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Running with Doug

I'm not what you would call a naturally gifted runner. My body was simply not designed to run fast for long stretches, say 50 seconds or more.

If there was any doubt before, I confirmed my running prowess in 1984 as I vomited while heaving across the finish line at soccer tryouts as a high school freshman. Fortunately, I was a goalie and was granted a bit more leeway, but still. Running and I were not friends.

Against all odds, running reemerged into my life roughly a decade after the incident at tryouts. As part of my reluctant training for the Chase Corporate Challenge, a 5k race in Central Park, I began jogging, not running. And by the late summer of 1994, I'd managed to log 3-4 miles on a regular basis.

I learned to enjoy the process without the pressure to win or even maintain a specific pace.

By the winter of 1995, I'd been running before work with my friend and roommate Doug. We'd find our way to Central Park in the dark three to four days during the week and run the 1.7-mile lower loop. Then, on the weekend, we'd hit the four-mile route.

You need to understand that Doug was a machine. At this point, he'd already run nearly 20 marathons. And, for fun, he'd compete in the annual stair climb race to the top of the Empire State Building. And when we finished our run, his warm-up, he'd usually hop on his rowing machine for his real workout.

On paper, Doug had it all. His Ivy League undergrad degree was topped-off with a joint JD/MBA from another Ivy League school. When we lived together, he was starting as an associate at a high-powered Wall St. law firm. But, humble to a fault, these symbols of social status meant nothing to him. He always made time for his friends and believed in amplifying the goodness of others.

People often think of running as a solitary sport. I disagree. At our slow pace around the park, Doug and I built our friendship mile by mile. Our conversations naturally explored our career development, dating, and our terrible taste in music. I can't imagine his cardiovascular system even realizing that he was in the midst of a workout. For Doug, fitness was never the point.

In early March 1995, when we got back to our apartment, Doug told me he had a serious question. With a devious smile, he said how much he enjoyed running together. He also said my fitness had subtly improved, maybe more than I thought.

He then asked if I'd run the Boston Marathon with him. Not someday, but in less than two months.

Doug handed me a copy of Runners World magazine featuring Oprah to drive home the point. "Oprah did it. So can you."

I laughed and rejected the idea a few times. And then he explained his thinking.

"We'll run the full six-mile loop this weekend. If you can run six miles at a steady-state pace, we'll try twelve next weekend. And if you can run twelve in the park, then you can definitely run twenty-six with thousands of fans cheering along the way."

The idea seemed absurd. But having grown up a few miles from the starting line, I was skeptical but hooked. Doug knew what he was doing. He'd been there before. And he believed in me.

"Ok. But you realize I've never run more than four miles."

Doug smiled, nodded, and we moved on with our day.

That Saturday, we finished the six-mile loop in the park with a bit of pep. I felt like Bill Rogers as we emptied our tanks for the final 200 yards. Our pace was at most ten or eleven-minute miles, but the milestone felt like Olympic gold. Doug loved it.

The following weekend we doubled the distance at roughly the same pace. And with that, I agreed to run Boston in a few weeks and began to believe in the impossible.

On the morning of April 17th, I spotted Doug at our pre-race meeting spot in Hopkinton. It wasn't hard to spot the 6'4" guy with bunny ears. He wore those in every marathon, so his family could find him in the crowd.

We lined up in the back with the rest of the bandits. Back then, you didn't need to qualify to run Boston. Savoring the moment, Doug told me to relax, to take it in. He also said we wouldn't move for 5-10 minutes after the race started. Apparently, it takes a while for 10,000 people to filter onto route 126 from Hopkinton's Town Green.

Over the next four hours, I chugged along at my stubborn pace. I didn't stop once, mainly out of fear that my legs would cramp and I'd be toast. Eventually, I rounded the corner onto Boylston Street and headed to Copley Square into the roaring crowd.

Earlier in the race, I freed Doug to run at his pace. But as I crossed the finish line, there he was, full of joy, waiting to give me a high-five and a hug. He never doubted that I'd meet him there.

Doug changed my relationship with running, which I now rely on for physical and mental health. At 52, my usual pace lags far behind the pace I once considered slow. But that doesn't matter.

When I'm running these days, my mind often wanders back to those winter training runs ahead of Boston in 1995. But, interestingly, it's not the big race that comes to mind. Instead, it's the time we spent together in preparation as Doug built my confidence, step-by-step.

Tragically, memories of Doug are all that remain.

In February of 2017, Doug lost a battle with his mental health, a struggle he effectively hid from those around him. Always putting others first, I imagine he incorrectly assumed he was sparing others from his pain.

I think about Doug often, but especially around this time of year. I think about the fact that I'm still here, and somehow, Doug is not.

In The Second Mountain, David Brooks writes, "One of the greatest legacies a person can leave is a moral ecology—a system of belief and behavior that lives on after they die."

Doug's gifts have stood the test of time. Through running, Doug helped me believe in myself and inspired me to stare down self-doubt. His memory reminds me that our daily actions can positively influence others in the present and long after we're gone.

Thank you, Doug. I miss you.

Other stuff

Bill Gurley on The Tim Ferriss Show I hesitated to include such a widely followed podcast, and I know Gurley is a controversial figure, but this one was excellent. Gurley shares lots of insight as a seasoned investor in public and private equity. A few topics that got me thinking: the power of Benchmark's equal partnership structure, approaches to valuation in Silicon Valley vs. Wall Street, why Meta's VR strategy will fail, and companies he'd like to see exist.

​Listen to the podcast (2 hr 17 mins)

The End of Organizing I've long loved note-taking as a learning process and have been increasingly excited about technological innovation in this area. In addition to maintaining a Readwise streak that recently crossed 1,000 days (humble brag), I'm also a Napkin investor and advisor. Improving how we access our notes and ideas was initially what drew me to Napkin's approach. Dan Shipper, a credible thought leader and builder (Lex) in this space sees AI as a valuable co-pilot to aid discovery, find connections, and eliminate the need for organizational systems.

​Read the article​ (7 mins)

Freelance Forward 2022 Growth in freelancing is transforming employment and careers, and the trends are accelerating. According to Upwork's survey, 60 million Americans participated in freelancing in 2022. What's more, freelancers report higher satisfaction. For example, "Two-thirds (66%) of freelancers say they feel more stimulated and 68% say they feel happier by the freelance work they do compared to a traditional job."

​Read the report (7 mins)

Snipd If you're a podcast listener and wish you could save insights while on the move, you'll want to check out Snipd. Just tap your Airpod while walking or hit "back" in the CarPlay App while driving. With this prompt, the embedded AI figures out the natural spot to extract a snip, converts it to text, and automatically sends it to Readwise for further review. You'll also find embedded transcripts, notes, and AI-generated chapter summaries. Is it perfect? Nope. But it's miles ahead of other podcast players, and it's free.

​Learn more about Snipd (not an affiliate link)

And a Farewell Photo...