Hey folks!
Messed anything up lately? Who hasn’t? Today, you can save yourself some heartache and learn from…
My 16 biggest life mistakes.
Mistake #1: Hiring without a process
From 2004 to 2015, my hiring process was driven by my gut.
I’d spend an hour with a candidate, feel my way through the conversation, then trust my intuition and make a hire.
I didn’t check references, I didn’t look at metrics, I didn’t have a candidate funnel figured out… it was the wild west.
Bad hires have cost me millions — and it’s all my fault.
(Next Tuesday, I’ll send you the hiring process I use today. It’s a lot more data-driven!)
Mistake #2: Nickels in front of a steamroller
There are lots of opportunities out there. But some of them are doomed from the start.
In 2009, we started a retail Halloween costume+decor business here in San Antonio. I figured with our fireworks company, I had a pretty good handle on seasonal businesses.
But I didn’t look at the big picture. If I’d really thought it through, I might have seen what’s obvious in hindsight:
Amazon was coming.
There was no way we could match their prices.
I regret starting a company into headwinds.
Mistake #3: Betraying a great boss
Early in my career, I had an amazing boss. He gave me a ton of opportunities and had faith in my abilities.
A few years later, I left his group and another colleague was coming in to take 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.
Loyalty matters. I blew it.
Mistake #4: Letting my appearance go
In 2003, I interviewed with a career-making investment firm. I thought I was a shoo-in.
Later, I learned one of the reasons they passed was that I looked unhealthy.
I had let my weight get away from me, and they read it as a lack of drive, self-awareness, and self-discipline.
Maybe I was that person at the time. I don't know.
But right or wrong, it got my attention.
Mistake #5: Living the life other people wanted me to live
In short, I used to be kind of a wimp.
In 2009, I was a pretty miserable SMB CEO. I was stuck in a grind-it-out, worry-about-details routine with very little room for creativity.
I knew I was more interested and excited about building new things and helping people, but I was a) scared to make the leap and b) bending to people’s expectations of me.
It took me years to find the courage to do what I was put here to do — no matter my fears.
Mistake #6: Not setting goals
Good life goals are quantifiable and challenging.
And that makes them scary.
So up until 2011, I just… didn’t. I figured if I didn’t set goals, I couldn’t miss them.
But life was slipping by one way or another. Looking back on those years, I could have gone further had I been less stubborn.
Mistake #7: Eating at Olive Garden
Never again.
Mistake #8: Getting serious too soon
Leaving college in 1997, I went straight into "adulting." I wish I’d played more.
Of course, that’s easy to say now, decades later.
But that time from 22-25 is when I could and should have been out having crazy adventures. Instead, I was too focused on my career.
Since I would become an entrepreneur, delaying the job wouldn’t have cost me anything.
(Obviously this may not work for more conventional career paths!)
Mistake #9: Not finding and sticking to a “rabbi”
In 1999, I interviewed for a high-powered chief of staff job with a pretty baller entrepreneur early in my career.
But when asked about salary, I made a ridiculously high request.
In retrospect, I should have offered to work for free. What I would have learned would have been worth 10x what I asked in salary.
But I overvalued cash in hand, and undervalued the opportunity to grow.
Dumb.
Mistake #10: Not continuing to learn
I read voraciously until about age 25.
But then, I’m ashamed to admit, I stopped for about 10 years. I wasn’t reading, learning, or searching for ways to improve myself.
I don’t have a good explanation for it. I guess I was just cocky and stupid.
It cost me nearly a decade of suboptimal performance.
Mistake #11: Not stretching
That decade I mentioned, when I let myself go? I lost a ton of my youthful flexibility.
If I’d spent 15 minutes a day limbering up, it would have saved me a ton of knee/back/ankle pain I suffer now.
I thought I was invincible!
Mistake #12: 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.
Our people said I was a bad idea.
I did it anyway.
The thing burned for 3 days.
The dumpster melted, and we had to pay for a new one.
I'm sure I wasn’t listening on many other items, either.
Mistake #13: Not making friends as an adult
I made tons of friends in college.
And when I left in 1997, I expected that I’d just keep making new friends in the working world.
What I didn’t factor in:
It’s easy to make friends when dumped in a dorm with 50 other 18-year-olds without attachments.
And the real world doesn’t work that way — you make friends by pursuing shared interests and activities.
I regret not figuring this out for the longest time.
Mistake #14: Not running away from a bad boss
The worst boss I ever had would constantly badmouth me and blame me when she underperformed.
It was so common I would hear about it from other people in the company.
She stalled my corporate career instantly. I should have quit as soon as I realized she didn’t have my back.
On the positive side, I got some valuable perspective on what not to do as a boss.
Mistake #15: Having a "this could go wrong" mindset
I often have the wrong mindset when it comes to new technologies.
I heard about Bitcoin over 10 years ago, and dismissed it.
I can afford to take some risks. So I should have been asking, “what could go right?”
Mistake #16: Building homogenous teams
In my 30s, I didn't understand that everyone is wired differently.
I’m an ideas person, and I like to talk to idea people. I would get annoyed by detail people.
The result: I built a bunch of teams that talked a lot but got nothing done.
These days, I recognize that different jobs need different kinds of personalities — and a team with variety wins every time.
—
And that’s it!
Each of these mistakes taught me an important lesson, even when it hurt.
But on the bright side, I’ve now gotten all my life mistakes out of the way — so it’s smooth sailing from here on out!
Thanks for reading, and have a great week!
Michael
