When Fritz and I agreed to this experiment, we had no idea what to expect. Who knew my sparkle bomb of an idea (sharing my own thoughts on retirement on this blog) would, well, set off so many sparkles! Thank you for the warm welcome in the comments. I look forward to continuing the journey with all of you.
As I said in our initial post, I want to share how my personal thoughts on retirement shifted from “Nope, Never” to “Maybe One Day.” It may sound subtle, but to me, it was seismic.
I never thought I’d retire. Then…I took a vacation and had an awakening. Share on X
Here’s how it happened…
A Personal Awakening
I love…
…accomplishing things.
…growing my company.
…contributing to my profession.
…mentoring those new to the financial planning career.
Give me three days off, and I’m itching to return to work.
That’s why this vacation was different. It was day 13, and I hadn’t been bored yet. We were in Beaver Creek, CO, where we got married. It’s my favorite mountain town.
Until this vacation, when people asked about my retirement plans, I’d casually say I planned to work until 70. But it wasn’t a carefully thought-out plan. It was simply the only path I could see.
Then, at 53, on that vacation, I experienced what a joyful retirement might feel like: a life centered around nature, health, and writing. Writing fills me with joy — when I can do it at a reasonable pace, not squeezed between emails, financial statements, and Zoom meetings.
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.
Pre-awakening: The logic was clear: I was supposed to save and plan for retirement. And, since I help others do that, I didn’t want to be a hypocrite.
Post-awakening: I was no longer planning for retirement out of obligation — I can see it one day. My future no longer felt like a murky unknown—it felt like something I could shape.
Here’s our Sept 2023 wedding photo from the top of the ski lift in Beaver Creek.
Dana’s favorite place in the mountains.
What Shape Will I Shape?
As I spent time thinking about the retirement I wanted to design, and how I would achieve it, a few things became clear:
1) I Can’t Go from 100 to Zero
Work full time – then stop all at once? No, such an abrupt transition doesn’t suit me. I must begin weaving in more time off now. That means planning more vacations, remote work weeks from Colorado, and learning to take weekends and holidays off like a normal person – weaning myself from the “always on” mindset of an entrepreneur. This is easier said than done.
2) I Work for Fun—So I Need More Fun
When I don’t have anything else exciting planned, I work. Because for me, my work is fun. So, the only way to scale back is to deliberately add other joyful experiences to my calendar. The first step? My husband and I booked a bucket-list hike along the Mont Blanc circuit in the Alps, spanning France, Italy, and Switzerland. We’ll hike about 99 miles over twelve days this summer.
3) I’m Not Building to Sell—I’m Here for the Journey
I needed more clarity around what I want from my eventual succession plan. Some business owners build to sell for maximum enterprise value. That’s never been my path. I’m building future generations of financial planners who will become owners of the firm. Two already have. This gives me something more valuable: maximum life satisfaction value. How do I continue to use this metric as my compass?
4) I Want a Long, Gradual Transition
I need to communicate to my team that I’m looking for shared responsibility. My goal is to scale down gradually over the next sixteen years. Yes—sixteen. It’s a long ramp, but it feels right for me. Each year, I must identify key tasks, determine who can take them over, train them as needed, and then I must let go of that item.
That clarity I found gave me energy.
Energy is a good sign that you’re headed in the right direction.
My Pre-Go Phase Begins (And Go-Go Starts Now, Too)
With my newfound clarity, I began working on a new book, which I hope to release this fall.
It’s called Living Off Your Acorns: Your Guide to the Four Phases of Retirement. It covers the mindset and financial shifts that happen in each phase: Pre-Go, Go-Go, Slow-Go, and No-Go.
When does each phase begin? It’s different for each of us.
My Pre-Go phase began on that vacation, when the light went on. While this phase typically spans the five to ten years before retirement, I realized I would need to overlay mine with the Go-Go phase—which for those with a more abrupt path to retirement, typically occurs during the first five to ten years of retired life.
If I don’t overlap mine with my current working years, I’ll reach 70 without having done many of the things I dream about. And at 70, my window to do them will be shorter. So I’m layering in my Go-Go experiences now. This is my path. And I’m intentionally making it happen.
The Financial Side
My financial plan was already in motion. I update it each year. But now, with a more clearly defined path, I approached several things differently in my 2025 update.
First, I stress-tested an earlier retirement.What if health issues force me out of work early? What if my feelings about work shift in my early 60s? I stress-tested a retirement as early as 65. I don’t think that’s my path—but according to the Transamerica Retirement Survey, 56% of retirees retired earlier than planned. I’d be foolish to assume it couldn’t happen to me.
Next, I ran our custom Social Security plan.When estimating future benefits, if retirement is far in the future, I use generalized assumptions in financial plans—often based on the Full Retirement Age benefit amount as estimated on someone’s statement. But as someone approaches retirement, we refine those projections. Typically, refinement begins around age 55. This year, I am 54 and my husband is 57. It was time.
Using specialized software, I input our historical and future estimated earnings through our projected last year of work. The program then calculates an actuarially recommended claiming strategy based on inflation, interest rates, and life expectancy.
This is where I got the surprise of a lifetime. I’ve run hundreds of Social Security analyses – I was pretty sure I knew what our recommended plan would be. I would have been wrong. And that?
That’s a story for my next post.
Until then… I’d love to hear from you in the comments.
Where have you found clarity?
What activities give you energy?
Where is retirement still murky for you?
And if you’ve had your own “light went on” moment—what was it like?
