How to Make a Choice

Davy Kesey
Feb 13 · 6 min read

Most people misinterpret Robert Frost’s famous poem, “The Road Not Taken” as an ode to individualism, a witty anecdote highlighting the importance of boldly zigging when the world zags. Don’t be afraid to swim upstream, that sort of thing. As the famous closing stanzas read:

I took the [road] less traveled by,
And that has made all the difference.

Seems clear enough, unless you’ve read the entire poem.

The two paths are in fact, quite similar. A few stanzas earlier the narrator describes the second road as “just as fair” as the first, observing that prior foot traffic “had worn them really about the same.”

In truth, the narrator simply doesn’t know which road is better—after all he only has the opportunity to travel one—but nevertheless anticipates later depicting his selection as hugely significant. Simply put, neither the reader nor the narrator knows which choice would’ve been the “right” one. (Enjoy a more in-depth synopsis here.)

My question today is this: how do we know what to choose? What’s the best way of making a choice? When presented with a proverbial fork in the road, how does anyone know what to do?

I ask because I myself don’t know. Questions constantly plague me. Is she worth double-texting? Should I spend time editing or marketing? Do I trust this person? Is it time to give up, or should I persevere? How hard should I push for this concept? What’s the best use of my money? The questions are endless.

Pro-cons lists, expert podcasts, and the advice of friends are popular solutions for some; others suggest journaling a few pages, sleeping on it, or “trusting your gut.” Still others prefer to outsource responsibility, hoping God or a controlling parent will tell them what to do. (It’s easier to let someone else make a choice and blame them if it goes poorly, rather than face it ourselves.)

Whatever our tools of choice, we tackle decision after decision and they generally seem to work pretty well.

Or do they?

While most of us have a choice or two that may not seem so good in hindsight, it made us into who we are today so why regret it? Even if it was a mistake, we learned so much from it, right?

That may be true, but we always “learn so much.” The default for humans is to learn. Choosing a different career path, a different relationship, or different city simply offers different lessons. And while our choices “made us into who we are today,” that doesn’t mean this “us” is the happiest, most fulfilled, or best possible version.

It’s classic human to defend past choices, as “The Road Not Taken” so cleverly illustrates. The road we’re on seems pretty good (and it may well be), but in truth we have no idea how the other one would’ve panned out. Even the seemingly obvious “right” choices in our past are subject to question. How can we know how the “wrong” choice would’ve turned out?

My point is not that pros-cons lists are useless or that our guts are lying to us or that we need to regret every choice we’ve ever made, but that our arsenal of tools for making choices is fundamentally limited and thus the wrong point of emphasis. Even if we can perfectly evaluate one choice versus another, it’s impossible to know what the subsequent ripple effects will be.

For example, my freshman year of college I decided to transfer schools. I applied two places: College of Charleston (in state) and University of Washington thousands of miles away. In trying to choose between the two, I weighed the academic merits of each, the size, the cost, the locations, and so on. I chose to be closer to home and attended College of Charleston.

What I couldn’t have known at the time is that my dad would get cancer six months later. Probably good I stayed close to home, right? Did I make the right choice? Maybe. There’s no telling what would’ve happened had I chosen the other school. Perhaps I would’ve met someone and gotten into a wonderful relationship. Perhaps I would’ve taken time off from school to be with my dad and later returned with an entirely different major, or not even not returned at all! Who can say?

Life is vastly complicated and intricate and dynamic and confusing. “Educated guesses” are totally overrated and far less “educated” than they purport to be. So again the question arises, how does anyone know what to do?

My theory is this: we never have enough information to make a truly “informed” decision. A better point of emphasis is choosing between the underlying motivations propelling us down one pathway or another— fear or hope.

I propose that our North Star, when choosing between anything, ought to be hope. Neither option guarantees a good outcome; we remain vulnerable to the unseen twists of life regardless. What is certain is that hope offers a more positive experience for not only ourselves, but those around us too—fearful people aren’t particularly pleasant friends.

I imagine there aren’t many proponents for fear, yet hope is still sometimes met with skepticism. When I say hope, some read naivety. May I respectfully say that your cynicism is showing? They are different words for a reason. Naivety suggests a lack of wisdom or experience, while hope simply suggests a dream or aspiration. Many of the greatest people in history have hoped for progress, for justice, for victory — that’s why they worked towards it! Yet no one would suggest that Einstein or Ghandi or Churchill were naive to the challenges.

Cool, hope sounds great. But how do we actually do that? The real challenge is (1) noticing fear and (2) subsequently choosing hope.

That first point is important because it’s so easy to miss fear. Some of the boldest people I know are unknowingly driven by a fear of being controlled or being trapped—their seemingly “bold” choices are actually driven by fear (and come with many of its nasty side effects).

Sometimes fear shows up in more mundane forms. I used to think my constant procrastination around work was due to laziness, but when I dug deeper I realized it was due to fear. I was (am) scared I’m not artistic enough, talented enough, or rich enough to pull together a photoshoot that will make everyone glad they worked with me. I’m scared of doing a bad job and getting criticized. Fear fear fear.

Noticing all this requires self-reflection, honesty, and time (the enneagram helps too). Most of us barely notice it though, as we opt for our preferred distractions: reading, drugs, Netflix, porn, socializing, work, relationships, alcohol, church…There are a million ways to avoid reflection in 2019.

In practical terms, I’ve tried the following approach: when I face a big decision (and sometimes even a little one), I list all of my fears for each route. I list everything that could possibly go wrong, all the ways I could be exposed, vulnerable, hurt. Then I list all my hopes for each option—what could be possible, what could go right. Putting it in such stark terms highlights when I’m leaning one way due to fear, rather than my supposed “objective” decision-making process.

We will inevitably make some choices out of fear, which is okay. Those fears arise from past wounds that ought to be unwrapped at great length in therapy, but the point is that they’re legitimate. It’s human; it’s normal. It makes sense. In fact, it’s hope that doesn’t make sense, especially since we’ve been hurt before and see dozens of treacherous obstacles littering the horizon. It’s very hard to choose.

Hope happens in a place of spaciousness, of safety, of abundance. It’s a maybe-things-will-work-out mindset. Choosing it is even more difficult than noticing fear, which is why I’ll have to unpack it at length in a future blog post. Surrounding ourselves with hopeful people and ideologies certainly helps. In the meantime, learning to recognize fear in ourselves is a good start.


Davy Kesey

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Big fan of banana bread. Also a photographer based in LA.