Anticipated Joy vs. Anticipated Regret

Last year I was pounding the table on The Bear (Hulu/FX) as one of my new favorite shows. I liked it so much I didn’t really know how a second season would go.

I finished season 2 this week and it’s not hyperbole to say it was one of my favorite seasons of any TV show I’ve ever watched. It blew me away how good it was.

It reminded me I actually wrote a post last year using one of my favorite scenes with Carmy and Richie waxing philosophical about life. And since it’s a holiday week I figured it would be a good time to re-up that post.



Frank Rabinovich was a portfolio manager and technology specialist at bond giant PIMCO in the 1990s.

The way his colleagues treated him was a microcosm of the culture at the firm in its heyday.

Co-workers would douse him with bug spray, claiming he smelled bad. They cut off the bottom of his ties when they didn’t like the look of them. They tackled him relentlessly in games of touch football since he wasn’t as athletic as the other employees.

One of the reasons PIMCO became a behemoth in the asset management world is because the culture was so aggressive. But that aggressive nature made for a difficult place to work.

Employees would regularly get nasty emails from their bosses at all hours of the day. People slept in their cars because they worked such long hours and rarely saw their families. There was political in-fighting and disrespect from colleagues.

The trade-off for all of that hard work and general unpleasantness was huge paychecks.

But those paychecks often came with an enormous cost attached to them.

Mary Childs recounts the story of former PIMCO CEO Mohamed El-Erian in her book The Bond King:

Mohamed El-Erian asked his ten-year-old daughter to brush her teeth. She ignored him. He said it again. Still she ignored him. He sighed.

It was not so long ago she would have immediately responded, he reminded her, and he wouldn’t have to ask multiple times; she would have known from his tone of voice that he was serious.

“Wait a minute she said,” and disappeared into her room. She emerged holding a piece of paper, a list she had compiled, of twenty-two important life events and activities of hers that her father had missed because he’d been working; her first day of school, her first soccer match of the year, a parent-teacher meeting, a Halloween parade.

“Talk about a wake-up call,” El-Erian said later.

Childs reported El-Erian had received a bonus of $230 million in 2013. That’s 230 with six more zeros tacked on.

What’s the point of having all of that money if you’re not going to enjoy it with the people you love? Why work so hard if it compromises the things that are truly important in life?

El-Erian later admitted, “My work-life balance had gotten out of whack, and the imbalance was hurting my very special relationship with my daughter. I was not making enough time for her.”

He would resign as CEO of PIMCO not long after that realization.

Life is strange in that there is no such thing as an equilibrium when it comes to the most important stuff.

Balance is required but always elusive.

A balanced portfolio means giving up some of the upside to protect the downside.

A balanced diet means occasionally eating some food you don’t like or foregoing some food you love.

Having a good work-life balance means sometimes you wish you were working harder and sometimes you wish you were spending more time with the people you love.

There are plenty of gurus and influencers out there these days that promise you can have it all.

Just follow these 10 simple steps.

Just read this one book and it will change your life.

Just read this thread I wrote on Twitter that solves all of life’s mysteries.

Just do what I did to become successful even though no two people on the planet share the same path.

I would love to share the secret to a happy life that’s perfectly calibrated. The truth is that there are no secrets to this stuff.

Plus you never really know if you’re taking a bigger risk by actually going out on a limb or being more defensive when it comes to life’s biggest decisions.

There’s a scene in my favorite new TV Show of 2022, The Bear (on Hulu), where cousins Carmy and Richie are waxing philosophically in the alley behind their family-owned Chicago restaurant while on a break.

I won’t spoil the show for those who haven’t watched it yet (seriously, you have to watch this one) but Carmy is working through a lot of personal, professional and family issues.

So he asks his cousin Richie, “Is there a name for that thing where you’re afraid of something good happening ’cause you think something bad’s gonna happen?”

Richie ponders this one for a second and then replies, “I don’t know…life.”

The psychological term for what Carmy was describing to Richie is anticipated regret.

There’s nothing wrong with being risk averse at times but if you’re always risk averse you’re going to miss out on life.

I think about this kind of thing a lot more these days when it comes to spending money.

From a young age I was always a saver. I never really enjoyed spending money on myself. I didn’t see the point.

I’m still a big saver but my views on spending have certainly evolved over time.

One of the hardest tightropes to walk in all of finance is finding that balance between spending money now and saving money for the future.

It becomes clearer to me every year that seeing my portfolio hit a certain number doesn’t bring me nearly as much joy as spending money on experiences.

Having kids and rounding third base to middle age has hammered this one home for me. I don’t want to die with a lot of money in the bank and no memories or hold off until I reach retirement age to enjoy myself.

Like most things in life, some trade-offs are required.

Investing itself is a form of regret minimization so I like to look at long-term savings as anticipated joy about how you’re going to spend those dollars in the future.

It’s important to save and invest because those savings can provide even more experiences as it compounds. Savings can provide a level of comfort and security so you don’t saddle your future self with unnecessary stress.

It’s also important to spend some money now on the things you love because time is precious. There’s no point in working for a paycheck if you don’t use that money to provide some enjoyment in life.

As long as you’re saving some money for the future you should also enjoy the present.

This post was originally published here on July 22, 2022.

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