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You are at:Home » The questions before the questions
Entrepreneurship

The questions before the questions

adminBy adminOctober 4, 2025No Comments3 Mins Read
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“I’m applying to work at Disney, do you know anyone who can give me a reference…”

“My two partners and I are planning a new company, can we ask you for feedback on our business plan before we go out to raise a seed round?”

“We’re moving to Centerville, which neighborhood should we consider?”

“Which famous college should I apply to?”

These are fine questions to ask. But they might be concealing the questions we need to ask first.

Thanks to the hype bubble, plenty of would-be entrepreneurs have decided that a real business needs VC funding. Some of the most fun you can have starting a business is hanging out with your partners, pre-business, brainstorming ideas, and the natural next step seems to be running the project as a team, as partners. Applying to jobs at famous companies feels like a safe thing to do. And moving to a town your friends admire feels like a smart move…

Except maybe you shouldn’t have partners. Maybe your business shouldn’t be investor backed. Maybe you’d be happier in an apartment in a city, or living overseas for a year…

Perhaps you should consider a gap year, or find a less famous but more effective university… or spend the time and money to learn a trade instead.

Before you start arranging the candles on the cake, it might pay to think about what flavor cake you’re going to get, whether you’re going to bake it yourself or whether there should be a cake (or a surprise party) at all… Once you fall in love with a future that has a cake in it, you’ve closed the door to all the other options.

Too much choice can be paralyzing, but too much choice is also a rare moment of freedom, a moment where it might pay to pause for a moment before backing into the obvious next steps. It turns out that just a few minutes spent reconsidering those obvious next steps can change everything for the better.

Here’s the actionable tactic: When presented with these moments of freedom, don’t simply articulate one plan needing improvement. Instead, find the time to create three different plans, plans that don’t overlap at all. Can you refine and improve each one enough that you’d be happy randomly choosing any one of them? Because by the time you’ve built out three independent plans, it’s quite likely you’ll have discovered the right path.

October 4, 2025





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