Regret Minimization
Three years from now, if an article is published about you, what would it say?
For years, I measured meaning through my work — chasing achievement, stacking accolades, proving my worth through external validation. COVID cracked that foundation, sending me into a deep journey of inner exploration.
A year and half ago, I felt stuck. I couldn’t put my finger on it, but the next phase felt s just out of reach. A mentor and long-time friend, Raman Kia, gave me an exercise that cut through the noise — a process so simple yet profound that it unlocked a new sense of direction.
We discussed my stuckness, and he said, “Go ride your horse up a mountain, and write this every day for 40 days.” From the conversations I’ve been having lately, I developed his advice into what I can call the Regret Minimization Exercise. It’s designed to help you strip away distractions, silence external pressures, and zero in on what actually matters. If you feel lost, uncertain, or stuck in transition, this practice can guide you forward.
A Regret Minimization Exercise
Every morning and night, for 40 days, sit for a few minutes and ask yourself:
The Morning Question
Each morning, before the day takes hold, ask yourself:
“Three years from now, if an article is published about me, how would it read?”
What’s the headline?
What does it say?
Who publishes it?
Why does it matter?
Step 2: The Evening Reflection
At the end of the day, ask yourself:
“Of all the things I could do or achieve in this lifetime, what’s the one thing I would regret not achieving before I died?”
This question forces you to confront your ceiling (your greatest potential) and your floor (your deepest fear of stagnation). It’s about eliminating false goals and honing in on what truly matters.
Step 3: Identifying the Pattern
After 40 days, compile your answers. Look for recurring themes in what you’ve written over the month.
If there’s a clear pattern, you know what you're building toward.
If there isn’t, you need to recalibrate — you don’t have clarity yet. Go back to the process again.
From what you’ve identified, break your vision into two years of focused action, setting six-month pivots that allow for adjustment and refinement.
Step 4: The Reality Check
Once you have clarity, and you’ve written your plan out — pressure-test it. Ask 2–4 people who know you best to review the plan and your goals — but don’t ask for encouragement. Ask them to be ruthless, ask them to to you:
Why won’t I achieve this?
Where am I blind to my own limitations?
What makes me think I’m capable of this?
This feedback, unfiltered, direct, and uncomfortable, is what sets the foundation for real success. Because if you don’t interrogate your weaknesses, they’ll be the reason you fail.