About a year ago, I was sitting across the table from a badass angel investor who is worth at least a half billion dollars and was on the board of over 30 companies. Back in the day he started and sold or took public several companies that have benefited perhaps a billion or more people over their span. In our meeting, he mentioned private jets, fancy cars, and houses in various locales and I couldn’t tell if he was bragging or just rambling and oversharing a bit with age. It was as though he was talking about doing the dishes, there seemed little joy in it for him.
We were trying to get him to write a check for our startup and he was talking about the challenges of money and how much to leave to various family members, the benefits vs. the handicaps of a handout, and the burden of having money with respect to others’ expectations and how it affects your relationships. I decided he was being sincere. He made a case that he would be happier if he just gave all of it away. We laughed but that only made him fight harder to make his case. It was absurd given the context. This was the same money that we were pitching him for and the same money that we hoped to make when after a few years of beatings and whiplash our startup succeeded (unlike the other nine out of ten that were statistically going to fail). He paused and looked at us both despondently and fondly, ”this is the happiest you will ever be. Remember this time,” he said.
The Happiest I Will Ever Be?!
I thought to myself, damn I really don’t feel happy now. I feel under appreciated, over worked, and vaguely like I am failing. I feel like I need just one more success to realize my potential or just 20% more money. I feel like if I were to slow down, I could lose my edge or maybe my lead in some unspoken race. The race where if you work hard and sacrifice the near term, some day you will be successful and rich. Once that happens there’s some vague implied promise that lots of your worries will actually go away and people will recognize you for the bonafide great person that you are. I know it’s so transparently stupid when I put it into words but you know it’s true that we all implicitly fall victim to this on some level. It pervades our culture. It makes it easier to sacrifice all that we do in the pursuit of this financial independence to say that once we get there then I can work on realizing my dreams and then I can be the person I’ve always wanted to be? When does that come in life and where does one draw the line to know that it has happened?
A Realization
Our society is not some conspiracy to keep us working, it has simply been set up over 1000s of years to serve human nature. Basic trade to satisfy our needs has evolved into this society where you work so that you can save money and create a better life. You work with dreams in mind of some day being rich and then you can live the happily ever after that we talked about. In the pursuit of this, human nature has built a pretty functional hamster wheel inside a damn entertaining maze that takes most people a lifetime to partially solve.
Hamster Wheel vs. Escape From The Maze
You work to get money to have that better life and in working you learn skills. You develop relationships with coworkers and then you have a community of people that validate you for your good work within this community. You are promoted to more respectable positions based on your accumulation of the aforementioned skills, some luck, and your general style and way that you make others feel as you all navigate the maze together. If you do this well, you get close enough to the edge that the walls start to break apart and there’s piles of cheese for you to munch on. You stare out at an undefined abyss and think holy crap what do I do now. Everything seems to really be clicking along well here inside this maze.
The Angel
This is where that angel investor made it to but I question what he did then. He had practiced skills to get to where he was but what if he needed different skills to function outside the maze? Did he ever get there? With all of his power, did he create balance in his life and make happiness a priority or just step back into the maze and repeat the pattern? I am not against work but I also refuse to say that only money making efforts have merit or virtue. It would seem that there is a difference between working because you think that you have to versus working because you know what it does for you and it is a net positive.
Warren Buffett truly seems to love his work when most of us would have retired long ago. As a billionaire living his modest lifestyle, he seems to have struck a balance that works for him so that is great. What I am raising here is that there are mazes to be navigated that can pull you into doing something that simply doesn’t serve you. You may need to work to reach financial independence but if you tie your self worth to your job can you ever stop working? I know too many serial entrepreneurs who are miserable but can’t seem to stop. I also know too many people who can’t even see that they have reached the edge of the maze. The maze is built on a foundation of endless productivity, vanity, and fear that all work to keep you scraping around its dead ends and seeking its safety enticing you to return to the center even as you reach the edge. So what is The Secret I didn’t know about being rich until I had money?
