Pickleball, Pulled Muscles, and Poor Planning
Why Growth Without Planning Can Leave Even the Strongest Teams Limping
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.
Bus Business Consultants, LLC
“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” before we sprint. And when we skip the warm-up, we pay the price.
Growth is thrilling, but growth without preparation is risky.
You’ve probably heard the phrase: “Opportunity doesn’t wait until you’re ready.” That may be true. But readiness doesn’t happen by accident; it’s something you build before the opportunity arrives.
In transportation, growth can be a powerful catalyst for change. It can boost revenue, increase market share, attract investors, and even put your company on the radar for acquisition. However, it also brings new demands to your people, equipment, systems, and leadership.
If you’re not careful, that exciting new opportunity can become a source of strain. Just as I strained my calf, companies strain their infrastructure and leadership when they leap without proper preparation.
Two stories, one common thread: growth without a solid foundation.
1. Orlando: The contract that nearly consumed the company
Almost 20 years ago, a transportation company in Orlando landed what appeared to be a game-changing contract with a high-profile, deep-pocketed client. The leadership at the time jumped at the opportunity. Who wouldn’t? But in their eagerness to secure the deal, they skipped a crucial step: planning.
Before the contract, the company was a seasonal charter operator that also ran one transit contract, which operated 200 days a year with no weekend service. After the contract, it was suddenly a full-time transit provider with a 24/7/365 schedule. The infrastructure hadn’t changed, but the expectations had.
By the time I arrived, the organization was under severe strain. Vehicles, drivers, dispatchers, and frontline leaders were overwhelmed. What was supposed to be a breakthrough had become a burden.
It took several years, marked by new fleet investments, organizational restructuring, leadership transitions, and cultural recalibration, before operations finally stabilized. The new contract had become so central to the business that, in retrospect, it was hard to tell which had been absorbed into which—the contract or the company.
2. A recent engagement: Outstretching the supply line
In a recent assignment, I collaborated with a company that had entered a new market, roughly three hours away from its base of operations. What began as a “temporary” contract quickly turned into a full-time obligation. But the company hadn’t secured a local facility, staffed adequately, or established support systems in the new area.
They had underestimated the logistical and operational challenges of managing a remote site. The result? Daily chaos. The home office was constantly pulled into troubleshooting mode, while the small team in the new market was left trying to hold the line with insufficient resources.
It reminded me of a military analogy: a unit advanced too quickly and outstretched its supply lines. The consequences were predictable—exhausted leaders, declining service quality, safety lapses, and a frustrated client. That’s when I was brought in.
Even with a clear plan, it still took months to rebuild the operation, establish a structure, and restore credibility. Though my assignment ended before the work was fully complete, we had laid the foundation for long-term improvement.
The lesson? Growth is not just a goal; it’s a responsibility.
It’s easy to celebrate new wins, new contracts, new markets, or new buses on the lot. But here’s the question every transportation operator needs to ask:
Are we truly prepared for this?
That means more than just having the fleet or a few extra drivers. It means asking:
- Do we have the operational bandwidth?
- Can our safety program scale with demand?
- Is our leadership team aligned and ready?
- Do we have processes to onboard and train quickly?
- Can our culture absorb this change without unraveling?
Because if the answer is no—or even “not sure”—then your next win could become your next pain point.
Don’t just stretch your fleet—stretch your foresight.
The truth is, I should have known better on the pickleball court. And honestly, so should most companies that leap into growth without planning. The signs are usually there. The excitement of opportunity often overshadows the discipline of preparation.
However, in business, as in sports, a warm-up is crucial. Planning isn’t a luxury; it’s insurance. It protects the people, the performance, and the promise of growth.
If your company is on the cusp of expansion and you’re unsure if your foundation is ready, I can help. At Bus Business Consultants, I partner with ground transportation operators to prepare, plan, and execute growth initiatives that stick, so you don’t just grow fast, you grow smart.
Because nothing derails momentum like a pulled muscle you could have prevented.
Brian Dickson is the owner of Bus Business Consultants and author of Ground Transportation Insights on Substack. Drawing on leadership roles in motorcoach operations and Disney’s Guest Transportation, he helps operators improve performance, culture, and growth—Bus Business Consultants: Driving Performance, Culture, & Growth in Ground Transportation.
This article was originally published on June 25, 2025 at Ground Transportation Insights.
