Sometimes I find myself stuck in the thought-trap that I am behind everyone else; I had opportunities in my twenties to follow a lucrative career path, to get married, to take a more "traditional" path. I did not take that path. And, approaching 40, I have paired down my possessions, traveled much of the world, and am engaged in work that is meaningful, but not money-making. The Torah tells us to be fruitful and multiply and this is what my Jewish grandmother hopes and asks of me. Should I have taken a different path?
-Obsessed Over Path Not Taken
Dear Path Not Taken,
I can’t know; no one - including you - can know what would have happened had you chosen a different path for yourself. I do believe that obsessing over “shoulds” is a trap, and that breaking away from this type of thinking will be good for you, whatever path you choose now.
There was a period of time, a few years ago, when I had a panic around sleep. I felt anxiety entering the separation from my baby girl that nighttime brought, and I did not want to surrender to the bizarre world of dreams.
I often have reoccurring dreams - featuring the same friend with whom I had a bad falling out, or a former boss I had disappointed. While revisiting these relationships- and my own fault in them - isn’t something I look forward to, I have come to appreciate how my unconscious tackles these unresolved scenarios in sleep, freeing me to deal with my actual relationships - in present time, in my waking life.
Another place where I get to inhabit such regrets is my creative work, a space that can hold an unlimited number of paths.
You have seen much of the world and are engaged in meaningful work; this is tremendous! (And something that many of the people who you feel “behind” may not have done) You have paired down the items that you don’t need: Add your regrets of the life un-lived to your discard pile.
If you have regrets about your thoughts or actions, take these days of awe and repentance to try to make amends. Then move forward in your actual life which sounds like it is already filled with great blessings and intentionality.
The lessons learned from regret are paid forward.
We are on the cusp of a New Year, and I do not believe it is one in which your Jewish grandmother wants you to torment yourself!
Pray for the things that you want to fill your life with, and point your heart in that direction.
All of my favorite writers published their best works after age 40 - many of them, their first work. And our prophets, too, found at this life-stage they were able to meet and overcome their greatest trials.
I hope that you are blessed to live to 120, but you can make today meaningful by living now.