Michael Girdley has tweeted about this as he reached a follower milestone in twitter. Here are my 16 biggest life mistakes. I am 46 years old. I still feel young, but old enough to have real regrets.

Hiring without a process

For the longest time (2004-2015) my hiring process was: Spend an hour w/ candidate->trust my intuition->make hire. No references, No metrics. No funnel. No nothing. Bad hires, especially in leadership spots, have cost me millions. All my fault.

Nickels in front of a steamroller

In 2009, we started a retail Halloween costume+decor business. It gelled with our seasonal fireworks co and seemed good. But e-commerce was coming including Amazon. It failed. I regret starting a company into headwinds.

Betraying a great boss

An early boss was a great guy. He gave me a ton of opportunity and faith. After a few years, I left his group. Another colleague took over my role. That colleague asked me for salary negotiation advice. I gave him info I shouldn’t have. I apologized eventually but I’ve never stopped kicking myself for that one. Loyalty matters. I blew it.

Letting my appearance go

In 2003, I interviewed with a career-making investment firm. I learned one of the reasons they passed was I had let my weight get away from me. My unhealthy appearance sent a message that I lacked drive, self-awareness, and self-discipline. Maybe I was that person at the time. I don’t know. Whether right or wrong — they got my attention.

Living the life other people wanted me to live

Being a wimp In 2009, I was pretty miserable being an SMB CEO. By then, I had realized I needed to be doing more of what I do now. Creating ventures and helping them from a board/investor role. But, I was stuck in a role that was a grind-it-out worry-about-details CEO job without a ton of creativity in the role. It took me years to get past that and to find the courage to do the things I was put on earth to do no matter what I felt others expected of me.

Not goal setting

Up until 2011, I resisted setting big goals. Good life goals are quantifiable and challenging. I was so scared to fail at goals that I just refused to set them. Looking back on those years, I could have gone further had I been less stubborn.

Getting serious too soon

Leaving college in 1997, I regret not playing more before “adulting.” Of course, that’s easy to say now 25 years later. But that time from 22-25 is time I could and should have spent out having crazy adventures. I regret being too focused on my career at that time. Given I’d become an entrepreneur, delaying the real job wouldn’t have cost me anything. I do think kids these days often try to “grow up” too early. But I also understand the pressure they’re under.

Not finding and sticking to a “rabbi”

In 1999, I interviewed for a high-powered chief of staff job early in my career with a pretty baller entrepreneur. When asked for what I wanted in salary, I gave a ridiculously high request. In retrospect, I should have said I’d work for free or even paid them to work in that role. What I would have learned would have been worth 10x what I asked for in salary. Dumb.

Not continually learning

I’m ashamed to admit that I read voraciously up until about age 25. I then went through a 10-year period where I wasn’t reading, learning, and searching for ways to improve myself through learning. I don’t have a good explanation for it. It cost me nearly a decade of suboptimal performance. I was just cocky and stupid. (Now I’m just less cocky and less stupid though, I think!)

Not stretching

As I mentioned earlier, I went through a decade from 1999-2009 where I let myself go and my youthful flexibility declined. I regret not spending 15 minutes a day limbering up. It would have saved me a ton of knee/back/ankle pain that I suffer now.

Starting a dumpster fire

In 2006, I was CEO of our family business. I got the great idea that we could save money by burning a bunch of excess cardboard inside of our dumpster. We set it on fire. The thing burned for 3 days. Melted the dumpster. We had to pay for a new one. It wasn’t so smart. I should have listened to our people. I’m sure I was also not listening on plenty of other items as well at this time.

Not using activities as a way to make friends

Leaving college in 1997, I expected the adult world to be easy like college with regards to making friends. It’s easy to make friends when dumped in a dorm with 50 other 18-year-olds with no attachments. Well, the real world doesn’t work that way. You make friends over shared interests and activities. I regret not figuring this out for the longest time.

Not running away from a bad boss

In my corporate career in 2002, I went from that great boss to a terrible one. This person would badmouth/blame me when s/he underperformed. It was so common that I would hear about it from others. On the positive side, I learned from this boss what not to do. On the negative side, a boss like that will stall your corporate career instantly by destroying your reputation. I regret not quitting on this boss the first time that I learned she didn’t have my back.

Having a “what could go wrong” mindset with lots of things, including crypto

I regret having the wrong mindset with regard to new technologies too often. It should be “what could go right?” I heard about BTC 10 years ago. I stupidly dismissed it.

Building homogenous teams In my 30s as a leader, I didn’t get that every person is wired differently

I would get annoyed by detailed people. Because I like to talk to idea people. So, I’d build teams that had lots of ideas but got nothing done.

Written by Michael Girdley

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