The dumbest decision I ever made (and the Nobel Prize that explains it)

Decision science, Family Guy, and why the “safe” choice may be the riskiest.

I know exactly when I ruined my life.

A touch overdramatic, yeah, but stick with me, because this story — about a single moment in Singapore 27 years ago — might also explain why you’re stuck in a job you hate, why you’re still living in a city that doesn’t set your soul on fire, or why you haven’t started that business or written that book or launched that podcast.

This was June, 1998. Semisonic’s Closing Time stood at the top of the charts, and I stood at the entrance to Singapore’s immigration building, my hand on the door. 

Source: Unsplash

I was coming to the end of one of the most amazing years of my life, doing a job I absolutely loved, in a country that had quickly become home. The only thing that stood between me and keeping all that going was one door. 

See, even though I’m a surgeon now, I never wanted to be one. Like actively, adamantly, deeply did not want to be a doctor. I wanted to be a rock star (because what little boy doesn’t want to be a rock star?) Or I wanted to be a linguist (because what little boy doesn’t want to be a linguist?)

But, I’m the first-born son of an immigrant family, so I really only had three options: doctor, lawyer, or failure.

I chose the first, and I hated it. Hated every single minute of medical school. In fact, not one month into med school, I made an appointment with my dean to tell her I was quitting. 

She suggested I take a year off instead. 

And that’s how I ended up in Singapore, teaching organic chemistry and cell biology at Ngee Ann Polytechnic. The comparison couldn’t have been stark: I hated medical school, and I loved teaching in Singapore. I loved the work. Loved the country. Loved the food. Loved the students. Loved my colleagues.

A brave person would have noticed the contrast, noticed how the depth of my hatred for medical school was perfectly matched by my love of what I was doing in Singapore. 

A brave person would have seen this dichotomy.

A brave person would have opened the immigration building’s door. A brave person would have started the process of leaving a career they hated for one they clearly loved. 

I am not a brave person.

I let go of the door handle. Turned around. And walked right back into medicine.

What the hell was I thinking?

Why did I walk away? Was I just an idiot? 

Or was something else happening?

The mystery box

First, watch this:

Let’s be honest — Peter Griffin isn’t exactly known for his good decision-making. And this is classic Peter: choosing a mystery box instead of a boat. 

What the hell was he thinking? 

(Says the guy who let go of that door handle in Singapore…)

Still, it’s an appropriate question. Peter’s decision? Dumb and indefensible. 

But what if I told you that my decision was just as dumb and just as indefensible? What if, even though medicine is a good career, I made the exact same mistake that Peter did? 

Risk, uncertainty, gain, and loss

It all comes down to some very fascinating (and Nobel-Prize-winning) science. 

To state the obvious, Peter was dumb to choose the mystery box. All his neighbors saw it. You see it. I see it. Sure, the box could have held anything. But the boat? That was a sure thing. He should have taken the money and run. 

Source: Unsplash

On the other hand, at least at first blush, it looks like I made a better decision than Peter. I chose the stable option. I chose the boat—the job security, the sure salary, the respectable career path. 

And, given what we talked about last month, that makes sense: after all, there’s no such thing as a certain decision, our brains are hard-wired to hate uncertainty, and two specific aspects of uncertainty—risk and loss—drive that hatred.

But I messed up. 

Back in 2002, Daniel Kahneman won the Nobel Prize in Economics for something called Prospect Theory. When Kahneman and his colleague Amos Tversky (who died before he the Nobel Prize was awarded) studied how we make decisions, they discovered something counterintuitive: We don’t always avoid risk. 

In fact, sometimes we very predictably take it!

When we’re offered a chocie between a risky thing (like a mystery box) and a sure thing (like a boat), we humans avoid risk only when the sure thing is good. 

In other words, a bird in the hand is worth two in the bush, only if you like birds. 

On the other hand, when the sure thing is bad, we become rabid risk-takers. 

Don’t believe me?

Imagine if, instead of offering Peter a boat, the salesman said, “You can choose the mystery box, or I put a bullet through your head”? What if he said, “You can choose the mystery box or I get your house?”

Would Peter still be stupid for choosing the mystery box?


The psychology that’s keeping you stuck

Not a single thing about the mystery box changed! The risk didn’t change. The uncertainty didn’t change. The box was still an unknown; it was still exactly as risky as it was before. 

And everything about the context did. What changed wasn’t the risk Peter was taking—it was the certainty. 

