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10 Regrets From a 58-Year-Old Douchebag

Oh Lord, it’s hard to be humble, but I could probably try harder

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Just to be clear, this is an illustration, not how I actually dress - Midjourney

After my last post about how great it is to be rich, I got a few comments that weren’t complimentary, suggesting that I came across as a bit of a douchebag. One reader said he suspected I was one of “those guys” at a party. I think it was an insult.

While this was going on, I read a post by Iva Ursano about her regrets as a 60-year-old woman. I’ve considered writing about regrets before, but since I like where I’ve ended up, I don’t usually consider anything a regret.

But not every regrettable act is life-changing, and in my mindset of being a douchebag, I started thinking about things in my past that have been pretty douchey. In the spirit of Iva’s article, here are some of my actual regrets — ones that didn’t result in any learning, just hurting someone for no reason.

  1. When I was an insecure 17-old on a student bus tour through Europe, I was asked for a hug one night by a girl who was even more insecure than me. I laughed and walked away, scared out of my wits that anybody would seek emotional comfort from me.

  2. On that same tour, to impress my roommate, I told him I had been accepted into MIT for the coming fall. I had only applied, and I was rejected a few weeks later. I had to confess that I lied when he wrote to me after the European tour, asking if he could visit me in Boston.

  3. At age 20, I was so craving status that I pestered my parents into buying me a sports car as a university graduation present, a red Mazda RX-7. Over the next two years, I got into three accidents and received 13 speeding tickets. It was pure luck I didn’t kill myself or anybody else.

  4. At age 24, in the office cubicle across from mine, our departmental secretary hung up her phone and burst into tears. As we made eye contact, she began wailing pitifully. I swivelled away and focused on my computer screen, unable to deal with strong emotions.

  5. At age 32, a girl I had been dating sent me an email asking about meeting up, and I forwarded it to a friend with some disrespectful comments. Instead of hitting ‘forward,’ I accidentally hit ‘reply.’

  6. At age 33, I corrected a girlfriend in public about using the word ‘comprise’ when she should have used ‘compose.’ She composed quite a good reply, comprising my many shortcomings as a boyfriend.

  7. When I was a 34-year-old superstar sales guy, I returned a rental car without filling it with gas first. When our bookkeeper questioned the gas surcharge on my expenses, I ranted at her for two hours and made her cry.

  8. When I was 35, a guy who flopped a straight flush in a game of Hold ’Em poker goaded me into betting more and more (I had a full house). I lost $500 on that hand and then another $5,000 over the next 8 hours as I refused to go to bed and made it my mission to take him down.

  9. At age 42, I was playing online World of Warcraft on my laptop in bed when my new wife jumped on me playfully. I screamed and rolled away, saying, “Agh! I’m in the middle of a battle, my team needs me!” My team would have survived. My wife didn’t talk to me for a day.

  10. In my 50s, when I was regularly investing in tech startups, I was also just discovering a love of EDM music and nightclubs. I used to insist that any potential entrepreneurs who wanted my money had to come party at my table or on my party bus. Juvenile. Not the party bus — the insisting.

A little too much zoom zoom — Midjourney

So am I a douchebag? Does it matter?

I definitely wrote a tone-deaf post conflating my self-worth with my money. But am I one of “those guys” at a party? Am I that guy?

That guy who doesn’t wonder if he’s a douchebag — because he knows he’s superior to other everyone else.

That guy who drives recklessly, wears sunglasses indoors, and leaves an airpod in one ear even when he’s not using it.

That guy who wears designer clothes with the brand visible, shows up late to every meeting, and over-uses hashtags.

That guy who takes selfies at funerals, pops his polo shirt collar, and name-drops celebrities and rich people.

That guy who hogs the conversation, parks across two spaces to protect his leased Maserati, and brags about his money and privilege in online posts.

That guy who tells you how to run your business and grabs your wrist to see the brand of the watch you’re wearing.

Do any of these remind you of someone you know — or of yourself now or in the past?

I’ve been that guy. Even now, I am that guy sometimes. I’ve done regrettable things, and I’ve hurt people with my behaviour. But getting treated for bipolar disorder, diving into psychedelic therapy, and experiencing internal family systems therapy have made me a better human.

I still wander into douchebag territory at times, but I don’t get lost there anymore.

We’ve all done things we’d undo if we could. We’ve all been horrible at some point in our lives. But there’s a solution.

Forgive yourself.

Be a little less horrible.

#dontbeadouchebag #Imnotadouchebag #Itwasjustonetime #sunglassesarealwayscool

  1. Iva Ursano’s post about her regrets as a 60 year old woman.

  2. My last post about how great it is to be rich.

  3. Dumb ways I spend money.

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