31 Lessons from 31 Years

Let’s get the lame stuff out of the way. I turn 31 on Monday. Yippee!

Last year, I wrote about the amazing growth that can occur in a single decade. Here’s that article: A Lot Can Change in Ten Years.

But for this 31st birthday, I went back and considered 31 valuable lessons that coincide with each year of my life. Some are specific to personal finance and investing, while others are general. Here we go…

1) It’s Tough Being Helpless

I, like you, was a helpless little butterball. Thankfully, human parents make huge sacrifices to help their helpless kids (thanks mom and dad!). Thank your parents 🙂

But that courtesy ends at some point. Eventually, you’ve got to learn to help yourself.

2) Be Nice to Bigger Fish

I was the youngest of three boys. If I didn’t play nice with my brothers, I might get shoved down in the snow.

The same thing happens in adulthood, but the shove and the snow look a little different.

3) Eat Cake!

There’s a photo of my 2nd (or maybe 3rd) birthday where I’m eating sour cream coffee cake. It’s still my favorite dessert.

Life is better with cake. Or whatever your version of cake might be. If we can’t eat cake, then what’s this all about?

4) Play Games

Some of my earliest memories at home involve playing games—rummy, Parcheesi, Magic: The Gathering—with my parents or brothers.

Turns out that real life, too, involves a little bit of math, strategy, luck, skill, politics, memory, pattern recognition, etc.

Games are more than just games.

5) Some People Want to Watch the World Burn

In kindergarten, Eric (still one of my best friends) and I built a sick tower out of foam blocks. And then Robert came over with zero hesitation and kicked the tower.

Our creation was strewn about the carpeted floor. Our 12 minutes of work turned to rubble,

The world has no shortage of Roberts. Good lesson to learn early.

6) Helping is Fun

1st-grade involved forays into arithmetic. It came easily to me. P.S. 6-year olds don’t “outwork” other 6-years olds to get good at multiplication…it’s just the luck of the draw.

But I also learned in first grade that I liked helping people understand their multiplication.

Helping people is fun.

7) Don’t Compound Your Negatives

Embarrassed about I-don’t-remember-what, I threw a kickball (in anger!) at my gym teacher when she tried to console me. Sorry Mrs. Markowski!

Teachers, it turns out, disapprove of students hurling kickballs at them. I compounded one small negative with a much larger one.

Don’t let your negatives compound.

8) Failure Happens

I was a good student, so getting a C on a math test in 3rd-grade was devastating. I did not have the tools to deal with (what I deemed) a massive failure.

It’s a good lesson to learn early. It’s certainly a lesson you’ll learn often. Failure happens. Dealing with failure is an amazing skill. I’m still practicing.

9) Some Things Aren’t Worth Learning

In the 1990s (and maybe still today), New York’s 4th-graders spend a month of Social Studies lessons learning about the architectural aspects of Iroquois longhouses.

Anthropology is important. Understanding other cultures is vital.

But I shudder when comparing the millions of people-hours (not an exaggeration) spent on Iroquois longhouses versus the utility of that knowledge in our lives today. Thatched roofs aren’t that important.

10) The Eye of the Beholder

During one of Mr. Gill’s entertaining 5th-grade science lessons, I yawned right in front of him. To me, it was a simple, innocent yawn. I was tired!

But when I saw Mr. Gill’s reaction, I immediately knew I had done something wrong. I paused, retraced my previous five seconds, and realized,

“Oh no. Oh no. Mr. Gill interpreted my yawn as disrespect. That I was openly and rudely signaling boredom.”

I quickly apologized and assured him I meant no harm. And thankfully, he saw my sincerity.

What an amazing lesson. Intentions matter, but so does the way our intentions are interpreted. And sincere apologies matter too.

11) Black Swans

Mr. Leone’s 6th-grade social studies classroom. That’s where I was when we turned on the TV to see the Twin Towers fall on September 11, 2001. Where were you?

Some events are unforeseen, unpredictable, and yet have colossal consequences. These are black swans.

12) First Impressions are Just Impressions

We had a new kid at school who was so cool. Within a couple days, he felt like an old friend.

And within a month, he turned out to be a real dick. Oops.

First impressions can fool you.

13) Strict is OK

Our 8th-grade math teacher—Mrs. Sweet—had a reputation for being strict. Yes, reader, it is ironic that Mrs. Sweet did not have a sweet reputation.

But she was the best math teacher I ever had. Learning algebra from her was so easy. Maybe because we were all scared to death about goofing off.

Hey, it worked! Strict = structure, and many humans need structure.

14) We Live Different Stories

In 9th-grade English, one of my classmates got into an argument with the teacher. He (the student) was sent to the principal’s office for punishment. Instead of complying, he opened up the classroom window, hopped out, and walked to the local diner.

At the time, I could never imagine doing this. But that’s because he and I lived different lives.

To him, the point of school—this lesson, this assignment, this discipline—wasn’t worth understanding. Looking back now, I get it. I understand (at least a little bit) his point of view.

Different lives, different lenses. Same world, different perceptions.

15) Work > Talent

I played basketball my entire childhood. I felt I was a shoo-in to be a starting guard on the junior-varsity basketball team in my freshman year.

Nope.

While my skills were there, I was chubby and slow. Even for small-school JV basketball, I didn’t have the athleticism to make an impact on the court. I was a liability.

That summer, I worked on my game and pushed to get faster. A ~4-inch growth spurt helped too.

