At my 20th reunion from Harvard Business School, it was great to see that so many friends had done so well.
Interestingly, many of those reaching notable financial heights had remained in the same industry, or even at the same company, for 10 or 20 years. This correlation makes sense. Equity rewards accrue disproportionately to “lifers” over the long term. Being a “lifer” is a smart career strategy, but is it a wise life strategy?
After working 20+ years, it’s worth asking:
What am I optimizing for?
Most haven’t deeply contemplated this question, and many will reply with answers that validate past choices. Those past choices, while successful, came with substantial trade-offs, as HBS Dean Kim Clark underscored at our graduation 20 years ago.
Should we reevaluate our trade-offs?
Are the trade-offs we made 10 or 20 years ago still the right ones? Today, with far more resources but much less time, should we reconsider past choices?
This thought experiment might be daunting. Realizing your current life is optimized for decade-old goals can be shocking. More importantly, have we fully acknowledged our own mortality? At some point, the music stops.
“Man looks in the abyss…At that moment, man finds his character.” – Wall Street (the movie), 1987
Few dedicate time to these existential questions. Investors analyze potential investments for months, yet rarely scrutinize their own lives. I know – that used to be me.
But when I got fired, I had a choice: return to a version of my old life or carve a new path. I chose the latter. While I’m not recommending dismissal as a catalyst, waiting for a crisis to reassess your life isn’t advisable either.
Your choices today determine how you’ll spend your remaining ‘best years’. Yes, we’re that old. Going forward, ‘how you feel’ will outweigh ‘what you’re up to’. So, let’s start at the beginning:
What are you optimizing for?