Lisa Featherngill spent more than four decades advising clients on their finances. But when she retired earlier than expected, she discovered that preparing for retirement and actually living it are two very different things.
Six months into retirement, she found herself checking her investment balances three times a day, questioning whether she wanted to return to part-time work, and gaining a new appreciation for the emotional side of leaving a career behind.
In the first of a series of conversations about her first year of retirement, Featherngill discusses what surprised her, what she wishes she had understood as an adviser and why having something to retire to may matter as much as having enough money to retire.
Below is a transcript of my interview with Featherngill, edited for brevity and clarity.
Why even financial planners can struggle with retirement
Bob Powell: You spent more than 40 years advising clients about their finances. But now that you’re retired, you’ve discovered that taking your own advice isn’t necessarily easy. What happened?
Lisa Featherngill: I would’ve been my own worst client. I can’t believe it. Forty-plus years of talking to clients about not looking at your accounts every day. And here I am on Monarch three times a day looking at my balances.
Powell: Let’s talk about how you got here. You had been planning to retire, but things didn’t happen quite the way you expected.
Featherngill: I had been thinking about retirement for a couple of years and working with a coach, so I had an idea of what I wanted to do.
In fact, I had talked to my boss last year. My plan for 2026 was to work full time until July and then work part time on a project basis at my employer until the end of the year.
Beautiful plan. Not what happened.
How a bank acquisition accelerated her retirement
Powell: What changed?
Featherngill: On Oct. 5 of last year, it was announced that Fifth Third was buying our bank. I knew that if I wanted to stay, I really needed to make another four- or five-year commitment.
And in my head, 2026 was my year to go out.
I would’ve been my own worst client. I can’t believe it. 40 plus years of talking to clients about, don’t look at your accounts every day. And here I am on Monarch three times a day looking at my balances.
So I raised my hand and said I was willing to be part of that first group that would be displaced, which happened on Feb. 1 of this year.
Powell: So the decision wasn’t entirely made for you, but the acquisition helped you make a decision you were already considering. How do you look back on that?
Featherngill: I consider it a gift because, if left to my own devices, I know I would’ve come up with excuses to keep going part time or even full time.
This really illuminated a path out for me.
But it’s given me an appreciation for the emotional aspect of retirement. I was not prepared.
Why her plans for part-time work changed
Powell: One of the questions people face is whether they should retire completely or continue working part time. You originally planned to keep working. What happened to that idea?
Featherngill: I thought this would be a semi-retirement. I thought that within three months I’d be doing some project work, maybe working part time here and there.
Friends kept telling me, “Give it six months.”
I said, “No, I’ll give it three.”
Well, I gave it three, and then three became six. It’s now right at six months, and I’m not even sure I want to go do part-time work anymore.
It feels like there’s hardly enough time to do the things I want to do in retirement.
But I do think it’s really important to have something to retire to, things that you enjoy doing.
What financial planning misses about retirement readiness
Powell: Advisers often focus on two questions: Do I have enough money to retire, and what am I going to do once I retire? How important is that second question?
Featherngill: I think you need to start a couple of years in advance.
I was fortunate in that I started working with our friend Andrea Miller, who’s a coach. She helped me organize my thoughts around how I wanted to go out and what I wanted to be doing once I retired.
I never focused on that as a thing. I was doing it, but I didn’t focus on how important it was.
And I wish that had crossed my mind as I was advising clients earlier.
I focused so much on the financial, and obviously that’s important, but there’s so much more than the financial.
I think that’s an area where advisers really can help clients. They can help them be comfortable that the numbers look good, but also think about the other side: What’s life going to look like?
Powell: Some advisers are reluctant to get into those conversations because they don’t see themselves as counselors. But they don’t necessarily have to become counselors to raise those questions, do they?
Featherngill: That’s why I’m so glad we’re talking about it. It wasn’t on my radar. It wasn’t something I was trained in, and it wasn’t a service I really offered to clients.
I hope other advisers will start considering adding that service or at least broadening the conversation.
As advisers, you see multiple clients going through the same life events, whereas the client really sees it only for themselves. So you have experience from things you’ve learned from somebody else.
What successful retirees have in common
Powell: Looking back at the clients you advised, was there a distinguishing characteristic between those who had a successful retirement and those who didn’t?
Featherngill: I think those who were successful really had something they enjoyed doing outside of work, whether that was traveling or golf or fishing, whatever the case may be.
Something that gave them joy, that they could spend time doing.
So when they were giving up one identity, they were moving toward something else that made them happy.
Powell: You had already started doing some of that before you retired.
Featherngill: I had worked pretty hard on having things I wanted to retire to.
As you know, I had taken up biking a few years ago. There were groups I wanted to be able to cycle with during the day, and I was always so jealous.
Once in a while I’d get out with them during the day and always felt like I was playing hooky.
So I knew there were things I wanted to do in retirement.
How financially and emotionally prepared must you be?
Powell: When someone is considering retirement, how buttoned up do they need to be financially and emotionally? Do they need to have everything figured out, or is being close enough sufficient?
Featherngill: I would say most of the way there, because it’s never going to turn out exactly as you plan.
Obviously, the first thing is making sure financially that you know how much you can spend, how much you need in order to retire, all those types of things.
Running the financial projections is key.
And then, second, the emotional aspect really can’t be ignored.
You’ve got to have something to retire to.
And it doesn’t mean giving up 100% of who you were during your working years. Maybe you keep some of that, maybe not, depending on what other things are important to you.
Retirement looks so different now than what it traditionally looked like.
How retirement changes when your spouse still works
Powell: Your husband is still working. How has that affected what retirement looks like for you?
Featherngill: I call this my gap year.
I told him I wanted at least one gap year where he’s still working and I’m doing all the things I want to do that he doesn’t necessarily want to do.
Online mahjong, for example. I have the mahjong card everywhere with me now.
I grew up around it. My mother and other women played, and I had taken a class last year.
Then somebody invited me to take another lesson, and I thought, “Wow, I could do that. I have time.”
So I did, and I got hooked.
Can retirement begin before you stop working entirely?
Powell: What advice would you give someone who wants to ease into retirement, perhaps by keeping some earned income, doing consulting work or working part time?
Featherngill: I keep hearing more presentations about how the road to retirement looks different for everybody.
Maybe it starts at age 50, when you begin doing project work or consulting, rather than following the traditional path of working full time until 65.
There are so many different options available now, especially with being able to work remotely.
I think it’s open for whoever wants to create what their retirement situation looks like.
What retirement means after decades of work
Powell: We’ve talked about your decision to retire, the importance of having something to retire to and how your expectations have changed in the first six months. How do you think about retirement now?
Featherngill: It’s a reward. It’s a reward for all the years of hard work.
What does it mean to retire successfully?
I’m writing a book and producing a multimedia series called Retire Successfully, exploring how people plan for retirement, how reality compares with their expectations and how their definition of success changes over time.
If you’re retired, I’d like to hear your story, whether retirement has gone according to plan or taken unexpected turns. Please consider completing my 15- to 20-minute survey. Your responses will remain confidential unless you agree to share your story publicly. You don’t need to disclose specific financial or medical information.
