Three months in I noticed something that should have been obvious. I can't plan past two weeks. The plans I made in January were wrong by February, the ones I made in February were wrong by March, and the one I'm trying to make today will be wrong by Tuesday.
For a while this bothered me. I was raised on the corporate version of planning. Quarterly OKRs, roadmaps, dependency graphs. The kind of structure where if you can't see six months out you're doing something wrong.
Then it clicked. If you can plan six months out you're not building anything new. You're executing on a thing that already exists. Big ideas don't have legible six-month plans because the idea changes shape every time you touch reality with it. Every meeting is a new insight. Every customer call rewrites the pitch. Every week of building reveals something the previous week was wrong about.
Not being able to plan is the signal that you're on the right ground. If your roadmap is stable, you're either solving a known problem (in which case the market is already crowded) or you're not listening.
The paradox I kept running into:
"I need credibility to win customers. I need customers to build credibility."
That sentence sounds smart. It's wrong. Or more precisely, it's a frame that traps you.
The frame assumes credibility is a binary state you either have or don't. It isn't. Credibility is granular. Every conversation has its own bar. A founder who has shipped three lines of code to GitHub has more credibility with the right prospect than a Fortune 500 vendor who has shipped nothing useful in eighteen months. The unit of credibility is "do they trust you to do this specific thing for them," not "are you a credible company."
Once you see it granularly the chicken-and-egg dissolves. You don't need a thousand customers to get the next customer. You need this prospect to trust you for this scope this month. The thing you ship them is the credibility. There's no other proof.
So the question changes. Not "how do I become credible." That's untrackable. Instead: what's the smallest thing I can ship to one specific person this week that would prove I can do the thing.
Same with planning. Not "what's the six-month plan." That's a fiction. Instead: what's the thing between now and the end of this week that has the highest impact on whether anyone cares about this in a month. Pick that. Do it. Look at what happened. Pick the next one based on what you saw.
Big ideas take long timelines, sure. But the timeline is not a plan you draw on day one and execute. It's a sequence of two-week loops where each loop's insight changes what the next loop should be.
First principles. Critical thinking. Granular. Three skills nobody teaches because they don't fit on a CV.
The plan, if you need one: pick the highest-impact next-two-weeks thing, do it, talk to the people it changes things for, repeat. That's it. Everyone who tells you they have a better methodology is selling you the methodology.
— Simon