I'm writing this from a hotel room in Nashville. I'm here for a business-planning conference—the kind of event where you finally step back from the day-to-day grind and think about where everything is headed. I've been to plenty of these events over the years, but this one feels different. Maybe it's because I've been running full speed for the past eighteen months, juggling new responsibilities at work and learning how to be a dad at home. Somewhere in all of that, I stopped planning—not intentionally, just one small deferral at a time until I suddenly realized I hadn't looked up in a while. This trip is my way of doing that.
The first exercise was deceptively simple: write down what went well this year. No dashboards, no spreadsheets—just reflection. And at first, nothing came to mind. The year felt like a blur of interruptions, changes, and constant motion. But after a few quiet minutes, the good started surfacing: a client relationship that deepened, a process that finally clicked, a decision that paid off after months of uncertainty. Quiet wins. The kind you don't notice in the moment because you're already sprinting toward the next problem.
That exercise hit harder than I expected. It made me realize how rarely we stop to appreciate the ground we've already covered. When you're focused on fixing what's broken, you lose sight of how much you've already repaired. Reflection isn't indulgence—it's maintenance. If you never check the dashboard, you shouldn't be surprised when the engine stalls.
Then came the hard part: the "stop doing" list. Habits, processes, distractions—the things we carry forward simply because they're familiar. As an MSP, I see this all the time. A business sticks with an outdated tool because it's "good enough." A workflow stays in place because no one wants to revisit it. The truth is, growth isn't always about adding more. Sometimes the smartest strategic move is subtraction.
But the exercise that surprised everyone was this: write a thank-you letter to yourself. Most leaders are wired for accountability, not appreciation—especially self-appreciation. But once I started writing, I realized how important it was. I thanked myself for the small wins nobody saw, the tough decisions that turned out right, and the simple persistence to keep going through a difficult year. It wasn't about ego. It was about acknowledging that leadership takes energy, and that energy has to be refueled somehow. We thank our teams, our clients, our families—but almost never ourselves.
Only after all this did we get to what people usually expect from a planning workshop—goals. One-year, three-year, ten-year goals. But instead of starting with revenue targets or KPIs, the facilitator asked a different question: What kind of business—and life—do you want to build? That reframed everything. You can't build a meaningful plan if you don't know what the plan is in service of.
It reminded me of why Systems Support exists in the first place. Our best work has always been rooted in being local, reliable, and responsive. We're not just fixing technology—we're helping businesses stay focused on what they do best. Every plan we make has to reinforce that identity. Every leader needs their own version of that compass.
We talked about non-negotiables next—the boundaries that keep you honest when things get busy. Not slogans, but standards. For us, that means responsiveness, integrity, and partnership. We don't cut corners on security. We don't disappear when things get tough. We don't treat clients like ticket numbers. Those lines in the sand protect your culture from short-term decisions that could damage long-term trust.
Opportunity came next, and with it, distraction. Business owners are constantly tempted by new ideas, partnerships, tools, and "game-changing" technologies. The hardest part isn't finding opportunities—it's filtering them. A good opportunity matches your values and strengthens your foundation. Anything else is noise. In the IT world, there's always a new platform or feature promising to change everything. But the only changes that matter are the ones that make you more reliable, more secure, and more effective for your clients.
Then there was crisis planning—the exercise everyone quietly dreads. No one likes thinking about what could go wrong. But pretending worst-case scenarios don't exist doesn't protect you. Preparation does. A few months ago, one of our clients faced a total system outage after a regional power failure. Because we had a continuity plan in place—backups, remote access, clear roles—they were back up within hours. That wasn't good fortune. That was the benefit of planning long before the crisis hit.
By the end of the week, I realized the most important part wasn't the worksheets or frameworks. It was the act of slowing down long enough to be intentional again. Reflection on what works. Clarity on what doesn't. Focus on what truly matters. Subtraction before addition. These aren't strategy buzzwords—they're the foundations of running a stable business.
That night, I re-read the thank-you letter I'd written earlier. It struck me that planning isn't about predicting the future. It's about preparing yourself for it. You can't know what's coming. But you can decide how ready you'll be. You can decide what kind of leader you'll be under pressure. And you can make sure your systems, your people, and your mindset aren't left to chance.
When I get back home, the chaos will be waiting. Emails, projects, client work, parenting—all the usual noise. But I'll return with something I haven't had in a while: a clearer sense of direction. Not a perfect plan, but a grounded one. The kind that helps you make better choices when the pace picks back up.
Planning isn't about control. It's about clarity. It's the simple act of stepping back long enough to remember why you started and where you want to go next. And sometimes, that's all the reset a business really needs.
