A surgeon’s guide to making hard decisions

Surgery lesson #465:
Never do a tonsillectomy with a hernia tray.

Back in the early 2010s, I spent a few weeks as a surgeon at a rural hospital in Haiti. I’m betting you can picture the place: dedicated staff, terrible infrastructure, overcrowded wards, and beautifully green outdoor covered walkways.

*The hospital in question, from their website*

On my second-to-last day there, a six-year-old girl presented to our outpatient clinic with chronic sore throats, massively enlarged tonsils, and bad sleep apnea. She couldn’t have had a more textbook indication for a tonsillectomy.

Since there were no ENTs scheduled for another six months, we got her on the OR schedule for the next day.

Anywhere in the world, ORs keep instrument sets for common procedures. Meaning, if a surgeon wants to fix a hernia, she doesn’t have to go into the instrument room to pick which scissors, retractors, needle holders, etc, she might need. All she has to do is request a hernia tray, and, 90% of the time, every instrument she needs is there.

Because this particular hospital rarely saw ENT patients, they didn’t have a tonsil tray—no pre-packed set of surgical instruments to do a tonsillectomy. And that meant that, right after clinic was done, the OR staff asked me to go through their individual instruments and pick the ones I needed for the next day’s operation.

Once I did, they whisked them away to be sterilized and I went home.

The next morning, I showed up ready to take these obstructing tonsils. My instruments, on the other hand, didn’t.

The morning staff asked me which instruments I wanted to use.

“Nothing special. Just the tray I put together yesterday,” I said.

The OR matron’s eyes widened.

“Last night, I put together a tonsil tray. Did that get sterilized?” I asked.

“No,” she said. “Nobody has any ENT instruments here.”

“So…wait. What instruments did you pull for this operation?”

“We got you a hernia tray.”

Needless to say. Don’t do a tonsillectomy with hernia instruments. It’s a slog.

But—and I promise I’m going to get better at transitions in 2025—this post isn’t actually about tonsils or hernias.

Instead, it’s about trying to do hard things with the wrong tools.

And in this case, it’s about how terrible of a tool the pro-con list is, especially for the really hard decisions.

Yet it’s also the most common technique we’re taught for making sense of hard choices. It’s kind of ridiculous how often it’s used.

Want to get a dog? Well, here’s a pro-con list.

Thinking of getting divorced? How about a pro-con list?

Considering having a kid? Believe it or not, pro-con list.

ADD GIF HERE

And the problem is? The pro-con list sucks. It’s the hernia tray of decision-making.

There are all sorts of reasons for avoiding it. But first:

The one good thing about the hernia tray

Is it possible to do a tonsillectomy with a hernia tray?

Turns out, yes. There’s one good thing about a hernia tray—and that’s that it’s got instruments in it.

Not the right instruments, mind you. But a surgical instrument is always better than no surgical instruments if you’re, you know, trying to do surgery.

And, well, the pro-con list is no different. It’s at least a tool for decision-making, and, in its defense, it’s at least the first stop on the decision-making pathway.

Specifically: it narrows your options.

And that’s a very good thing. Last year, we talked about decision paralysis, the Infinite Elevator paradox, and why dating apps suck so much. Specifically, the anxiety of dating apps comes from the fact that, the more choices you have, the less satisfied you will be with what you choose—no matter what your final choice is.

(Man, decision science is sometimes hard to explain in a single sentence).

In other words, let’s say you’re choosing an ice cream flavor. At Gelateria Tres, there are only three flavors: strawberry, chocolate, and salted caramel. At Gelateria Trentuno, there are thirty-one flavors, including salted caramel.

Even if you were to choose salted caramel at both places, your experience at the first gelateria will be better, explicitly because you only had three flavors to choose from.

I bet you’ve seen this play out in your own life: how many times have you found yourself in complete paralysis because a restaurant menu was too long, because there were seventy-two flights to choose from, or because you’d spent all day swiping Feeld?

You’re not alone. Analysis paralysis is a thing.

And that’s where pro-con lists absolutely shine. You simply can’t make a pro-con list for seventy-two flights. (I mean you could, but who has the time when Season 3 of The Floor is about to drop?)

Narrow framing

But that’s where their usefulness ends.

There are two big problems with using pro-con lists for life’s biggest decisions.

The first is that they tend to paint decisions as black and white. And sometimes, they are—you can’t half have a kid, for example. However, that tendency pushes you toward seeing decisions as binary choices.

And real-life choices don’t work that way. Let’s say you want a dog in your life. You could:

Get a dog.
Volunteer at a pet rescue
Join a dog sitting group
Join a dog walking group
Foster puppies
Become a vet
Volunteer with a therapy dog organization
Work as a dog groomer
Work as a dog trainer
Specialize in pet portraits
Volunteer with programs that teach children how to interact safely and respectfully with dogs
Join a dog advocacy group

And so on…

Imagine tackling that with a 24-column pro-con list!

The same thing is true with even bigger decisions. Say you’re considering a job change.

You could—and pro-con lists would nudge you to—view this decision as binary. Either I stay in this job, or I quit and find a new one.

Alternatively, you could explore a “layered career” approach: Maybe you don’t need to leave the job altogether quite yet. Maybe you could start thinking about your professional life in layers. Maybe all you need to do right now is shave a little bit of time away from one job so that you can dip your toes into a different pond.

And no pro-con list is up to that task.

Fixed preferences

The other major issue with pro-con lists is that they tend to see preferences as fixed. The reality is, they’re not.

Now, any decision-scientist reading this blog will push for my excommunication from the guild of decision science after that sentence. After all, one of the fundamental, deeply-held tenets of decision science is that preferences are fixed and stable.

