The Plan to be a Writer and the Life I Actually Lived

In 2000, I finished an MA in fiction writing at Johns Hopkins University and did the next most logical thing. I built a software company.

The internet was new and exciting at that time, and I had a problem at my nonprofit marketing job that I knew the internet could solve. How do you connect people who care about the same causes and help them act together at scale? An online marketing for nonprofits pioneer named Mark Rovner served on a committee at my nonprofit’s national organisation and he invited me to present my ideas for solving this problem. The result was that I designed an online community platform called FedWeb that is still in use today by hundreds of Jewish Federations across North America.

While I was looking for an agency to build FedWeb, I met Laura Kittleman and Tom Yeatts who had already built out some very effective advocacy and community organising software through their company VirtualSprockets. They asked me to join them. I said yes. They taught me what it meant to be an entrepreneur and I was hooked.

Building a product turned out to require the same things that fiction requires—an instinct for structure, an attention to what value people will get out of what you’ve made, and a willingness to keep revising until it works. I didn’t experience the pivot as a departure. I was still making things that would change people’s lives. I just wasn’t making them out of paragraphs.

What followed was two decades of building technology for social good. VirtualSprockets served the ACLU, Amnesty International, Habitat for Humanity, Feeding America, and others. My next company, Good Done Great, helped Nike, IBM, Marriott, Toyota, and Home Depot manage their philanthropy programs. I have sold every company I have ever built. This is either a business strategy or a character trait, depending on when you ask me.

The satisfaction this work gave me was real. Not the satisfaction of completion, which was always brief, but the satisfaction of making something that moved money and effort toward good work in the world. To date, the companies and nonprofits I founded and supported have helped raise more than $4B in philanthropy and volunteer effort for almost 300,000 nonprofits. That is a more meaningful legacy than I had any right to expect.

The writing kept coming back, every few years, in the gaps between companies. I would return to the page, begin something, feel the pull of a new problem, and set the manuscript down. I attributed this to a natural restlessness in my character and did not examine it further.

I was fifty-three when my doctor told me I had ADHD. Most of the preceding four decades suddenly made more sense. The particular asymmetry I had been living with is not an inability to focus—it is an inability to sustain engagement with something once the hard problem has been solved. Once a product was generating revenue, I needed to move on and find the next unsolved thing. I had spent forty years calling this restlessness, not knowing it had a clinical name. I still remember my mom asking when I was a teenager, “why don’t you ever finish anything?”

Understanding this changed how I read the pattern. A novel needs to be finished in a way a software product doesn’t. There is no version release with a novel, no point at which you have answered the central question and can hand it off to someone else to keep enhancing. I had, without quite knowing it, been circling the one kind of problem I struggled with most, seeing something all the way through to its completed state.

After my last company, I took time off to be with my children and moved to Vancouver with my family. I then came back to professional work as a fractional executive—helping other entrepreneurs through the stages I had already been through. It’s remarkable how many of them had a restlessness similar to mine.

In September 2025, the conditions that had kept me from writing finally changed. My children were older. My wife enjoyed engaging in interests and projects that didn’t always overlap with mine (she will confirm that you don’t want to hear me sing). I was between things in a way I hadn’t been for a long time. I needed something entirely my own, something where the question was mine and the only standard that mattered was my own.

I went back to the 1996 screenplay that became A Frictionless State. Why and how that happened is covered in another essay. I’m not sure I could have written this novel in 2005 or 2015. Understanding how systems fail from the inside, what it costs people to build things that outlast them, what it means to be responsible for decisions that affect lives other than your own—these were things I learned by building companies, not by studying them. The novel needed a person who had done real and difficult things.

David Everett, the director of the writing program at Johns Hopkins, told our cohort that completing the degree would help us, but the only thing any of us actually needed to call ourselves writers was to write. We didn’t need to publish, just to sit down and do the work.

For thirty years, I kept finding other things to build. I don’t regret any of them. But I have now sat down and done the work.

David Everett was right. I just needed a while to take him up on it.

A Frictionless State is free to read, one chapter at a time. Start reading →