#18: How to make hard decisions

Knowing what you want and WHY you want it

Dec 24, 2021

I dread decisions. I spend so much time agonising over all the things: purchases small and large (Christmas gifts included); career moves; the right words for a two-line holiday card; the right time to publish this post. I excel at seeking data and outside opinions instead of trusting my own knowing heart.

Of course, I earnestly try to bend hard decisions into neat black and white shapes; to talk it all out. But when my pro/con columns or thoughtful friends point out the advantages of one option over the other, I go all “Yes, BUT” on them, round and round until I bury myself into a lonely circle of despair.

In the end, I rarely regret a choice after I’ve made it, but I regret the time and energy that I lost making it.

And the anguish! Sometimes I add guilt to the mix, because how bratty is it really to complain about OPTIONS? Poor spoilt you, deciding between two graduate schools / fifty types of pie! Or I feel deficient, cut out from my desires, like they were pencilled lightly on a wrinkled piece of paper that I swallowed whole before anyone could read them out.

What I've learnt through many many hours of dithering is that the specifics of what I want are usually less important and interesting than why I want it.

Why would I take on that work assignment? Maybe I enjoy working with that person / I feel anxious about money / I want to learn a specific skill. Or say you’re picking a name for your children. What’s important for you about that choice? Is it loyalty to your ancestors? That your kids will stand out / fit in? In what group? That they write down their name easily on forms? That those names sound melodious / sophisticated / commanding when you shout them across the playground? Why?

Here are other ideas that soothe me when I feel gripped by a hard choice:

Indecision doesn’t have to be a defining trait or a curse. It can be just a situation you find yourself in.
Some decisions feel momentous and final when you make them, but are reversible and not that big of a deal in hindsight.
There rarely is a superior option; there is the path you choose and the other paths. (More on that below.)

Here are handpicked sources that have helped me through the years—not to make the right choice, but to understand and marshal the motives behind it. They’re the ones I find myself re-reading and sharing with friends periodically, and they feel like a gift every time.

The philosopher

Let’s start with philosopher Ruth Chang, a professor of jurisprudence at the University of Oxford in the United Kingdom. Watch her TED Talk* below. Read this Q&A^. Go on, I promise it’s a doozy.

Chang disabuses us of the assumption that there is a best option, and invites us to look instead for the option we can commit to. Those commitments, she says, help us to become who we are:

“Suppose you go to medical school and you had no idea how tough medical school was going to be. If you’re not committed to being a neurosurgeon, you’ll take this as evidence that you should be doing something else. […] But if you have committed to it, you’ll take the fact that it involves a lot of work as a kind of challenge. […] So by committing to things, we can actually create reasons for ourselves to continue on that path.”

And yes, this often means closing the door to other options. That’s kind of the point of hard choices, and that’s how you become a “wholehearted being”, as Chang puts it. The alternative is drifting. Which I think is what makes you look back at years of your life one day with fury in your belly, wondering how the hell you got there:

“Drifters allow the world to write the story of their lives. They let mechanisms of reward and punishment—pats on the head, fear, the easiness of an option—to determine what they do.” *

The writer

I often come back to The Ghost Ship That Didn’t Carry us, a beautiful column penned by Cheryl Strayed in 2011, when she was still writing anonymously as agony aunt Dear Sugar.

Sugar advises a 41-year-old man who’s wondering whether he wants to become a father. I could quote the whole thing here—each paragraph is beautiful and wise—and urge you to read it. In a way, Strayed’s words echo Chang’s:

“And so the question, sweet pea, is who do you intend to be. As you’ve stated in your letter, you believe you could be happy in either scenario—becoming a father or remaining childless. You wrote to me because you want clarity about which course to take, but perhaps you should let that go. Instead, take a figurative step into the forest like that man in the poem and simply gaze for a while at your blue house. I think if you did, you’d see what I see: that there will likely be no clarity, at least at the outset; there will only be the choice you make and the sure knowledge that either one will contain some loss.”

Okay. Now we have a framework to ask ourselves questions that will hopefully yield deeper answers. But if you’re anything like me, you still want help tidying up the underlying data and options.

The surgeon

I recently discovered this risk analysis matrix by neurosurgeon Ben Carson1, who served as Secretary of Housing in Donald Trump’s government. In his book Take the Risk, Carson explain how he uses four simple questions to decide whether or not to do a risky surgical intervention, or whenever he faces a hard decision in his life (like letting his teenage son drive a family car after two accidents):

Carson also explains how he goes through the four questions several times to assess risk from different perspectives: for example putting himself in his + his patient’s + his hospital’s shoes.

He also considers the Why: what are his motives and personal values? For instance, recalling a very risky surgical case, he says:

“From my own perspective there was enormous potential risk to my reputation if we experienced a negative outcome. My personal value system, however, made it relatively easy to discount any worries about my reputation and focus more on my patients’ perspective.”

The careers guru

When I have dozens of decision criteria fighting for my attention, I sometimes use the prioritising grid from Richard N. Bolles’ job-hunting bible What Color Is Your Parachute?

Screenshot of Richard N. Bolles’ Prioritising Grid, from his book *What Color Is Your Parachute?*

As Ruth Chang says:

“The first step is to figure out what matters when it comes to choosing between your options. Is it your wellbeing? Is it what other people will think of you? You have to figure that out, but most people don’t, and that can lead to flip-flopping because you’re changing your mind about what matters.”

Do you have other goodies in your toolbox that have made a difference to your decision-making? I’d love to know about them.

Why Would Anyone

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