What Kahneman and Tversky discovered was:

  • Humans are risk-averse when they focus on gains

  • But when the certain option is bad, we’ll take all the risk we can get our hands on.

In other words, Peter’s not dumb for taking the mystery box. Peter’s dumb for taking the mystery box in that specific context.

Which brings me back to the Singaporean immigration building—and why my choice in 1998 is even less defensible than Peter’s.

Because I looked at it all wrong. 

Fundamentally, I faced a choice between an uncertain (but so far positive) future in Singapore, and the certain (and certainly unpleasant) future waiting for me back in medical school.

And all I could see was the risk. All I could focus on was the uncertainty.

So of course I chose the certain thing—even though the certain thing was bad! 

If I’d reframed the choice like I should have — if I’d compared the mystery box of a life in Singapore with the certain loss of happiness waiting for me in medical school — maybe I’d have made a different choice.


Your Turn: A 6-Minute Exercise That Might Change Your Life

Alright enough nerding out. Let’s do something about this. 

Is the psychology of the mystery box keeping you stuck?

Give me six minutes, and let’s fix it.

First, take out a piece of paper, open your Notes app, whatever. At the top, write down the big decision you’re wrestling with. You know the one. Maybe it’s:

  • leaving your stable but soul-crushing job

  • starting that terrifying side hustle

  • finally writing the book that’s been living in your head

  • moving to a new city

  • asking that person out

  • having that difficult conversation you’ve been avoiding

Now, set a timer for 3 minutes. For those three minutes, I want you to take a deep breath, close your eyes, and imagine making that choice. Like, really imagine it. Sit with it. Visualize writing that resignation letter, moving to the new city, asking that person on a date.

Got it? Ok, start the timer. I’ll be here when you get back.





How did that feel? Specifically, what did your internal monologue tell you? I bet it obsessed about the risk of the new thing and the safety of your current situation. I bet it focused on all the things that could go wrong, the departure from the safety. The steady paycheck. The known devil. The “sure thing.” I’d put money on it.

That’s because your brain’s making the mistake I made in Singapore. 

So, let’s use Prospect Theory to our advantage. Let’s flip the script

Set another 3-minute timer. This time, focus on what you’re losing by not choosing the mystery box. Think about the creativity you’re stifling. The relationships you’re missing. The life you’re not living. The slowly accumulating regret of playing it safe. 

And every time your brain tells you to focus on the positive, chastise it. I want you to spend three minutes focusing on the negative. (Don’t worry, it’s just 180 seconds).

Ready? Start the timer. Focus on the negative.





Feel different? 

That’s because you’ve just hacked your own brain. When you reframe your choice from “what might I gain?” to “what am I currently losing?”, suddenly that mystery box starts looking pretty good.


The Power of the Mystery Box

Here’s what I wish I’d understood nearly 30 years ago, standing outside that immigration building in Singapore: 

The “safe” choice isn’t safe. Sometimes, the riskiest thing we can do is stay put. Sometimes, we need to choose the mystery box.

When we face big life decisions, our brains naturally frame them in terms of risk. Specifically, our brains ask: Is what I might gain worth giving up what I already have? 

But maybe that’s the wrong frame. 

Maybe the better question is: What am I losing by not taking this risk? What’s the cost of staying put? What’s the price of choosing the path of certainty?

Because here’s an uncomfortable truth: There’s no such thing as standing still. We’re always moving forward; the only thing we get to choose is what path we’re on

And maybe, when we think we’re choosing safety, we’re actually choosing loss.


I’m often asked, “Since you hated medicine for so long, would you do it the same if you could do it all over again?” It’s a hard question to answer—I love what I do now, and what I do now is a direct result of choices I made in the past.

But I won’t lie to you—I often wonder what would have happened if I’d chosen the mystery box back in 1998. 

I know I can’t go back and change that decision in Singapore. But I can help you think differently about yours.

So the next time you’re facing a big decision, remember Peter Griffin and his mystery box. 

And remember that guy standing outside an immigration building in Singapore, choosing certain unhappiness because he was too afraid to take a risk.

Then make a better choice than I did.


What big decision are you facing? I want to hear about it! Contact me with the button below, or book a free call with me. Let’s figure out if it’s time for you to choose the mystery box.

And PS: If this post resonated with you, share it with someone who might be standing at their own immigration building door right now.

Sometimes we all need a little push into uncertainty.

Previous
Previous

Unfinished business, and why your brain won’t let it go.

Next
Next

Your brain’s already been hacked