I am 20 years younger than my father and he is 20 years younger than his father. It’s one of those strange coincidences of life but one that makes it easy for me to visualize my future self and ask a very important question.
When I am my Dad’s age what will I wish I had done when I was the age I am now? When I’m my Grandfather’s age will I be proud of the life I am living or will I wish I had lived my time here on Earth a differently?
The other day my friend Gary Vaynerchuk posted the following photo of a quote he gave during an interview. He called it “A (by accident) Manifesto”
The fact that Gary mentioned “Why didn’t I go to Austin?” in his quote lit a fire under me to share my thoughts on the topic. Note: I moved to Austin in 2011.
Shortly after my son, ShortMan as he’s known on the interwebs, was born I remember saying to myself that someday I am going to tell this little boy that he can do anything in life. And then I made a decision that I would do my best to lead by example. It was at that very moment that I decided to pursue my dreams of becoming and entrepreneur. I hated working at a big corporation and wanted to create something of my own.
My wife, being as amazing as she is, when I talked to her about my ambition to do more than just work at a big company told me that I should do it. In her words she said “I’m more afraid of you looking back when you are 60 and regretting the life you lived.”
So, was it a Disney fairytale from that moment on? Hell no!
In typical entrepreneurial fashion it has been a roller coaster ride of epic highs and despondent lows followed by new highs and more lows and so on. I was lucky enough to be at the forefront of the social media revolution and count many phenomenal entrepreneurs and thought leaders as friends. However, I also ran completely out of cash at one point and was literally reduced to tears a couple of times over the past 7 years. Looking back on it now and looking ahead to when I am 61 or 81 I know I’ve chosen wisely to live life like it’s an adventure.
Very few people will have the courage to do what I have done and what my family has done. Most people as Thoreau said “lead a life of quiet desperation.” And for conquering those fears I am very proud of myself and my family.
I decided to write this post not to brag or urge you to follow in my footsteps and quit your job. I wrote it to remind you, and continue to remind myself, that the future, older you would give anything to be the younger you again.
If you have trouble visualizing what is possible ask someone who is 10, 20, 30 or 40 years older than you what he or she would do if they were your age again.