When I was in my 30s, I would fantasize about someday being able to retire. At the time, I was working for tech startups. I enjoyed the work, my colleagues and the challenges. I liked that my income was going up rapidly. I liked having a reputation as a “go to” guy who made things happen.
Part of what ruled my fantasy of retirement was reading about all the Dotcom millionaires who became stupendously wealthy overnight. Steve Case , Mark Andreessen, Bill Gates, Steve Ballmer, Steve Jobs, Elon Musk, Mark Cuban and others. They did it and I assumed I would too.
I was so naive.
Fantasy
I thought of my retirement in two phases – the retired with my wife phase and the old, alone phase. Since my wife was 18 years older than me, I figured I might outlive her – although to be honest, I rarely thought about that being a possibility.
Phase 1: Retire early as a multimillionaire. Own several houses – one on the beach, one in the mountains and a villa in France. We’d travel between the houses seasonally so we could always enjoy the best weather. We would drive Mercedes luxury cars. I’d have a few small boats. I wouldn’t need yachts, just something to putter around the lake or the ocean. We’d have a few pure breed designer dogs. We’d have maid service for our homes. I’d start one or two small businesses to set up our kids for success. We would eat out at fancy restaurants, drink a lot of wine and enjoy life together. I wanted to be an active investor, advisor and board member for tech startup companies.
Phase 2: When I was old and alone – which I figured would be way down the road – I’d buy a small stilt home in Florida on a marshy bay or lake. I’d have a small flat boat to run around in. I’d workout every day, get pleasantly drunk every night and grill a lot of steaks for dinner. I’d spend my days reading, swimming, snorkeling and spending time with my dogs. I’d still be a millionaire of course, but by this time, I’d be making sure the kids were set for life and my “legacy” was established through my charitable donations.
Reality
By the time I reached my 40s, I figured I’d never be able to retire. None of my Dotcom dreams of getting rich came true. My career (and earnings) had gone up and down. Instead of having stock options worth millions, I was living paycheck to paycheck struggling to stay ahead of debt payments.
I never did have any Dotcom stock success. But my earnings went up, our debt got paid off and we reduced our living expenses.
I stopped fantasizing about having a Mercedes. Instead I was proud to have two vehicles that were in decent shape, were over 10 years old and hadn’t required a monthly payment in years.
I still thought I’d likely have to work forever, but my goal was to build up a nest egg so that no matter what, my wife would never have to worry about money. If I died, our savings plus my life insurance policy would ensure that.
Then my job was eliminated (again).
Then I started a consulting business.
Then my wife was diagnosed with lung cancer.
Then she died.
I’ve been retired for 4 years.
It is pretty fabulous – but unlike anything I had fantasized about.
I live off of my investments. I make deliberate frugal choices that involve trade offs. I don’t go out to fancy restaurants. I live in a small, sensible home. I drive an inexpensive car. I don’t have health insurance. I minimize my purchases of goods and services.
I haven’t gotten drunk in 18 years so that part of the fantasy is also gone.
I do workout everyday. I spend time with my 2 dogs. I don’t have a maid nor do I want one.
I have gotten back into drumming and have learned how to draw and paint. Exercise, art, writing, chores and my dogs fill my life.
I am alone.
No wife. No kids. A few friends who range from long distance friends I rarely see to casual acquaintances see often.
I have zero interest in striving for money. I’d like to have more. If I did, I wouldn’t worry as much when I need to pay for healthcare. I’d eat more expensive food. I’d get a membership to a private pool so I could ensure I always had a lane.
If I was über rich, I’d have a second home in California or Florida where I would go during the winter. I’d also build my own lap pool so I never had to rely on public pools.
I might invest in risky startups, but maybe not.
I’d contribute more to charities.
Maybe I’d get a villa in France or Italy. But maybe not – what would I do with the dogs?
After a lifetime of wanting to be rich, I no longer care about it at all.
I’d take it, if it came.
But it won’t. I know that now.
And that’s perfectly fine.