"Oh, are you Rich But Sad?"

Getting unstuck from the cognitive dissonance of success and achievement

Oct 29, 2024

I once saw Alec Baldwin seated at Irving Roasters, a basement coffee shop in New York City.

Most people connect my name to him. Either him or, surprisingly, Alex Trebek, although you see it, right? Alex? An Alex is NEVER mistaken for an Alec. But “Alex” is the name that goes on my Starbucks cup 78% of the time. Otherwise, it's written as “Alik,” which I cannot comprehend.

Mr. Baldwin is no doubt the most famous Alec. There's no one even close.

There are so few of us, I figured I'd walk up to him and say hello in that cramped coffee shop, and we’d be instant best buddies/name brothers.

But he was having a pretty intense conversation with (what seemed like) an assistant. Actually, I'm shortchanging it. He was steaming mad. So I stepped past the land mine.

I don't like to approach celebrities unless I'm a legitimate fan and have an encouraging word to say. I never ask for a photo. I'm not trying to TAKE something from them. I want to GIVE.

That's my rule. My golden rule.

“Do unto celebrities what you would want done unto you.” (2 TMZ 4:11)

By Any Other Name…

The name Alec is quite rare; it's the 1978th most popular name in the United States.

How then, did I come to be named Alec?

Two readers here know the story quite well: my parents.

They went to see a little movie called Star Wars in 1977 when they were—er, one of them was—pregnant with me.

As the story goes, they saw the name “Alec” in the credits, and liked it.

That’s it? That’s it.

It supposedly had nothing to do with the actor or the role, but who are we kidding?

I was named after Alec Guinness, the actor who played Obi-Wan Kenobi.

I was named after a Jedi Master.

Or rather, I was named after the classically-trained English actor best remembered for playing a Jedi Master.

Here's the thing, though.

He hated the fame that came from Star Wars.

He bristled at the outlandish success he found later in life.

“The success of Star Wars is a bit of a surprise to me, and I remain somewhat bewildered by the phenomenon it became. I would never have imagined that after years of performing in Shakespearean roles and receiving accolades for serious films, I would be most remembered as a mystical Jedi Knight.”

Wait, what?

This ran deep. This wasn’t a gotcha sound bite from a bad day.

He doubled down in his two autobiographies:

“I am still astonished by the fervor with which people approach me about Star Wars. It is as if they have all found something deeply spiritual and profound in it. I have been asked to give blessings, to write out prayers as if I were some real-life holy man. It is absurd. And yet, this has become the reality of my life—constant bombardment by people who only know me as a character in a space opera. I can only conclude that the world has gone mad.”
“I couldn't believe the dialogue. It was unspeakable. I kept waiting for some deeper, more meaningful scene to emerge. It never did. After a few days, I went to George Lucas and said, ‘I can't go on with this. It’s rubbish.’ I asked him to kill me off—a quick and painless end to what I already saw as a lost cause. George thought I was joking, but I wasn’t. He eventually agreed to it, but I couldn’t bear the thought of continuing for three more movies.”
“Apart from the money, I regret having embarked on the film… I shrivel inside each time it is mentioned.”

Yikes. These aren't the good vibes you're looking for.

This guy, my namesake, DESPISED the very role that made him a worldwide celebrity.

He worked hard, trained, took chances, and led an actor's life... leading to massive, worldwide accolades.

Who among us wouldn't instantly sign up for such a life?

And yet his success—the result of that enviable life—left him not just unfulfilled, but discouraged. Frustrated. Burdened.

For anyone who loves Star Wars (especially those of us whose 80s childhoods were shaped by it), doesn't it cut deep to know the truth? That it wasn't Obi-Wan goading Darth Vader to "strike me down,” it was the actor begging George Lucas to "cut me out.”

And for the rest of his life, unsavory interactions with generations of fans left him pondering how he had stumbled upon such "good misfortune."

My Good Misfortune

I've spent my entire career making things. Conducting experiments. Posting things online (even back when the only "online" was American).

Psrshhhkkkkkkrrrrkdingkakingkakingtshchchchchchzzzzstdingdingding

I dabbled in lots of things: from Shakespeare to HTML, improv to branding, Photoshop to Final Draft.

These creative experiments—some successes, most not—led to something great: founding one of the first-ever social media advertising agencies with a longtime friend and business partner.

McBeard began as the "Mc" (me) and the "Beard" (Alan Beard), but quickly grew to a cast of hundreds, serving top-tier clients like Disney, Netflix, Coca-Cola, and AT&T.

