I zipped up my backpack. My folded uniform inside was left unwashed with everything still in my pockets. As if I had just vanished out of it one day and it remained as a time capsule of that exact moment, that sheer break in my life where I was living in a post-dream world. A world where my biggest accomplishment was behind me and a new civilian life was what I had left.

This was made much more potent by the simultaneous divorce I was in. But on the bright side, the Army made sure that I had a great LinkedIn page that said I was a “Manager” that could “remain calm in high-pressure situations” and they set me off to find a new identity.

This was indeed a high-pressure situation. No education, no connections, and really the only skills I had were walking with a big rucksack and shooting you from the next postcode. I was pretty good at waiting in line for days on end for any reason (or no reason at all) and I had things I was interested in… but that was it. No marriage, no uniform, no purpose, no future. Remain calm, like my LinkedIn said.

So, when entering a new area, you do a Recce, right?

I sold the little I had and travelled the world on a shoestring. Thailand, Australia, Cambodia, Germany, I went to as many places and met as many people as I could. I learned about as many walks of life as I could find and tried as many jobs as I could get into and established a left and right limit of what I could do to give myself a life I wanted. After a year I realized I liked to work with my hands and I liked to make decisions. I learned that.

And if you can see it… you can shoot it, right?

Back in America I knew I had a lot to learn, and it would be guided by those two things. So, I started finding and scoring targets. “What company could I infiltrate to learn as much as possible, as quickly as possible, to catch up with the other men my age?” then I would break the trigger on those roles.

And so it began and continues to this day, 12 years later.

I would continuously select companies and roles that could teach me what I needed. One step at a time, but never knowing 2 steps ahead. The knowledge I gained in each role informed the needs of the next role resulting in a ruthless OODA loop of self-inflicted psychological trauma with very little safety net and no defined end point. A summitless mountain. But I was pretty used to it after my upbringing.

I was into extreme sports - flying parachutes and wingsuits and scuba diving in caves - you name it. I was used to pushing through physical pain, thinking through frustration, setting my own goals, assessing my own risk. It was these soft skills, these personality traits, that helped me persevere.

It wasn't anything relating to college - I didn't go. It wasn't professional military education - I didn't have one. It wasn't connections - I didn't know anyone. It wasn't money - I made $2.10 an hour before I joined the Army and only a bit more while I was in.

It was, and still is, entirely down to a single solution to a universal problem:

You can pick your pain.

But (1) how intense you make it + (2) how long you can stand it = your level of success.

You Pick Your Pain

In this world everything hurts. Sitting at a desk all day kills the spirit of an adventurous man. Plumbing a toilet kills the spirit of a proud man. Excel spreadsheets kill the spirit of a creative person (and me). Everything we do has an innate and unique pain that must be dealt with in a healthy way if you want to do it for any period of time. But the good news is that - you get to choose what pain you get. 

How Long Can You Bear That Pain?

So you have chosen your pain, now you must nurture it and bear it. Nurture it by making it as excruciating as you can and bear it by balancing that intensity with duration. Just like shooting - learn the fundamentals slowly and painfully. Dry fire your rifle standing while your shoulders burn every day for as long as you can without skipping a day. Focus on trigger squeeze. Sight Picture. Do it tired, do it hungry, put your hands in an ice bucket and do it stiff. Take the rifle apart and study every piece. Put it together and feel the levers and springs move as the trigger breaks - with gloves on. Then go to the range and shoot with no sights. Earn every single mod on your rifle, on your person, and in your life. 

How do we apply this to a non-military role, though? Something less tactical and more cerebral?

My Pain as an Example:

The pain I chose was simple - I am always the dumbest man in the room. But pain comes in two metrics, and the balance of intensity and duration has many factors, some outside of your control. So what situations can I put myself in where I absolutely maximize the knowledge disparity between me and every other person? How long can I keep that up before I get fired or something breaks inside of me? 

I talked my way into the right jobs, but places I had no right to be in. I started out as a mechanic who had never fixed a car. While I was there, I learned to fix a car. Then I ran a service program for a big OEM when I had never done program management in my life. While I was there, I learned how to do it. Then I led commercial strategy for a huge autonomy company with 2 MBA interns working for me - I learned how to lead that. I let each of these roles guide the next role and I never told a lie to get in the door; I just made friends who believed in my potential.

But the most insidious part of this pain is that every single day you feel like shit. Every single conversation you are on the back foot. You are never right. In every human interaction you recognize you are lower on the totem. You are always asking the questions, putting out lower quality work than your peers, and you are never celebrated, promoted, or acknowledged because you are punching way above your weight.

But… if you can stand that consistent rejection… You get smarter faster than anyone who came from a place you did. The longer you can stand it the higher your velocity up the ranks.

And when you look up from your work. When you take a second and look at how far you have come… you remember why that pain is worth pushing through.

My biggest accomplishment wasn't the Army and I don't know what it will be. But I know I probably won’t recognize it when it comes, because I’ll be working on the next one.

So what pain will you choose? How long can you stand it? You can have the whole world if you want it, you just have to want it bad enough.

The Salty Rolex, 2x Defense Tech Founder/CEO, 4x Unicorns, Army Infantry, Highschool Dropout.

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