I've reached that age where life stops being all sweet moments and starts throwing real curveballs. In the past few years, I've lost close friends, watched people get terribly sick, and seen carefully laid plans crumble. Your late 30s hit differently as you start seeing your parents age, get sick, and the roles reverse, while you're simultaneously juggling your own career, family, friends, and health.
Suddenly life feels less rosy and more... finite.
This led me to regret minification, which comes down to one simple question:
When I'm 80 years old, would I regret not doing this?
If the answer is yes, then it's time to do it.
This mindset really started a decade ago, when I ended up packing up my life in Copenhagen and moving to North America in my late 20s, and was further validated when back in 2017 I realized my health wasn't as good as I thought. That health scare crystallized something: time isn't infinite, and the window for certain experiences has an expiration date.
It's this realization that led us to New York City. Would I regret not living in NYC in my 30s when I could finally afford the lifestyle I'd dreamed of as a kid? Absolutely. This extends to material decisions too, like the sports car. Would I regret not driving one while I can still get in and out without groaning? So I bought one.
Most recently, this framework led me to a career pivot. The question was clear: would I regret not exploring this path while I had the chance? The answer was yes, so here I am.
Look, these might be financially questionable decisions, influenced by reading Die with Zero, but when I'm 80, looking back at my life, I'd rather have good stories, lots of memories and some stupid purchases and decisions than a fat bank account and a list of regrets and big "what ifs."
Life is short. The Tail End is coming faster than I anticipated, and the plan you have will never be the plan that happens.
So when I'm facing those gnarly one-way trap door decisions — like moving continents for a new life or pivoting my career — optimizing for minimizing major regrets is how I'm choosing to live my life at the moment.
The guiding question remains: Would I regret not doing this?
Onwards.
/k