It was an amazing success, and unexpectedly so. The work was fun. The business was profitable. The culture was kind. The hoodies were plentiful.

We were approached to sell McBeard a decade ago, and after a few months of negotiations, we said yes.

We announced the acquisition on May 4th, 2015 (May the Fourth! The irony!).

I had achieved the kind of success that, again, most people would instantly sign up for.

I am incredibly grateful for the luck—yes, hard work and shrewd decision-making and overcoming the risks of entrepreneurship—but ultimately, the fortunate timing and opportunities that led to this good thing.

I’ve said often that, given the chance, I would choose to sell again 10 times out of 10.

Like I say to my kids about tattoos:

It was the right timing, the right situation, the right acquirer.

It was—and continues to be—a life-changing moment in my life.

And yet.

And yet…

I have these lingering, unnamed, overwhelming negative feelings that stem from that decision, even a decade later.

Good Misfortune.

The success didn't solve any of the underlying issues in my life. My shortcomings didn’t get fixed. In fact, they were laid bare.

It's that adage about lottery winners: the money doesn't change them. It only amplifies what was already there.

It pours gasoline on the fire.

If you're greedy, you're about to be unbridled.

If you're bad with money, you're about to be everyone's sucker.

And if you're a people-pleaser who gets his self-worth from what he thinks others think of him…

…the success will throw you for a loop.

I wasn’t ready for it. How could I be? Whose template was I following? Who else did I know that could have warned me about this? Who else built a company from 2 to 150 people in three years and sold it?

I have many, many caring and well-meaning people in my life.

But I didn’t have someone who had done that.

And I didn’t have the words to even ask for what I didn’t know I lacked.

“Oh, Are You Rich But Sad?”

These days, I tell my friends that I'm going through a "very reasonable midlife crisis” (i.e., no new cars, no new wives).

But really, it's this.

It's the Alec Guinness-style cognitive dissonance of my good misfortune.

My inner monologue has said, “I have this success that I know I should be grateful for, but I have some underlying disappointments. Is it OK for me to have problems? No one wants to hear about my rich guy problems. I'll just stuff these down for a while. Maybe let’s drink those away for a while.”

For years, I worried that if someone heard that I had a problem with my outrageous success, they'd tell me to “wipe my tears away with some of that privilege.”

This fear was mostly unfounded… but occasionally confirmed.

I’ve been getting up on stage at storytelling shows like The Moth this year, and at one of them, I added a slip of paper into the pot, to be read by the emcee. The theme was “Surprising Turns,” and I anonymously wrote that “selling my company was both great and disappointing at the same time.” When the emcee read it, she laughed and mocked, “Oh, are you rich but sad? Is there someone here who’s rich but sad? I can help you out with one of those things… my bank account number is…”

Everyone laughed, but I shrank down to nothing, right there in my seat.

I didn’t want sympathy. I shouldn’t have sought it in that room. My mistake.

I don’t need sympathy here…

And yet.

How do I hold both gratitude and struggle at the same time?

I once heard a Ray Romano joke: “My wife doesn't like it when I use something from our fights on stage. But I tell her that if she doesn't like it, she can go cry into her big pile of money.”

I took this joke, stripped away the humor, and internalized it.

For too long.

I've been grappling with the idea that I got everything I wanted in my career, and it didn't fix anything. Didn't even come close.

Jim Carrey once said:

“I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it's not the answer.”

Can you believe this guy? What an ass! How dare he! It’s so TRITE for a rich man to say that. Especially one who once dreamt of achieving that very thing.

Ellen Degeneres opens her new Netflix special “For Your Approval” with this:

“You know, I used to say that I didn’t care what other people thought of me. I realize now, looking back, I said that at the height of my popularity.
If I look older than when you saw me last, it’s because I’m older than when you saw me last.
And also, I stopped doing Botox and filler.
Yeah. I used to do Botox back when I didn’t care what other people thought of me.”

Survival of the Bleakest

The more I dig into this idea, the more common I find it to be.

Here’s a video I recently recorded in the back of a driverless Waymo:

I just started reading a book called Strength to Strength, which is a “second half of life” type of book, which, on the one hand, I'm VERY into, but on the other, I don't like AT ALL… “You're old now!”

The OPENING CHAPTER of this repugnant but amazing but repugnant book is “Your Professional Decline is Coming (Much) Sooner Than You Think.”

Screw you, book!

Not me!

I'm the tagline of Fame!

