Running Probably

Running Probably

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Running Probably
Running Probably
Shakeout: Doing stuff

Shakeout: Doing stuff

Using fitness for fun, not just performance

Paul Flannery's avatar
Paul Flannery
May 27, 2025
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Running Probably
Running Probably
Shakeout: Doing stuff
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On Sunday, I went for a 14-mile run with my friend, Josh. In addition to being great company, Josh is an expert trail guide. When he offered to show me how to connect my local trails via his own network of interconnected routes, I didn’t have to think twice before saying, yes.

What made my decision making process easy was understanding how my base level of fitness would translate across a 2-3 hour run in the woods. Quite well, to be honest. Thanks to my Boston Marathon training, I knew I could manage the run aerobically and physically. More importantly, I knew that my fitness would allow me to enjoy the run. There’s few worse feelings than knowing you’re dragging down a social outing because your fitness is lacking.

Fitness doesn’t have to be reserved solely for racing. It can be cultivated and developed in such a way that it allows you to go out and experience cool stuff with interesting people whenever the opportunity arises. And that’s how I wound up climbing over a swamp on a ladder over by the interstate.

Having a blast. Photo by Josh.

In this week’s Shakeout, we’re headed to the track for another workout in my ongoing quest to drop a sub-6 minute mile later this summer. But first, a quick story about offering old-school wisdom to a new school runner.

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