As a sophomore, I started at point guard on our varsity team.

16) You Control the Pace

Basketball was great fun, but I was most at home on the pitching mound in baseball. And all good pitchers know this lesson (thanks, Dad!):

The pitcher controls the pace of the game.

If you feel rushed, step off the mound and re-group. If you’re in flow, then get set and force the batter to step up to the plate. Nobody can push you to go faster or slower than you want to.

Life doesn’t always allow you to control the pace. But it usually does, and it’s your life. Don’t let other people set your pace for you.

17) Once in a Lifetime

Despite my basketball and baseball stories, Red Creek was a soccer school. We had a Hall of Fame coach and great players, winning three New York state titles in 4 years around my graduation.

I didn’t play during my junior and senior years. Why? Because I would have sat on the bench all season. I spent my autumn working on basketball and baseball instead.

But I missed opportunities to hang out with friends, play for a great coach, and sit through rainy Fall nights on hard aluminum benches, watching my teammates push towards a state title.

In retrospect, I should have played. I missed that once in a lifetime chance.

Instead, I got a life lesson: take advantage of your precious opportunities.

18) The Wide World

Leaving little Red Creek to head to the “big” city of Rochester and the truly international University of Rochester was a life-changing choice.

Go see the world!

19) Life is Delicate

January 2010: In our intramural basketball championship game, I watched my teammate Jeff soar through the air and throw down an NBA-style putback dunk.

January 2011: Jeff got in a fight at a fraternity house, was stabbed in the chest, stumbled outside, and died in the delicate Rochester snow.

Life, too, is delicate.

20) Just Try It

At the end of my sophomore year at Rochester, I picked up a squash racket for the first time. Now 12 years later, I’m still playing squash 3-4 times a week.

Trying new things can change your life.

21) Message vs. Messenger

Great content from a good teacher is a home run. We all know that. A good teacher can also turn bad content into a useful lesson.

But a bad teacher can turn good content into a dull lesson. You might miss important lessons because the teacher was bad (not the lesson itself).

It’s all-too-easy to confuse the messenger for the message. The better you are at separating the two, the more you’ll learn.

22) “Holding Onto Anger…”

“…is like grasping a hot coal with the intent of throwing it at someone else; you are the one who gets burned.” –Buddha.

Thanks, Buddha. Great point. Have I mentioned my sports background? My competitive nature has led to plenty of on-court anger. I’m still faulty, still trying to improve.

And 99.9% of the time, I’ve been burning myself.

23) Tough Conversations are Tough (But Vital)

When I look at my failed relationships—platonic or romantic—one common denominator is my hesitation (or inability) to have “tough” conversations.

My alternative usually involves a form of bottle-’til-you-burst. That bottling-up of emotions is much, much worse than having the tough conversation in the first place.

24) Know When to Quit

I quit studying plasma physics in grad school because it was too complex for my Newtonian monkey brain. I quit my Ph.D. program because the publish-or-perish lifestyle didn’t interest me. I quit two jobs that weren’t working out.

Quitting is hard. You might regret it (but probably not). If your gut and brain both think it’s right, then it’s probably right.

25) So Many Fish, So Much Noise

The sheer number of people in the world still catches me off-guard. So many experts. So many opinions. So many thought-leaders and pundits.

My biggest hesitancy behind the Best Interest is the nagging question, “Am I just another armchair expert who is adding more noise than signal?”

I continue this work because I believe I’m providing signal, and you readers frequently say as much. But it’s an important lesson nonetheless. In this chaotic global ocean, we should all strive to output more signal, less noise.

26) Surround Yourself With Smart People

“You are the average of the five people you spend the most time with.”

“If you’re the smartest person in the room…then find a different room.”

This is so cliché. But it’s also true. Two quick anecdotes.

1. I work with a bunch of satellite engineers. Learning from smart people is fun.
2. I’m proud of the way my friend groups have succeeded in life, and I absolutely attribute it to our ability to inspire one another and grow with one another.

27) “This is Water”

No description here. Just an amazing video that helps me during quarter-life crises.

I highly recommend you listen to it during you next media-consumption session.

https://www.youtube.com/watch?v=DCbGM4mqEVw

28) There’s Not Enough Time

We’d all love to have 30-hour days. Same sleep schedule, but give me six (or more) extra daytime hours.

But that’s fantasy land. In this world, we’ve got to make life work with only 24 hours a day. That means we have to “kill our darlings” or say no to things that we enjoy.

My two cents? Develop a bimodal mindset.

29) Write More

Self-bias here. Writing makes you better.

Whether it’s journaling, a diary, a blog, a book, a newsletter, an email to your friends…writing is good for you.

30) Be Nice. Give Compliments.

I am far from a social maven. But I do have “this one trick!” that I lean on. Socializing is easy when I use it and hard when I don’t.

The trick is 1) be nice and 2) give compliments. The trick-within-the-trick is that you have to be genuinely nice and give genuine compliments. Don’t bullshit people. They’ll know.

If people associate you with positivity, happiness, kindness, generosity, etc…then the world will open up for you.

31) Listen to Your Partner

Kelly knew that I’d enjoy fostering dogs before I knew it. I pushed back against the idea. And now, of course, I love having dogs in our house.

Kelly was right. I should have listened. I’ll be better!

Thanks for reading, guys. I’ll probably turn this into podcast form, too (check out the Best Interest Podcast!).

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