Where were you at 30?

I was in the Moat of Low Status

I recently met up with two business school pals for dinner. As we waited for our table and enjoyed a cocktail in the bar, we started talking to a couple of younger guys.

Oh to have more hair than money…

They were recent Kellogg MBA grads who worked for a very large online retailer. (I won’t say which one, but it’s as big as a South American river.)

Friendly and respectfully curious, they asked us about our career paths. They were duly impressed with my accomplished classmates—a hedge fund manager and former start-up executive who has rung the bell a few times. I’ve done all right myself.

Then one of the guys asked an excellent question: “Where were you at 30?”

I laughed, pointed to the software leader, and said, “When I was 30, I was deep in debt, sharing a two-bedroom, one-bathroom walk-up with this guy, and working in an industry that was unravelling violently.”

The young men smiled at my unimpressive answer. I elaborated.

On my 31st birthday in March 2000, the stock market was in free fall. The Nasdaq Composite index lost 1/3 of its value in four weeks, on its way to shedding 80% over 18 months.

LAUNCH.com, the digital music company where I worked was vaporizing alongside the rest of the Internet 1.0 economy. Three rounds of layoffs eliminated four out of five of my colleagues, and I barely survived the cuts.

I had sold exactly none of my stock because, foolishly, I believed holding onto it was a sign of loyalty. And when Yahoo! finally bought us for loose change that Jerry Yang found in his couch cushions, my payout bought me a desktop PC running Windows Millennium Edition.

Around this time, I confessed my financial situation to a new girlfriend—a dotcom multimillionaire who was smart enough to cash out. Despite my full head of hair and low-carb-lean body, she was not impressed.

The new grads laughed at my pain. When I divulged that liquidating my equity would have paid off my $80,000 in loans—$150,000 in today’s dollars, they traded fist-bumps hearing a balance similar to their own.

I often tell jokes in public. Come see me. (This silly theme goes back to me playing with divinity-themed AI image creations for my last post)

Then my hedge fund buddy shared his story. Right out of business school, he had taken the strategic consulting route. The lucrative pay package funded a nice apartment and the ability to chip away at his tuition debt.

But he found the work unsatisfying and decided he wanted to be an equities trader, a position for which he was positioned poorly. So, he quit the consulting gig and gave up his flat. He lived like a monk for almost two years while taking trading courses and networking with a seemingly irrational persistence, until he finally cracked the industry.

The bold bet on himself worked. Today, he’s reaping meaningful rewards in the form of both career satisfaction and financial compensation.

My other friend at 30 years-old was on a more consistent progression up the success ladder, propelled by a brilliant financial mind and a .1% work ethic that has barely diminished almost three decades later.

One of the benefits of having an ally like him is his ability to see the bigger picture. On a drive to the airport back from an early 2002 ski trip—as single, childless dudes, we could still find a few bucks for the important things—I was lamenting my situation. He put it into perspective.

“Okay, this girl’s not into you. Whatever,” he said. “You’ve got a good job at Yahoo! and stock options that could be a game-changer. Just keep your head down and keep moving forward.”

That’s what I did, and that’s exactly what happened.

Three years later, I was a millionaire.

How am I doing?

I took the young Amazonian’s question as a rhetorical check in—was he doing okay? Up to this point in life, he has done all the right things. Yet, despite having an impressive degree and a great job, he feels as if he’s not where he should be.

This is natural. Young people think careers are linear. Older folks know they can be jagged and often chaotic. And that’s okay.

In her forthcoming book You Can Just Do Things, author Cate Hall—a former drug addict, poker champion, and tech CEO—discusses the importance of embracing the “Moat of Low Status.”

Hall argues that many people spend part of their twenties and thirties in a bit of a ditch—an uncomfortable stretch where your peers seem to be pulling ahead while your own life feels uncertain, underfunded, and unimpressive.

Pre-order Cate’s book here.

But the moat has advantages. It shrinks your ego. It forces you to adapt. And you persevere because you have no choice.

Over time, however, good things happen. Opportunities arise that were not visible from the other side of the moat, and the path makes itself known. It happened to me, to Mister Hedge Fund, and it happened to Cate.

I’ll bet you a desktop PC that it will happen to these two young guys as well.

On their way out the door, my new friends swung by our table to say goodbye. I did my best to return their Gen Y daps, and gave them the best advice I could.

“Keep your heads down, boys. And keep moving forward.”

THE END

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