JTBD: Triathlons

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The end of the high school track season was bittersweet this year. A few senior boys, who I got to know well, didn’t quite run well enough to advance in the post season.

But being high school senior boys, they soon had another idea: a sprint triathlon.

There’s a great place in Clermont Florida (Choice of Champions) that runs an accessible sprint series each summer in May, June, July, and August. “When are you signing up,” I asked, “I’ll sign up too.”

It’s great to gloat over them with a rare win and they give all the trash talk back (and more) when they beat me.

“July,” Nick said.

“No!” his mom protested, “it’s going to be too hot.”

That’s the point. It’s not really about doing a triathlon, it’s about having an experience. Yes, times kind of matter, but only in the scope of the experience. For a crew of high school swimmers and runners, it might be a better experience and greater stories if it’s the race in July.

Maybe it will be, maybe not. But it’s the right direction. This was an early lesson in Bob Iger’s experiences. He thought sports was about the game, but really it’s about the story. Talking about the wins or losses are meaningless without comparison because context gives us a narrative.

This summer then, take the trip, do the thing, make mistakes. It’s not actually about the outcome – it’s about the experience.

JTBD: Falafel

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Google’s Liz Reid, VP of Search:

“One of the interesting things about the evolution of AI is that people stop talking just in keyword ease as much, and they start expressing more of what they want, and then that becomes much easier for us to give an answer. If you say, tell me about someone versus what’s new with someone, that’s actually much easier for us to figure out how to give better results than if all we just say is someone. We used to talk about an example query in a different way is falafel.

What do you want to know with falafel? Some people don’t know what falafel is, they want a definition. Some people want recipes.

Some people want to find where to eat. Some people want nutritional information. They all just use the word falafel, and that’s just harder to figure out how across all of them do that.”

From Odd Lots: Google’s Liz Reid on Who Will Own Search in a World of AI, Apr 23, 2026

That’s jobs to be done! Take something that someone said, and figure out the why and progress they want to make in their life. This whole section of the podcast is good because it’s about the idea of translation.

In the case of Google, it’s about a computer translating what progress a person wants to make. But that’s the whole idea of JTBD.

May the fourth be with you.

Track it

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Building off last week’s idea about fleeing time.

My friend is a big fan of Jesse Itzler. I haven’t quite figured out how to use his calendar. But his ideas led me to keeping my own calendar and tracking what matters.

Often the days just run by. Like a book you read, are excited about, but finish, and wonder: What was that all about?

Weekly plannings take the place of quality time.

This all felt off. Like, were we doing what mattered?

My biggest note from The Art of Spending Money was how rich is your camera roll? It’s not about watches or trucks (Florida!) or house size (Florida!!). It’s not about vacations skiing or trips to Europe. It’s about the pictures on my phone. If there are lots of pictures with people I love doing fun things that’s all that matters.

This also lives on my calendar so I can track it. Whether digitally or on paper, if I have a nice coffee with the kids, go to a concert, visit a beach – something special together – it gets a pink heart 🩷. That shows me at a glance how many things we’ve been doing and if we need more of them.

Life is fast. By the time you read this it will be graduation season. Then college orientation. Then a family trip. Then the fall semester. Whoosh. Take some pictures, be with your people.

Track it to do it.

Do it now

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The last project in my business and entrepreneurship class is to create a business plan. But in the weeks before that, kind of a middle what-do-we-do-between-units, we spent a week on business case studies. We did Geometry Dash (which they loved, but then wanted to play Geometry Dash), Life Time Fitness, and movies (naturally).

The Life Time fitness lesson was a riff on 25IQ: Take a current business concept and contrast it with quotes from others/specific leaders. For the Life Time it was Buffett and Munger.

Munger’s contrast-misreaction (number 16) is the idea that we are relative thinkers and we contrast one thing against another to understand its place. Munger’s warning is not to spend 40K on a boat and then buy the $400 cooler add-on. Those coolers only seem cheap relative to the price of the boat.

That same week my daughter picked up her high school graduation gown.

And man, it feels like I’m out of time. It’s gone. Suddenly.

