How much (financial) independence?

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Our end-of-year school ceremony included two band performances and two cheer displays for America’s (checks Google) semiquincentennial (half-five-hundred). And that was just for staff. That American feeling is here.

I also spoke with a financial advisor. I got to ask reverse financial advice. There’s no self-inflicted wounds. But it got me thinking, how much financial independence do I want?

A favorite book claims someone can live on twenty-thousand dollars a year. And they can! But the number of freedoms they have are limited. They aren’t free to grocery shop whenever for whatever. They aren’t free to fly on airplanes. They aren’t free to join gyms. They lack a whole bunch of freedoms.

But everyone lacks certain freedoms. There’s no carte blanche. So the question shifts to which freedoms would you like?

These are simple but not easy questions. The advisor asked what I would like my retirement income to be. Uh, whatever it is now, I guess. There’s no way to answer those questions.

During this season of celebration, enjoy your freedoms!

Ruby Ridge: Part 2, Groups

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These are ideas about communication after listening to The American Scandal Podcast about Ruby Ridge.

Humans feel more than they think.

Humans want to feel safe. Groups make humans feel safe. Humans feel the need to be members of a group.

Adolescent weirdness is part of this. Children have familial feelings, teens less-so. But everyone needs to be part of a group.

Humans join groups and then find adjacent groups. Viewers also watched.

Groups form worldviews.

Group members communicate well. Information is less idiosyncratic. Time is more. Quality forms from shared experiences.

Group to group collaboration requires more energy than group to individual or individual to individual. There’s more “mass”. If you want to go fast, go alone. If you want to go far, go together. Groups are slow, but powerful.

Some of the groups involved at Ruby Ridge: white nationalists, the FBI, Federal Marshals, the United States government, the Weaver family (and extended family), Idaho neighbors, a hostage rescue team, the media, the legal system.

The Ruby Ridge story was a tragedy. It was a mess because of poor communication and unappreciated group dynamics. I’d forgotten the explosiveness of that time (Ruby Ridge ’92, Waco ’93, Oklahoma City ’95).

The American Scandal podcast ends with an episode about the threads of Ruby Ridge to current politics. That part felt less convincing that the narrative story. But in the summer of America’s semiquincentennial, I hope you find peace and joy.

Ruby Ridge: Part 1, Communication

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These are ideas about communication after listening to The American Scandal Podcast about Ruby Ridge.

Trust and information make up communication. 

Trust is the combination of quality and time. Quality is the depth of common experiences. Time is the lengths of common experiences. Relationships with frequent and deep experiences are strongest. 

Information is idiosyncratic. People overlap in their understandings – to some extent. It’s difficult to convey “information” about black swans to someone who has only seen white swans. 

Obstacles to communication. 

  1. Time: quantity is its own quality. 
  2. Quality: be vulnerable, deflate the ego, collaborate, be meaningful. 
  3. Information: everyone is a Bayesian, but we all have different priors, observations, and probabilities. 

Communication enablers. 

  1. Speed: slow down and increase time, allow quality, and refine information. 
  2. Gather their information: what assumptions have they made? 
  3. Walk in their shoes: what direction does this information lead? 

“Consumer profile” is a business-speak analogy. The less overlap with the groups communicating the more energy has to be put in the system. 

Three things from three years ago

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In early June 2023 these are the top stories and ideas floating around. Let’s see how important they are in three years.

  • “UFO Whistleblower”
  • Apple Vision headset
  • AI (LLM) development

If you were a technology optimist in the 1950s you may have predicted that practical storage would become 1,000 times larger. Maybe 10,000 times larger, if you were swinging for the fences. Few would have said “30 million times larger within my lifetime.” But that’s what happened.

The Psychology of Money

What’s it like teaching high school?

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Our school ends Memorial Day weekend, and aside from having a high school graduate!, it’s a calmer time. Tests are done and preps can wait.

But there’s an apt analogy for what it’s like teaching high school and it’s AI.

Teaching high school is like working with a different AI model each day. It might be a good one and it might by gobbledygook. This also depends on the person.

I stand at the front of the room, next to their desk, and online via Google Classroom and I make a request: Please read this article (sometimes it’s only blog posts from here) and write three sentences about what you learned.

Three sentences! Well, the AI never complains about that.

Often the work is okay to great – just like AI. Sometimes it’s nonsensical. Just like AI.

Early on, teaching felt overwhelming because I tried to do too much. It’s like parenting in that sense, only you have 120 kids. Jim Gaffigan has a good joke about this: what’s it like having a fourth kid? Imagine you’re treading water and someone hands you a baby. Students aren’t your kids, but they’re also not not your kids. I’ve hugged crying kids, fed hungry kids, listened, counseled, and encouraged. Kids are messy too.

Teaching got easier when I simplified my goals: pass the state exam, build relationships, be safe. If I’m working towards two or three of those things at any given time then we are making progress.

Teaching is a good situation to see the adage that people overestimate what they can get done in a day and underestimate what they can get done in a year. The kids change so much. It may not always be in the way I hoped – but it’s often in the way they need.

Have a great summer.

Full Hearts

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My biggest takeaway from Morgan Housel’s The Art of Spending Money was to have a rich camera roll. I want my wealth represented by the photos I take of the experiences and people in my life.

But life is busy.

Before writing this post, I spent 15 minutes updating my daughters’ and my family calendars through the next three months: high school volleyball, college orientation, college move-in, work dates, doctor dates, date dates.

To make life less busy, I track good moments. Using the year-at-a-glance calendar, I make a heart on days when something good happened. Often it’s small things: funny movies, coffee dates, just hanging out. If a few days have gone by with no pink hearts, then I know it’s time to make some plans and have some good moments.

My moments are fleeting.

In two-weeks my 16 year old sits for her driving test. In seventy-nine days my 18 year old moves into her college dorm. Just last week, she graduated high school.

Man, it goes fast. It flies by. So take today, and fill your heart.

Stop counting pushups

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I was never good at push-ups. But good is subjective. If the pool of push-up people is small enough, I’m the best, and if it’s large enough, I am not.

Better is better. Better shows progress, and that’s what life is really about. Progress, walking your path, stumbling, succeeding, and meeting people along your journey.

I did pushups wrong. I counted push-ups, not minutes. I was thinking about the wrong number.

in my class, we do an accountability partner assignment. Students choose two areas to improve, and an accountability partner for each one. I offer – if needed -to be their accountability partner.

One student, Aaron, wanted to do 100 push-ups a day. I was his accountability partner.

This was too many for me. But it was because I was doing 100. If I change the metric to minutes of push push-ups per day, it became more achievable.

Set a timer for one minute. Do as many push-ups as possible. When not doing Push-ups just be in the push-up position with arms extended.

That’s it!

My guess for the effect is ambiguity and familiarity. How many sets? How long will this take? Do I have time for this?

Nothing in my life is denominated in number of push-ups. There’s no context. But minutes, I’ve got minutes everywhere.

Where else could this work?

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.