Planning to Retire? Don’t Skip These 3 Mental Prep Steps

I’ve been thinking a lot about retirement lately—not because it’s around the corner tomorrow, but because it’s starting to come into view. And the more conversations I have with friends and colleagues who’ve already taken the leap, the more I realize how little attention we give to the mental side of this transition.

We talk about the money. We talk about the logistics. But we don’t often talk about the emotional weight of walking away from a career that shaped us, or what it takes to build a fulfilling life afterward.

This post is part reflection, part preparation. It’s me trying to work through some of the big questions before the moment arrives. If you're in a similar spot—still working, but starting to wonder what comes next—I hope this gives you something to chew on.

Retirement always sounded like freedom to me—no more meetings, no more 6 a.m. alarms. But I’ve been thinking lately about what actually happens when you step away from work. No one really talks about that part: stepping away from structure, purpose, and sometimes even your sense of self.

Most of us plan for retirement with spreadsheets. We calculate. We save. We wait. But from what I’ve seen and heard, the harder part isn’t financial. It’s internal.

Here are a 3 things I’m trying to think about now—before that moment comes.

1. Prepare for the Loss of Mental Stimulation

For years, our brains are in constant motion—solving problems, making decisions, navigating personalities. Then suddenly, that pace disappears. I imagine at first it might feel like a break, but I’ve heard from others that it can quickly feel like a void.

It’s easy to underestimate how much work keeps your brain active. When that disappears, you might find yourself itching for something to solve, something to build, something to learn.

I’ve started thinking about what might keep my mind happily buzzing when the time comes. Not with busywork, but with things that genuinely light me up. I have many ideas, more than I can probably follow through on. But some of them, I’m starting now in my spare time to build momentum.

2. Expect an Identity Recalibration

I haven’t retired yet, but I’ve thought about who I am when I’m no longer starting with, or including, my job title and description to talk about myself. Who am I when that is gone, when it becomes who I was?

For a lot of us, work is more than a paycheck. It’s where we feel competent, needed, and known. It’s our source of big puzzles, camaraderie and new challenges. Losing that role frees up your schedule but, it can mess with how you see yourself.

I think about who I am outside of work, and in some ways, see a version of myself that’s more true – artistically creative, curious about everything, mindful of what really matters in life. The “job” version of me is just a subset of who I am, not the whole.

How I view myself today is different than when I started my career. Some of what I continued to carry through my career is less important today than it was 10 or 20 years ago and I’ll be okay leaving some of it behind. It served it’s purpose won’t be needed.

3. Get Comfortable With Unstructured Time

A wide-open calendar sounds pretty appealing most days. But I can imagine how easy it would be to feel a little lost without the built-in structure of a workweek.

Some people wake up wondering what the point of the day is when every day is a “Saturday”. And while I’m not there yet, I think about days without work when I don’t have a schedule or plan. I can meander through the day wasting time on trivial, nonessential things.

This is a signal to shift from external structure to intentional structure.

I’m starting to think now about what a “soft rhythm” could look like—things like a morning walk, a creative project, or a weekly meet-up that brings shape to the day. I’m not short on ideas!

Let Yourself Grieve the Chapter You’re Closing

Even if you’re ready to retire—even if you’re excited—it’s okay to feel a little sad.

You’re saying goodbye to a chapter that shaped you. To the professional network and people who were part of your daily life. To moments that tested and stretched you.

Not all of the people will carry over into your next chapter. And that can feel like a loss. You world can suddenly feel smaller. Prepare for that. Accept the change and build new.

I’ve already started reflecting on some of those memories, and I imagine when the time comes, they’ll hit even harder. That part of life matters. It deserves to be honored.

Retirement isn’t just a new beginning—it’s also an ending. And endings deserve their space too.

Talk about it. Remember the good stuff. Say goodbye on your own terms. Embrace the opportunities ahead of you.

As I Think About What’s Next

Retirement isn’t a destination. It’s a transition. One that asks you to not just stop working, but to reimagine who you are without the role that once defined you.

I’m still in the thick of work life, but I’m paying more attention to what comes next. Being curious and honest now feels like the best prep I can do.

If any of this stirred something for you too, I’d love to talk. No pressure—just a real conversation about what’s next.

Let’s talk about your Next Chapter—on your terms.