I put a premium on interestingness. Venkatesh Rao has helped give voice to an instinct I’ve always had when he talks about the zone of maximal interestingness.
In business, this tends to be a high-risk, high-reward approach. I’ve often stumbled upon business models we could move to that would be easier, more practical, and very solid surfaces for respectable growth. But I always opt for the harder, riskier, but way more interesting model. I like to do stuff that, if it works, alters everything. I like approaches that rely on the fewest possible status quo assumptions and require the most new behaviors and mindsets.
Of course it’s a game of constant compromises navigating where to go for interesting swings vs. boring bunts. Not everything is interesting. I like to ask myself, “Even if X was wildly successful, would it excite me?”, and, “Even if Y totally failed, would it excite me?”. If answer one is no and answer two is yes, I go for Y. The interesting one.
Building a better version of something that already exists and changes no patterns of human behavior and opens no new vistas of possibility doesn’t do it for me most of the time. I do not look down on it. That’s mostly how the world progresses. I love that people do this all around me. I almost wish I had less of an appetite for interestingness. But I just know I’m not going to be happy if I’m not working on something that has the potential – even if a longshot – to upend everything.
So I opt for that as much as I can. When it doesn’t work, you don’t gain much. When it does, you gain everything. But I find a bit of recklessness necessary for my sanity.