The Finger Locks of Success

“I’m jealous of everyone who had the balls to do something that made them happy” lamented a seasoned portfolio manager at his fifteenth Harvard Business School Reunion. As the protagonist in Charle’s Duhigg’s recent Sunday New York Times ball-breaker America’s Elite: Wealthy, Successful and Miserable, this professional investor worked 12 “insanely stressful” hours per day, with colleagues who were constantly undermining him and doing work he found meaningless. The ball and chain that kept him tethered to his misery: $1.2 million dollars. What was the saying about money buying happiness?

In my mix of life skills, cojones – and specifically having them – is not a virtue that’s high on my list. For the most part, I’ve played it safe: majoring in engineering, accumulating credentials (umm, 900 CFA hours), and hugging the well traveled path of Wall Street.

As I read the article, I found myself transported back to my Wall Street self and nodding along in agreement. And while I eventually made it out, the old me shared similarities with Duhigg’s protagonist (let’s call him Sherman in homage to Bonfire of the Vanities). I was rife with envy at those who had the balls to jump out of the escape hatch. And my own taste of spectacular compensation became a clear obstacle from taking agency over my own life.

Meet Sherman, our $1.2 mm man. (Actually, I just Google’d “preppiest dude on the Internet”) [IG: @kjp]

Comply or get destroyed

There’s an illegal maneuver in MMA called finger locks. It’s a high-leverage (yet seemingly innocuous) tactic that applies extreme pressure to an opponent’s fingers; Wikipedia describes it as “disrupting the interconnectivity of the system of smaller joints within.” It’s like an arm bar for your digits! The lucky recipient is forced to choose between two bad options: submission (tapping out) or having your digits snapped into pieces.

Despite his $1.2 mm annual bounty, Sherman was trapped by the finger locks of success. In his own words, “there’s no magic salary at which a bad job becomes good.” Five years ago, I remember a similar feeling. Despite my extreme good fortune, how did I manage to feel cornered and powerless in my own career?

Half a butt cheek on a melting ice cube

The day I took the PSAT was when I committed my life to triumphantly ascending the corporate ladder. This is the weird behavior that occurs when you have zero chance of getting laid in high school. And so the journey of Yale → Investment Banking → Fund Management (sprinkled with some good timing and ‘battle field’ promotions) landed me that coveted Managing Director title at the ripe young age of 31. Game on.

Once you reach the summit, your slice of the financial pie grows exponentially. But my own ascent had a very significant asterisk. It had spanned the global financial crisis, which had savaged the industry and left it a shadow of its former self. The growing pie was now a melting ice cube. And I had half a butt cheek on this ice cube.

What was I to do? I was so conflicted. Those pesky finger locks! The ice cube had years (maybe a decade) to melt – but I was 31 years old and hoped to contribute 30-plus energetic and inspired years of work.

Did I want to spend my prime in an industry that was atrophying away profitability and talent? Be a growing guy in a shrinking industry? And let’s not even mention the hot mess of a bunch of grown men trying to slide their pasty cheeks onto a glistening ice cube.

The shackles of spending

Back to Sherman. In the NY Times piece, it turns out he’s actually discovered a key to escape his $1.2 million golden handcuffs. It’s “an offer at a startup, that he would love to take.” But the dalliance is short lived. This role would require a 50% pay cut (yes, to $600k) and Sherman was “locked into a lifestyle that made this pay cut impossible.” His wife concurred, “laughing when [he] told her about it.”

Calling this lifestyle creep is akin to calling a hyena a kitty. It’s part creep, part what-the-heck-are-you-thinking and a complete misalignment between how you spend your money and what you value. Yet, in Sherman’s defense, even Bloomberg believes that living in NYC while making $500k can seem hard (and result in a paltry $7,300 leftover spending).

Thankfully my path diverged from Sherman’s as Lisa and I had not succumbed to the demons of lifestyle creep. That didn’t stop the uncertainty of our spending from gnawing at us. At the time, we had a one year old and as an artist, Lisa didn’t have a W-2 income (nor access to employer-based healthcare).

Ironically, our financial paranoia wasn’t around the big-ticket spending, but around the fear of going back. We had clarity around things like health insurance (18 months of COBRA then Obamacare), home ownership (not an option for 5+ years), a vacation home (no interest) and private school (probably a stretch).

Even without lifestyle creep, there was comfort in not caring about the prices of things – Economy Plus upgrades, my umpteenth Air Max purchase, a spontaneous facial at a hotel spa and replacing a lost iPad without hesitation.

