Something to Play For

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The new year is a fresh start, time to think about and assess our lives, direction, relationships and so on.

However, if you need a little extra framing, Bill Simmons spoke about how the Celtics are doing so well and why. It might be because…

“Every single guy has some sort of hunger for something. So it’s like Jalen Brown, Tatum’s not here. I’ve always thought I could carry a team like this, so he’s in. Derrick White. I’ve always thought I could do a little more offensively. Here we go. Same for Prichard. Simons, contract here. Cada, I’ve never gotten a chance.Hauser, finally getting more minutes. You’re going down line. Jordan Walsh. I would fucking kill somebody to play 25 minutes a game. Hugo, I’m 19, I’m a rookie. Josh Minot, thank God I’m finally playing basketball.”

It’s great. Each guy, no matter what level, has something to play for.

Monte Carlo Mistakes

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“I’m going to work until my next birthday,” a near retiree friend told me. We were having dinner and she’d already punted on retiring her previous birthday. But this next one would be it – unless she wanted to travel more. 

Alaska was last year, Galapagos is this year, Africa the year after.  “I met with a financial advisor who ran a Monte Carlo simulation,” she said, “if I save a little more and take vacations from my income rather than savings, it’s more likely I’ll be better off.” 

Monte Carlo simulations, I thought, that sounds like a task for an LLM. After entering some approximate figures and going back and forth, Gemini ended with this: The Median Outcome: Even with this safer spending, the median outcome is ending up with $10M+ at age 83. This highlights the “Saver’s Dilemma”—to guarantee you don’t run out of money in the worst 10% of scenarios, you usually end up with a massive surplus in the other 90%.

Humans are feeling creatures, and it was a good feeling to know the spending “floor”.  (See also: Maxims for Thinking Analytically, extremes). In almost all situations $X is your spending floor. 

Decisions are a constant tradeoff of: what kind of mistake are you willing to live with? 

When I returned to teaching the cheating whack-a-mole was a whole new level. Twenty years ago laptops were a minority, now Chromebooks are ubiquitous. 

Imagine you’re running a marathon against one other runner. You’re neck and neck through the first five miles. You pull ahead. But then you notice something. There’s another runner ahead. You misunderstood. You’re running a marathon against a relay team. 

That’s the whack-a-mole challenge. Pop one area, a fresh one arises. 

Teachers have the same choice as retirees running Monte Carlo simulations (and all of us!). What side do I error toward? There’s no bullseye because there’s no right answer, just blunders one way or another. 

In the classroom, I give grace. Punishing a kid who worked hard and had questionable (LLM?) answers is worse than catching the number of cheaters +1. Retirees aim for grace too, only from the market. 

It’s like an alarm system. Do you want it to go off at false alarms or miss real events? 

This is the same spirit at the heart of 4000 Weeks – mistakes are inherent, are we choosing which ones to make?

Framing Resolutions

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Reframing metrics is catnip. In book form this is Moneyball, but there are many posts about framing and metrics.

How might we frame a meaningful life? And what metrics?

“Ultimately, the number of things you did can’t be definition of a. meaningful life. It’s got to be what you did and whether you did it in the spirit of showing up for it.”

That’s Oliver Burkeman’s advice to Rich Roll (November 2025). Burkeman’s book, 4000 Weeks, was one of my favorites last year. Happy New Year.

2026 Calendar

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Last year I bought Jesse Itzler’s Big Ass Calendar but found it to be too much friction. I wanted something to see my plans (which it did well), track activities (less well), and take notes and reminders (not well at all).

The only part I used – but loved – was the year at a glance. A 22″ by 14″ spread, by May it hung above my desk.

But it wasn’t great. I loved planning, doodling, and reflecting on adventures. Though my daily notebook dominated the tracking, noting, and reminders – the year-at-a-glance was a great reminder about what we got to do and what we still might yet.

Here is a Google Sheets version of that calendar. Under print settings, you may need to customize the layout. I print out four pages (January – June with dates 1-16 is one page for example), then craft it together.

