A few years ago I was outside my Chicago garden apartment in Little Italy washing my Cannondale after taking it out for a ride along the lake. It's an aluminum frame from the early 2000s with a totally sweet, blue-fade paint job that looks amazing when shiny and clean. It was a warm, sunny day and I was content.
I looked across the street. One of my neighbors had put out a "For Sale" sign in front of their row house. The place was a disaster, a complete gut job. Still, I knew I couldn't possibly afford it. But I was so happy and content that day that I said to myself, "This is what I want. I want to be here, in Chicago. Put down roots. Own a little two-flat and fix it up. Make a baby. Drink beer and grill in my backyard." I knew I would be happy forever if I could just own even a small piece of how I was feeling that day.
My garden apartment was cold in the winter. The forced air system couldn't pump heat out fast enough to keep up with the drafts on brutally cold days. It was damp and musty smelling under the stairs and there were spiders. The kitchen was mundane with standard appliances and finishes and I couldn't change anything because I was a renter. If only I owned my house, I could make it exactly the way I wanted it to be.
On the train to work the next day, I started thinking. My job was boring. It didn't challenge me, and I didn't own my own work and I had no control over the scope of my projects. My commute was at least 2 hours each day. I had too many managers. We used version control software from the 90's. Our "deployment script" was a guy named Bob. If I owned my own company, I could use Git. I wouldn't be bored, I would be challenged!
Fast forward to today and I own my own company. I've created and made over $80,000 in profits from two separate products, plus scads more consulting. I'm now friends with all of the entrepreneurs I used to envy and admire from my padded, borg cube. I bought and fixed up a beautiful brick two-flat in one of the hippest neighborhoods in Chicago. I can walk to multiple breweries or Michelin star restaurants in less than 10 minutes. The blue line is a 5 minute walk. I still have my blue-fade Cannondale and now I also have a matching orange/yellow version I keep in Arizona for my yearly winter vacation. Isaac joined our family 20 months ago, and he's more amazing than I could have ever imagined. I'm living the dream I had all those years ago.
So I'm happy and content right? Every day I should feel like I did while washing my bike that day years ago because I got everything I wanted. And yet, last year I was more depressed and anxious than I've ever been in my life. I had to take drugs and see a therapist. (I'm way better now though, if you were worried).
Everything went off the rails when I saw the For Sale sign and started dreaming about a better life. If instead I had stopped and realized that I was happy and content right then, and I had everything I needed in my life to be happy and content ...obviously, because I was happy and content! And yet, I was unsatisfied. I thought I would be happier if only I had a better job, bigger house, more money, fame, recognition, more vacation time.
It was an illusion.
I'm not saying that I shouldn't have started my own company or bought a two-flat. But I do think my motivation was all wrong.
As denizens of the first world, you and I likely have everything we need to be happy. I'm never starving, I eat fancy home-cooked meals every day. I have almost infinite entertainment delivered to my house for $7/month. I can talk to any of my friends and family instantly from anywhere for $12/month. I have a roof over my head. There's no war raging outside my windows. The list for people like you and me goes on and on, we have a lot to be thankful for. But we all suck at appreciating it.
I think that being happy is very likely a skill, and if I took half the energy I put into getting a new house and starting a business and instead put it into learning the skill of being content with what I do have, (and then not worrying about losing it), I would be the happiest person you know.
I say "skill" because it's not something that comes naturally. Our brains seem wired to do the opposite. A problem appears in my life so then I imagine terrible versions of the future where I lose everything, and then I work hard to come up with ways to avoid that outcome. Or I feel gloomy because it's cloudy in Chicago and I miss the sun, so of course I'd be happier if I was in Arizona. Then I'm plotting ways to buy another house in Tucson. I have literally been doing this exact thing for the past few weeks.
My brain takes every pain and tries to protect me from it and sees every pleasure as something I have to protect at all costs. My brain is so good at finding problems to fear or pleasures to seek, I think I'd be miserable if I was a billionaire.
My problems won't be solved with another house. I won't be happy if I just have a little more money. I want to learn the skill of being thankful for what I have and to not fear losing it. I know in my soul it's better to spend my energy learning to be happy than trying to create the perfect life. I already feel more thankful for everything I have.