Friday Reflections: What Are We Optimizing For?

Happy Friday!

Here are a few thoughts, reflections, and musings from the week.

Intentional Living

Designing Summer.

The kids wrap up the school year next week, which means we're all getting ready for summer around here. Today's 97-degree high certainly helps set the mood.

This year we've got some good things planned and are hoping to make some great memories for ourselves and the kids.

I've got the opportunity to attend a couple of World Cup matches later this month with some friends. As soon as I get back, the family and I will fly up to Maine for a few days at my mom's place, followed by a week on a lake in a small rental cottage.

Hopefully we'll spend our days swimming, fishing, kayaking, reading, eating, chatting, and relaxing.

Then my wife will head home while the kids stay with Grandma for another two weeks. During that time I'll be working remotely from... somewhere. Friends' houses, coffee shops, maybe a library. I'll figure it out.

Later in the summer we'll head down to Hilton Head with my wife's family for nearly a week, and sprinkled throughout the season the kids will attend a few day camps while my wife and I continue working.

It's quite a bit of time away from work for me. And unlike many out there, for me, when I don't work, I don't get paid.

The consultant part of my brain notices that immediately.

But I keep reminding myself that this is exactly what I've spent years saving and investing for. Summers with young kids are finite. There will come a time when family vacations become harder to coordinate, when the kids would rather spend time with friends, and when opportunities like this become increasingly rare.

It's easy to say that family experiences are important. It's harder to prioritize them when they come with a real cost.

For me, intentional living means making those tradeoffs consciously.

I'm trying to maximize for time, experiences, and memories—not income.

And by that measure, it's shaping up to be a pretty good summer.

Financial Independence

Thinking about what's next.

I'm currently 48 and increasingly finding myself thinking about life after full-time work.

In some ways, I'd be happy to walk away tomorrow.

Work hasn't been particularly satisfying lately.

At the same time, I have to acknowledge that I have a pretty amazing setup. Good flexibility, decent pay, interesting projects from time to time, and a level of autonomy that many people would envy.

So why do I keep thinking about retirement?

One thing that gives me pause—and if I'm being honest, a little fear—is that I'm not entirely sure what I'd do with my time.

I know myself well enough to know that I won't be happy sitting around all day.

I need challenges.

I need projects.

I need opportunities to learn and grow.

Writing might become a bigger part of my life. Perhaps consulting on a smaller scale. Maybe taking classes, volunteering, mentoring, or even pursuing something completely different.

The funny thing is that I feel pressure to have the answer before making any decisions.

But maybe that's unrealistic.

Maybe retirement isn't something you plan perfectly in advance. Maybe it's something you discover through experimentation.

What I find myself returning to again and again is the realization that financial independence and retirement aren't actually the same thing.

Financial independence gives you options.

Retirement is just one of them.

For now, I don't have a clear answer. But perhaps that's okay.

The important thing is that I'm beginning to ask the question.

Health

Too many beers.

I went out with some friends last weekend and visited a fun rooftop beer garden near our home. The weather was perfect, there was a fun cover band, and the beer was delicious.

I had a lot of fun. Too much fun.

The next day I was not feeling well.

Of course, with two young kids, and a not so sympathetic wife, I still had to get up out of bed and do all the things.

It was a struggle all day.

I managed to take the kids to the pool for a bit, and we did some other things, but I definitely was not the best Dad that day.

Since then I've gone the last five days without a drink.

I guess that's not a real cause for celebration, but sometimes for me it is.

Between regular happy hours, night caps, and occasional binges - I do sometimes worry about my level of drinking.

As I get older, it affects me more and I want to be mindful.

During COVID my drinking got to be a little too much (in my opinion) and that led to me keeping a daily tally of how many drinks I have.

I try to keep the monthly average number to less than 2.

More recently I track the number of "dry days" per month as well, aiming for 15.

At the end of each month I tally up the stats and reflect on what was going on that made me drink more, or less, and how it impacted my life.