This version’s lines are lighter than Jesse’s and the boxes are slightly larger. I use pencil because life happens. I’ll also throw on stickers and crude drawings for events.

The layout is so nice, to see horizontally where we are in a month and vertically where we are in the year. It also makes it easy to see if we are “a month away or more” from events.

What it’s missing is birthdays and holidays, but I’ll post other tweaks as they arise.

How to Make Air Travel Better with Orthogonal Thinking

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Orthogonal thinking and alchemy means solving problems with nonintuitive variables.

A lot of great finance book use orthogonal thinking. Rather than ask: how to shop for Christmas on a budget, orthogonal thinking moves past money and asks something closer to: how to create meaningful Christmas moments.

That reframing changes the variable from dollars/gifts to moments/meaning. To get in that spirit, Blake Scholl told Tyler Cowen how to make air travel better (no indentation).

The other thing that we need to do, and this is part of why it’s not a solved problem, is we need to fix checked baggage. Because baggage check is unreliable and slow, we have people carrying onto airplanes things they absolutely do not want to carry.

If we fix airports such that baggage check is fast and reliable, then we can stop having carry-ons, and we can get on and off airplanes much, much faster than we can today. That would actually be the biggest win. Imagine an experience where you take your Uber to the airport. The bag that today you would carry on is in your trunk. You step out of the car, someone, maybe even a robot, grabs your bag from the trunk. You don’t see it again.

After you land, you get a push notification on your phone that says your Uber’s in slot seven A, and by the time you get to your Uber, your bag is back in the trunk. The customer experience is your bag teleports from the trunk of your Uber at your origin to the trunk of your Uber at your destination. That’s how they should work. Then you don’t carry on all this stuff and it’s much faster to get on and off airplanes.

Reasoning from Extremes

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“No one,” Zach Lowe told Bill Simmons, “is arguing for a longer season. No one wants more than 82 games.”

“I’ve never seen a study,” Dr. Longo told Rich Roll, “showing that if you do 12 hours of fasting a day you’re going to have a problem.”

Both of these November episodes fit within maxims for thinking analytically. Not all of life will include common ground, but when it does, we can start there and decide how much to move away from there.

2025 Books

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Previous editions: 2024, 2022, 2018 , 2016

Best of the best

A Woman of No Importance. Wow. A work of nonfiction that reads like fiction. Forget David Goggins, get some Virginia Hall in your life. Not since Hillenbrand’s Unbroken did I read a book that was so powerful and inspiring.

4000 Weeks. Though I’ve read a lot of time management/ productivity books and followed hustle porn online, this book was different. It fit with a shift towards timelessness, depth, long term goals and thoughts, etc.

10 to 25 and The Anxious Generation were the best parenting, teaching, and coaching books I read this year. The former reinforces the effects of status, and what the authors call “earned prestige”. The latter goes beyond infinity pools and shows how the life of young people has changed (since the 90s) and what the adults in their life can do. Along with Good Inside, these are my favorite family books.

Your Money or Your Life. The classic is classic for good reason. Reading it after Early Retirement Extreme is backwards, but it was a reminder about why we talk about money so much, because we need that much help to live better.

Second tier

Revenge of the Tipping Point. Enjoyed this much more than expected. Gladwell was the non-fiction author who got me interested in reading as an adult but I didn’t care for much of his recent work (and don’t follow his podcast). But this was great!

The Art of Frugal Hedonism. This book wasn’t great – but it was fun! It’s like Your Money or Your Life but written by a pair of Australian hippies. It’s the most fun “personal finance” book I’ve ever ready.

Thinking in Systems. Another classic that was good, but resonated differently because we’ve been playing with these ideas.

Self improvement

The Four Agreements and Who Moved my Cheese are life compasses. We need to regularly read things to get our bearings.

Fun Fiction

Theft of Fire, a science fiction space trip. Overall fun and the first true “space travel” book I’ve read. I continued to enjoy the Slow Horses series to the point of bugging my daughters about the exploits of Jackson Lamb. The show is on Apple TV.

