Bucket List or Compass? Design a Retirement You Love

People arrive at retirement for different reasons and in varying degrees of readiness. Often, the overarching goals are to spend time with loved ones and keep busy. But here’s the question worth asking: is that enough to build a successful retirement?

Why We Retire Isn’t Always About Work

According to the Ontario Securities Commission in 2024, the #1 reason people retire (whether they’ve already started or are about to) is to spend more time with friends and family. That speaks volumes about the importance of human connection.

But here’s the challenge: in today’s increasingly virtual world, nurturing real connection is harder than ever. We get seduced by the idea of accomplishing more, often from the comfort of our pajamas, instead of creating the relationships and experiences that actually make us feel alive.

The Busy Trap

People enter retirement and immediately find ways to keep busy. They are accustomed to getting things done and feel that their value is somehow linked to productivity.

The problem? Busy doesn’t always equal fulfilled. And it often steers us away from the very connection we longed for.

I know this firsthand. This past summer, I buzzed from one project to another: painting, fixing, checking things off the list. It was energizing, but I had to intentionally step back and break the habit of cramming something into every minute. For me, time and space spark creativity which is one of my top values.

The Bucket List Isn’t Enough

When we think of retirement, visions of travel and hobbies appear. And yes, those can be wonderful.

A retired friend of mine took a pizza-making class on the Amalfi Coast earlier this year. Honestly? That sounds like heaven to me.

Still, I know that kind of trip would be a delightful break, not a way of life for me. A bucket list is good for keeping dreams in view, but it can also become another to-do list.

And here’s the hidden risk: what happens if you work toward a long-held goal only to discover you don’t actually want it? Do you bail? Or do you push ahead just because you promised yourself (and others) that you would?

The Compass Approach

Instead of chInstead of chasing activities, what if we asked how we want to move through the world?

Consider these questions:

• Peace of Mind: Does “slowing down” or “traveling more” give you permission to choose for yourself without guilt? Does it let you step off the hamster wheel?
• A Sense of Self Beyond Work: How would it feel to measure your worth without tying it to deadlines or milestones?
• A Little Adventure: What new experiences could awaken your curiosity and wonder?

A compass, anchored in your values, can guide you toward opportunities that help you grow and evolve.

👉 This is exactly the kind of exploration we do in my Remarkable Retirement program: helping you uncover your compass so that meaning, not busyness, drives your days.

Designing Retirement Around Who You Are

For me, retirement is about staying grounded in values, peace of mind, and being comfortable in my own skin. It’s about designing life around who I am, not just what I do.

Like many of us, I have to be mindful of my tendency to stay busy. If I don’t intentionally choose meaning over activity, I’ll slip back into my old programs of doing rather than being.

We Retire as Ourselves

Here’s the truth: we retire as ourselves. That sounds ridiculous, doesn’t it? Of course we do! But think about it.

If I retire as a workaholic, my comfort zone will always be finding “stuff” to do. Even if I’ve dreamed of traveling the world, I might avoid booking that trip and instead busy myself with endless tasks around the house. Things get done but not the things that move me toward the life I truly want.

I’ve seen this with women I’ve coached: one client entered retirement thinking her worth came from a packed schedule. By our second session, she was confidently designing her mornings around reflection, art, and time with grandchildren. The shift wasn’t about doing less, it was about doing what mattered most.

The Real Question

We’ve spent a lifetime saving money and preparing for the future. But were we ever taught to play, to explore, to discover what brings us joy?

I didn’t often ask myself what I wanted outside of family vacations. Even then, those precious east-coast summers with my parents and children were crammed with activity. Looking back, the gift wasn’t the full schedule. Rather, it was the simple connection across generations.

That’s what lingers. That’s what matters.

Bucket List or Compass?

So I’ll leave you with this question: Do you want a bucket list… or a compass?

If you’ve been nodding along, this is your moment to pause the busywork and design retirement around who you are. That’s exactly what we’ll explore together in Remarkable Retirement, beginning October 15th on Zoom – the last group of 2025.

You’ll be alongside women asking the same questions: What’s next for me? How do I want to live these years fully?

✨ Ready to find your compass?