The Thought Experiment That Led To My Three Kids

Welcome to The Purpose Memo, a newsletter where I give you ideas for wrestling your life back from digital technology and living a principled life. 

If someone forwarded you this, join them and other readers here.

Read time: 7 minutes

I got married a few months after I graduated college.

During the time my now-wife and I were engaged, we were frequently asked about our plans for having kids. I fielded a surprising amount of questions about a “honeymoon baby” and when there would be news of “a little Peyton” on the way.

Consequently, I had a few reps to tweak my response. Toward the tail end of our engagement, were you to ask me about children, I would say, “If you hear about us getting pregnant before our fifth anniversary, just know it was an accident.” 

Excusing the unnecessary punchiness (still in college, remember?), this answer served two purposes, one explicit and one implicit:

I wish I could have a conversation with that younger version of me. If I could travel back in time and meet him, I think I would simply hold up a picture of my (our?) three kids—all of which were born before that fifth anniversary—and smile.

You almost missed out on the best thing to ever happen to you.

Thankfully, I married the right girl. One massive, correct decision can overcome scores of wrong ones.

Today’s newsletter is not about family planning. It’s about a decision-making tool, a razor, that fundamentally altered my future. And it has the potential to do the same for you.

There’s a feel-good song called Like the World Is Going to End that’s a take on the question, “What would you do if you found out the world was ending soon?”

According to the songwriter, you might:

I like the song, but I’ve never cared for the premise of the question.

Of course I’d make dramatically different decisions if I had one week to live. But I don’t. And if I lived like I did, my future self would be very upset with me.

In my opinion, a far more salient question is this:

What am I likely to regret on my deathbed?

This hits closer to home. Death is inevitable, and so, it seems, is regret.

Even further, the inverse of the question points toward what we ought to do, not just what we should avoid:

What am I unlikely to regret on my deathbed?

This is a powerful question. Change the framing, and often, the right choice becomes clear.

Consider how likely are you to regret…

Answer: very likely.

Conversely, how likely are you to regret…

Answer: very unlikely.

I call this exercise The Unlikely Regret Razor—and it’s the reason I have three kids.

The Unlikely Regret Razor:
When facing a difficult decision or evaluating your habits, consider which choice you are less likely to regret on your deathbed.

During the first year of our marriage, my wife asked my thoughts on trying for a baby.

“We’re not supposed to have this conversation until year 5, remember?”

But there was a sincerity in her question that forced me into a reckoning with my actual opinion. After some brief introspection, I realized I didn’t have one.

Nonetheless, somewhere along the way I had developed a working version of the unlikely regret framework, and this seemed like the perfect chance to test it out.

So I asked myself: “Which of these choices am I less likely to regret: having kids young or waiting five years to start the conversation?”

The more I thought, the harder it became to ignore.

I couldn’t picture a world where I would hold my newborn baby for the first time and think, “Man, I wish I would have waited five more years for this!”

Then other thoughts began to pour in like a river breaking through a dam:

The evidence mounted and I changed my position, thankfully. I can’t imagine life another way.

I have dozens of examples of how the unlikely regret razor has proved a clarifying tool in my decision-making.

If you start using it, prepare for three things to happen.

1. You’ll take more risks.

Risk avoidance is a short-term strategy. Over the long haul, gains acquired by avoiding risk start to feel insignificant. “I wish I would have taken more risks” is one of the most painfully common deathbed regrets.

2. You’ll do the obvious thing.

All of us have an obvious choice we’re avoiding. As Sahil Bloom says, “If your life was a movie, what would the audience be screaming at you to do right now?” Does the TV need to come down from the wall? Is it finally time to give up social media? Is that difficult conversation past due?

The breakthrough you’re searching for might be waiting on the other side of an obvious choice.

3. You’ll live a story-worthy life.

Benjamin Franklin once said, “either write things worth reading, or do things worth writing.” If you’re telling your grandkids about it around the campfire, you aren’t regretting it on your deathbed.

Instead of droning on about the TV you watched, the hours you scrolled, the sterile, corporate job you loathed and how you let your health deteriorate, you’ll have tales of attempting grand things and failing, daring to be different, laughing uncontrollably, weeping bitterly, and living fully.

There’s an opportunity in front of you right now—a choice, a conversation, a leap of faith—that could change the rest of your life. Which one are you less likely to regret?

The choice might be clearer than you thought.

You just have to make it.

Enjoyed this week’s post? Let me know in the comments.

Two ways you can share this with a friend: forwarding the email or sharing this link.

Not subscribed? Subscribe here to for more posts like this one: peyton-welch.com

See you next week.

PW