I consider 35 to be a significant age. I’ve now done some things, accomplished some things, and seriously f-ed up some things as well. For that reason, I now feel qualified to make this list. Here are the 5 biggest mistakes I’ve made in my life (so far).
#5: Not Going Back to School
After college I worked at an education technology start up called TeleParent Educational Systems after college, eventually becoming the CFO and raising over $2 million in debt and equity capital for the business. I left after a couple years, realizing that my real passion was for design and online business development.
What I should have done was go back to school to learn the skills I needed to grow an online business. I had money coming in from accrued payroll, no kids, and no job. Instead of just going back to get another degree or technical certification, I taught myself the skills necessary to build websites and online businesses, making mistakes throughout the process. Yes, I now know how to do it, but taking a couple years in formal training would have sped up the process significantly.
#4: Not Traveling More When I Was Younger
This is a common regret, but it’s worth stating. Time seems so short when you’re young. I was hustling when I should have been experiencing. I hear people in their 20’s talking about having “no time” because of school or a job, and I want to slap them (not literally, but kind of).
Once kids and real responsibilities really hit, you find out what “not having time” really needs. I now try to wake up at 4am every day because I literally NEED TO to keep up, and even then it’s tough. Travel is something I need to plan 6 to 12 months+ in advance.
#3: Selling My First Successful Business
I wrote a whole article about selling my first business, but here is the gist of it. My goal was to sell a business since I was in high school. What I realized after selling was that the hard part of building the business was getting it rolling in the first place. Instead of cashing in on the growth and propelling the business to bigger and better places, I sold it. Lesson learned. Now I work on long term growth.
#2: Not Giving Enough F’s in General
I was a sensitive kid. I remember growing up and being impacted emotionally by almost everything that occurred in my life. My son Declan is the same way. He loves people and his family and his toys and writing and drawing and a million other things. I love that about him and it reminds me how I used to be. A big, sensitive goofball.
I haven’t been like that in a long, long time. As I grew older I built a thicker skin. I got tougher, more cynical, and more reclusive. People were not something I enjoyed, they were things I misunderstood and feared. For that reason, I discounted personal relationships and ultimately exacerbated the problem.
The purpose of this “hardening” was to desensitize myself to emotions I didn’t want to feel. The problem is that emotions don’t work that way. When you deaden yourself to one emotion (like dread, sadness, regret, fear, etc), you deaden yourself to ALL emotions. There are so many good emotions… love, passion, commitment, excitement, encouragement, gratitude, happiness, hope, interest, amusement, etc.
So, I’m going to stop being so closed off… hence this article ;)
#1: Marrying My High School Sweet Heart (Now My Ex-Wife)
Everyone says not to do this for good reason. You’re not mature enough (or possibly lucky enough) to meet your life-long partner in HIGH SCHOOL. I actually knew this, but was too stubborn to admit it.
It ended long before the 10 years that we spent “together” did. Turns out she was cheating on me and actually had a BOYFRIEND for 7 of the 10 years. Some may say that I was stupid not to realize and do something about this, but the truth is a little worse; I was too principled and disciplined to find the proof of the cheating, and instead relied on straight-forward questioning when I was suspicious of her cheating. She would say “no” and I would accept it because she was my wife and that’s what I believed was right. I was wrong.
The implosion that followed the break-up was very rough. I not only questioned my intelligence for wasting 10 years of my life with a devious and terrible person, I questioned my core principles, faith, and overall life objectives. I’m fully recovered now, but being with such a POS for any amount of time was definitely the biggest mistake I made in my life.
Even so, such a bad relationship makes me appreciate my current marriage that much more. My wife Jamie, the mother of my sons Damien and Declan, is an incredible person that showed me how a good marriage really looks like and feels.
