Ground Transportation Insights

Ground Transportation Insights

Growth & Strategy

Pickleball, Pulled Muscles, and Poor Planning

Why Growth Without Planning Can Leave Even the Strongest Teams Limping

Brian Dickson's avatar
Brian Dickson
Jun 25, 2025
∙ Paid

Last night, I played pickleball for the first time—and let’s say I found myself in a bit of a pickle.

About ten minutes into the game, I felt what I thought was a ball hit the back of my left calf. The sharp pain got my attention. I scanned the court, spotted a ball by the fence, and asked my partner if one had come flying over from another match.

“Nope,” she said.

That’s when I realized the truth: no stray ball had hit me. The pain I felt was coming from me, specifically, from a calf muscle that I hadn’t bothered to stretch. I had done what too many of us do: I jumped right in without warming up, like any self-respecting 53-year-old who still thinks he’s 25. And now, nearly 24 hours later, I’m hobbling around, wishing I’d taken a few minutes to prepare.

It made me think about something I’ve seen repeatedly in the business world, especially in the ground transportation industry. Whether it’s launching a new service, entering a new market, or scaling an operation, we often fail to “stretch…

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