lawyers charge $300-infinity per hour or they take a case pro bono, for free.
at some point every craftsman has to make this transition. in 2020 i found myself rejecting phone calls to “pick my brain,” even when the person offered hundreds of dollars. meanwhile i’ve responded at length to 100s of messages from strangers, pro bono.
[trigger warning] no matter how great you are, an hour of your time is probably not worth thousands of dollars. we’re all familiar with the 5 minute “it took a lifetime” Picasso doodle, or the fired IT guy who negotiated $50k to fix a 1-liner critical bug. but the former example was never about time, and the latter is actually a cautionary tale in systems design.
the IT guy is worth about whatever he was paid as an employee, and their manager’s negligence was worth about whatever the IT guy was paid to save the day. that is the lesson. investing energy in extortion scenarios is to fail the business ethics Rorschach test.
pondering my own earnings through this lens reminds me of Derek Sivers’ Hell Yeah or No philosophy. if someone offers $500 to chat about their app idea for an hour but i’m not thrilled to help, it’s unethical to counter at $600. better to say good luck or put a couple thoughtful minutes into a useful email.
so here’s what we’re trying to figure out: how much do we need to earn from our craft to stop thinking about the money?
in college i always had 2-4 jobs and was still broke. if you asked me what the Good Life looked like i probably would have said “able to live alone, go out to eat whenever i want, travel 1-2x per year.” i still think this is a great standard of living.
but as we age we realize: life is kinda long? we plan for the future. suddenly, having enough to cover rent in 3 weeks is not enough. and i don’t mean that in the slippery slope, never enough sense. i mean objectively. what will happen when i’m no longer able to work? how can i survive another 20 years?
the answer to this question dovetails into finding the optimal “hourly rate.” first, calculate how many years we’ll need to cover in the future. next, soberly determine how much fulfillment we get from our craft. if we can keep going for several years, we can subsidize fewer years, charging less along the way.
as an entrepreneur i’ve never said i love what i do because most of it sucks. i don’t enjoy firing people, being “pinged,” meetings, giving the government $100s of thousands in annual taxes lest they put in me in prison. i don’t enjoy working 7 days a week, covering for others, dealing with backseat drivers. i dislike monthly bookkeeping, all species of admin work, reminding people for the 5th time to put their work in the shared folder. entrepreneurship is endless suck in exchange for occasional kind customer emails (jet fuel) and sometimes getting rich (score board). often it’s just a clever way to lose everything.
the problem is i’m good at it. i’ve never lost a single dollar. so i keep going, but i recently began planning my departure. it took all of 2025 to accept that “good at” != “fulfilled by.”
after accepting this nuance and (of course) acknowledging that i’m lucky to even consider not working for a stretch of time, i’m pumped to share that my escape hatch is in good condition.
in 2026 i’m hitting Eject. there is no longer an amount of money that makes me say Hell Yeah.