You can no longer stand behind a beefy title or company name. Your identity is less tied to one job and more so intertwined to your lifestyle. And technically it feels like you can always be doing more work, at any/all hours of the day/week. And the fears, let’s talk about those.
The logistics behind owning my own business sort of terrified me. And it can feel like freelancing (even if an LLC or S-Corp) puts you in this odd in-between. The murky lines were unsettling, and I didn’t want to miss a tax rule or deadline because I wasn’t a full-fledged business with all the bells, whistles, and experts to boot. I went through several invoicing/accounting systems and more than a handful of tax/growth question marks to make sure things ran smoothly.
At some point, old coworkers were writing for help and I just didn’t let fear get in the way anymore. I instead became hungry for knowledge.
I couldn’t start out knowing it all, and I couldn’t know it all if I didn’t start. So I kept re-honing my process, asked questions (so many questions!) when I needed, and learned not to second-guess myself.
I was chatting with a few longtime self-employed writers the other day, and they expressed the same fears. But also the same gratitude and appreciation that they’ve kept it up and had time for their families, kids, and life when they needed to shift things around a bit. It made me realize how glad I am that didn’t let that nagging fear get in the way, because it’s made the last few years invaluable.
If it’s something you want, look fear squarely in the face and take it one step at a time. And don’t be afraid to ask for help on that road to learning!