When I arrived at the airport a few weeks ago, the porter at the curbside check-in greeted me with a smile.  There was no line at the counter, and I smiled back.  He asked me for my name and destination, and proceeded to look up my flight.   

“Aisle seat, you’re lucky,” he said. 

“I know, especially since I wasn’t able to select a seat online when I bought the ticket.” 

“You must have checked-in early,” he said.  I told him I did. 

He then chimed in with, “You’re Pre-Check TSA too.” 

“Lucky again!” I laughed.

I’ve been thinking about luck a lot lately.  In the course of the U.S. 2016 presidential campaign, I’ve listened to all the candidates lament how the middle class has been squeezed, and how economic upper mobility in the U.S. is under pressure.  I’ve been wondering about how I would feel if I had gotten “lucky” in my career in technology.  Of course, there’s the old trope credited to various sources, “The harder I work, the luckier I get.”  That may have been true decades ago, but I don’t know anyone who doesn’t work hard any more.  Even the low-wage service worker who often has to hold down several low-paying jobs just to get by works a lot harder than most professionals I know.  And most professionals I know are exhausted more than they are energized, and nearly every one of them questions what price their work ethic is paying on their families.

As a young, single mother, I knew the only way I could become financially independent was if I had a college degree in a growing field.  When I graduated with an Associates degree, I had great job offers because of my high G.P.A.  Yes, hard work was a prerequisite to balance straight A’s with single parenting. Luck didn’t really play a role in my early career at all, yet I’ll acknowledge the head-start privilege I was granted as a pretty, white girl. Gradually though, as I accumulated skills, a network, experience, and a bit of a personal brand in my field, I started to believe I deserved the American Dream too. 

I was able to go from young welfare mom to an internationally recognized professional who owned two homes, two cars, one truck, and two businesses. I once furnished an entire house with cash.  I was also able to renovate a second home which included the addition of that surefire trophy of suburban success: a built-in heated swimming pool. I even paid for my wedding and honeymoon with cash.

Midway through my career, I left a six-figure executive position with a consulting firm to join a startup where my new partners lured me away with with a generous stock package.  It was the first time I thought I could actually “cross over” to a life of not having to worry about money at all.  If those stock options could be converted to a cash payout, I would be A-OK. 

Of course, like so many others who count their stock options ahead of time, that didn’t happen. The company went bankrupt and the options were worthless.  I think something even illegal was going on with the founding management as well, but I was long gone before that weirdness emerged. That company was the first in a string of unsuccessful moves I made to join startups where the payout would be awesome, if only… the company could exit via the public markets and I could cash out.

One of these startups involved one of the largest investment banks in the world, Morgan Stanley.  I convinced myself that if Morgan Stanley was investing in this company, it must be a sure thing.  Nope, the company folded, and I lost the investment I made in the founders’ shares I bought originally to join the executive team.  Another company was headed up by an entrepreneur known to have a large ego who had been fired from his last startup. That company was backed by one of the most prestigious local venture capitalist firms in town.  I thought to myself, “His ego won’t allow him to fail twice, so this must be a sure thing.”  Nope.  The company was dismantled and liquidated in a fire sale.

So, no luck for me.

What I’ve been wondering is how I might be a different person if I had gotten lucky?  If I had been able to cash out with a windfall of stock options that catapulted me into the 1%, would I have believed I was more deserving?  Would I have believed I was special, because I worked hard to rise above the economic circumstances into which I was born?  Would I look with disdain on people who had fewer material assets than I had?  Would I be living in the home showcased in the photo above?

Would I be (gulp) a… Republican?

So many of my career friends who had soul-sucking jobs that involved carrying bags for executive miscreants were able to cash out. Now, they live lives of comfort. I pitied them then, but are they pitying me now?

I watched a documentary again last night, “Park Avenue: Money, Power, and the American Dream.” I forgot I had already seen it, but got pulled into it again once I started watching it.  In the film they highlight research conducted by Berkeley Psychologists Paul Piff and Dacher Keltner. The team ran several studies that looked at how social class (measured primarily in terms of wealth, private education, and prestige) had an inverse relationship to caring about others – especially those who had less. The film demonstrates how even in an obviously rigged game of Monopoly, study participants adopted an air of entitlement.  Piff gave a TED talk on this topic:

The point of this long piece is, the older I get, the more grateful I am that I was not warped by the excesses of capitalism. Losing my affluence has made me more human, more empathetic, more interested in achieving sustainable gains for a greater swath of the general population.

My American Dream didn’t turn out the way I expected, or once had hoped. Yet, my dramatic personal economic rise and fall has forced me to see humanity more clearly. In the end, I’ve come to realize I am far luckier than I ever imagined I could be. Devoid of the trappings of wealth and materialism, I’m a better person, a more grounded person, and much more in tune with the human race and what being fortunate really means.