The Weekday World I Never Saw
I can still remember the smell of beans being freshly roasted, the low sound of them being stirred in endless circles in a distant corner, smoke rising through the roof to the street beyond. I was in my twenties, sitting at the same wooden corner table I sat at every weekday morning, a large refillable cup beside me, floor-to-ceiling windows looking out over Main Street in a college town of forty thousand. The Blue Ridge wasn't visible from that chair, but it was close enough to feel. Just beyond the edge of town, those mountains sat the way they always had, patient and permanent, pulling at something restless in me that wanted adventure and variety more than routine. I didn't have to see them to know they were there. I've felt the same way about God through the busiest seasons of my career.
I had spent my teenage years hiking the Appalachian Trail on weekends, camping with friends, learning what it felt like to be small in the presence of something ancient and permanent. Those mountains had spoken to me since before I had language for what they were saying. And every weekday morning in that coffee shop, with the trail just a few miles east and the ridgeline close enough to shape the horizon, they were still the thing I oriented toward.
I was working through a book of the Bible most mornings, taking notes, writing out prayers, journaling about the applications. The journals had themes. One was called "Beauty All Around." I printed out quotes and taped them inside the cover, clipped a photo of a Van Gogh painting as I read Letters to Theo, glued in a picture of a pear next to a line from Augustine’s Confessions about stolen fruit. It was prayer, Scripture, wide reading, and looking for the connective tissue running through all of it. I was young and free and sitting at a table where nobody needed me for anything, soaking up God and life and learning.
I was life rich and money poor.
With our child on the way, I traded it. I spent the next twenty-five years building a career, raising a family, and saving aggressively toward financial independence. The coffee shop became a weekend luxury. The journal moved to the predawn hours on the days when the schedule allowed. The mountains disappeared from my daily view for a season until I moved West to Arizona and they came back into focus. The time to think got replaced by time to produce, and the production was good. It paid well and most days I don't regret the trade.
But I'm getting ready to trade it back. Different mountains now, visible from every direction in a desert valley with wide-open skies I've come to love. And this time, when I walk into the coffee shop, I won't have to leave.
The Preview I Wasn't Expecting
A few weeks ago a big project wrapped after months, and the next several are in a planning phase that doesn't need me yet. A rare gap opened between deliverables, and instead of filling it with busywork, I decided to use it.
I've already mapped out an ideal Tuesday. Now I had a chance to test pieces of it, not in theory but on actual weekday mornings while I'm still employed. These weeks felt like an advance scouting trip into a life that isn't mine yet, with nobody knowing I'm about to move in.
The Gym at 10am on a Monday
An early meeting earlier this week made my normal 5am workout impossible. I've always had some schedule flexibility, but on most Mondays I'm too locked in to step away especially mid-morning. With a little slower pace at work, this time I went.
The parking lot was full. I had to walk five times farther to get inside than I do before dawn. There was a line of people waiting to scan in. You would have thought it was a holiday. A group fitness class was running in a side room, bass reverberating through the whole gym. Every bench press, incline and decline, was taken. I expected a room full of traditional retirees. Instead there were people of every age and fitness level, many of working age, and I never would have guessed it was a weekday.
I improvised. Placeholder kettlebell exercises while I waited for the equipment I came for, working through my routine out of order. I made it through, but it took creativity and patience.
On the way home I revised one small piece of my retirement plan. I've been looking forward to sleeping in for the first few months after I downshift. While I still will, maybe it will not be quite as late as I'd originally imagined. There's something to be said for getting there before the crowd.
The Coffee Shop, Thirty Years Later
Last week I spent two hours at a coffee shop on a weekday morning. I had my leather-bound journal and my fountain pen open in front of me. A large window looked out on palm trees and flowering trees outside instead of the Blue Ridge.
I poured out my heart to God, processing this last season of full-time work, asking for wisdom about situations I'm carrying, praying for the faithfulness to do well the work I still have in front of me. I felt a greater clarity into my own heart and a sense of what the future may look like. Only time will tell.
The same God. The same desire to understand my own heart and seek wisdom outside of myself. A different decade and a different window, and the practice still fits like it always did. It’s one I want to become more of my daily rhythm.
