Why Is the Wisest Advice in the World so Hard to Follow?

Many years ago I came across some words of wisdom from Mark Twain that have both inspired and haunted me ever since:

Twenty years from now you will be more disappointed by the things you didn’t do than by the things you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.

Mark Twain

Ironically, those words were similar to advice my late father gave me: “Son,” he said, “make your errors in this life ones of commission and not omission. There are far worse things in this life than fucking up. You can always start over again. But if you fail to take that leap, it will haunt you forever.”

Or, to quote that wise 20th Century philosopher :

When you come to a fork in the road, take it

Yogi Berra

And yet we all realize (a) the deep wisdom of that advice, and (b) the difficulty of following it. Think of it as the lifetime equivalent of the first time you stood at the end of the high diving board staring down at the water below–or maybe at the edge of a cliff a good twenty feet above the lake. Should I jump?, you ask yourself. C’mon, just jump, you wuss. You can do. Just do it already!

Well, we’ve all been there. Over and over. At so many decision points in our lives–big ones, such as a new career opportunity, and little ones, such as what to order at a restaurant. And, as we look back on those decision points, we realize how often we decided not to jump, decided to back away from that cliff. Inertia is a powerful force in all of our lives. But then think of the times you did take that leap. Take a moment to gather some of your fondest memories–big and small–and how many of those would not exist today if you hadn’t taken that leap. Perhaps those memoires include a rock concert you decided to attend at the last minute, a hike you took in a national or state park, an oddball class you enrolled in during college and loved, a trip to someplace you’d never been, a yoga class, a guitar lesson, or any of dozens and dozens of other memories you are so grateful to have.

But then there are the bigger (and scarier) opportunities–your career, your relationships, your move to a new town or even a new country. The leaps you took, and the ones you didn’t take.

In a class I taught for years at the Washington University School of Law, I encouraged my students not to focus too narrowly on what they believed was the optimal career path, which many viewed as a clearly marked, well trod stairway up to that treasured tier known as “success” in a law firm or business. “Look at the careers of some of the most admirable people you know,” I would tell them. “I guarantee that none of them got to their present position following a straight line. Each of their life paths is a dizzying set of crisscrosses, screw-ups, back steps, and re-directs.”

Whether your personal hero is Barack Obama or Jeff Bezos or Ruth Bader Ginsberg or Ernest Hemingway or Lin-Manuel Miranda or Phil Knight or Oprah Winfrey or some other woman or man you admire (and even envy), take a moment to track their career paths and you will see the wisdom and the deep challenge captured in that timeless Robert Frost poem, “The Road Not Taken”:

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

 

Then took the other, as just as fair,

And having perhaps the better claim,

Because it was grassy and wanted wear;

Though as for that the passing there

Had worn them really about the same,

 

And both that morning equally lay

In leaves no step had trodden black.

Oh, I kept the first for another day!

Yet knowing how way leads on to way,

I doubted if I should ever come back.

 

I shall be telling this with a sigh

Somewhere ages and ages hence:

Two roads diverged in a wood, and I—

I took the one less traveled by,

And that has made all the difference.