One thing a lot of freelancers and entrepreneurs don’t talk about enough — especially not between cries of ‘You get to be creative and make your own hours!’ and ‘There’s no ceiling to how much money you can make!’ — is just how often they’ve thought about throwing it all out the window.
It happens, of course it does. I’m positive to the point of insanity, and it happens to me, too.
So: is the desire to quit an every day thing? Absolutely not. But once every few months of running your own business, especially when you’re reliant on your own service and manpower only to bring in that paper, you start to think romantic thoughts about a secure, boring-but-simple 9–5.
And it’s no wonder, right?
Freelancing and entrepreneurship are essentially a tightrope walk between skyscrapers.
Sure, there’s no ceiling, and boy is the sky beautiful. But there’s also no floor… and it’s a long, long way down to the bottom.
So when we lose our balance on that tightrope — when a contract drops, a project goes belly-up, or we miss a bid for that dream client — we naturally become fixated on the endless chasm below us. It looks, at least from a distance, like the darkest, endless pit of failure.
And because humans are masochistically curious, we start to wonder what would happen if we fell. What we’d lose. What we’d break. What we’d have to tell our moms.
That’s where the vertigo happens.
That’s when monotonous days spent in a cubicle, clocking in and out, and working for someone else in a quiet office somewhere starts to sound absolutely glorious.
At least if I fail there, it doesn’t matter too much in the grand scheme, right? At least if I screw up I’m not forced to come nose-to-nose with my own perceived mediocrity, frustration, and rage in the same way I do when I’m flying solo. Because when it’s just me, there are no co workers to talk to about how “crazy” my boss is, or laugh about how “it’s not life or death, and it doesn’t really matter”.
Because it does matter. For solopreneurs, it matters a lot.
And I’ll admit in my darker moments it gets tempting to fix up my resume… Just to see what would happen.
Yet, I don’t. And here’s why:
Eventually when vertigo sets in, and it will, you have to figure out if the no ceiling/no floor is right for you. You have to judge whether the highs are worth the lows.
It’s also a good time to remind yourself how far you’ve come. How, by not quitting those 15 million times before, you’re miles away from where you started, and you’ll be miles even farther soon.
After all, you’re not sitting at home in your PJ’s because having to pay for your own health insurance is so great. You’re doing it because you want to build something.
When you want to quit, remember: the longer you stick around, the more you build, and the bigger you an grow.
Don’t stop. Adapt.
Client flow running dry? Bank account looking sad? Adjust. Wait it out. More will come.
And while it might feel like you’re alone in your work space, home office, or living room with these worries and fears — just remember there are millions of people who’ve felt and are feeling exactly the same thing you have. Some quit, and some keep going.
There is no shame in stopping if you’re finding the highs are simply not worth the lows. But before you throw in the towel, consider your position. Have you exhausted every resource? Have you knocked on every door for help? Have you reached out to past clients, people you admire, or mentors for help?
If the answer is no to one or all, keep thinking. Get creative. Don’t be shy about asking — because asking is part of your livelihood now. Shyness is no longer your friend.
This is the game of self-employment, how it is, and how it will be. You can stop standing on your tightrope for a second, and hook your arms and legs around it to feel more secure. Crawl if you have to. But don’t stop, and don’t let go unless you’re absolutely ready to.
All is never lost and that chasm below only really exists in your imagination. Money will come. Clients will come. They always do.
Just keep going. Hang on. Don’t quit. And keep walking that rope, kid.
Photo is of the author, by NYC-based photographer Juliet Warren. There’s more great stuff on her Instagram, too.
