Dear Bear: do you feel doubts about your unconventional career path?

Ellsworth Kelly’s Austin, photo by Victoria Sambunaris

Housekeeping: Hi! Matchmaking results are out for 95% of people, the rest will be out in the next day or two. Some people got the same matches as last time because of a bug so just email me if that happened to you and I’ll fix it!

Context: a reader suggested letting our community contribute to some Dear Bear questions. I really appreciate these answers and wanted to share them, as well as answer the question myself, since I both love and occasionally feel tortured by my weird career. I’ve been writing my Substack for almost five years now!! (Btw: you can ask me (and Rishi) Dear Bear questions here.)

Dear Bear (am I starting this correctly?) -

I recently started freelance work and have plans to start my own business. I'm aiming to be self-employed from this point forward, which feels daunting, but also the right path. Did you ever experience any doubts with pursuing writing full time? Any advice for someone pursuing an unconventional path away from the 9-5? And how did you build routine or maintain a sense of community while doing so?

- Toiling and Spinning

Answers:

Ved: Not an answer: But I started freelance work as well and it's been daunting because I have no idea what I'm doing.

I'm part of a writer community which gives me some support

For unconventional paths, have you checked out the Pathless Path by Paul Millerd?

Build a routine: Setting a rhythm with writing and freelance work is important. Seth Godin also mentions that self employed time management is different from normal work because it’s more intense in many ways. So don’t expect to do 60 hour weeks self employed if that was the expectation at work.

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Finn: I’m someone who started their career freelancing and is now very happily employed because freelancing/self-employment was pretty bad for me. When people look for serious relationships, common advice is to figure out what makes a relationship good for you—shared interests? Emotional support? Similar life planning regarding marriage, kids, etc.? Cultural overlap?

Few people do the same for work. I realized that I can be emotionally volatile, get stuck in my head and I need to be working with someone who can snap me out of that. I also realized that the assumption of “If this project is cool, I will be doing literally all of it” led to me just not doing many projects and that having collaborators is actually super important to me—and which is why I am 100x happier as an employee in a small startup than as a freelancer.

This is not an anti-freelancing sentiment at all (I know many, many people who love being self-employed/freelancing and for whom it’s exactly right). It’s just about being intentional.

The advice is this: I’d figure out what matters to you in a good working situation—and then see how you can build that while being self-employed.