I’ve noticed that the two most common sources of regret for my last 20-30 years of experience are:

• Missed opportunities
• Coulda/Woulda/Shoulda thinking when a disaster strikes and I didn’t see it coming

The risks taken that paid off – what would I regret? For example, when taking my first mortgage, it felt like a great risk. The payment was a significant portion of my salary at the time, the period was long, and the apartment we bought was not great but we couldn’t afford anything better. The interest rate was high, and the seller had some non-disclosed debt and some people wanted their money back. It ended up fine, we renovated the property over the years and resolved the issues. Turned it into a home.

When I take a risk that doesn’t pay off, I also seem to not regret it if it was a deliberate informed choice taken without influence. I stopped insuring my previous car for theft and accidents. It got stolen. The saved premiums for 3 or 4 years didn’t cover the loss of value. Did I have regrets? I didn’t. I made a choice based on the amount of time I lost each year to deal with things like paint damage and vandalism. Covering the cost myself would’ve been cheaper and quicker than going through the insurer and the police on every occurrence. The same happened with previous vehicles, none of which were stolen. It didn’t pay off last time but I felt zero regret because it felt like it was an expected, although unlikely result of my math.

Most of the time when I felt regret, I didn’t see the negative outcome coming at all even if there were obvious signs in retrospect. For example, I played basketball. A second later I was on the ground with a dislocated knee. I didn’t see it coming. Lots of coulda/woulda/shoulda followed. However, the outcome was predictable, and the risk was taken when I agreed to play with unfamiliar clumsy kids. I blogged about bias, assumptions, and intuition, a couple of times this year.