Our Last Three Months: Late Nights and Calloused Minds

It was February 19, and the snow came early. I was supposed to be in the middle of New Jersey for a client strategy session in two days, but with this weather it wasn’t looking good. Weeks before I had decided to take the trip by car since there weren’t any quick flight options from Richmond.

That decision didn’t seem so smart now, as I only had 30-minutes to gather my stuff and hit the road a day early to avoid the oncoming ice and snow. I made it to the hotel by 1:15 AM and settled in to eat the vegan takeout food that I had picked up in Philadelphia. A dream realized.

This is the story of our last three months.

I promised that we would write a series of quarterly updates to let you know how things are going over here at The Impossible Company. This is the second in that series. And that trip to Ewing, New Jersey really does sum it up well. Because when I took that trip, I was shot. The weekends and weekdays started to blur, the hours of operation felt more like a 7-Eleven, and no number of advanced degrees could get QuickBooks to do what we needed it to.

Of course, this is a great news story at its heart. There was paying work! Our first project was a brand and website for a really exciting new consulting firm in Singapore (more on that later). Then we started another story-powered branding project for a new company looking to expand healthcare access in rural America. Add in a few keynotes, strategy sessions, and short-term storytelling projects, and we ended up with a pretty good quarter. And for that, we are completely grateful.

But nobody can escape ‘The Struggle’.

In Ben Horowitz’s book, “The Hard Thing About Hard Things,” he outlines an array of advice and insights for aspiring entrepreneurs. Central among them is the concept of The Struggle. Essentially, it’s the idea that no matter how successful your young company is, you will face a number of challenges that leave you questioning why you started the company in the first place. It’s the lost proposals, lack of time, cash constraints, red-eye flights, late nights, and lessons learned the hard way. Horowitz sees it as the rite of passage for any new venture.

When I read that book just after we launched, I didn’t really think much of it. I just wanted to put my head down and do good work. But the pace these last three months gave us a taste. It taught us that the struggle is indeed real. That when you go all in and obliterate the line between your work and life, you will run out of gas at some point. And when you do, you will question everything.

For me, it all hit in that hotel room in New Jersey. Watching the snow fall and melt on the glass roof of an aging indoor pool, I asked myself why I was working so hard, and what exactly I was doing with my life. That’s when I remembered a story from 15 years before.

On the calloused mind.

When I was 22-years-old, I started a graduate program in mathematics. If you walk the halls of any math department, you will find two types of people. The first are savants. Those who can effortlessly derive elegant solutions to most any problem.

That wasn’t me.

The others are more grit than genius. Blue collar types who work late nights just to try to keep up. This was me.

After a very long night working a proof, I came in to the lounge an hour before class to find a colleague just starting his assignment. He opened the book, sat quietly for a few minutes, and then wrote down the correct proof. My all-nighter was his 20-minutes.

It was devastating.

So, I went to find my mentor professor to tell him that I didn’t think I had what it took to be a mathematician. I walked him through my struggles, telling him that there was no way that I could be the one to discover new truths in mathematics.

He smiled, and gave me advice that would change my life. He said, “Matt, you have been given a gift today. Every mathematician hits this wall that you just did. It’s the edge of your ability. But every great breakthrough is on the other side of that wall. So, the real secret to success is not in being a savant, but in the struggle. It’s in the calloused mind.”

And that’s just it.

I could tell you that the company is good, pipeline is strong, and that the work is fun to do. That we are starting to find more balance, and a more efficient and sustainable operating rhythm is taking shape. It’s all true. But that’s not the whole story.

Because when we take leaps, set bold goals, and go all in, we should know that the path is not paved by our impossible dreams. It’s paved by the calloused mind.

Thank you for a great three months.

Onward to the other side,



If you like this one, you can subscribe to the weekly newsletter below.