In 2015, I was a relatively green young tech salesman at a software company called NationBuilder. Our company's vision was grand and our community was tight-knit, but the numbers just weren't lining up. The company was in deep trouble. On a devastating spring morning, our CEO made an announcement that would change our trajectory for years to come.

He had decided to lay off about 40% of the company's workforce, he said. The decision didn't come easily - he was welling up with tears and shaking as he spoke. But he had no choice: if he didn't, the company surely wouldn't survive. By lunch, nearly one hundred employees - close friends and dear colleagues - were out of work. The remaining staff and those recently departed collectively shut down the office and wandered down the street in a daze to a dingy Irish pub.

This thing happens when compassionate first-time CEOs lead their companies through "war-time" operations: when they need to cut employees, they're often reluctant to cut deep enough. And so, often, they need to cut again. About two months after our first layoff, we found ourselves axing another 10% of the company.

I was still employed. But, still, I wandered back to my desk to pack my things and join my former colleagues at that same Irish pub down the street.

As I packed my backpack, I watched as a colleague, friend and mentor grabbed his laptop and shuffled into a conference room, headset around his neck.

"Ryan, you coming?" I asked.

He hesitated for a moment.

"I know it might sound insensitive," he mumbled, "But I really need to work."

I wasn't quite sure what to say. It did sound insensitive, to my ear anyway. He saw my face tense, and I think he saw the inner mechanics of my confusion grinding away.

"I have two proposals to write," he said. "I'm going on paternity leave soon, and as bad as it sounds, the office is quiet right now. I need to take advantage."

I rubbed my neck, threw my bag over my shoulder and walked out the door.

I had plenty of respect for Ryan. He had proven time and again to be an empathetic, compassionate and thoughtful colleague and friend. There was no reason to believe he had changed as a person. I wasn't quite sure what I was missing.

Almost exactly five years later, in the spring of 2020, the world collapsed.

By my own design, I was unemployed when Coronavirus struck. I had left my job at NationBuilder in July of 2019 when the company had finally secured more firm footing after a turbulent, exhausting five years. I boarded an airplane to Colombia with a one-way ticket. "Six months," I told myself. "And then I'll be refreshed and ready for my next professional step."

In early 2020, I was refreshed. I was treating applications like a full-time job: reconnecting with my network that I let erode during the prior six months, requesting introductions and applying for gigs. I actually received two offers. I declined them both - they didn't quite feel right, though I didn't know why. Anyway, I had more in the hopper and other opportunities brewing.

And then the virus hit and the phone stopped ringing. Follow-up emails went ignored. I was ghosted more in March of 2020 than a catfish on Tinder has been ghosted in their entire life.

I banged my head against a wall for most of March and April. The whole world seemed to be doing the exact same thing. Everyone was confused. Everyone was cooped up on their couch in a haze.

But then I remembered that moment with Ryan in 2015. There's opportunity in this moment.

And, here I am, declaring that May and June of 2020 were the most productive, important months of my life. And it sounds insensitive and terrible. But there was an opportunity created in what I couldn't do. I could apply for jobs all day, but the fact of the matter was that the jobs for which I was qualified - the ones I truly wanted - simply didn't exist. And, fortunately, I still had enough money in the bank to pivot.

So I started writing. Nonstop. For ten or twelve or fourteen hours a day. What else was I going to do?

And then I realized my laptop came with this silly pre-installed application called GarageBand that I had literally never opened. And then I realized that people were craving stories about human connection and adventure. And that there was this huge open space on the world's creative canvas. And, and, and.

It all started with that moment of recognition - the realization that there is truly opportunity in life's tense, difficult moments. It may sound insensitive and it is, to a degree. After all, the opportunity available to me wasn't available to those without the means to survive without a steady gig. But from pain comes growth, and from the little nooks and crannies in difficult experiences lives opportunity, if you're creative enough to seize it.

It wasn't easy. Every third or fourth day I'd poke my head up and wonder: what the hell am I doing? It took commitment and an unwavering dedication to the choice I made.

But here we are, at the very beginning of 2021, and I regret nothing about my 2020. I've launched the Baggage Claim podcast, I'm building and growing an audience, and I'm spending all day, every day doing the two things I love most: building relationships and telling stories about the human condition.

Finding opportunity in life's dark moments takes courage and creativity. Or, if you're me, it takes remembering one odd, destabilizing interaction with a person you respect in a dark, unforgettable time.


This website doesn't exist to sell you anything. I just enjoy telling stories about humans, interactions and travel. If you're in the United States or Canada, text CONNECT to (332) 877-9540 to stay connected. If not, click here.

Will Conway


Former political software guy. Now a traveler and adventurer, which isn't a job, and host of the @heybaggageclaim podcast, which really isn't either. Travel stories no one tells.