By Patrick Lee, President of Chesapeake Think Tank and CEO of Spark Business Institute
Business owners often come to me overwhelmed by the sheer volume of decisions they face daily. The constant noise, the pressure to move quickly, the feeling that everything needs attention now—it’s no wonder many lose sight of where they’re actually trying to go.
I’ve witnessed this countless times throughout the Chesapeake Bay region– and beyond, particularly here in Anne Arundel County: talented entrepreneurs working incredibly hard but feeling like they’re running in circles. They have a vision, maybe even a strategy, but somewhere between fighting daily fires and attempting quarterly planning, they’ve lost their connection to a clearly defined path forward.
What’s missing? Waypoints.
Think about any road trip you’ve taken. You don’t just have a destination—you have a series of interconnected points that mark your progress. There are highway changes, rest stops, fuel breaks, and maybe overnight stays if the journey is long enough.
Each of these serves as confirmation that you’re on track and provides natural decision points. You don’t stress about which exit to take for dinner when you’re still three hours away—you focus on the immediate next step.
Yet in business, I watch owners constantly making decisions about metaphorical “Route 38” when they’re two days away from even approaching it. They’re worrying about scaling problems when they haven’t solidified their core offering. They’re designing complex marketing funnels before establishing whether customers actually want their product.
Without clear waypoints, everything feels equally urgent and equally important. That’s a recipe for decision fatigue and misdirected energy.
Here’s something we don’t talk about enough: waypoints aren’t just checkpoints to ensure you’re on track—they’re opportunities to celebrate progress.
When I work with clients to establish clear benchmarks, something magical happens. The first time they hit one of these pre-defined markers, there’s tangible evidence that their strategy is working. We can measure it, acknowledge it, and most importantly, celebrate it with their team.
This creates something I consider the third currency in business. You have time, you have money—what’s the third leg of the stool? Momentum.
By celebrating these milestone achievements, you generate momentum that carries your organization forward. Your team becomes energized. Your stakeholders gain confidence. You personally gain the psychological fuel needed to tackle the next leg of the journey.
Recently, I worked with a client who was facing significant business headwinds. Their original plan wasn’t yielding expected results, and they were beginning to feel like everything was crashing down around them.
But because we had methodically plotted waypoints throughout their strategy—complete with contingency plans at each junction—we were able to respond quickly and decisively. When certain metrics weren’t met, we already knew exactly which expenses to cut, which initiatives to pause, and which opportunities to double down on.
While my client could clearly see the challenges ahead, they weren’t experiencing the financial freefall they had feared. The pre-established waypoints and corresponding contingency actions provided guardrails that kept their business on a sustainable path despite the turbulence.
Without specific, clearly defined waypoints, how do you evaluate your progress? Too often, it comes down to how you’re feeling that day.
Did you wake up energized and optimistic? Then maybe things are going great! Did you start the day stressed after a poor night’s sleep? Suddenly everything looks like a disaster.
This subjective evaluation creates a rollercoaster that no business can effectively navigate. When waypoints lack specificity, they become subject to reinterpretation based on mood, bias, or resistance to change.
When you establish crystal-clear criteria for each waypoint—”We will achieve X revenue by Y date with Z profit margin”—you create an objective reality that can’t be ignored or reinterpreted.
You may choose to adjust your strategy based on what you learn, but you can’t pretend you’re somewhere you’re not.
At Chesapeake Think Tank, one of our most valuable services is helping clients develop their critical path with clear, meaningful waypoints. We work with you to:
This approach transforms vague aspirations into concrete roadmaps. It reduces overwhelm by clarifying which decisions need attention now versus later. And perhaps most importantly, it provides regular confirmation that you’re making meaningful progress toward your ultimate vision.
If you’ve been feeling lost in the noise of running your business—making countless decisions but unsure if they’re moving you forward—perhaps it’s time to establish some waypoints. They might just be the navigation system your business journey has been missing.
Copyright 2025 | Chesapeake Think Tank
