The Dog That Caught the Car

What Comes After Enough?

Last post, I took a break from the physician-leadership series because my family apparently decided to spend the summer evaluating whether bones are better broken or not.

My wife broke her foot. My son broke his pitching arm. My daughter and I went to blues camp anyway, finally performed together after five years of talking about doing it, and somewhere in the middle of all that I found myself flying across the country on a same-day ticket, buying a chest freezer, and filling it with enough food to keep a one-armed college student alive through the beginning of his semester.

There’s a Fugitive joke in here somewhere. I just don’t have the energy.

The thing that struck me was not the orthopedic absurdity. It was how much of the chaos was manageable because of things that had been built years before anyone knew we would need them.

That observation collided rather neatly with another conversation my wife and I had already been having about retirement, money, and what decades of discipline are actually supposed to buy you.

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The Dog Catches the Car

When I retired from the Army four years ago, people kept asking what I was going to do next. This is apparently as mandatory when someone retires from the military as the retiree growing facial hair.

Twenty-four years in uniform. Pandemic. Clinical work. Research. Leadership. Organizational shenanigans that I have neither the time nor blood-pressure medication to revisit here.

So what’s next?

My smartass answer: build Legos.

I hadn’t had the personal freedom to actually do the snarky thing that jumped into my head to say ( Some have accused me of using sarcasm as my love language). Once I did have that freedom, there was something clarifying about it. After two decades working to create some degree of financial flexibility and professional optionality, I actually had some.

It is the proverbial dog that caught the car.

Now what?

In my case, part of the answer turned out to be music. Blues camp with my daughter was literally the first thing I did after becoming a civilian. I started playing more seriously, went to a couple of midlife-crisis guitar fantasy camps, met people I had listened to for decades, and met working musicians who were spectacular teachers and eventually became my private instructors.

Somewhere along the way, the guy whose best friend once described his backup vocals as so out of tune that they “actually worked as harmony” started singing in front of people.

For the record, they only worked as harmony in the way that whatever the hell Yoko Ono did onstage with Lennon and Chuck Berry worked as art.

My friend was being charitable; so stipulated.

Now I’m calling songs at blues jams, performing with my daughter, traveling to Italy for music workshops, and wondering whether music will occupy a much larger part of my life whenever I finally transition out of clinical medicine.

That transition is becoming less theoretical because my wife and I have also started seriously talking about her retirement. We aren’t starting with the financial aspect. Here’s our jumping-off point:

What do I want my life to look like when work stops organizing it?

For years I’ve joked that in retirement I intend to become my wife’s Italian hot-tub boy. We don’t have a pool, so Latin pool boy was unavailable. She rolled with my smart-assery and countered that she intends to become Henrietta, the Welsh gardener.

Yeah, I married up.

The more serious version came up while we were looking at retirement budgets. What does she actually want?

Her answer was remarkably simple. She wants to be able to see each of our kids, wherever they are living, at least twice a year. In addition to that, she wants us to be able to take a handful of trips each year. Maybe a cabin somewhere nearby. Maybe Vegas for a weekend. Maybe Hawaii. Maybe Europe. She wants to channel her inner gardener, putter around in her greenhouse, do some land and hardscape projects, and take up painting, photography, or whatever other artistic endeavor grabs her.

Most importantly, she does not want to sweat it.

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What Are We Optimizing For?

I’m sure many of you who have contemplated retirement have had similar arguments with AI as I did while looking at the numbers underlying our retirement plan.

Do we need a financial advisor? What does a Monte Carlo simulation look like for the portfolio? What is the optimized rate of return?

All useful questions.

But the more interesting one became: what exactly are we optimizing for?

The financial analysis, the advisor, the Monte Carlo software are not a waste. If all that “squeeze” produces sufficient “juice” and gets you to your goal, fabulous.

My point is: don’t skip the part where you define the goal.

