I wrote this line five times in one tweet last month. Didn't explain it. Two weeks after quitting I can.
Honesty isn't "don't lie", almost nobody lies. It's saying the thing you actually think when it's expensive. In a job, the cost of saying what you think is friction with a manager, a peer, a roadmap somebody else owns. The move, mine for years, was to soften. Round the corners. Hedge. After enough rounds you stop having the thought at all, there's nowhere left to put it.
Self-employment doesn't make you brave. It removes the audience that was rewarding you for being careful. Same thought, no friction to dilute it. Some people stop talking to you. The ones who don't are the ones that matter.
Tolerance is what lets honesty survive contact with other people. Without it, honesty turns into being right at people, which is the opposite of useful. It doesn't mean agreeing. It means letting the other person have their reason without pre-judging it. Hardest moments are when someone is wrong for a reason you've heard ten times before. You want to roll your eyes. Don't. Let them say it. Then say what you think. You'll be right with them, not at them.
Congruency took longest. Do the thing you said you'd do, including the things you only said to yourself. Job version of me thought I should write in public. Didn't. Thought I should build products. Shipped side projects that died on Sunday. Thought I should be honest with prospects. Rounded the corners.
None of that was a lie to anyone else. It was a lie to myself, repeated daily, in doses too small to show. The cost compounded anyway. After years of it the version of me on a job application didn't match the version of me on a Tuesday morning, and you forget which one is real.
Self-employment closes the gap by force. If you said you'd write, you write. If you said the prospect isn't a fit, you tell them. The action is the proof.
Before anything that takes more than a day now I run three checks. Honest about what I actually think, including the parts that cost me. Tolerant of the people I disagree with, even the ones I think are wrong. Does this match what I told myself I'd do when nobody was watching.
Yes to all three, the work goes somewhere. Anything less, it doesn't, even when it looks productive.
Only personal philosophy I've found that doesn't decay.
— Simon