14 lessons from 14 years of self-employment

At 14 years of self-employment, you would think that I have everything—whatever that means—down. But the double-edged sword of being your own boss means that you are constantly learning and adjusting. Really great for DIYers, “learn by doing” people, and those who thrive on having multiple projects. Self-employment is not for the faint of heart. Over the years on this anniversary, I’ve shared freelancing lessons—ones I learned, ones I’m still learning. This year, I’m sharing 14 lessons that have endured multiple pivots across multiple industries. 

1. Listen to your gut. One I have shared many times before, but not to be confused with imposter syndrome, where your gut is overpowered by your brain telling you you’re not good enough. 
2. Systems are never done being built.
3. You can plan for policies, but there will always be that one client who makes you edit or create a new one. And repeat.
4. SOPs are for solopreneurs, too. Ever since writing out my processes, like bookkeeping, I no longer fumble around trying to remember how things go. 
5. The more specialized someone is as a coach/consultant/teacher, the more they’ll charge and the more they’ll (hopefully) help you.
6. In the beginning, you’ll be a generalist, and that’s okay. You need to try a little bit of everything to figure out what makes your heart sing. 
7. When you start to feel stagnated, bored, and not creative, and you’re NOT in burnout, it’s time to pivot or expand. 
8. You do not need to grow all the time. It’s okay to build slowly and stay solo. 
9. It is fine to benchmark, but don’t get lost in that comparison. You don’t know their circumstances, and to be honest, the ones I’ve benchmarked against a few years ago are out of business now. 
10. If you have a partner, it is imperative that they emotionally support your dreams. A bad partner will tear you down, reorient attention to themself, and slowly sink your vision. It is doubly difficult to build something if you’re stressed at work and at home.
11. The thing you avoid doing the most is the thing that’s going to sink you if you don’t confront it. Hate accounting, and you’re not going to learn or outsource it? You’re going to have cash flow problems.
12. If you’re having trouble with what makes your service unique, ask inquiring clients as part of your consult. “Why do you want to work with me? What part of my work appealed to you?” 
13. Work at the optimal times for you. This may change. My schedule is a loose 11 am-5 pm (creative & admin work), 8-10 pm (photo editing). If you’re going to be your own boss, you should set the best schedule for yourself.
14. Find people who are like you, who will celebrate with you. In my case, I mean other solo business owners because they know what I’m going through. What I do is not the same as what a tech startup founder goes through, and it isn’t the same as what a restaurant owner goes through. 

These last few years have been HARD. Beyond what I prepped for or could’ve known. Living in the epicenter of AI, going all in on only writing and photography, I’ve had a front row seat to what’s been eroded in creative fields. But you know what? If you’ve gone deep in what you specialize in, dig your heels in. I’ve tried AI culling and editing (It found monolid photos to be closed eyes. It doesn’t understand a blurry foreground composition.), I’ve tried AI “writing,” and it was fucking terrible. AI editing makes things stale and voiceless. AI-generated headshots teeter on the uncanny canyon rift and often fall right off the cliff. Don’t get me started on graphic design.

I can’t believe 14 years have passed already. Solopreneurship is a battle. You question your sanity and your life choices. It will have the best highs and absolutely terrible lows. It’s truly one of those things where you have to believe in yourself first. I’m ending this on a high note that I shared with paid subscribers last week: this month has had the most amount of money I’ve ever invoiced in one month in all my 14 years. Onto Year 15!

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