There are a lot of ways to look at this. Die With Zero. Your Money or Your Life. Mr. Money Mustache and the FIRE community. I might not like all of their answers about what constitutes “enough,” but huge respect to all of them for ASKING THE DAMN QUESTION.

That feels strange because so much of early adult life runs in the opposite direction. We don’t contemplate “enough” because we are pre-wired to focus on “more.”

I have written before about how people resist things that are simple but difficult and instead become enamored with things that are complicated but appear easy. Finance is fertile ground for this.

Earn money, spend less than you earn, invest the difference, don’t panic when markets fall, and keep doing it for twenty or thirty years.

This is not intellectually difficult.

It is behaviorally difficult as hell.

There is no hack. No options-trading system. No AI agent. No secret portfolio that turns you from twenty-eight and irritated that you are not rich yet into independently wealthy by next Thursday.

To quote Ryan Reynolds in The Hitman’s Bodyguard: boring is best.

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The Four-Hour Workweek Comes After the Work

Which is why the story people tell themselves about Tim Ferriss and The Four-Hour Workweek has always amused me.

People see the endpoint: four hours, automation, employees making decisions without bothering you, you and your copy of Vagabonding sitting somewhere rustic checking email between adult beverages of choice.

Except that is not what made the system possible.

Ferriss had already spent an enormous amount of time running the business. He dealt with customers, answered questions, made decisions, screwed things up, fixed them, and lived through enough versions of “What would I do if this happened?” that eventually he could write down the answer and give somebody else a rule.

You cannot automate judgment you have not developed.

The four-hour system was not a substitute for all the work. It was built from the work. Being an incredibly engaged and disciplined entrepreneur enabled him to write the ultimate “success as a slacker” book.

Discipline enables being a slacker?

That sounds like a paradox.

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Costco Chicken Economics

My son is near the beginning of one of these paradoxical processes.

His current financial insight is that a Costco rotisserie chicken may be one of the greatest investments available to a twenty-year-old college student.

He is not wrong.

Five bucks. Multiple meals. Minimal effort.

Compare that with spending thirty-five dollars because Uber Eats will transport one dinner from a restaurant four miles away.

There are times when convenience is worth paying for. There are also times when paying seven times as much because you do not feel like driving to Costco is fucking stupid.

Part of my son’s financial job right now is learning the difference. He saves. He invests. He feeds himself cheaply. Then, when he and his girlfriend both have time off, he can take her somewhere nice for dinner and enjoy the experience without pretending every dollar spent is a moral failure.

Thrift enables luxury?

Sounds paradoxical.

Delayed gratification enables gratification?

That seems less paradoxical. You are supposed to eventually get gratified.

I am thirty years ahead of him, and interestingly, I still buy Costco chickens.

When I travel for clinical shifts, I work twelve hours, go back to the hotel, sleep, wake up, eat something, sleep again, and go back to work. I do not need haute cuisine. Don’t get me wrong, I can now hear someone say “pommes frites” and not roll my eyes when I know damn well they are bringing me some kick-ass French fries.

But on a clinical week? I need enough decent food in my pie hole to make it through the next shift.

A chicken. A bag of greens. Some cereal. A protein shake. A hotel breakfast buffet that includes powdered eggs.

It’s a military thing. We just get used to stuff.

Done.

The difference is that thirty years of making decisions like that means when my son breaks his arm three thousand miles away, I do not have to give the furry crack of a rat’s behind what the plane ticket costs.

I buy it.

Those two decisions are not inconsistent.

They are the point.

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Delayed Gratification Still Includes Gratification

Earlier this summer I listened to Die With Zero while my wife and I were thinking about retirement. There are parts of the book I found genuinely useful, and there are parts where I found myself wondering what the hell the author was talking about.

One example describes someone borrowing money from a loan shark to take a trip to Europe and treats that as a wonderful example of prioritizing life experience.

Dude…I have questions.

If your vacation-financing strategy includes the non-zero possibility that someone named Ratso breaks your legs because you cannot repay the debt, I am not entirely sure we have discovered the optimal path toward human flourishing.

