I’m about 20 months out from retirement, and instead of waiting for a finish line, I’m treating this time as a design phase. As I started looking at this process, I realized that I need a timeline with clear markers—similar to watching mile markers on the highway to understand where you are and how far you still have to go.

By creating this timeline, I can focus on transition rather than the end of something—a concentrated work life. I want to stay focused on intention, not rush the time away just to get there. No doubt I’ll have moments of both impatience and fear, but being grounded in planning and design helps keep it manageable and focused. This can feel like a challenge for those of us who have spent a lifetime working and who find ourselves needing an alternative to the traditional retirement plan.

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Where I Am Right Now

Until a year or two ago, I had a very different mindset about retirement. I assumed I would retire at 70—if then. I was tied to my career for familiar reasons: identity, finances, and expectations. It had also been a long time since I had traveled far beyond the college campus and my local neighborhood. As I took time to think about what I was doing and what I wanted next, I began exploring alternative ways to live. How could I do what pleased me instead of what I “should do,” without being irrational or irresponsible?

As you’ve probably picked up, I’m still working full-time—sometimes more than full-time. The hours are long, and the stress can be overwhelming in cycles. My biggest challenges mirror those of many in management roles: juggling priorities and making sure people are in the right place, mentally and physically.

My home base is an in-progress townhouse that will require decisions fairly soon. Initially, those decisions are straightforward—updates to bathrooms, closets, and similar projects. Later, the question of whether to rent or sell will be on the table.

The pup, Bobo, remains top of mind in both my planning and current travel. His comfort matters—whether he’s at home, on the road with me, or at the daycare and boarding facility he’s used since he was about a year old.

I continue to travel periodically for both work and pleasure. My personal travel is mostly cruising right now. My most recent trip was a two-week cruise over Christmas and New Year’s. I have three more booked for 2026 and will begin looking at options for 2027.

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The Non-Negotiables for My Retirement Lifestyle

While I don’t have all the details worked out, I do know some things that are required in my retirement lifestyle. Thinking through these now helps establish parameters for planning. Here are a few you’ll see reflected as the process unfolds:

• Solo travel is not optional. The plan must include meaningful travel, whether full-time or periodic.
• Comfort matters. Comfort—for both me and Bobo—is important. I don’t want to be so budget-conscious that I end up in places that don’t suit us.
• Mild weather. Having lived with both heat and cold, I want to be able to step outside without feeling like I’ll pass out or freeze.
• A manageable budget. As much as I wish otherwise, staying within what my finances can realistically support is essential.
• No rushing. Pace matters. I need time for thinking and writing without feeling like I “have to” do everything.

Ultimately, I’m trying to keep things simple and manageable.

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What I’m Actively Working on This Year

Over the coming year, preparation will be key. I’ve already mentioned the house updates, but I also need to focus on paying down credit cards. Those two goals may be in direct opposition, which is something I’ll need to weigh carefully.

I’ll also be traveling—primarily through lower-cost cruises and long weekends. The goal is enjoyment and relaxation, but also the opportunity to test a few travel theories I’ve been considering.

Another major part of this transition is building this blog. It matters to me to share what I’m learning and, hopefully, help others navigating a similar path. This lifestyle isn’t mainstream, and examples can be hard to find. If nothing else, I can offer transparency—and you can learn from my mistakes, which I’m sure I’ll make. We’re aiming for flexibility, not perfection.

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How Travel Fits Into My Countdown (Not After It)

To stay grounded—and to begin testing this new travel style—I’ll continue traveling while planning for retirement. Solo cruising is a major part of this. By taking advantage of school holidays and break closures, I can experiment with longer trips and better understand the difference between slow travel and fast-paced vacations.

Experimentation before retirement is essential. It allows me to monitor energy levels, confirm costs, and test the rhythm of taking things one day at a time. It also helps me learn what brings joy—and what turns out to be a pain.

Bobo is part of this experiment too. He’ll be joining me on longer trips and adapting to different locations. I suspect he’ll be quite pleased with the extra opportunities to put his nose down, catch a trail, and pull me halfway down the road in pursuit of something that passed by a few hours earlier.

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What I’m Not Doing (and Why)

For now, I’m preparing for decisions that will eventually be more permanent. While I’ll get the house ready for sale or rental, I won’t be making housing changes in the short term. Given my specific financial situation, that wouldn’t be a smart move.

Although I’m drawn to the idea of full-time slow travel, I’m not committing to it yet. This planning phase is about exploration—creating experiences that help me evaluate both what I want and where I want to be.

And while I’ll continue optimizing my finances, I’m not willing to give up living and traveling in the present. Balancing those priorities will require thought and planning. Fortunately, I like spreadsheets.

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What Success Looks Like at the End of These 20 Months

So what happens when I reach the end of this countdown? I won’t have every answer, but there will be fewer unknowns. I’ll have greater confidence in how this different kind of retirement can work. My home will be ready for its next phase, and I’ll have clarity around finances—along with a realistic sense of what’s possible and what isn’t.

Most importantly, I’ll have a flexible plan that makes me feel excited, not scared or exhausted.

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If You’re on a Similar Timeline…

If you’re on a similar timeline, you don’t need to have everything figured out. Retirement planning can be done in phases, allowing room for change—in you or in the world around you. If it resonates, I invite you to follow along as I navigate this in real time.