Hey Reader,
Every. Single. Founder. If you are so lucky, will feel overwhelmed, underperforming, late, early, missing something, not clever enough, not near enough, not fast enough, not leader enough. Searching for a playbook that doesn't exist, and feeling that you're winging it, with a perpetual fear that you're one day away from it all crashing around you.
The more qualified you are on paper. Domain expert, PhD, MBA, researcher, somewhat accomplished someone, the harder this all feels.
This is not imposter syndrome. You wish!! You should be so lucky to be so new, and so arrogant to believe you actually get that excuse.
Nope. This is way simpler. Reality has a surprising amount of detail. Detail you can only find by doing the thing.
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This is understanding you are exactly where you are supposed to be, being new, fresh, first-time, doing the riverdance in a minefield IS THE superpower. You've heard me say it before, ignorance is a superpower (until it's incompetence!).
Nothing taken for granted. And just to remind you, if there was a playbook then you wouldn't be in business, success would be the norm, would be the commodity. This is exactly what the journey to experience feels like.
It's not lost, it's just early in the part of the journey where the map stops working, the zero GPS mountain range between “let’s do this” and “what the f are we actually doing” so of course you feel lost. It’s a reasonable expectation.
Which leads me to Harvard Stupid. The founder who believes they can think and strategize their way through reality without actually doing it. It’s all the fluff, all the work that feels right, without realizing reality’s detail only reveals itself when... you actually engage with it.
It’s the arrogance of intelligence that lets you think you’re good enough to skip steps, it's the founder who lowers the price because you know too much about what’s wrong, it's discounting your own competence because you can see every gap, and most of all calling a task, or effort, or idea, or option done before reality has had a chance to humble you (doing enough to pretend you have given it a fair shake).
Harvard Stupid isn’t about being dumb. It’s what happens when you’re smart, prepared, perhaps even qualified, and that preparation becomes a trap. You know too much to just start, see too many risks to just move. Building maps of a place you’ve never been.
This is not me telling you you're stupid and that's fine. It's about telling you that you are encountering complexity you couldn't have known and now you have to go engage with it. Fast.
The cure. Get. In. Traffic. Or more explicitly. Realizing that reality has a surprising amount of detail!!
Which takes me to this. Read it. Mandatory rite of passage for every founder. As in don't quote Zero to One, Hard Things, Lean Startup, The Mom Test, Do Unscalable Things, and not Salvatier and his piece: Reality Has a Surprising Amount of Detail.
His premise is simple.
"At every step and every level there's an abundance of detail with material consequences. If you're trying to do impossible things, this effect should chill you to your bones. It means you could be intellectually stuck right at this very moment, with the evidence right in front of your face and you just can't see it."
He uses the example of building stairs, something a child could draw but the moment you try to do it yourself, it gets exponentially harder at every single step. Shockingly, a lot of detail goes into building a single step. The amount of detail that has to go right and the amount of stuff ready to help you fail. The wood warps. The screws pull the bracket off-angle. The measurements that looked right on paper are wrong in your hands.
Which is my point to you. The details are invisible until you're holding the wood. They're specific to YOUR wood, YOUR tools, YOUR hands, YOUR stairs. The only way to see them is to start.
And what makes this extra cruel is that once you've held the wood and felt it warp it becomes so obvious it doesn't even feel like something you learned. It just feels like common sense.
It's why experienced founders seem unreasonably good, thousands of details that are almost invisible, but are first principle facts.
THE BALANCE
I'm not telling you to be reckless, knowledge has huge value and matters, but most founders treat preparation as a floor, this weird non-negotiable they must navigate, when it's actually a ceiling. It limits your ability to see how this plays out in your specific startup, your specific moment in time, your specific view of the world.
At some point, your research is just intellectual procrastination. Cue the "told you so" newsletter Planning vs Preparation (TL;DR plan to learn, prepare to adapt. But you have to actually start before either one kicks in.)
THE REAL REASON YOU FEEL BEHIND
Your engineering feels slow. It is. That's you discovering how your specific product, your specific stack, your specific team actually works. Detail you can only find by doing.
Your sales aren't closing. Not because your product is wrong because you haven't yet absorbed the micro-details of how your specific buyer actually makes a decision, the flow, the keywords, the triggers.
Your fundraise feels impossible. It's exactly as hard as it should be. You're learning what investors actually care about, which is different from what they say they care about, which is different from what LinkedIn says they care about - for these investors and your specific startup.
This is not failure. This is reality revealing itself AND it only reveals itself to the founder who is in the room, hands on the wood, making the stairs. Get it now?
Reality Has a Surprising Amount of Detail.
THE REFRAME
So, if you agree with the premise. Then you agree you are not behind. You are not underprepared. You are not missing a playbook that everyone else has. You have it, literally, exactly where you are, that's the playbook. This is the playbook.
The confusion you feel isn't a bug it's the feature, it's to be weirdly celebrated.
You NEED TO REALIZE the mess you are trying to fix, the mess that feels like the weight of the company on your shoulders, that MESS is the learning.
Hurry up. The stairs won't build themselves.
If I can be of service, feel free to grab time.
LFG.
- James
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