Six months ago, in my first Retirement Manifesto guest post, Retirement – My Journey From “No, Never” to “Maybe One Day, I wrote:
“Suddenly, retirement wasn’t a vague checkbox I advised others to prepare for—it was something I could see for myself one day. Not a fully formed picture… but like being in a room with the light off and then a dimmer switch turns on, casting just enough glow to glimpse a path forward.”
It’s time to check in on that glimmer.
Has my “retirement room” gotten any brighter? Or is the dimmer switch still at that soft glow?
How do you know when you’re ready to retire? Today, Dana shares personal thoughts from her journey. Share on X
When You Know
At the monthly Women’s President Organization meetings I attend, we do an exercise called issue processing. One person presents a challenge, and everyone else is only allowed to ask questions—not offer advice. Issue processing forces you to come up with your own answers. Retirement is much the same.
At a recent meeting, Cathy (not her real name) shared how burned out she felt about her work as a business broker. She’d spent the last year training someone, and to keep that person busy, she lowered her usual criteria for the kinds of business transactions she takes on. This burned her out.
She’s feeling zero motivation about work, and a heaviness sets in each time she tries to get back into it. What she wanted from us was advice on how to get that motivation back.
I don’t know Cathy’s financials, but I do know she’s in her early sixties and has talked about slowing down for years. So my question to her was simple:
“Why? Why do you want to reenergize?”
As the question settled in, Cathy’s posture straightened, and her face softened. She became visibly lighter.
“Wow, thank you,” she said.
Cathy is ready to retire.
I’ve seen this countless times with clients. Their “retirement room” is far away and dimly lit. And then one day, the light comes on enough that they recognize it immediately. They’re ready to walk in.
After the meeting, I thought about my own energy. I hit a rough patch this past summer. A few things drained me for a month or two. But right now? My work battery is fully charged. If someone forced me to stop working today, I’d be heartbroken.
My retirement room is still dimly lit. Do I work on moving that dimmer switch, or leave it alone?
As I pondered this, I found a surprising companion in the conversation: Warren Buffett.
Warren Buffett
Warren Buffett steps down as CEO of Berkshire Hathaway at the end of 2025.
How did he know it was time to retire?
“There was no magic moment,” Buffett, now 94, said in an interview with The Wall Street Journal. “How do you know the day that you become old?”
He added:
“I didn’t really start getting old, for some strange reason, until I was about 90… But when you start getting old, it does become—it’s irreversible.”
Warren began feeling his age at 90. And he’s retiring at 94.
Did anyone chastise Warren to give it up at 65? 70? Even 80? Perhaps they did. Maybe he ignored them and kept doing what he loved anyway. Would we say he didn’t live a balanced life? That he should’ve stopped working earlier to pick up pickleball or travel more?
I doubt it.
I’d guess that for at least the past quarter century, Warren shaped his work life around the things he loved and excelled at, delegating the rest.
Perhaps Warren’s story is missing from this perspective on retirement.
There are plenty of people like him, past the conventional retirement age, doing what they love, filled with purpose and passion, and part of a community they value.
Maybe that’s the path I’m on. Something about that idea feels light and energizing to me.
Keep on Sprinting
About twenty years ago, my business partner at the time told me this Hunter S. Thompson quote fit how I lived my life:
“Life should not be a journey to the grave with the intention of arriving safely in a pretty and well-preserved body, but rather to skid in broadside in a cloud of smoke, thoroughly used up, totally worn out, and loudly proclaiming, ‘Wow! What a Ride!’”
So when Fritz wrote Retirement is a Sprint, Not a Marathon, it struck a natural chord with me. “Yes,” I thought, “This is the way!”
But what I didn’t ask was, “Is this the way for me?”
I’ve been sprinting for twenty years. I love sprinting. But sprinting requires rest.
This past year, I finally got better at rest. I scheduled more time off. Still not a ton, but far more than I had in the previous two decades.
And I learned something about what works for me: partial time off.
In November, for example, I did a four-day morning pickleball clinic and worked in the afternoons. Earlier in the year, while training for our Mont Blanc hike, I spent a week in Beaver Creek, CO, working in the morning, hiking in the afternoon.
When I get enough rest, my work battery stays full.
As I write this over Thanksgiving weekend, I’m genuinely eager to get back to work on Monday. We’re launching a new YouTube channel. My new book is coming out. My team is growing. Work feels exciting again because, lately, I haven’t overdone it.
Is this the happy medium Warren Buffett found?
Maybe so.
In Conclusion
Has my retirement room gotten any brighter? Yes, just not closer. But the picture is a little clearer.
It involves more rest. More half days. More “staycation” weeks where I can focus on big projects without interruption, and delegate more of the day-to-day tasks.
It’s looking more like the Warren Buffett path. No specific age in mind. Instead, paying attention to how I feel, where I add value, and what brings purpose and joy.
Your Turn: If you’ve created a nontraditional retirement path, or if this resonates with you, I’d love to hear your story in the comments below. Am I crazy, or are there others with this perspective?