(he reads on)

The opening story of this offensive book—and this devil chapter—is about Charles Darwin (yes, that one), who was (you guessed it) successful but unhappy (not my man Charlie D!).

In his last years, Darwin was still very famous—indeed, after his death he was buried as a national hero in Westminster Abbey—but he was increasingly unhappy about his life, seeing his work as unsatisfying, unsatisfactory, and unoriginal. “I have not the heart or strength at my age to begin any investigations lasting years, which is the only thing which I enjoy,” he confessed to a friend. “I have everything to make me happy and contented, but life has become very wearisome to me.”
Darwin was successful by the world's standards, washed up by his own. He knew that by all worldly rights, he had everything to make him “happy and contented” but confessed that his fame and fortune were now like eating straw. Only progress and new successes such as he enjoyed in his past work could cheer him up—and this was now beyond his abilities. So he was consigned to unhappiness in his decline. Darwin's melancholy did not abate, by all accounts, before he died at seventy-three.

“Consigned to unhappiness” ???

No way. He must have been weak! Talk about Darwinism in action!

Surely, he’s the only one.

The book continues:

I'd like to be able to tell you that Darwin's decline and unhappiness in old age were as rare as his achievements, but that's not true. In fact, Darwin's decline was completely normal, and right on schedule. And if you, like Darwin, have worked hard to be exceptional at what you do, you will almost certainly face a similar pattern of decline and disappointment—and it will come much, much sooner than you think.

Decline and Disappointment aren’t for me! Those are for the nerds who played the other D&D: Dungeons and Dragons.

In Good Company

With a small amount of research, I’ve found that the hits keep coming:

Kurt Cobain (Nirvana): “I never wanted to be the voice of a generation… It’s something that was thrust upon me.”

J.D. Salinger (Catcher in the Rye): “I’m known as much for my retreat from the world as for any book or story I’ve written.”

George Reeves (the original Superman from the 1950s): “It’s a bird, it’s a plane, it’s my grave.”

Mary Shelley (Frankenstein): “I have been judged all my life for that one creation, as if I did not have other thoughts, or creations beyond that story.”

John Montagu (the 4th Earl of Sandwich): “I invented it only to keep working, yet I am remembered more for a piece of bread and meat.” (I know I’m supposed to be sad for him, but this is legitimately hilarious)

Florence Nightingale (founder of modern nursing): “My greatest work was not in hospitals, but in the analysis of how we could prevent sickness.”

Eadweard Muybridge (who created the first motion picture): “I am more than a man who showed a horse in motion.”

Ray Kroc (McDonald's): “I was always looking for the next big idea, but people couldn’t see past McDonald’s.”

Howard Schultz (Starbucks): “I’ve built Starbucks, but I’m also a leader, an advocate for change. Yet, people can’t seem to see me outside of coffee.”

Ingvar Kamprad (IKEA founder): “IKEA is just one part of my life, but people think it’s all that defines me.”

Martha Stewart: “People see me as just a homemaker, but I run a media empire, I’ve built companies, and I’ve managed crises. There’s more to me than just baking a perfect cake.”

Let’s add to the pile this couplet from the Bible (ahem, not TMZ)…

“What good will it be for someone to gain the whole world, yet forfeit their soul?” (Matthew 16:26)
“I have seen all the things that are done under the sun; all of them are meaningless, a chasing after the wind.” (Ecclesiastes 1:14)

What do YOU want, Alec?

I don't know how to tackle these deep feelings of identity, inadequacy, and the deep desire to find meaning—even success!—in my work.

I want to keep going, but how?

I can keep reading this offensive book, to see where it goes. :)

I can ask God for peace and guidance that I cannot find on my own.

I can be more open with friends and family on this subject (though my tendency is to go all Enneagram 3 and project the image of success!)

And I can find solace in the fact that I am not alone in these feelings—they're felt by famous people, by rich people, by successful people, and, more importantly, by ordinary, good, everyday people.

Some of this is about money, sure, but it’s more than that. It’s about finding self-worth amid all kinds of struggles. It’s about detaching from achievement obsession. It’s about making space for something more than mere greed.

Perhaps even about embracing contentment, whether you have a little or a lot.

Or maybe it’s just me shouting into the void that my deep struggle can still matter, even if I have some of that privilege I’ve read so much about.

And wondering if others feel the same.

Maybe that’s you.

You're not alone in this.

I am not alone in this.

Like Obi-Wan says, “This is the hope I'm looking for.”

Alec Guinness and Pamela Brown in Macbeth, 1956

Thanks thanks thanks for reading.

Give a shout in the comments if this is you.