Retiring without retreating

Did you know that retirement doesn’t have to mean retreat?

If you want your retirement to be a retreat — a time to relax, travel, and enjoy the fruits of decades of hard work — that’s wonderful. You’ve earned it.

But that’s not everyone.

Some of the most rewarding coaching conversations I have are with seasoned leaders who are leaving their job but aren’t ready to just go away. They’ve spent decades investing in people, building teams, and accumulating hard-won wisdom. And they want to keep sharing it.

The challenge? They can’t always see how.

The Two Fears

Something I’ve noticed when working with leaders approaching retirement: most are carrying two very different sets of fear — personal and professional.

On the professional side, there’s the backward-looking fear. You’ve poured yourself into your team for years. Maybe it would take three people to replace you (not just one). You don’t want to see everything fall apart when you walk out the door. You’ve nurtured this, built this, created this…and the thought of that legacy disappearing the moment you close the door is gut-wrenching.

Then there’s the forward-looking fear, the personal one. You’re not sure what comes next. You may not know if you’ve put enough aside financially. And even if the money is fine, there’s a deeper question: How will I bring value to the world when this role was so much of my identity?

You’re asking, “What’s my next step?” But the answer feels foggy.

Retiring Without Retreating: A Path Forward

If this resonates, I want to share a process that can help you move from foggy to focused.

Start with the end in mind. Before you do anything else, get clear on what you actually want this next chapter to look like. How much money do you need? Is the desire to keep working driven by a financial gap, or is it about purpose and contribution? Both are valid but they lead to different strategies.

Choose a likely path. Think about what energizes you. Are you an introvert who thrives in deep one-on-one conversations, or an extrovert who lights up in front of a room? Do you want to serve many people with accessible offerings, or go boutique with a few high-investment clients? The options are broader than you might think — speaking, coaching, training, consulting, or some combination. And if you’ve been thinking about writing a book, test the material first with talks and workshops. See if there’s a market before you invest a year of your life.

Define your uniqueness. This is where tools like values assessments and leadership preferences become invaluable. What’s your hardwiring? What are your core values? What’s your mission for this next season? And here’s a question I love asking: What irks you? Where do you see something in your industry or community and think, “I know I could do that better”? That frustration is often a signpost pointing you toward your unique contribution.

Beta test it. Don’t build an entire business in a vacuum. Instead, define your best customer. Are you serving individuals or organizations? What age and career stage? Where do they live and where do they hang out? What are they wrestling with? Then go interview them. You don’t need a formal research project — just genuine conversations. Say something like, “I’m doing an informal research project on [your topic]. Could I ask you a few questions?” You’ll be amazed at what you learn.

You Still Have So Much to Give

The leaders I work with in this season aren’t winding down. They’re gearing up for something different. The goal isn’t to replicate what you were doing — it’s to take everything you’ve learned and channel it in a way that fits the life you want to live now.

You can leave your current role well, leave your team intact and equipped, and develop a plan for what comes next — one where you retire without being retiring.

If that sounds like something you’re wrestling with, I’d love to talk. You can apply for an exploratory call here. And if you want to start exploring your uniqueness, check out the Leader’s Journey and values assessment.

Your wisdom shouldn’t retire when you do. Your next chapter is waiting. Let’s figure out what it looks like.