The Road Not Taken

James Kerr

LAST MONTH MARKED two years since I leapt into the unknown and left the security of the corporate world to begin a second act as an independent writer. How’s it gone? Have things panned out as I hoped, financially and otherwise? 

Let’s be clear upfront that this move was never about making money. It was about taking a shot at my long-held dream of being an author. I’d put that dream on the back burner for three decades as I did what was necessary to support my family. Now, with my kids out of college and some savings in my pocket, I wanted to take a chance on myself before I ran out of time. I didn’t want to get to the end of my life and find I’d never taken a shot at living life on my own terms. 

Two years later, I’ve achieved things that money can’t buy:

  • Seeing my first book in print and my blog gain a dedicated following
  • Going to book signings and readings, and interacting with readers and followers
  • Spending my days pursuing my passions rather than managing emails and responding to the latest corporate fire drill
  • Having the chance to travel and spend precious time with my kids, including camping for an entire month under the big skies of Colorado, where my middle son lives.

It’s safe to say I wouldn’t have been able to do any of these things if I was still running 12 hours a day on the corporate hamster wheel. But I’d be fooling myself if I said that all these things didn’t come at a price. I haven’t made a penny on my book, which is still earning back its upfront costs for the publisher, or on my blog, which is ad- and subscription-free. 

My current writing project is a multigenerational novel about a Pennsylvania lumbering family that’s facing an existential crisis following the death of its patriarch. I’ve spent two years researching and writing the book, and I’ve loved every minute of it. I can’t wait to get up in the morning, sit down at my desk, and see how the story and the characters unfold. 

Still, I harbor no illusions that I’ll ever see a financial payback for all the time I’ve spent on this crazy project. Even if I’m fortunate enough to find an agent and a publisher for the book, the odds of making any money on it are about as long as winning the lottery. 

The fact is, everything we do has a price, and that price is our time. As I write in my debut novel, The Long Walk Home, time is our most precious resource, and every choice we make about how to spend our time has an opportunity cost—an alternative road not taken.

My own opportunity cost for the past two years has been missing out on earning a six-figure salary and all the things I could have done with that money, including investing in the financial markets at depressed prices. I made that choice willingly because I had something burning inside me that demanded attention, but I’m well aware of what I lost whenever I glance at my portfolio and see what could have been, had I continued to earn money and invest over the past two years. 

And it’s not just the money that I’ve lost when I made the decision to exit the corporate world. I miss my old teammates. I miss the camaraderie of being part of a team and an organization with a shared mission. I miss the feeling of accomplishment that comes from seeing my efforts make a difference for a big, publicly traded company.  

Would I make the same decision again if I had to?

Yes, yes—a thousand times, yes. There’s nothing more fulfilling, I’ve found, than being able to spend my time doing what I love. To gain that freedom was well worth the opportunities I lost. 

At the same time, I’ve gained a greater appreciation of the things I took for granted while working: the money, the friendships, the camaraderie.

My advice: Whether you’re considering jumping into retirement or taking a shot at a second-act career, be clear not just about what you’ll be gaining with the move, but also what you’ll be losing. Quantify them if at all possible. Ask yourself what your time is worth and how best to utilize it in pursuit of your goals. Think through the different uses for your time. Life’s journey is inevitably uncertain—but carefully weighing the alternatives should help you make the best decision possible.

James Kerr led global communications, public relations and social media for a number of Fortune 500 technology firms before leaving the corporate world to pursue his passion for writing and storytelling. His debut book, “The Long Walk Home: How I Lost My Job as a Corporate Remora Fish and Rediscovered My Life’s Purpose,” was published in 2022 by Blydyn Square Books. Jim blogs at Follow him on Twitter @JamesBKerr and check out his previous articles.

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