The Secretary Problem, Asymmetric Risk in Your 20's, and One-way & Two-way Door Decisions

Welcome to Letters of Wonder, where I explore the truths behind clarity, creation, and a wonderful life.

The Secretary Problem and Dating

How do you make the biggest decisions in your life?

There’s actually a mathematical answer.

Naval Ravikant brought this up on a podcast with Chris Williamson.

And I became fascinated.

The idea is that you find the most optimal output by following an algorithm.

Without going too deep into the math (I'm more of a words guy myself), here's how it works.

Let’s say you have to choose the best secretary.

Here’s how to statistically get to the best one:

1. Reject the first n/e applicants (that’s the total number divided by Euler’s number, ~2.7 — for my fellow word guys, it just means “the first third-ish”)

2. Hire the first candidate who is better than all the candidates you have seen previously

This way you are much more likely to select the best secretary.

To me, this concept is most fascinating in relation to finding a life-partner.

At first, it may seem silly.

Go on a bunch of dates and reject people.

But the idea is that you don't even know what you're looking for.

You may not have to reject them outright.

But dating around gives you a higher chance of finding a partner.

So how do you figure out your n?

It’s not an exact science.

But it’s based on how many people you realistically think you’ll date before committing.

If you’re 21 years old, n might be 20 or 30.

You’ve got more time to explore, figure out what you like, and calibrate your preferences.

But if you’re 29 and thinking more seriously about long-term commitment, n might be closer to 10.

You won’t know the perfect number.

But even just estimating it gives you a better strategy than going in blind.

Reject the first ~37% (that’s n/e), then commit to the first person who’s clearly better than everyone before.

That’s how you find the most optimal partner based on mathematics.

This applies to any big decision you have to make in life:

• Dating to Find a Life Partner
  → Go on several dates early without committing. After a while of dating around, commit to the first person who’s clearly better than everyone before.

• Hiring for a Critical Role
  → Interview a set number of candidates. Don’t hire until after a good amount have been interviewed. Then hire the next standout.

• Choosing a City to Settle In
  → Travel to 10 cities? Explore the first 3–4 without pressure. Settle in the first one that feels better than any previous.

• Buying a Home
  → View the first few houses just to get a sense of them. Then choose the first one that feels right.

• Picking a College or Grad School
  → Visit a bunch. Don’t jump at the first one that feels “pretty good.” Wait, then choose the one that clearly outshines the earlier ones.

• Choosing a Long-Term Business Partner
  → Talk to a handful of people. Don’t jump at the first person who’s cool. After a few convos, commit when someone clearly clicks above the rest.

Now obviously it’s a bit difficult to make everything so algorithm based.

The bigger lesson here is to try more things before committing.

You don’t have to follow this rule.

It’s just the highest probability way to get what you want!

The Risk Curve of Your 20s

I was recently chatting with a mentor who told me to go "all in".

In other words, don't settle for the middle path.

Thanks to his advice, I’ve decided to commit to building Trendify.

Still writing newsletters though - oops!

The middle path is mediocre (not the Buddhist one).

I was recently reading "Die with Zero" by Bill Perkins.

He talks about a fascinating concept of "asymmetric risk".

When you have less to lose, you should take bigger bets.

In other words, you risk more for a much greater reward when the downside is low.

1. If you lose, you’re basically where you started

2. If you win, you’re up massively

I'll give you an example.

If you're 23 and starting your career, you can risk a whole lot and still end up fine.

You could quit your job, start a business, fail and still have all the time in the world to figure things out.

But what if you're 45?

Now it becomes much more difficult.

You now have to figure out how to support your spouse and little ones too.

And if you fail in your business, you're now putting their quality of living on the line.

In our 20's, most of us have a lot more we can risk and still be fine if things go south.

That’s why this is the decade to experiment like hell.

And I’m slowly learning to take bigger bets, even when they scare me (here are a few I’m learning to do more of).

1. Take a shot at your dream life.

   • Build that business. Start writing that book. Let go of the things that don’t serve you.

2. Approach the people who intimidate you.

   • Reach out. Say what you truly think. Connect with people. You never know what might come out of it.

3. Share that thing you’ve always felt scared to share.

   • Post that video. Start that podcast. Write that newsletter.

4. Say yes to weird opportunities.

   • Go to that random event. Intern for free with someone legendary. Build a side project with friends.

That's the concept of asymmetric risk.

And even if you’re past your 20’s you can craft that dream life as well.

It may just be a bit more difficult to do so.

But if you want it bad enough, you can always find a way to make it happen.

One-way & Two-way Door Decisions

I’m realizing more and more that it’s okay not to have things figured out.

Maybe it might even be a good thing.

In your 20’s, you’re still figuring out what you do and don’t like.

For some of us, it’s clear and we go for it.

For most of us, it’s a slow path of exploration and we take our time.

The important thing is to make sure it doesn’t take too long. As young as we are now, we will get older eventually.

Let’s talk about decisions.

Your partner, the city you’ll move to, your career, these are all massive decisions that will impact you for the rest of your life.

That’s where One-way & Two-way Door Decisions come in.

Jeff Bezos introduced this idea. And it’s fascinating.

1. One-way doors = big, irreversible decisions (marriage, career, moving)

2. Two-way doors = easily reversible choices (switching an app you use, side projects)

So technically you can reverse the 3 decisions I mentioned above.

But they are extremely difficult to do (divorce, moving again, quitting your career).

So I’d say they are closer to one-way doors.

And whenever you make a one-way door decision, you better take a lot of time to really weigh out your options.

Bezos says that by recognizing the type of decision, you can allocate the appropriate amount of time and resources to it.

So recognize if it’s a one-way door decision and spend far more time (if you can) on it.

Go Where You Feel Light

Your intuition is pretty powerful.

Sometimes you just know deep down that something is not right for you.

And other times, you feel a sense of inter-connectedness to everything.

It’s this feeling of feeling “light” as Harvard-educated sociologist Dr. Martha Beck says.

That’s how you keep leaning into your purpose/calling.

So go where it feels more light for your body. Where you feel in sync.

I strongly believe if you keep following that as your inner guide, you will build a beautiful life around you.

I'm not sure if this agency path is the most optimal thing in the world for me forever.

But I do know that I enjoy it a lot and it's giving me the freedom I've longed for.

There might be a different path in the future, but this right now feels great.

It's interesting because I myself never explored other paths.

I followed wherever my body felt more “light”.

And that led me to stumble into this path of content and building a content business.

So if you have already committed to a path/career/person, that can also be very fulfilling.

You don’t need to apply these complex decision making principles.

You can absolutely make the most out of what you do have now.

• Showing up better for your current partner

• Learning to enjoy your work more

• Exploring whatever city you live in

There’s a lot of joy in all of the above.

But if you haven’t committed yet — great.

You have the whole world at your hands.

You can try different things, explore and reflect.

Then slowly commit to what feels the most fulfilling to you.

If you can’t find that thing — keep exploring.

But remember this - at the end of the day, all paths are beautiful in their own way.

And with that, I’ll leave you with a beautiful quote: