Don’t Forget the Pandemic

In every well-laid plan, no matter how carefully orchestrated, there comes a moment when things fall apart. It doesn’t matter how organized, methodical, or well-prepared you are; at some point, the gears grind, the system breaks, and you find yourself in chaos. It could happen at the beginning of a project, the middle, or right near the finish line. But it’s going to happen.

I’ve talked about this idea a lot—how everything breaks at some point and how you need a certain kind of person to handle the fallout when it does. It’s not a matter of if it will break; it’s when. What I didn’t expect was to see this idea hit everyone, all at once, across the entire world when the pandemic hit in 2020.

Before we get to that, let me take you back to a conversation I had in my backyard office, a shipping container I’d turned into a workspace. My friend, Stefan, was hanging out with me that day. Stefan is one of those people I love talking to about my work because, like me, he’s got a DIY background. But unlike me, Stefan spent a good chunk of his life working for Amazon—a company that, on the surface, seems like the ultimate in professional organization, process-driven, and meticulously planned.

Stefan had all the inside stories about Amazon—the wild pivots, Christmas deadlines, the impossible scenario  behind-the-scenes chaos that shaped the company. Despite its reputation for being a hyper-efficient machine, Amazon, like everything else, had its share of battles and scrappy moments. Stefan understood that, and that’s why we connected. He gets the messy side of things, even in the most polished organizations.

We were talking about all this one day when the pandemic was just starting to shut the world down. We were watching the chaos unfold, and I remember Stefan saying something that has stuck with me ever since.

He said, “Darren, the world is living in a broken football play right now.”

And immediately, the image came to mind. A football team running a perfectly orchestrated play—the quarterback drops back, the linemen execute their blocks, the running back gets the handoff, and everyone does their job with military precision. The play goes off without a hitch, and the running back glides through the defense, untouched, for a touchdown.

But then, on the next series, something goes wrong. The ball is fumbled on the snap, and suddenly, everything that was supposed to happen is irrelevant. Chaos erupts. Everyone is running around, scrambling to pick up the ball, improvising as they go. It’s a broken play, and nothing is going according to plan. People freak out. They get scared. No one looks like an expert anymore. Oh, and people are looking to take your head off. 

That, Stefan said, is what the whole world was experiencing when the pandemic hit. “Everyone thought they knew how everything worked, how the game was supposed to be played. And now, the snap’s been fumbled, and they’re all panicking.”

Then he looked at me and said, “Darren, the reason you feel so comfortable right now is because you’ve been living in a world of broken plays for your entire career. This is your world.”

He was right. The more I thought about it, the more I realized that the pandemic had forced everyone into the kind of scenario I’d been navigating my whole life. Everything was upside down, and the so-called professionals, the ones who had everything planned out, didn’t know what to do. Their playbooks were useless now.

But me? I was right at home. The world had entered my world. For the first time in my life everything was falling apart and it wasn’t my fault. It wasn’t one of my plans, ideas, or crazy scenarios that got me in trouble this time. As a matter of fact, it was pretty clear all the “professionals” were the ones that got us in this mess. And now everyone from tech leaders to the medical community didn’t seem so trustworthy anymore. All the respected, grown up, organized, mature leaders were, well, failing. And losing credibility by the minute. 

For years, I’d been the guy who took on the projects that had no clear path to success, the ones where things were already broken or on the verge of falling apart. I never waited for the “perfect” plan because I knew there was no such thing. I never needed everything to be lined up in neat little rows before I started moving. For me, the chaos was where I thrived. I knew how to adapt, how to pivot, how to make something work when all the professionals had thrown their hands in the air.

And suddenly, in 2020, everyone was being forced to live in that space. The pandemic fumbled the snap, and now the whole world was scrambling.

The professionals—the ones who had always relied on their polished processes and carefully planned models—were stuck. They were panicked, confused, trying to figure out what to do next because the game wasn’t following the rules anymore. There was no playbook for this. And here I was, looking around, thinking, Welcome to my world.

It was in the midst of this global broken play that I found the most success I’ve ever had. Everything I’d been saying for years about how things would eventually break, how you had to be prepared to get dirty, to throw out the rulebook, was now validated. The world was learning a hard lesson that I had known all along: nothing stays neat and tidy forever.

The pandemic was the ultimate broken play, and it forced everyone to face the reality that no matter how well-organized you think you are, no matter how many plans you’ve made, eventually, you’ll have to deal with chaos. And when that happens, the question isn’t whether you have the right plan—it’s whether you can adapt in the moment. It’s whether you can handle the dirt, the mess, the scramble.

That’s why, when everything shut down, I didn’t stop. I leaned into it. Because broken plays don’t scare me—they’re where I do my best work.

This chapter isn’t about the pandemic itself. It’s about what the pandemic revealed: that no matter how much you plan, no matter how professional you think you are, the world is going to throw you a curveball. The snap is going to get fumbled. And when it does, the real question is: can you run the broken play? Can you pivot, adapt, and still find a way to get the ball down the field?

In the end, everything breaks. It’s not a matter of if, but when. And when it does, you have to be ready to throw out the playbook and get to work. That’s the reality I’ve been living in for years. It’s a reality the whole world was forced to confront in 2020. And it’s the reality that’s always been at the heart of what I do.

The professionals don’t always see it, but it’s there. Everything breaks, and eventually, everyone has to get a little scrappy. The pandemic just made it impossible to ignore.

So, as you read through this book, keep that in mind: don’t forget the pandemic. It was the moment the whole world got a taste of what it’s like to live in a world where nothing goes according to plan. And for me, it was the moment that everything I had been talking about was laid bare for everyone to see.

Everything breaks. But that’s where the real work begins.