Speaking of which, the Murderbot stories continue to thrill though the Apple TV show didn’t resonate with me. Stick with these books first.

I read a handful of Jack Reacher books this year, mostly comfort rereads. It’s great to have a series of books that are plentiful enough to be different but also follow familiar trails.

ChatGPT was helpful to find older fun fiction: The Old Man from Thomas Perry, The Bourne Identity, and The Kill Artist. The Bourne Identity has a heavy Vietnam shadow, something that was part of all the movies I watched as a kid but few of the books I’ve read.

Misc.

Two books that were great but I need to think about more were Inner Excellence and Designing Your Life.

This year was a shift in reading patterns. Of the 29 books (not all listed) 16 were fiction. What used to be a handful is now more than half. Happy holidays and happy reading.

Easy Diets

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In November 2025, Rich Roll release a podcast about fasting. This compilation episode included an overview of why fasting works, how to fast, an additional details. But, what stood out was the importance of design.

Dr. Valter Longo spoke about the effectiveness of a 12/12 fast. That includes a twelve hour eating window and a twelve hour non-eating window.

Roll pushed back, asking is that enough non-eating time?

Yes, Longo explained, there are positive health effects but more importantly it’s easier to do.
Dr. Michael Greger said the same thing – only in reverse. Greger’s early advice was about a daily dozen set of foods people should eat. A dozen foods a day?

Inconceivable! Vizzini shouts.

That led to a lot of explaining by Greger. It’s aspirational. It’s a suggestion. It’s something to work towards.

Actions are based on frictions. How easy is something: to understand, to follow, to fit with my current worldview?

Better fits may not be perfect fits, but they’ll happen more.

Olsen’s Little Things

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Greg Olsen is a former NFL player and current NFL broadcaster. He also coaches a middle school football team. What’s nice about Olsen’s perspective is that he’s played at the highest levels (“The U”, The NFL) and still says it’s the little things that matter. (Apple Podcast) ““The shit that Luke and I are yelling at the kids when we’re trying to coach seventh and eighth grade defense is the exact same coaching points the good coaches are trying to give pro bowlers. It’s all the same.”

What are those things? It’s not the highlights, flash, plays, or scheme. It’s “little technique, fundamental habits. How do we do pat and go in football? Like no one spends any time on that. And I think if people realized how much that would move the needle, they’d be shocked.”

Okay. So it’s the little things that matter. How do you coach them? Specific solutions

“But what I’ve learned is like you can be loud and you can be boisterous, but you have to give them solutions. You have to give them, it can’t just be, we got to tackle better.

“You missed that tackle, tackle them. Like, you know, go get them, go get them. Yeah, what?

“I don’t know, coach, I’m trying, but like, I don’t know what that means. So to your point, what I’ve learned is like, when you are yelling instruction, it’s got to be very specific. Alex, Alex, you’re tackling the wrong hip.”

The wrong hip. That’s specific. That’s fundamental. That’s helpful. It’s the little things.

Texts from School

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My daughter’s high school (where I teach) has a new software program this year called Parent Square. It’s an app/service that allows school messages to be delivered more consistently, more immediately, and (unfortunately) more often.

During our training meeting where the administration sung the app’s praises I couldn’t help but think like an economist: oh this is too easy.

We all want to be informed parents. Or do we? Do parents want to know everything going on their children’s lives?

Regardless of if we want it (I don’t think we should) – we can’t!

Around the same time as my frustration with so many notifications, Kris Abdelmessih was asked about how to be a trader. He gives helpful advice. He’s a great writer, a good dad, super smart, and kind online. But part of kindness is honesty, he wrote:

“It’s gonna sound maybe harsh, but I tend to think that if you’re gonna figure it out, you just kind of are. You’re gonna find what to read; you’re gonna find the right things. And it’s like, if you’re unable to do that meta work, you’re just not cut out for it.”

Don’t bring information to a design fight. Want to change behaviors? Make it easier to people to take actions. Want to not change behaviors? Give people (more) information about the world. The ones who want it will get it.