Leadership Thought of the Day: Getting Lost

Jake Wilder
3 min readJan 11, 2022
Photo by Leah Kelley from Pexels

“How will you go about finding that thing the nature of which is totally unknown to you?” asked the pre-Socratic philosopher Meno. It’s something I read years ago in Rebecca Solnit’s A Field Guide to Getting Lost and it’s stuck with me ever since. Amidst our hyper focus on productivity, how do we explore new, unknown ideas and experiences? As Solnit wrote,

“The things we want are transformative, and we don’t know or only think we know what is on the other side of that transformation.”

Some of our greatest joys in life — wisdom, inspiration, happiness, and fulfillment — come best when they take us by surprise. We find them only after we stop chasing them. As Viktor Frankl wrote in Man’s Search for Meaning, “Happiness cannot be pursued; it must ensue.”

Yet taking time away from our direct pursuits, in the hopes of wandering our way into success, seems like a waste of time. It’s counter to everything we know about productivity and efficiency.

Which is, perhaps, the very problem we’re facing today.

We spend more and more of our lives chasing success and fulfillment at work, yet the vast majority of people remain disengaged with their jobs. Despite all our plans, to-do lists, and schedules, we’re not moving the needle on fulfillment at work.

We’ve never been more productive. But if that productivity doesn’t translate to fulfillment, is it really worthwhile?

Napoleon Hill said, “Every adversity, every failure, every heartache carries with it the seed of an equal or greater benefit.” It’s worth nothing that he didn’t say it leads to benefit. It’s not guaranteed. It only offers the seed of transformation for those willing to cultivate it.

The one thing that we can all count on is that our futures are uncertain. We don’t know whether our jobs will be here in ten years, how our lives will change, or what will happen to those that we love. How we respond in these times of uncertainty depends on our ability to respond to it. If someone’s never gotten lost in their life, they’ll be ill prepared when life gives them some unexpected turns. In contrast, for those who are comfortable in the unknown, getting lost stops being a cause for panic.

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Jake Wilder

I don’t know where I’m going. But at least I know how to get there.