Revisionist Me

In the 2000s, I built several businesses--all within the mortgage and real estate industries--and bought several commercial rental properties in Colorado. I was worth millions... on paper at least. In 2007-2008, the American mortgage and real estate markets tanked. In 2009, I filed a personal Chapter 7 bankruptcy, lost everything, and applied to grad school. Those are the basic facts of the story of my late-20s to mid-30s. How I've told this story has evolved quite a bit, becoming a story of its own.

Originally, I was too shell shocked to even know how to tell the story. Before long, the original story I developed--and fully believed--was that I had had some success as an energetic young entrepreneur, went through an extraordinarily difficult time personally and professionally, was a victim of the market crash at the same time I was part of the cause of it, and that I needed to take a few months to recover my physical and mental health after the stress of it all. I emerged cynical and humbled, slightly worse for wear, much more cautious, and hopefully more than a little wiser than the blindly and foolishly optimistic idiot I had been in previous years. I had poor foresight and even poorer timing. I realized I still had a lot to learn, so I went back to school and found some mentors. Not terrible perspectives, and not unreasonable reactions, but I've come to see how this story limited me in certain ways.

Eventually, however, I realized how lucky I was and am to have experienced success in my late 20s and subsequent failure in my early 30s. I truly couldn't have become the seasoned entrepreneur I am today without having failed so spectacularly. Everyone fails big eventually, especially great entrepreneurs. By failing big relatively early--and I considered this failure to be a nuclear bomb dropped into my life, and in many ways it was--I had plenty of time to try again and again and again. "Fall down seven times, stand up eight" became my mantra. This gave me courage, knowing that no matter how bad things get, I'll get through it. As long as I keep breathing, keep waking up each morning, I can choose to take actions to make my situation better. Even bankruptcy, foreclosure, ulcers and other health issues, ended relationships, not eating for days on end, and living in my car weren't, in fact, that scary. What I feared most couldn't, in fact, hurt me. I can take risks again if I want. What's the big deal?

Further, I became a much more empathetic person. Living out of my car, I learned how hard it is for the truly disadvantaged to get by. At least I had a car and a college degree. Thus, I began to see the true limitations of capitalism. That is, if a nice, honest, intelligent, highly educated, ambitious, hard working, straight, cis-gendered, able-bodied, middle class, white guy from the US can make millions and get wiped out in a blink, what chance does a woman of color from a low-income background have, or, say, anyone from the slums of Buenos Aires or Manila? I won the privilege lottery at birth, and it's still damn hard to be financially successful sometimes. And even at my broke-est, I still had a college degree, career options, a supportive family, and generous bankruptcy laws allowing me to start over mostly debt-free (i.e. student loans don't go away). I came away from this experience asking myself daily, "How can I help others less fortunate than me? How can I make things better?" My story isn't just about me anymore, it's about all of us.

My story's evolution didn't stop there. More recently, I don't think of the story much at all. When I do, I see it as a helpful blip, an interesting period of my life, or an interesting story that might help others... not a nuclear bomb. I tried, fell down and skinned my knee a little, got back up, learned a lot, and went on to the next fun adventure. This period of my life was merely a temporary but perhaps necessary setback, not a failure at all.

I've also realized that while life without money is difficult, money ultimately doesn't have to matter much. Paradoxically, the happiest times in my life all happened when I had next to no money at all, and my most stressed out, unhappiest, least fulfilling times have all come when I've had the most money. I'm not saying money causes unhappiness, but lack of balance, free time, meaning, community, and perspective certainly can. More importantly, choosing new perspectives can help us heal so we can lift ourselves back up, and then lift up our less fortunate brothers and sisters too.

That's the story I like telling now. The previous versions weren't wrong, per se, but this evolution of the story serves me better. Perhaps it helps me serve others better as well.