From G.E. to GameStop, investors have a long history of following the herd right off the cliff

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No doubt you’re familiar with FOMO — the “fear of missing out.” It’s the angst we feel about being left out of the fun. It’s what drives us to go to social events we aren’t particularly interested in, because everyone else is going and we’re afraid of being the only loser sitting at home.

FOMO isn’t just a social phenomenon, though. I spent two decades as an investment manager, and I saw it time and again with individual investors. …

A story about Monty Python, Toad the Wet Sprocket, and the importance of shipping your work

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What do the legendary ’70s British comedy troupe Monty Python and the ’90s American rock band Toad the Wet Sprocket have in common? Weird names, for one. But how the latter got its weird name has a lot to do with the former. And it’s a great example of how, when we put creative work out into the world, we just never know how or when it’s going to inspire someone.

There was no shortage of strange band names in the 1990s — probably because the rockers in the prior decades took all the good ones. …

We all have imaginary “super-people” who threaten to destroy our confidence. Here’s how to take yours down.


“Comparison is the thief of joy.” — Theodore Roosevelt

I’m not what you’d call a natural-born exerciser. I’m a big guy, and I don’t run so much as I lumber. I don’t get “jazzed” to work out. You wouldn’t want to be next to me in your Cross Fit class, unless you like being next to a sweaty middle-aged dude who’s constantly asking you “how much longer?” I frequently procrastinate about exercising, even though I know it’s what I need to do.

When I’m feeling particularly down on myself about my poor exercise habits, my mind often goes to my…

The Beatles had it right: All you need is love

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My daughter is in college, and she told me something recently that really jarred me. “My friend and I were talking the other day,” she said, “and we realized we’re two of the few girls we know who have a good relationship with their fathers.”

It was one of those weird life moments where I felt happy and sad at the same time. Happy that I was one of those two dads. Sad that so many of her friends have no emotional connection with their fathers.

No doubt about it — parenting is hard. And the hardest part of all…

How to go from self-critic to self-coach

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I recently watched a 2018 Netflix special with David Letterman and Jerry Seinfeld in which the two legendary entertainers took turns interviewing each other on stage. What struck me most was how much the two differed in their approach to compliments: Seinfeld was gracious and appreciative whenever Letterman noted his incredible career success while Letterman rejected or downplayed any positive comment Seinfeld made about his career.

It came off more as self-loathing than modesty. “I should have left [the show] 10 years ago,” Letterman said at one point, “because then I could have taken some of that energy and focus…

Community doesn’t just happen — we have to make it happen

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When I decided to sell my company and start a new chapter in my life as a one-man show, I was excited. No more 8 a.m. staff meetings. No more deadlines set by others for projects I wasn’t particularly enthusiastic about. No more personnel problems to deal with.

As the saying goes, the world was my oyster. I would finally be free — free to focus only on the things that interested and inspired me. Free to learn new things and think new ideas and plot the course I, alone, wanted to take.

As another saying goes: It all looks…

Rewards are fun — but the fear of pain is what keeps you focused

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I have a freelance writing contract that requires me to deliver a newsletter of around 2,000 words to my client on the second Wednesday of every new calendar quarter. It’s a hard deadline; if I don’t deliver the newsletter, the company can’t bill their clients, which blows up their quarterly operations calendar and gets a lot of people pissed off. At me.

Some quarters, the work on this newsletter flows easily for me and I’m done well before the deadline. Other quarters, I struggle for ideas and direction; when that happens, I invariably procrastinate and wait until the last minute.

We’re not climbing a mountain; we’re navigating an expedition

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Thirty years ago, when I was in my mid-twenties, I remember going through goal-setting exercises. I read books and watched videos and did worksheets to help me determine what I wanted to accomplish in my life, personally and professionally. I was determined to get clear about my long-term goals and then, like Arnold Schwarzenegger, I was going to crush them. (Remember, it was 1991.)

Like most people, my big-picture goals were focused on the final destination — some hazy endpoint far-off in the distance where I would finally have all the things I wanted. …

Here’s how to silence the constant critic in your head

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The other day, I did one of those random acts of kindness for a stranger. I won’t go into specifics, because I don’t want to be that guy. I’ll just say it was nicer than holding the door for someone but not as nice as donating a kidney.

What was interesting to me, though, was the way my inner monologue played out afterward. When I got back in my car, I sat for a moment and enjoyed the warm, glowy feelings of doing something nice for a stranger. I thought, “Hey, that was a kind thing you did. Good job.”

New details are emerging about the tragic death of former Zappo’s CEO Tony Hsieh on November 27 from injuries he received in a house fire.

Recent articles in Forbes and…

Jack Calhoun

20+ years as managing principal of a wealth advisory firm. I write about the principles of sound investing, the solopreneur life and the wisdom of experience.

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