The Exit Interview

On Courage, Doubt, and Staying Engaged in Life

Photo by Michael Dziedzic on Unsplash

I got the eye of the tiger, a fighter
Dancing through the fire 'cause I am a champion
And you're gonna hear me roar
Oh, louder, louder than a lion 'cause I am a champion
And you're gonna hear me roar-Roar, Katy Perry

I’ve been retired from corporate life for many years now. I started my own company, and my only employee is the Director of Security—my dog, Jax.

But every now and then, I find myself pulled back into a leadership or business role that requires dusting off skills I once used daily. This week was one of those moments.

I offered to conduct an exit interview for an organization I work with. An exit interview is a “final, structured conversation between a departing employee and an employer to discuss why they’re leaving, share honest feedback, and offer suggestions for improvement”. For confidentiality reasons, I won’t share any details. What I can share is how deeply impressed I was by the employee I spoke with.

They were confident. Thoughtful. Clear-eyed. And fearless in their belief that the new role they were stepping into would be exactly what they were looking for. Even more striking was their trust that if it wasn’t—something else would appear.

This person is likely in their 30s, when the world still feels wide open and full of possibility. And that’s what stayed with me long after the conversation ended.

What happens to that kind of confidence as we move through middle age and beyond?
Why do some people stop reinventing themselves, stop learning, stop growing, stop taking chances?

And maybe the most personal question of all: how do we not let that happen?

The word that kept coming to mind was courage.

The poet David Whyte writes:

“Courage is the measure of our heartfelt participation with life, with another, with a community, a work; a future.”

That definition feels especially relevant at this stage of my life. Courage isn’t about bold leaps or dramatic reinventions—it’s about staying engaged. About choosing not to withdraw.

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I see this courage all around me. Friends in middle age and beyond who refuse to stop growing. One earned her Ph.D. in her 50s and has published several books. Another launched a new brand. One continues practicing law despite “threatening” to retire for as long as I’ve known her. Another expanded her retail business—doubling both the footprint and the risk. Another started a fitness business for older adults. And there are so many people I know who have also started writing on Substack, sharing their thoughts, dreams, and opinions. Trust me…this can be scary. None of it is easy. All of it requires courage.

As Psychology Today wrote:

“It’s hard enough to admit you don’t know what you’re doing when you’re an insecure, cocky 20-something. But it’s even harder to admit when, in your 40s or 50s and beyond, you’ve reached a level of proficiency—if not mastery—in one field. You’re recognized. People come to you for your expertise. And now—boom—you’re in terra incognito.”

That resonates deeply with me.

For me, courage looked like going back to school in my late 50s.
Before I did, I had real doubts. I wondered if I was simply too old to learn something this detailed. If my brain could still retain facts and concepts the way it once did. It’s one thing to take a risk when you’re young; it’s another when the question isn’t just Will this work? but Can I still do this?

Today, my business operates as a Virtual CFO, helping small businesses structure, plan, strategize, and use financial reports to improve performance. I came from a generalist executive background, where highly skilled experts brought me the data and recommendations, and I made decisions based on their expertise. (Cathy L. if you are reading this...I am talking about you!!) When I started my company, I needed to create those reports myself.

So I went back to school for accounting. Yikes.

It wasn’t just debits and credits. It was new technology, new systems, and the very humbling experience of being a beginner again. The learning curve was steep—but I persevered. And I’m so glad I did. I truly love the work I’m doing now…for as long as I want to do it. Who knows?

I don’t have answers. What I do have is curiosity—and a desire to start a conversation.

How do we stay motivated to keep learning?
To keep growing?
To keep taking risks?
To stay engaged with life and open to the unknown?

What doubts have you had to face in order to keep growing—and what helped you move forward anyway?

Courage, my friends.

Peace + Clarity

Much love!

Thanks for stopping by Leaving Middle Age! If you found this interesting, please share it with friends, family, or anyone who’d appreciate the journey.