This feeling has been building like warming water and since spring break it’s started to boil. There’s so many game nights we missed. Vacations we didn’t take. Experiences gone.

You hear it goes fast but don’t feel that until it’s gone.

It might seem like you have a lot of time left with your kids. And you kinda do. But just because it seems like one thing doesn’t mean that it necessarily is. Take time today, see, call, text your kids. Do it now.

Do the work

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As a high school teacher I use LLMs a lot. My peers do too. It’s just too easy not to have a model type out all the text in whatever format for (all the different) software programs we use.

One quirk of the LLMs is they always make the correct multiple choice answer the longest multiple choice answers. When in double thirty years ago we just chose “C” – now, students choose the longest answer.

But there’s something lost. TNSTAFL. Maybe not in the busy work of typing out questions, but maybe so. It could be a feature, not a bug that audiobooks (and books), are so long. It’s more time to sit with an idea.

In that spirit, here are two ideas and inspirations about doing the work:

Ezra Klein: “Having AI summarize a book or paper for me is a disaster. 

It has no idea what I really wanted to know and wouldn’t have made the connections I would’ve made. I’m interested in the thing I will see that other people wouldn’t have seen, and I think AI typically sees what everybody else would see.

I’m not saying that AI can’t be useful, but I’m pretty against shortcuts.

And obviously, you have to limit the amount of work you’re doing. You can’t read literally everything. But in some ways, I think it’s more dangerous to think you’ve read something that you haven’t than to not read it at all.

I think the time you spend with things is pretty important.”

Daryl Morey: “They (Bill James) said, ‘Hey intern, you go work on this project, see if you can look at point differential and how it affects the NBA.’

So that was my very first analytics project, which is in the ’93 basketball book. Yeah, I remember coming up—like, literally worked on it 24/7 because I was like, ‘This is my moment to try and prove something to Bill James,’ who, by the way, didn’t care at all when I did it.

He, you know, he probably thought it was derivative because it sort of was. But it took a while to come up with the idea of modifying the exponent. That was obviously the first time Bill’s ideas were adapted to basketball.”

Pesky Proclivities

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My friend Stephen wakes up and immediately checks the news. That’s not good, he said.

He’s trying to quit. Or do something else. Or read the news with more mindfulness. Or prayer. Or something.

But history can help us, maybe not check the news, but at least remember that crazy is the norm. Henry Oliver told Tyler Cowen in March 2026, “Obviously, Shakespeare is always writing about the Reformation, and he’s always writing about the tension between pre- and post-Reformation culture, not the least in terms of, there’s now an official policy, but everyone remembers what it was like, and they miss ordinary life in pre-Reformation times, and their mothers did things differently.”

In the 1500s people pined for the good old days.

And more recently too! David McCullough ‘Wrights’ that when bicycles were first introduced people did not like them. Adults thought they were for lunatics. Teens were forbidden from riding them. The innocent bicycle began as pariah.

Change is uncomfortable. Ambiguity is icky. But it’s the norm. Immediately checking the news probably isn’t good. But taking note of people’s proclivities probably is.

Are you committed capital?

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Investor John Arnold told Patrick O’Shaughnessy there were two things, early on, that helped him become one of the greatest investors.

First was, “a lot of retained earnings, and then new investors came in.” Makes sense. If you have a great idea with lots of room to grow, let it grow!

Second was committed capital, “Whenever we had a down month or a downtime period, which we had, they weren’t calling to redeem, but they would call up and say, do you need more capital?”

This is an idea we’ve seen before, notably with Buffett – but this time it hit different: is this how I act in my relationships? The answer wasn’t good.

When my daughters are being teenagers, do I lean in and offer more love? When they’re frustrated, am I a good set of ears? When there’s a down period, do I ask them if they need more?

Hearing Arnold talk about it make complete business sense. Like, heck yeah, let’s do this together. But I didn’t feel that in my relationships: too short, poor listening, too transactional.

Oof.

But now we have that question. Guidance. Are you committed capital?

