the outsider, the naïve one.
People who say “I’ll help build you a website” then ghost, leaving you with broken promises.
It’s not just institutions. Sometimes it’s family. Sometimes it’s friends. Sometimes it’s colleagues and mentors.
🕯️ The Loneliness of It All
Entrepreneurship is lonely. You can sit in a room full of pro bono lawyers, nonprofit leaders, or well-intentioned workshop facilitators and still feel like you’re navigating it alone.
Because at the end of the day, it’s you who has to face the invoices. You who has to wonder if that grant report will get approved. You who has to balance the hope of making art with the reality of making rent.
đź“š Books That Have Walked Beside Me
There are books that helped me not feel so alone, even when 90% of the advice around me felt useless:
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Lead From the Outside by Stacey Abrams — a reminder that leadership often starts in spaces that don’t see you coming, and that power can be claimed even when the structures aren’t built for you.
The story I can’t stop thinking about: two women — one Black, one white — trying to get their startup into retail stores. They had to take out loans just to pay accounts. They were broke, stressed, and raw. I see myself in that. The hunger, the stress, the endless cycle of pushing forward even when the system is designed to keep you out. -
We Should All Be Millionaires by Rachel Rodgers — part pep talk, part strategy manual for women and marginalized folks carving out wealth in systems not built for us. A wake-up call that wealth isn’t just for the privileged few; it’s a survival tool and a right. Rodgers breaks down the poverty mindsets that keep marginalized folks underpaid, while giving concrete steps to start charging what you’re worth, delegating, and building wealth unapologetically.
The story I can’t stop thinking about: Rodgers talking about raising her rates and refusing to apologize for wanting wealth. I see myself in that — knowing my work has value, even when the world wants me to surrender to failure. -
Walk Through Fire by Sheila Johnson — raw and real about building an empire while facing personal battles most people never see. A testimony that success doesn’t mean the absence of struggle. Johnson shares how she built BET and her business empire while navigating betrayal, sexism, racism, and personal heartbreak. The fire didn’t destroy her — it forged her.
The story I can’t stop thinking about: Johnson enduring public and private pain while still building something world-changing. I see myself in that — holding grief and ambition at the same time, still pushing forward when most people would have quit. -
The Perfect Day to Boss Up by Rick Ross — a blueprint for hustling through chaos and claiming power on your own terms. Proof that hustling through chaos requires mindset, discipline, and multiple streams of income. Written in the middle of the pandemic, Ross shows how to turn setbacks into strategy and why bossing up is a daily choice, not a one-time win.
The story I can’t stop thinking about: Ross grinding through uncertainty, mapping his empire in the middle of crisis. I see myself in that — still plotting my future, even when the world feels unstable and the rules keep changing.
🎧 How I Access These Books
I recommend checking out Libby (libbyapp.com) — it’s free with a library card anywhere in the 50 states of the USA. This is where I listen to audiobooks while practicing my daily Vipassana meditation — an ancient technique from India that centers on breathing with your eyes closed, sitting with steady posture in a chair, on the floor, or even in bed. By focusing on the breath moving in and out of the nostrils, I can regulate my nervous system and approach entrepreneurship with more clarity.
I know meditation and audiobooks aren’t accessible to everyone. If sitting still isn’t your lane, you can:
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Try short daily walks or listening with earbuds — one chapter at a time, no pressure to finish.
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Use BookWatch (a subscription app that plays books like videos) if you prefer more visual learning.
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Or go low-tech: check your local library for print or e-books you can download to a phone or e-reader for free.
The point isn’t the format — it’s finding ways to keep these stories close to you while you’re living your own hustle.
🌱 Why I’m Still Here
Yes, this life is hard. Yes, it’s lonely. Yes, it often feels like spinning in circles with gatekeepers at every door.
But here’s the part I hold onto: Entrepreneurship gives me sovereignty. I get to be messy and still be the Executive Director and CEO of my own life. I get to reject gatekeepers, even if it means cobbling together scraps until my work speaks loud enough to be undeniable.
Freedom with weight is still freedom. And I’d rather carry that weight than carry someone else’s silence.
✨ If you’ve felt this too — the paradox of freedom and gatekeeping, the loneliness of being your own boss — I want you to know you’re not foolish, and you’re not alone. We’re out here, building messy, brilliant, imperfect empires in the dark. And even if only 10% of the resources feel useful, sometimes that 10% is enough to keep us moving — beyond survival, toward thriving.