17 Jul 2025 What If You Don’t Know When You Want to Retire?

One of the lessons I’ve learned—and keep learning—as a financial advisor is the importance of asking good questions. But in my early days, I asked a lot of mediocre ones.

High on the list was this classic: “When do you want to retire?” I asked it of everyone—whether they were 30, 40, or 60—and almost always got the same answer: “Tomorrow.” It was said with a laugh. Sometimes it reflected a longing for relief or change. But more often, it was just another way of saying, “I have no idea.”

At the time, I thought I was doing my job. Retirement is a major milestone, right? It only made sense to plan around a specific date. But over time, I’ve come to realize that for many people—including myself—it’s not such a simple question.

I’m 53. And if you ask me when I want to retire, I honestly don’t know. I love what I do. I genuinely enjoy helping people think clearly and make wise decisions about their lives and their money. At the same time, I know there will likely come a time when I’ll want to slow down—or even stop working altogether. I’m just not sure when that might be or exactly what it will look like.

The truth is, it’s hard to pin down a date—especially when that date might be decades away. Even people approaching traditional retirement age often struggle to commit to a specific endpoint. Some are eager to stop working. Others can’t imagine stepping away from the work they love. Still others aren’t sure what they’d do with their days if they did retire.

So over the years, my questions have changed. “When do you want to retire?” became “Would you like to not have to work at some point?” which became “How do you envision your 60s, 70s, and 80s?” I’ll probably find an even better version of the question in the years ahead. But for now, I think it opens up a more honest and helpful conversation.

So what do we do when we want to plan wisely for the future—but we’re not exactly sure what we want that future to look like?

It can be tempting to just put our heads down and delay the conversation until change is upon us—either by choice or due to some unforeseen event. But I think there’s a better way. It starts by taking time to consider our hopes and dreams for the future—but it doesn’t end there.

In his book Clear Thinking, Shane Parrish draws a helpful distinction: preparation is what you do when you can predict the future; positioning is what you do when you can’t. Positioning is about setting yourself up to adapt—making thoughtful decisions now so you’re better equipped for whatever comes, even if you don’t know exactly what that will be. The smart decisions we make today set us up to make even better ones tomorrow.

I believe that Parrish’s distinction is helpful in financial planning. Even if we’re unsure what we want the future to look like, it’s just as important to focus on smart decision-making. The kinds of decisions that allow us to make the most of life now and give us the flexibility to adjust when the time is right.

So how about you?

If you know when you want to retire, are you actively preparing for it? And if you’re not sure yet, you’re not alone. That uncertainty doesn’t mean you can’t plan. In fact, it’s all the more reason to start positioning yourself now—to build a future with more freedom, flexibility, and opportunity.

Here at Beacon, we love these kinds of conversations. Let us know if you’d like to talk.