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Not made any truly expensive $ mistakes thankfully, but time mistakes, yeah. I regret almost all the time I’ve spent on commissioned business writing, for business/marketing type gigs. Wasn’t fun, probably made my real writing worse.
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I did a high profile gig early in my career and got so psyched about it that I wrote a detailed blog write-up of the whole thing including technical details. I know of at least 3 next gigs I lost because of that
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All mistakes of omission Not learning breathwork sooner Not making YouTube videos sooner Wasting too much time/energy on deadbeat friends Etc But can’t overcorrect because there is value in my slow deliberative process, patience, etc
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