Why Talking About Money and Happiness Matters

What we can learn from Bono, Brian Cox, and Jonah Hill

For four years, I’ve been exploring the connection between money and happiness on my podcast, Crazy Money. I come at the topic mostly through conversations with highly accomplished people and authors who study fulfillment.

Sometimes I wonder if the mission is worthwhile or whether I’ve reverse-engineered an idea that fits my experience of having made some money and wrestled with its often confusing impact on my life. Either way, I found it interesting when the universe—or maybe it was just my Facebook news feed—recently presented copious evidence that the struggle for money and status is an unavoidable human tendency that begs our understanding.   

Over the Christmas holiday, I inadvertently came across the work of three well-known artists who offer insights into their own struggles with money. In Bono’s memoir, Surrender, Jonah Hill’s Netflix documentary, Stutz, and the Channel 5 (UK) series, How the Other Half Live with Brian Cox, each of these masters of craft confesses to the difficulty they’ve had handling success or, more specifically, how their challenges handling life drove them to succeed.

It speaks volumes that on the second page of a 557-page book, covering over four decades of U2’s epic creative accomplishment, Bono writes:

There are some dirty little secrets about success that I’m just waking up to. And from. Success as an outworking of dysfunction, an excuse for obsessive-compulsive tendencies. Success as a reward for really, really hard work, which may be obscuring some kind of neurosis.

It’s not the only thing, but one of the primary conclusions this international superstar and humanitarian wants you to know: maybe all the accolades and fame are as much the symptoms of the quiet despair he’s harbored since losing his mother at age 14 as they are the by-product of his innate work ethic. Motherless Bono couldn’t win the attention of his emotionally-paralyzed, widower father, so he set out to win the world’s adulation instead.

Is it over-simplification? Maybe. But it makes sense.

Similarly, in Stutz, Jonah Hill introduces us to his therapist, Phil Stutz, who has helped the actor, writer, and two-time Oscar nominee grapple with the childhood inadequacy that even a dazzling Hollywood career can’t extinguish. Jonah sought Phil’s help at a time when he had “an incredible amount of success,” but also an intense “desperation to get happier.” Despite his fame and serious Hollywood cred, Jonah still saw himself as a “14-year-old kid with acne who is very overweight…and feels very undesirable to the world.”

Before Jonah found Phil’s unique set of coping tools, he engaged in an If/Then relationship with his career. “I thought, if I got successful, they wouldn’t see (the fat kid).”

Jonah doesn’t specify who “they” are, but he elaborates on his thinking that “success and awards will absolve me of the pain of life,” and “…when it didn’t cure any of that stuff, it made me beyond depressed.”

Yes, Jonah Hill still worries about who he was in middle school. So do I (you can read about my pimple here), and—I suspect, on some level—so do you. As Stutz told Esquire in an interview about the problems of movie stars: “at the end of the day, after you get done flying privately or being recognized, the problems are the same. Exactly the fucking same.”

Third, Brian Cox, the Scottish actor who grew up destitute but now makes millions portraying  media magnate Logan Roy on HBO’s Succession, just released a mini-series for which his goal is, “to find out what money does to you, to me—how it affects all our lives” ­because “money is very much my own personal demon—something I’ve avoided confronting until now.”

All this talk by the most prosperous and prolific creators about the nature of success and its attendant bounty begs the question: Why? Why are these wildly accomplished dudes bringing their struggle with accomplishment to the surface? They need neither the work nor our pity, and I doubt any editor, producer, or publicist begged them to talk about how hard it is to be rich and famous.

Instead, I think these guys want to share a secret that only a small number of people who make it to the financial mountaintop get to learn: wealth doesn’t deliver the existential glee almost all of us believe it will. They want others to understand that, beyond having enough and doing interesting work, our faith in the redemptive power of money and fame is wildly misplaced.

Before I made money, I thought wealth would get me more than a big house and some cool cars. I actually believed, if only on a subconscious level, that it would liberate me from the slow-burn anxiety I feel every day. That its attainment would scrub away my self-doubt and the persistent, nagging feeling that I don’t deserve to be happy.

Looking back, it’s easy to see how silly the logic is. I spent years working my ass off, thinking, “I’ll show those motherfuckers!” I never stopped to specify who “those motherfuckers” were, but when the intense labor paid off in spades, I didn’t feel any different. I started wondering, “Wait, which motherfuckers was I going to show?”

We think achievement will vanquish our straw man opponents who have been conspiring to keep us down, but we learn quickly that—while money can buy all kinds of cool stuff and experiences—it can’t buy freedom from the voices in our respective heads. Like Bono’s dad and Jonah’s non-specific “they,” it’s our negative self-talk that turns out to be “those motherfuckers” we’ve been trying to outrun the whole time!

So maybe the quest to explore money and happiness isn’t a contrived and self-indulgent exercise. Maybe if we were more self-aware of what success, however, we define it, can and can’t do for us, we could focus on the things that really do pay off. Or, more importantly, we could get to the core issues that hold us back from loving ourselves.

Yeah, maybe my doubt about the sincerity of my mission is just one more of those motherfucking voices in my head.

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The fifth year of Crazy Money podcast starts today, featuring my conversation with Katherine Blanford, my friend and fellow comedian whose career has taken off in the past year. We talk about her appearance on The Tonight Show, opening for David Spade, new fame, envy, having cash in her pocket for the first time, and the Ollinger family’s incredible basement.