Slack founder Stewart Butterfield refers to this as the 3 stages of wealth. He described this hierarchy to Guy Racz on the How I Built This Podcast. Level one is when “people no longer worry about their credit card bills or their student loans.” Level two is:

“I don’t care what stuff costs in restaurants. You know, you’re like, I really want this thing, but it’s $18. But the other one’s $12. SO I’ll get the $12 one. There’s a level where it really doesn’t matter what you spend on a particular meal.”

And the ultimate level of wealth is:

“I don’t care what vacation costs. Like, I don’t care how much the hotel costs or which flight we go on.”

Lisa and I had sprung past level two and were at the precipice of three. As kids, neither of us thought we’d ever reach this ultimate level. And we panicked that Sherman’s path was the only way to reach – and stay – at that ultimate level.

Damaged goods syndrome

Here’s a true story. Years after I left finance, I discovered that our marriage had made it into the rumor mill. An industry peer had told others that they knew how my entrepreneurial journey would play out. First, I’d fail as an entrepreneur. Then, we’d spend way more than we anticipated. Which would come at the ultimate price: Lisa would leave me (maybe for another Sherman).

Thankfully, I didn’t hear this in my early days of entrepreneurship; it would’ve rattled my then-fragile core. Just like we didn’t want to “go back” to our childhood financial situations, stepping off the current trajectory racked me with the fear of becoming damaged goods. After all, one of my back-up plans was returning to the finance industry (obviously with hat in hand). It’s a human instinct to contemplate the possibility in that horrific rumor. What if the person I loved most saw me as damaged goods?

An Excel-lent life

“When I die,” wondered Sherman “is anyone going to care that I earned an extra percentage point of return? My work feels totally meaningless.” There’s a story that financiers tell themselves about the mission behind their work. That extra percentage point of return is the elixir that enables pensioners and endowments to live their best lives.

I believed (and still do believe) that finance plays a central role in the global economy. But like Sherman, I didn’t feel like moving numbers across Excel spreadsheets made for an Excel-lent or well-lived life. Epsilon Theory’s Rusty Guinn evaluated this conundrum through the eyes of a banking analyst who views the higher purpose of their job as “something something matching capital with those who can deploy it.” But like Sherman, deep inside they feel that this narrative (and thus the work itself) is a sham. And over time, their true function reveals itself:

To permit his immediate boss to signal competence to her immediate boss, a chain of signaling which ultimately ends with a client who wants to do something (e.g. buy another company) while offloading some of the various types of risk and accountability associated with that thing to the most credible third-party sources (i.e. you).

But is the pursuit of mission and meaning yet another instance of the pesky finger locks? We’ve leapt into a post-meaning world where Facebook’s desire to “bring the world closer together” or Twitter empowering “power to create and share ideas and information instantly without barriers” are met with a suspicious eye roll.

Like Sherman, I had a legit question: what is meaningful work? How many meaning-based companies existed in the Fortune 500? Was the only option for bankers and consultants to flip the switch into professions like surgeons, public advocates, pastors or journalists?

And more importantly, would that ultimately lead to happiness?

Giving back the winning ticket

This all culminated into the feeling that I held in my hand the winning lottery ticket. Yet I was on the cusp of making the grave, irreversible mistake of giving it back. The countless sacrifices made by my first generation parents, the 10,000 hours reading white papers on quantitative investing and the thousands of breakfast networking meetings – would become the sunk costs of my former career.

This reminded me of Warren Buffet’s quote that he believes that he “won the ovarian lottery.” In 2013 he shared a thought experiment with a group of MBA students and had them imagine that a genie could teleport you back to your birth lottery. There, you’d get a chance to pick one ball out of 6.8 billion (the world’s then-population) which would determine your individual birth attributes:

You could be born intelligent or not intelligent, born healthy or disabled, born black or white, born in the US or in Bangladesh, etc.

Buffet concludes this thought exercises with a challenge:

If you could put your ball back, and they took out, at random, a hundred other balls, and you had to pick one of those, would you put your ball back in? Now, of those hundred balls (…) roughly five of them will be American. (…) Half of them are going to be below-average intelligence, half will be above. Do you want to put your ball back? Most of you, I think, will not. (…) What you’re saying is, ‘I’m in the luckiest 1% of the world right now.’

So back to the lottery. Does Sherman, does Khe Hy, or do you want to put that ball back and draw again? Chances are no. This – by definition – puts the impetus squarely on us to live each day like the luckiest 1% in the world.

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