Immediate gratification is not automatically wisdom. Heroin is also immediate gratification. Jogging requires considerably more effort before the endorphins show up. That does not make heroin the superior wellness strategy.

But the book is right about something important. Experiences have timing.

There are things you can do at thirty that you may not be able to do at eighty. There are trips your children can take with you now that may make no sense twenty years later. There are opportunities to help people you love while you are alive rather than maximizing the size of an estate they inherit after you are dead.

My wife and I have done some of this almost accidentally. We set aside substantial money for our children’s education because we would rather watch them begin adult life without student debt than congratulate ourselves for leaving them a larger inheritance decades later. We have traveled while working. We have gone to ball games, hockey practices, recitals, birthdays, school events.

We worked hard too.

Those things were not mutually exclusive.

Now we are reaching a stage where the balance is shifting again.

We have gone to Italy for music workshops. I am going back. We are meeting people at similar stages of life who can trek to Tuscany, play Beatles songs with people they met the year before, bring their spouses, make friends, eat ridiculous amounts of good food, and not spend the entire week worrying about whether they have committed an act of financial irresponsibility.

When my wife and I reflexively wonder whether this is a responsible expenditure, the response comes in the form of a question:

Why the hell did we work this hard if it isn’t?

Which makes us sound terribly frivolous.

Except we still look for a good deal. One workshop offered to lock in the prior year’s price if we prepaid for two future sessions.

Don’t threaten me with a good time.

Apparently discipline enables frivolity.

There’s another paradox.

Maybe “frivolity” is not quite right.

Discipline enables optionality, flexibility, and choice.

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When the Habit Works Too Well

It lets me look at a $1,200 same-day plane ticket and say, “My son needs me,” without turning the decision into a financial summit. It lets my wife imagine a retirement where she never has to worry about whether she can afford to fly across the country to see one of our children. It lets me tell someone helping with my business, “I’m offline for two weeks because my son broke his arm,” and then actually disappear.

The business is supposed to enable the life.

The life is not supposed to enable the business.

The same thing increasingly applies to clinical medicine. I still love it, and it still produces income. As long as one or both of those things remain true, I may continue.

If someday it is not financially necessary and I do not enjoy it anymore, then why exactly would I continue?

Habit? Identity? Because I spent decades becoming good at it?

At some point, that is just another dog staring at the car it caught.

This is where successful discipline creates a strange new problem. The habits work. Saving becomes automatic. Working becomes normal. Delaying gratification becomes admirable.

Then one day you have enough, and the psychological machinery does not necessarily receive a software update informing you that the objective changed.

I have seen people who have saved for decades remain deeply uncomfortable spending even when their resources are more than adequate for the lives they want. At the other extreme, I have seen people save for a few weeks, notice that they are not yet wealthy, and decide the whole exercise is pointless.

Both lose track of what the behavior was supposed to accomplish.

Neither accumulation nor spending for its own sake qualifies as a bona fide purpose.

The purpose comes first.

For my wife, part of the purpose is uncomplicated access to our kids.

For me, apparently, it involves guitars, family, travel, teaching, writing, some amount of medicine, and occasionally building Legos.

Inevitably, your mileage may vary. And while I am rooting for you to get wherever you want to get, professionally, personally, financially, whatever-ly, eventually you will face the same dilemma:

Now what?

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Back to Our Previously Scheduled Programming

That question is also where this two-week detour from physician leadership ends.

But the detour was worth taking.

Because if leadership, mentoring, judgment, and development are supposed to help us live better rather than merely work better, occasionally it is useful to look up from the professional conversation and ask whether the life all that effort was supposed to support is actually getting lived.

The ironic part is that this entire departure sets up where I was headed next in the physician-leadership series anyway.

You got that leadership position. How’s that working for your identity?

And ultimately: do we need physician leaders, or leaders at all for that matter?

Apparently the dog caught another car.