People often think of a financial plan as something permanent: printed, bound, heavy enough to feel like a serious piece of work. There’s comfort in that weight because it looks like certainty. But after more than twenty years in this field, I see planning very differently. To me, it’s much closer to landing a shuttle on Mars.
NASA begins every mission with a meticulously designed flight plan. But the moment the craft leaves the pad, outside forces start rewriting the route. Tiny shifts in gravity, unexpected weather, new data from the spacecraft—they all require continual adjustment. The plan isn’t abandoned; it’s refined. That’s how you reach the landing site.
Retirement planning works the same way. The plan gives you direction, but it’s not the final word. Markets move. Tax laws change. Health and family needs evolve. Your own priorities shift as retirement becomes lived experience rather than theory. A plan built to sit on a shelf doesn’t help you navigate any of that.
The problem with oversized plans is not the effort behind them; it’s the illusion they create. When a plan tries to account for everything in advance, people assume the future will honor those projections. It rarely does. Instead of flexibility, you get rigidity. Instead of clarity, you get clutter. And instead of confidence, you get a document that looks impressive but offers very little you can actually use.
A better way is to approach planning the way mission control approaches spaceflight: expect change, prepare for it, and understand the structure well enough to adjust intelligently. I often think of the investigative boards you see in police dramas—the ones that map the whole operation. Not because planning is dramatic, but because those boards show how the pieces connect. Income sources, taxes, investments, healthcare costs, estate plans, timing decisions. When you understand how each piece affects the others, you can anticipate likely scenarios and build contingencies that reflect reality rather than wishful thinking.
That’s the real work of planning: interpreting new information without emotion, adjusting before small drifts become major detours, and staying oriented toward what matters most. The plan you walk away with is important, but the ongoing process matters far more.
A strong plan is simple enough to use, clear enough to understand, and flexible enough to evolve. It gives you a reliable framework, not a rigid script. And it helps you make good decisions in a world that refuses to hold still.
In the end, the map will never match the territory. But with a plan built to adapt—and someone guiding the course with you—you still arrive exactly where you intend to go.