Goodbye, Paper Route. Hello, Leadership Lessons.

When I was fifteen years old, a business disruption ousted me from my very first job.

I had a paper route for several years, one that I had inherited from an older boy whom I looked up to. It was a great job for a kid, and it gave me valuable work experience. I learned about overcoming challenges (60 percent of the route involved walking up what was akin to a small mountain, appropriately named “Hill Street”), meeting schedules and deadlines, managing expectations, providing customer service, handling collections, and much more that has served me well since then.

In retrospect, I was likely one of the very last kids to hold a paper route, and I never saw the change coming. One day, the newspaper replaced me with a guy in a station wagon who delivered papers on multiple routes. And that was that.

I haven’t thought about my paper route in a very long time, but as I work with clients grappling with disruption, succession, business sales, and retirement, I occasionally reflect upon my experience. I think about it because I never had the opportunity to retire or “move on”; in modern business parlance, my “exit” was unexpected and unplanned.

So, what does my experience delivering newspapers have to do with your work? The short answer is that the disruption to my career as a paper route mogul taught me a few valuable leadership lessons that you can benefit from.

Three Leadership Takeaways from Losing My Paper Route

1. It’s critically important for leaders to try and understand both their industry and the wider world on a macro level.

Living in an era of exponential change has continually reinforced this lesson for me. I cannot stress enough the importance of environmental scanning and attempting to grapple with the world’s impact upon your organization.

2. Leaders need to plan for disruption.

Losing my paper route didn’t put me on the street or take food out of my mouth (Thanks, Mom and Dad). It did, however, make me acutely aware that I had no plan of which to speak. Good leaders always think in terms of contingencies and backup plans. As President Eisenhower once said, “Plans are worthless, but planning is everything.”

3. No matter how complete or thorough plans are, they must always be adapted and adjusted when reality smacks them from your hand.

As the Prussian military strategist, Helmuth von Moltke the Elder wrote, “No plan survives contact with the enemy.” Phrased differently, a flexible mindset will enable you to bend, not break, when the unforeseen arises.

Extra! Extra!

In the entire history of newspaper delivery, there is likely only a handful of us who had our routes disrupted by the changing times. I recently drove up Hill Street revisiting my old paper route, though, and I am grateful for the entire experience—including the way it ended. It enabled me, at an early age, to understand firsthand how swiftly change comes and what that means.

If you’re facing change and are concerned that your paper route might be taken away from you, give me a call. We probably need to talk.