I generally think looking back is a complete waste of time and energy. I have little to no regrets and feel that thinking like that simply weighs you down. The more weight - the more I have to carry and the more I have to carry - the more friction I have for the things I want to get done.
I am moving quickly through my 50"²s which means one thing for the purpose of this article; I have a lot of potential baggage to carry through my day. More years equals more baggage just by simple math. What kind of baggage am I carrying you ask?
I left MapQuest too early to completely maximize a financial return. (No multi-coast beach houses yet.)
I turned down an excellent role in my most favorite industry due to a wicked combo of ego and arrogance and never returned to that industry. (I still bleed consumer mapping and navigation.)
I was pushed out of an existing retail business some friends had asked me to join wasting valuable time & energy and ruining a number of great friendships. (We ended up moving for a fresh start.)
Though I consciously don't think about these experiences, it is obvious that they continue to impact me as at least one to two times a year I have a dream involving the people involved with each one of the businesses. Every one of these dreams has a basic narrative where I am coming back to the company. The storyline is always the same, the entrance to the company is brutally awkward. I am obviously subconsciously carrying some pretty meaty baggage.
This can't be good.
A few weeks back I was traveling for a long weekend and decided to reach out to one of my former partners in MapQuest who I had not seen in more than 18 years. Back then, he and I were both young, competitive, and driven. We sparred a little. Our sparring probably created some friction between us as well as throughout the organization. Maybe great things happened because of it and if so I am happy for what MapQuest came to be. But I was still carrying some personal baggage.
So we met for drinks and dinner with our wives a few weeks back. We caught ourselves up to date on kids, jobs, startups wins and startup failures. We reminisced about stories remembered and stories forgotten. Turns out we were born about 3 days apart in the same yar which I never knew. It was a fantastic evening.
As my wife and I walked back to the hotel, she remarked that it appeared that a weight had lifted off my shoulders. She added that I might have just slayed one of my dragons. Maybe no more dreams. I hope so.
In the last 15-20 years, I have experienced at least 10-12 of these highly-charged dreams filled with angst about my departure. I wonder how many decisions, strategies, and opportunities were impacted by that baggage. And I wonder now, if I could have released that baggage sooner. It would have been so easy to not reach out - don't we all make those easy decisions every day? Some of this I can probably chalk up to age; the immature crap fades away with time and the more honest stuff seems to come to the surface.
Think how many better days and nights I might have had if I had acted on this sooner.