The Questions You Must Not Answer

Sam Gerstenzang
2 min readJul 10, 2017

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There are some answers that aren’t worth knowing. At least not right now. It might take too much effort to find. The question might be wrong. The world might change. It might be unknowable.

The traditional analytical approach is to “do the work” to understand what you don’t know, piece by piece. To framework the world and to fill in all the details.

But I think this approach doesn’t work with big unknowns, or when you’re trying to make big jumps. It doesn’t work in research. It doesn’t work in startups. It doesn’t work in writing.

Because what you must do is let a new question hang open wide, and use that to go find concrete answers elsewhere. The market is between 1x and 100x its existing size if we reduce the cost by half. We can make this 30x faster but we don’t know who will use it, or what can now be built. Let’s assume we have ten times as much computing power.

And in exploring, you discover new questions and new answers. Maybe you were wrong but it didn’t matter because the question was the wrong too. Or an adjacent possibility is born, from your own work or from pure luck.

This suspension of disbelief is critical because our models of the world are very poor. Even if we build all the spreadsheets and all the TensorFlow models, the unmodeled world dominates. We just don’t know.

The role of the researcher, the essayist, and the businessperson are similar in this way. Success comes from successive suspension of disbelief.

But to make great things you have to get the ordering right; to hold just enough consistency while letting the pieces wobble themselves out. And of course, not answering some questions will kill you.

It’s a little bit like living in a house made of jello. You must run from collapsing beam to collapsing beam, massaging each to hope it stays put for a little bit longer. The rain is pouring down through the roof, the neighbor walks by, and you must insist “it’s a house, I swear!” Because if you don’t, it will all come falling down.

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Sam Gerstenzang

Building @askumbrella. Previously building products, teams, and companies at @sidewalklabs & @imgur, investing at @a16z http://samgerstenzang.com