My 16 Biggest Life Mistakes

Here are my 16 biggest life mistakes.

I am 48 years old.

I still feel young, but old enough to have real regrets.

A thread:

— Michael Girdley (@girdley) June 3, 2023

** Betraying a great boss.

An early boss was a great guy.

He gave me a ton of opportunities and faith.

After a few years, I left his group.

Another colleague took over my role.

— Michael Girdley (@girdley) June 3, 2023

(cont'd)

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.

— Michael Girdley (@girdley) June 3, 2023

** 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.

(cont'd)

— Michael Girdley (@girdley) June 3, 2023

My unhealthy appearance messaged 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.

— Michael Girdley (@girdley) June 3, 2023

** 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.

— Michael Girdley (@girdley) June 3, 2023

(cont'd)

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 position.

It took me years to get past that and find the courage to do what I was put on earth to do — no matter what I felt others expected of me.

— Michael Girdley (@girdley) June 3, 2023

** Not goal setting.

Up until 2011, I resisted setting big goals.

Good life goals are quantifiable and challenging.

I was so scared to fail that I just refused to set them.

Looking back on those years, I could have gone further had I been less stubborn.

— Michael Girdley (@girdley) June 3, 2023

** Eating at Applebee's.

OK, this one was too easy.

I went there once.

Never again.

(Sorry, @chilis. I’ll never betray you again.)

— Michael Girdley (@girdley) June 3, 2023

** 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.

— Michael Girdley (@girdley) June 3, 2023

(cont'd)

I regret being too focused on my career at that time.

Since I would become an entrepreneur, delaying the job wouldn’t have cost me anything.

I think kids often try to “grow up” too early.

But I also understand the pressure they’re under.

— Michael Girdley (@girdley) June 3, 2023

** 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.

When asked what I wanted in salary, I made a ridiculously high request.

— Michael Girdley (@girdley) June 3, 2023

(cont'd)

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.

— Michael Girdley (@girdley) June 3, 2023

** Not continually learning.

I’m ashamed to admit that I read voraciously 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.

— Michael Girdley (@girdley) June 3, 2023

It cost me nearly a decade of suboptimal performance.

I was just cocky and stupid.

(Not cured, but I think I’m less cocky and stupid!)

— Michael Girdley (@girdley) June 3, 2023

** Not stretching.

As I mentioned, 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 I suffer now.

— Michael Girdley (@girdley) June 3, 2023

** 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.

— Michael Girdley (@girdley) June 3, 2023

(cont'd)

The thing burned for 3 days.

Melted the dumpster.

We had to pay for a new one.

It wasn’t so bright. I should have listened to our people.

I'm sure I wasn’t listening on many other items, either.

— Michael Girdley (@girdley) June 3, 2023

** Not using activities as a way to make friends.

Leaving college in 1997, I expected to make friends in the adult world as quickly as I did in college.

It’s easy to make friends when dumped in a dorm with 50 other 18-year-olds without attachments.

— Michael Girdley (@girdley) June 3, 2023

(cont'd)

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.

— Michael Girdley (@girdley) June 3, 2023

** Not running away from a bad boss.

I moved from under a great boss to a terrible one in my corporate career.

This person would badmouth/blame me when s/he underperformed.

It was so common that I would hear about it from others.

— Michael Girdley (@girdley) June 3, 2023

On the positive side, I learned from this boss what not to do.

On the negative side, a boss like that can stall your corporate career instantly.

I regret not quitting on this boss the first time I learned s/he didn't have my back.

— Michael Girdley (@girdley) June 3, 2023

** Having a "what could go wrong" mindset with many things, including crypto.

I regret having the wrong mindset about new technologies too often.

It should be “what could go right?”

I heard about BTC 10 years ago.

I stupidly dismissed it.

— Michael Girdley (@girdley) June 3, 2023

** Building homogenous teams

In my 30s, I didn't understand that everyone 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.

— Michael Girdley (@girdley) June 3, 2023

tl;dr:

I'm 48.

I have a ton of regrets and mistakes that I've made.

Thanks for listening.

This was one of the most challenging posts I've written on here.

I hope it helps some folks.

(If you want more stuff like this, give me a like+RT+follow, thanks!) https://t.co/RfZK5Yov0z

— Michael Girdley (@girdley) June 3, 2023