The Reality Check Every Creative Needs
I never planned to be a business owner. No matter what job I wanted at any given time in my life, I never once imagined I wouldn’t work for someone else.
Yet twenty years later, here I am with a thriving design studio, supporting myself and several contractors, with flexibility in my schedule and the freedom to take on whatever projects I want.
But let me be clear: it hasn’t been easy. The expectations I had when I started were completely off base. I envisioned myself working peacefully from a cool-looking office space, with ample time for long lunches, and big projects with bigger budgets that would naturally fall into my lap.
Reality looked nothing like that.
The Questions Nobody Asks Before Starting
If you’re reading this, you probably have the self-employment itch. Maybe someone’s pushing you toward it, or maybe you’re just daydreaming about being your own boss. But before you turn in that resignation letter, you need to ask yourself some hard questions.
And I mean really ask them. The honest, uncomfortable, ego-bruising kind of questions that reveal whether this path is actually right for you.
Why do you want to start a business?
Is it flexibility you’re after? Creative control? More money? Less commuting? The ability to work on passion projects? These are all valid reasons, but here’s the thing: can you get any of those by negotiating with your current boss or finding a new position elsewhere?
Sometimes the grass isn’t actually greener on the entrepreneurial side—it’s just different grass with different maintenance requirements.
Are you disciplined enough to get up every day and do what needs to be done?
Nobody’s going to tell you to start working. Nobody’s going to notice if you spend three hours scrolling social media instead of sending that proposal. You need to be able to motivate yourself, day after day, even when you really don’t feel like it.
Think of times you’ve faced big obstacles. What did you do well? Where did you struggle?
Can you handle the uncertainty of an irregular paycheck?
This is huge. Some months you’ll make more than you ever did at your day job. Other months you’ll wonder if you can pay rent. Your bank account might be empty one minute and flush with cash the next.
How do you handle uncertainty mentally and emotionally? Do you have cash reserves? Or a partner whose income can support you while you get started?
How do you handle failure?
Because you will fail. A lot. You’ll lose clients. You’ll underprice projects. You’ll make mistakes that cost you money. You’ll say yes to the wrong people and no to opportunities you should have taken.
What skills and support do you need to develop to become more resilient?
So Should You Do It?
Here’s what I know: the worst day of being my own boss is a million times better than being bossed around by someone else—even if they’re one of the good ones.
No one else will ever give me the flexibility or the money I can choose for myself. The freedom to design my life around my needs and values is worth every bit of hustle, sweat, and occasional tears.
But it’s not for everyone. And that’s perfectly okay.
What’s Next?
If you’re still reading, chances are you’re seriously considering taking the leap. Good. That means you’re thinking critically about one of the biggest decisions of your professional life.
The questions I’ve shared here are just the beginning. In my book Good Work! Practical Advice for Starting & Scaling Your Creative Freelance Business, I walk through everything I wish I’d known before I started—from setting up your business structure and creating your first contract, to finding ideal clients, pricing your services, and building systems that let you actually take a vacation.
Ready to find out if you’ve got what it takes? Grab your copy of Good Work! and let’s do this—together.