I think most people talk about retiring as a moment in time–you clean up your desk, hug a few coworkers, and walk out the door for the last time. While that moment serves as a marker, retirement isn’t a moment. It’s a transition. From a planning perspective, it’s really the five years leading up to it that are some of the most pivotal in your entire financial life.
We refer to this period as your retirement glide path. It’s where clarity and confidence are built—or where avoidable mistakes can take root.
There are two core areas we focus on in those final working years: the financial plan itself, and the emotional validation of that plan.
1. Clarifying the Financial Picture
The most foundational part of your retirement plan is understanding what life after work will actually cost.
That sounds simple, but for high-income families who have never needed to put much effort towards a budget, cost of living is often one of the most challenging numbers to pinpoint.
When income has always exceeded spending, it’s easy to live well without tracking where dollars go. In retirement, income becomes structured—strategic. A few thousand dollars a month of underestimated spending, compounded over a 30-year retirement, can drastically change your glide path.
This is where we spend real time with clients, not just reviewing past expenses but projecting forward:
- What kind of lifestyle do you want?
- What will travel, healthcare, and family support cost?
- How might your spending shift over time?
When we get these numbers right, everything else in the plan becomes sharper.
2. Building Emotional Readiness
As the financial plan comes into focus, something else happens; confidence builds.
In client meetings, we revisit the plan often in the five years before retirement. Each update is a moment to stress-test, refine, and reaffirm. You’re not just making decisions—you’re internalizing them.
By the time retirement arrives—whether that means selling a business, stepping back from full-time work, or something in between—your plan is pre-emptively answering the concerns most retirees face.
That emotional readiness is just as important as the numbers. Retirement isn’t just about stopping work—it’s about trusting the plan you’ve built to fund what comes next. The goal is that as life unfolds, you can consistently say, “We planned for this.”
If you’re five years out—or even ten—it’s never too early to get clear on the numbers and start building that glide path. It’s about preparation, and the sooner we begin, the smoother your landing.