For as long as I can remember, I’ve been looking for the things that will make me okay. That will prove, finally, that I was good enough. It’s taken on different forms as I’ve gotten older, but it usually entails achieving something or obtaining something that makes me distinguished in some way. The things I’ve had my mind set on, like getting a promotion, a beautiful wife, a new car, or a stellar vacation, won’t be unfamiliar to most.
And there’s nothing wrong with any of this. Goals are a sign of being alive. Wanting things in life and being willing to work for them makes the world go round.
As a young man I became interested in stock market investing. I learned that a lot of people were creating financial security for themselves by predictably saving and avoiding spending foolishly. I gravitated to buy and hold strategies and understood that many became wealthy buying and holding shares of good companies for decades. Surely I could do that.
But then a boss offered me a chance to buy shares in an innovative medical products company that was still privately held through some personal connections he had. I thought to myself ‘this is how fortunes are made!’ Here was a deal available to only a select few who got in early and were later rewarded for their foresight. Finally, I would prove to the world that I was somebody! I had worked hard to make the right connections and was willing to put my money where my mouth was. Let everyone else complain about how unfair life is.
So for two and a half decades the company held on through multiple rounds of funding and transfers of ownership. With each passing decade my enthusiasm and hope only grew. I eagerly awaited their quarterly reports about FDA approvals and record sales. Some day, hopefully soon, they’re going to be bought by a big industry player and all this waiting and anticipation will have been worth it.
Now mind you, all this time I had been working and saving, slowly building my assets and resting easy at night. My investments did well. I was a homeowner and had ample reserves so my investments never had to be drawn down, even during bouts of unemployment. My buy and hold strategy worked very well.
But the relative peace around my finances overall were in sharp contrast to the feeling that I would one day live on easy street thanks to the incredible foresight I had to get in on the ground floor of this company. I didn’t want to hear that most start ups are not successful and finding the ones that are is largely a function of random chance.
Finally, the day arrived. I was informed that the company had been bought by a bigger player and I would be receiving a check in exchange for signing over my shares. I had been vindicated at last! I grabbed the paper-thin envelope out of the mailbox and proceeded to the kitchen, wondering if it was enough to quit my job THAT DAY.
I calmly pulled the check out of the envelope and looked at the box in the upper right hand corner. So the $5,000 dollars I had invested in 1998 were now worth . . . a whopping $6,040. Oh.
I dimly held on to hope that this was a mistake. This must be the initial “good faith” payment, with more on the way. I contacted my old boss who explained that our shares had been diluted with all the additional rounds of funding. This was the final payment and there was no mistake.
So my get-in-on-the-ground-floor fantasy was a bust. I had to face the fact that I had invested an inordinate amount of time and energy into something whose potential for return was a function of chance. That I was choosing a fantasy over what was right in front of me.
The days and weeks that followed my sobering lesson have been a good time for evaluating what’s important in my life. Am I connecting regularly with the people I love? Am I making progress on my mission? Am I delivering value in my work? Am I making a difference?
I’m also far more aware of how I am investing my energy. Mind you, there’s nothing wrong with making investments in long shot ideas. Some of those investments do pay out and someone gets wealthy as a result. But you need to ask yourself what is driving that investment. Take it from me: a desire to prove yourself worthy on the uncertain and unlikely success of a startup is a surefire way to invite existential bankruptcy into your experience.