Guided wandering

In the 2018 Amazon letter to shareholders, Jeff Bezos talks about the power of wandering:

“From very early on in Amazon’s life, we knew we wanted to create a culture of builders – people who are curious, explorers. They like to invent. Even when they’re experts, they are “fresh” with a beginner’s mind. They see the way we do things as just the way we do things now. A builder’s mentality helps us approach big, hard-to-solve opportunities with a humble conviction that success can come through iteration: invent, launch, reinvent, relaunch, start over, rinse, repeat, again and again. They know the path to success is anything but straight.

Sometimes (often actually) in business, you do know where you’re going, and when you do, you can be efficient. Put in place a plan and execute. In contrast, wandering in business is not efficient … but it’s also not random. It’s guided – by hunch, gut, intuition, curiosity, and powered by a deep conviction that the prize for customers is big enough that it’s worth being a little messy and tangential to find our way there. Wandering is an essential counter-balance to efficiency. You need to employ both. The outsized discoveries – the “non-linear” ones – are highly likely to require wandering. ”

Jeff Bezos, 2018 Letter to Shareholders

While reading this, a question I thought of is: if it’s highly likely that wandering will lead to outcomes that are outsized discoveries, why is wandering disincentivized in most institutions?

In high school, most people I knew were looking to get into good colleges. In college, those same people were looking to major in lucrative fields to get good jobs. Once they’re in those jobs, they’re looking to jump to bigger companies that pay more and are growing.

It seems like there’s actually very little incentive in the system to wander. Schools teach just enough for people to be useful. Jobs pay just enough for people to not leave.

I’m always fascinated by people who zagged while everyone else zigged. In big companies, people who love their jobs fascinate me just as much. Oddly enough, to love a job in a big company is contrarian.

Most of my friends and I who’re in the process of starting companies struggle to sell our visions, raise money, and get customers for novel solutions to existing problems.

When we pitch our projects, most people will give us a list of reasons detailing why our proposed solution will fail. If founders were paid for listening to unsolicited advice they wouldn’t need to raise funds. Yet, it’s those very same people that act like they knew an innovative product was inevitable once it’s widely available and acceptable.

Why the contradiction?

My working theory is that people like the concept of innovation in the abstract. When founders pitch visions for a new world they make most people uncomfortable as it may threaten the status quo.

If you hear someone tell you a new idea, don’t shut it down. Challenge yourself to think of a world where it may actually work.

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