For me, it's another part of intentional living. One of the lessons I've learned as I've gotten older is that self-awareness matters more than rules. I'm not interested in never drinking. I'm interested in being honest with myself about when drinking is adding to my life and when it's subtracting from it. Tracking helps me do that.

Family

A Soccer Life.

We're gearing up for a 3v3 soccer tournament that my son is playing in this weekend. It looks like it's going to be HOT, but it should be fun.

He enjoys playing, and I have to admit, that I LOVE, watching him play. For the parents in the crowd, I imagine you can relate. There's just something about watching your flesh and blood out there on the field, competing, trying hard, and slowly getting better at something.

Recently, we wrote the check for another year of soccer. He's only seven years old, but because of his age and skill level, he's now moving into the club's "Juniors" program.

Or as I like to call it: the gateway drug to travel soccer.

It's funny because this isn't really where I expected things to go.

When we first signed him up, my goals were pretty simple. I wanted him to get some exercise, burn off a little boy energy, make some friends, and learn what it means to be part of a team.

That last one is probably still the most important to me.

I think sports can teach kids a tremendous amount about life. How to contribute to something bigger than themselves. How to deal with success and failure. How to persevere when things get difficult. How to support teammates and be supported by them.

When I think about what basketball has given me throughout my life, the list is long. Exercise. Stress relief. Fun. Friendships. A reason to get out of the house. A community.

I want those things for him too.

The challenge is that youth sports have a way of becoming more and more serious over time.

One team becomes two.

One practice becomes three.

Local games become travel tournaments.

Before long, entire weekends revolve around a sport.

It feels a bit like watching the first domino tip over and wondering where the chain reaction eventually ends.

The funny thing is that I never set out hoping to raise a travel soccer player. I simply wanted my son to enjoy sports and gain some of the benefits that come with them.

And that's what I'm wrestling with now.

At what point does a healthy activity begin demanding more from the family than it gives back?

Maybe that's the wrong question, though.

The purpose of youth sports isn't necessarily to create college athletes or future professionals. It's to help kids build confidence, friendships, resilience, discipline, and a lifelong appreciation for physical activity.

The challenge for parents is figuring out how much structure and commitment is enough to get those benefits without allowing the sport to consume family life.

I'm not sure where that line is yet.

For now, we'll continue taking it one season at a time and see where the journey leads.

And if ten years from now I'm sitting in a folding chair at some soccer showcase tournament halfway across the country, feel free to remind me that I once wrote this article.

Side Note: For others in the kids sports world, I'd highly recommend the book "Playing to Win" by Michael Lewis. It dives deep into the topic and is in my opinion, mandatory reading for anyone with kids who are serious about sports.

With the above in mind, I think I need to give it another read sometime soon..

Fun

Books, TV, and Video Games.

I finished The Almanack of Naval Ravikant this week and thoroughly enjoyed it.

The book is packed with short observations and insights, many of which I've found myself highlighting and revisiting. My Kindle now contains 56 highlights from the book, which is a very large number by my standards.

One of the reasons I enjoyed it so much is that Naval's ideas often challenge conventional thinking.

He talks frequently about leverage, independence, wealth creation, and designing a life on your own terms.

Not surprisingly, many of those themes resonate with me as I think about work, money, family, and the future.

One quote that particularly stuck with me was:

"Whenever you can in life, optimize for independence rather than pay."

I suspect that's one of those ideas I'll find myself returning to for years.

With my wife out of town this week, I also found myself spending a little more time than usual watching television after the kids went to bed. I finished Narcos: Mexico on Netflix and thought it was excellent.

One thing I appreciate about both Narcos series is how naturally they blend English and Spanish dialogue. Characters simply speak whichever language makes sense in the moment, which adds a level of realism that many shows lack.

Between books, TV, and a little Zelda with my son, it's been a pretty enjoyable week.

Not every form of entertainment has to be productive. Sometimes it's enough for it to simply be enjoyable.