The Painful Gift

My wife and I are anxiously awaiting the arrival of twins this spring. I’ll be honest – I don’t have a clue what’s in store for me.

And how could I? Sure, I’ve read the books, done the baby classes, built the crib, and installed the car-seats, but knowledge and experience are two different things. Right now, I’m the source of a good hearty laugh for weathered parents who know what’s ahead.

As a soon-to-be parent, I find myself wondering what they’ll look like, who they’ll be, and what their life will be like…and dare I wonder…will they want to play sports?

I hope they do. Ok, I REALLY want them to.

But maybe for a different reason than what you might think. Yeah, teamwork, discipline, hard work, pushing past your limits – all that stuff is excellent and sports are a great facilitator of those lessons.

But what I’m most looking forward to might be unpopular.

I’m looking forward to them losing.

For every glorious come-from-behind-victory or tear-jerking championship run, there’s always the other side: the loser.

Winning is glorious, but I want my kids to understand the brutal lessons sports dish out:

  • Someone’s always better than you
  • Hard work doesn’t always pay off
  • Injuries are random and keep you from playing
  • Team bonds are broken as you grow up or graduate
  • Sometimes things just don’t go your way – for no good reason

These lessons are painful to go through. Losing may seem like the worst thing that can happen, and how it should be the end of everything, but the world turns and life goes on. It doesn’t wait for you.

So you learn to come back to the gym the next day and get after it. You learn grit, and you learn that losing won’t stop you.

That might be even better than winning.


I was sitting in a packed conference in NYC in 2017 listening to the ever-witty Josh Brown interview my all-time favorite finance writer, Jason Zweig of the Wall Street Journal. They were talking about Bitcoin (remember Bitcoin?!) back when it was all the rage and some people were making tons of money for having these digital tokens.

Zweig said something that has stuck with me ever since. He talked about winning with Bitcoin and winning big. I’ll paraphrase what he told the crowded room:

There’s nothing more poisonous to an investor than making massive amounts of money in a short amount of time.

Unchecked winning can be a curse. You think you’re brilliant and your ego leads you to continue playing – but then your luck runs out when you’ve bet everything. Or it can make you crazy because you become so fearful of every little event that could be your downfall. James Clear calls this the ‘The Shadow Side of Greatness.’

A good investor knows losing money begets making money. This tweet from Morgan Housel shows the returns earned for each decade and the losses experienced during those time frames in order to earn those returns:

Losing is the investor’s best friend. The friend that keeps it real with you by pointing out your blind spots and keeping your ego in check, so that you can become a better person.


Last night, the Virginia men’s basketball team won the NCAA championship a year after falling in the first round to UMBC. The loss last year was the first time ever a #1 seed lost to a #16. Virginia coach Tony Bennett called their loss to UMBC ‘The Painful Gift.’

Painful as it was, Virginia showed us all the gift of losing. I’d argue they were already a big success by getting after it and having a great season this year. But they ended up winning the whole thing, which makes for a great bow on top of this story.

In a world where parents are robbing their children of adulthood, I will look forward to the day when the kids take their first hard loss. Life will go on, you’ll get back up, and dad will still take you out for ice-cream.


Now here’s what I’m reading/listening to:

The 7 minute rule (Against the Rules – Michael Lewis)
The shadow side of greatness (James Clear)
James Harden needs 1.16 points (WSJ)
Benign myths in financial advice (Bps And Pieces)
Jimmy Butler: I will beat Kevin Hart with my left hand (YouTube)
How wealth changes you (The Cut)
How to pass CFA level 1 (Alpha Architect)
Jordy Nelson and the back-shoulder fade (ESPN)

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