In other words, if von Neumann and Morgenstern are right, then your preference for salted caramel gelato is unchanging. If you’d choose salted caramel instead of strawberry when you’re 21 and in living central New Jersey, then you’ll also make the same choice when you’re 65 and living in Paris. Your preference for chocolate over strawberry is stable across time and space.

But, we all know it’s not.

I grew up hating tomatoes. Like, abhoring them. Couldn’t stand their gooey insides. Would always, always, always choose something without tomatoes, even if it meant a pizza with no sauce.

Now? I can’t say I love tomatoes, but I can also say that I’ve had some pretty transformative tomato encounters.

*A transformative experience with tomatoes, Dirt Candy, August 2023*

My preferences about tomatoes have been neither fixed nor stable.

Professor LA Paul has done some fascinating research on the effect of “transformative experiences.” In her seminal book, she posits that transformative encounters have two effects on us: they transform us personally (I’m no longer as anti-tomato as I used to be), and they transform us epistemically.

This epistemic transformation is deeper. It’s the you-don’t-know-what-you-don’t-know transformation.

In other words, you can’t fully know what’s on the other side of a decision until you make it. All decisions are uncertain, and so are you.

You can’t fully know what life is like before having a kid—until you have a kid. You can’t fully know what life is like as a fifty-year-old child-free person—until you’re 50 and child-free.

Transformation is epistemic. You are a different person—fundamentally, epistemically—on the other side of a transformative experience than you are now.

And pro-con lists simply can’t handle that. In fact, they assume the exact opposite—that the pros now will still be pros on the other side of the decision.

Which is far from guaranteed.

Wrap your choices

There are so many better decision frameworks. So many better instrument sets than pro-con lists.

And here’s one.

In their book, Decisive, Chip and Dan Health proposed a different framework for making the hard choices better, more confidently, and with more clarity. They called it WRAP:

Widen your frame
Reality-test your assumptions
Attain distance
Prepare to be wrong

Here’s what it looks like in practice. Try this out with a big decision you’re facing.

Widen the frame

As with all my exercises, start by taking out a sheet of paper and writing your big decision at the top.

Let’s say you’re a nurse trying to decide whether you want to stay in nursing. Write “Should I stay or should I go?”

Now cross it out!

That’s the old you talking. That’s the pro-con you talking. That’s the binary decision.

Instead of “Should I leave nursing?” reframe the question so that it’s open-ended. Something like, “How could I evolve my career?”

And just like that, you’ve widened the question.

Now widen your options. List three and solutions, instead of either / or. A solution could be, “I stay in nursing, and I pursue my teaching certification,” or, “I leave full-time nursing and I keep a per-diem job.”

Reality-test your assumptions

OK, now that you have some options, it’s time to reality-test them.

For example, in the first option above, I’ve made the assumption that you could stay in nursing while pursuing a teaching certification. If this were my decision, I’d want to know if that’s actually true.

You can do that in a few ways:

Identify a couple of people who’ve made a similar transition. What would you want to know? Call them! Honestly, there’s nothing people like more than giving advice, so use that.
Consider rolestorming—brainstorming, but with a touch of role-playing. Instead of brainstorming as yourself, take on the persona of a supportive partner or a disgruntled parent or your own therapist or, heck, Oprah herself. And then brainstorm from within that role. What does Oprah think about your assumptions? What does your mom?
And then finally, test-drive your assumption. If you’re considering adding a teaching certification to your career, then seek out a six-week course at your local community college, adult education center, etc. How does it feel to do that?

Attain distance

As the third step in the Solving for Why Navigation System, my clients have to engage in a time-travel exercise.

I ask them to envision themselves at 86 years old (why 86? You’ll have to sign up to find out). And then I ask them to ask their 86-year-old selves three questions:

What things do they wish they prioritized as they made big decisions? And what things do they wish they’d de-prioritized?
Imagine the decision “failed”—how did they recover from that failure?
Now that they’re nearing the end of their lives, what do they want their epitaph to read?

Prepare to be wrong

Believe it or not, this last step is my favorite, because it forces the widened frame more than almost any other step in this process.

Since every decision is made under uncertainty, I ask my clients to start thinking more probabilistically. What are the chances of this working? Have you seen others do this? How big of a risk are you taking—and are you willing to take that risk?

I make them get granular with it: what’s the financial investment, what’s the time investment, and what’s your cushion in each of those domains?

And then, we do a pre-mortem. As in the time travel, I ask them to imagine that their decision failed. What happened for it not to work? Where did they mess up? And what can they do now to make sure that doesn’t actually occur. These anticipatory autopsies really help get you unstuck.

The Power of Expanded Thinking

In late 2024, I worked with a surgeon who initially saw her choice as “stay in surgery or leave medicine entirely.”

In our time working together, we discovered multiple possible paths she could pursue: reducing clinical time to do more research, transitioning to administrative leadership, combining clinical work with consulting, using her expertise in medical device innovation, or starting a bookstore (which was her initial “should I go” option).

Now, let me tell you. This framework didn’t make the decision for her. What it did instead is reveal options that her stress-narrowed vision hadn’t considered. Options that she could then stress-test, pre-mortem, and time travel with.

No framework is perfect. Just like no surgical tray is perfect.

But that’s ok. The goal is never to make the perfect decision (because they don’t exist).

The goal is to make the good decisions.

And then to act.

→ Want more weekly content about making the hard decisions with confidence and clarity? Join my mailing list!

→ Ready to transform this insight into action? Get my free guide, “The Anatomy of a Good Decision,” where I break down the exact framework that helped me navigate my transition from surgery to decision science.

→ Are you a medical provider struggling with exhaustion, burnout, and indecision about how to craft a purposeful career? Check out my free 20-minute webinar on the Solving for Why Navigation System here.