Last January, I went skiing with three friends to Jackson Hole, Wyoming. It was an amazing trip and one of my favorite mountains I’ve ever visited.
It didn’t hurt that Wyoming is home of the Walt Longmire books, the best mystery series I’ve read in years. It was my first time to the state and worth the trouble of getting there from Nashville. (Our flight was cancelled and we had to rent a car for the five hour drive over the snow covered Teton pass at midnight.)
One afternoon, while riding up in the gondola, we met a young woman who was on a ski adventure. She and her friends were driving between some of the best mountains in the West. They hit Alta, Snowbird, Big Sky and Jackson Hole. She was in her late 20s and seemed to be having the time of her life.
While talking to her, a thought hit me, “I wish I had been that in touch with the things I loved doing when I was 27.”
I didn’t have a whole lot of self-awareness when I was 27. I didn’t know what type of things I really liked and I certainly didn’t invest time or money in them. It’s taken me decades to figure out what I like doing. I never would have had the courage to organize a six-day ski trip through the west when I was in my 20s.
During moments like that, I usually feel discouraged. It’s like hearing how great compound interest is if you start investing when you are 18. That’s amazing information unless you’re 38 years old and then you feel like it’s way too late for you.
But this time, instead of thinking, “I wish I had gone on an adventure when I was 27,” I thought, “What would the 53-year-old me wish the 43-year-old me had done?”
Wishing you had done something when you were younger causes regret.
Wondering what the future you will wish you had done causes wonderment.
Ten years from now, what will the older you wish the younger you had done?
Is it a trip you’ve always wanted to go on?
Is it investing more in relationships?
Is it making a list of the skills you wish your parents had taught you and then deliberately teaching them to your own kids?
Is it finally writing that book?
Is it moving to Colorado? Or Montana? Or Manhattan?
Think you don’t have enough time?
You’ve got ten years to accomplish it.
Don’t look back in regret.
Look forward in hope.
It makes life a whole lot more enjoyable.
P.S. Ask the 10-year question and then read this.