May 2026: The same lesson at different ages.

I’ve been turning 43 over and over in my head for weeks. Maybe it’s the 15-month-old who’ll see me almost 70 by the time he’s off the payroll. Maybe it’s the daily death-defying stunt of walking down the stairs. Maybe it’s the harsh realization that I’m no longer the young, ambitious professional I once was, and not just some mid-career guy either. Whatever it is, it’s hitting hard.

So I’ve been taking a look back at the non-linear path that got me from the Class of ‘00 to Head of Strategy and Modernization at The Select Group. That’s the theme of this month’s newsletter: looking back to understand the path forward.

Enjoy.
-AM

Anger fueled motivation.

I spent most of high school caught between the things I was interested in (motocross, BMX, writing code) and a string of teachers and counselors telling me I was too dumb to carry lumber on a job site. Seriously. That is what my HS guidance counselor told me. A lot of kids I grew up with never reached their potential because they believed what those people said. Me, it pissed me off.

By the time my Pennsylvania-mandated Senior Project came around, I had a chip on my shoulder, and it stayed there for a lot of years.

By the time I graduated I had already built one startup (16327Online, a dial-up internet service provider and web design studio), was building my second (Carzz, a platform that let auto dealers manage inventory on their websites), and was running an early motocross eZine with my friend Grant called MotoXtreme.com.

This phase took me through Edinboro University, 18 months in Phoenix, and a summer in Minneapolis. It taught me that anger can be a powerful motivating force, and that nobody can or should put limitations on what you’re capable of. Most importantly, that you should never put limits on yourself.

Skipped: the car business, cross-country roadtrips, lifelong friends.

Nobody is coming to save you.

After Minneapolis I went back to Pennsylvania to help my dad get ready to sell my childhood home. By then I’d made an exit from Carzz and was struggling with what to do next.

I distinctly remember sitting in church one Sunday, and the moment I asked God for a sign of what should be next, a vivid image popped into my head: US Army. I signed the contract that Thursday.

The next several years were an intense motion of training, train-up, and deployment that didn’t slow down until I was sitting in a hospital bed in Baghdad following a failed assassination attempt.

In about two hours I had gone from a man with a purpose and friends to being absolutely alone. I came home alone. I recovered alone.

It was in the months following my injury that I realized nobody owed me anything. If I wanted to get through what I was facing, the only person I could count on was myself. I had to reinvent. That’s a lesson I carry to this day: you are responsible for your circumstances, and only you can change them.

Skipped: homelessness, fuzzy nights in Savannah, managing up.

It’s not what you know, it’s who trusts you.

Facing medical retirement in Savannah with a new mortgage, I had a fast-approaching deadline to figure out “what’s next?” I went back to the only other thing I knew: software.

To this day I’ll never know why the recruiter from VeriSign pulled my thin resume from the stack, but I’m glad she did. I interviewed with Bill Holliday and Doug Winters, and the offer Bill made me saved my life. It was my path out of the dark hole I was in, and the beginning of an interesting non-linear career.

Engineer, to engineering manager, to consulting company founder, to Global Product Lead of Military and Law Enforcement at Under Armour (that’s still a WTF moment for me, but the most culturally significant part of my career). The seven years following the moment life slowed down in that Baghdad hospital bed were a whirlwind of people, relationships, and learning.

The most important takeaway from the first time I met Bill, until Adam Silva introduced me to Brian Offutt and Kip Fulks at Under Armour, was this: it’s not what you know, it’s who trusts you. If people trust you to perform with integrity, they will give you an opportunity.

Skipped: lessons in real estate, fashion boutiques, boat ownership, early online dating.

Trust and influence open doors.

After the Under Armour detour I went back to building and back to consulting. This time, things looked a little different. Based in Nashville, I served as a Product and Technology consultant and built a pretty good practice. One thing led to another and I found myself in a series of rollups: Davisbase Consulting, SolutionsIQ, eventually Accenture. I finally got off the acquisition bus through an invitation from Scaled Agile.

During this 12-year phase I helped a lot of companies solve some very big problems, helped others find themselves professionally and build amazing careers, and found my footing as a technology thought leader and speaker.

How did a kid who was too dumb to carry lumber on a job site end up keynoting a technology conference in Paris? When you push yourself, put yourself out there, and consistently deliver what you promise, you build a reputation. The reputation builds trust. The trust gives you influence. And influence is what opens the doors you couldn’t have knocked on yourself.

“Earn it everyday.” Maybe I had a hunch.

Skipped: trail running, when PE comes to town, international (business)man of mystery.

Family is all that matters.

Through all of this I have made no mention of relationships or family. That’s because through all of the learning and growth I outlined, I was absolutely horrible at personal relationships. Probably the worst you’ve ever seen. I was so busy trying to prove myself that if anyone stood in the way of the path forward, I ruthlessly cut them from my life.

Jenelle helped change that pattern. She has been my rock, partner, and best friend over the last 9 years. What made it work in the early years was that while building our relationship, we maintained our independent trajectories.

COVID brought us to Raleigh, and things started to shift. We became much less focused on what we wanted as individuals and much more focused on what we wanted as a couple, and as a legacy. We lost our little girl in early 2023, and the grief was the first thing in 20 years that I could not outwork. Through a ton of very hard work medically and emotionally, we welcomed Ford Michael into our family in February 2025, and everything changed.

After Ford was born I went almost immediately on an 8-month rotation of international travel. The travel that had previously made me feel alive was now weighing heavy on my heart. By the time October and my sabbatical came around, I knew I had to make a change. The stress and the travel were no longer “it,” and for the first time in my professional career I didn’t have a plan or a path. And that was ok.

I jumped without looking, because nothing mattered more than Jenelle and Ford.

Skipped: Family vacations, a cycling venture, too many cars.

Looking back to look ahead.

Thank you for entertaining the thought experiment, and thank you for making it this far.

The five lessons I pulled out walking through these 20 years are not separate lessons. They are the same lesson at different ages.

The chip on my shoulder taught me not to let other people define what I’m capable of. Baghdad taught me not to wait for anyone to save me. VeriSign taught me that trust is currency. Nashville taught me that trust compounds into influence. Jenelle and Ford taught me what all of it is for.

You are the only person who gets to decide what your life is in service of. Nobody is going to hand you a plan, and nobody is coming to tell you that you’ve earned it. Nobody owes you the next opportunity. And once you accept that, the freedom on the other side is the whole point.

My goal from here is simple: I want Ford to know that his mom and dad always have his back. I want him to make all new mistakes, not the ones I already made for him. I want him to understand what it means to be free, and how to earn it. And I want to be there, every time, when he calls.

Everything I do professionally from here serves that goal.

Cheers!
-AM