Proximity to Money

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Reading The Art of Spending Money by Morgan Housel inspired this thought. And it felt like this was the heart of, not the book, but my interpretation. It was like, this is the idea to organize your actions around.

The closer something is to money, the less value it contains.

Like a Venn diagram, the more a thing overlaps with money, the less ultimate value it has.

Money as the first example. Money is money. Complete overlap. Money is good but because of the things it allows, not itself. You can’t eat money. You can’t stick your toes in money, well you can but it doesn’t feel like sand at the beach.

Nouns can be a second example. Money buys food, which leads to sharing meals. Money buys pickleball paddles, which leads to time exercising, laughing, and seeing friends. Money buys cars, which travel to beaches where there is sand.

Verbs. Money pays people to landscape, which leads to time with family. Money pays for tax services, especially this time of year. Money pays for haircuts, which help us feel better.

This frame of money is so heavily tilted by JTBD theory and Early Retirement Extreme I can’t get away from it.

Both JTBD and ERE point past the initial assumption and ask what’s really the goal?

And both rely on creativity to find a solution which leads to that goal.

Now, thanks to Morgan Housel, there’s a question to ask when making choices: What is this proximity to money? If it’s close, it’s probably not what I want.

Two Problems with Net Worth

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In the early days of blogging, the Rational Walk was an easy entry to investing. Focusing on Buffett and Berkshire, they made an intimidating topic accessible.

One of their suggestions was to track net worth (this was early in my education in finance and investing). Rather than income or savings, net worth was how much a person was actually worth. It was the proper way. The intelligent way. And who doesn’t want that?

So I tracked it.

It’s been great! To see a number rise thanks to mortgage payments, investing gains, and raises feels wonderful. It doesn’t go up every time, but the number goes up over time.

However, like a lot of numbers, it provides a false sense of authority. It’s just a number, and it has two problems.

First, it’s not cash. Our net worth includes a house, 401k, and brokerage accounts. To convert all to spendable money is a task. Selling a house is an ordeal, a 401k included penalties up to a certain age, and brokerage accounts need liquidity. Someone has to buy what a person is selling. Plus, you know, crypto.

Second, it’s not the solution. Money may lead to a solution, but it’s not the goal. This is the heart of one of my favorite books, that there are many creative ways to live well and we stink at coming up with them! We can pay for services – or do them ourselves. The latter just takes some time and the right YouTube instructions.

It’s nice to be reminded of these things. Life is dynamic and asks for balance. Have things boiled down to a number? It might not help, but it’s probably not the answer.

The Need for Finish Lines

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“I learned this in SEAL training,” said Chadd Wright, “the evolution that we lost the most guys on during hell week was this: the instructors set two cones out on the beach. They put the class out there and they said, ‘All right, run from one cone to the other‘, it was a one mile stretch.

“And they just said, ‘keep doing that until we tell you to stop.’ It was just a one mile run back and forth up and down the beach there in front of the ocean at your own pace. We got a couple hours into this thing and guys just were just quitting like in droves. And I’m like, “What is going on? Why are all these dudes quitting?” Like, well, the reason they were all quitting is because the instructors didn’t tell us that this is a 4-hour evolution. They just said, “You’re going to keep doing this.” And we were in hell week, so we knew it could go on for 3 or 4 days if they wanted it to. They couldn’t see the end. Everybody’s looking for a finish line, and there’s no finish line in life.”

We have ambiguity aversion. There’s an innate dislike of the unknown. It’s part of our system.

But we know this. We can use this.

Last fall my dryer was “crying”. It was making a squeaking noise that got louder each cycle. I’ve never fixed a dryer before and felt the ambiguity: what if I break this more, what if it’s challenging, what if it’s electronics, what if I hurt myself, etc.

There were two problems: the broken dryer and my feelings around it.

Well fixing my feelings (and the dryer) was just a YouTube video away. Of course there was somebody, fixing the same washer (the only difference was the color of the machine), who posted an amazing tutorial. Thanks to u/Bearded Appliance Repair, and one Amazon parts order, the dryer got fixed.

For those things floating from to-do list to to-do list because they don’t get done, there are really two things to address. The thing, and our feelings about it.