Unlike the gym, the coffee shop was mostly empty. Two retired friends catching up at a leisurely pace, sharing about their lives and laughing. A couple of people working on laptops, one on a video call in a corner. There were a smattering of stay-at-home parents after drop-off. It was wonderfully quiet.
What excited me most was watching the two friends. They were in no hurry to leave. They lingered, had great conversation, laughed and they were slow in parting. I want more of that. Whether with my wife over lunch, or with a friend on a weekday afternoon, I want the kind of conversation where nobody checks the time.
Where the Gap Appeared
The temperatures finally broke over the weekend, and I went for one of the first good hikes of the season early on a Sunday morning. Off season, the snowbirds are not yet back. Parking lot nearly empty, sky open and clear. I can only imagine how much emptier it would be on a Monday.
In the busiest seasons of my career, hiking alone has been how I clear my head and get re-grounded. In the next chapter, I want it to become something I share with the people I care about: my wife, a good friend, another couple. The version of the dream I kept returning to had other people in it.
That surprised me. And it led me to look more honestly at what was actually waiting.
I assumed a weekday world was built and waiting for me. In some ways it is. The gym is packed. The coffee shop is there. The trails are beautiful. But the version of that world that's mine doesn't exist yet.
I went looking for a midweek men's Bible study. My wife has been part of women's groups for years and currently leads one. The churches near us run multiple women's studies during the day, some of them ten minutes from our house. Surely there's a men's version.
There isn't, at least not the version I was looking for. Our church has a midweek evening study, but nothing during the day. A large national group runs another larger men's study on a weekday evening, but twenty to thirty minutes away. The same organization runs daytime groups for women within ten minutes of our house. The demand for a daytime men's group isn't there, and where it does exist, I suspect it skews towards men in their seventies and eighties.
Whatever your version of that search looks like, whether it's a creative writing group, a woodworking co-op, a volunteer crew, or a weekday hiking club, it's worth finding out now whether it exists, whether you'd need to build it, and how that changes your picture of the first year.
That was a small jolt. And it led me to count honestly.
I have one close local friend. Several strong acquaintances. One or two couples we're close to. Two or three lifelong friends in other cities I could call for anything, but they can't readily meet for lunch on a Wednesday.
When the job goes away, so does the social contact it supplied whether I wanted it or not. I've been working from home since 2020, which means I've already been living a version of this for six years. But the calls, the meetings, the travel, the dinners with colleagues, those still filled the space. After the downshift, they stop.
The money was the easy part to plan. The people are harder, and I have work to do there to build more local friendships - particularly among friends who have flexibility to take hikes or play pickleball on a weekday.
What I Heard From People Who've Already Made the Leap
A few weeks ago I was at a personal finance conference and organized a dinner with a group that included several people who had retired or downshifted in the past five years. A counselor at the table, whose practice focuses on marriage, money, and the emotional weight of major life transitions, put it plainly: the financial planning is the easier part. People spend years on their number and almost no time on what they want a typical weekday to look like or the friends who make it meaningful.
Three things from that dinner I'm still turning over.
The relationship adjustment is real and takes time. Those who've been through it said roughly a year before a new rhythm feels natural. Not a year of struggle. A year of recalibration. Worth knowing before you get there.
One or both partners can experience a real loss of identity as earner and provider. The math is solvable. That part is harder.
And the asymmetry the counselor named is exactly what this series, and this blog, exist to address. The number gets twenty years of attention. The life behind it gets almost none.
What I'm Starting to Build
I keep coming back to a kayak dream. Flatwater mornings on a weekday, maybe with my wife or a recently retired friend. Wild horses along the shoreline, canyon walls catching the early light, birds I'll need to learn to identify. Community built around nature and a shared activity rather than around a conference room. I'm still researching whether my sedan can haul a pair of kayaks, which tells you how far along I am. I may rent one in one of these slower blocks and see what it’s like hauling it out there and paddling around on a midweek morning.
Beyond that, I'm thinking about starting a lunch once or twice a month for men who've stepped away from full-time careers, or are about to. Not a support group. Just a table with people who understand the transition and want somewhere honest to talk about what comes next. I'm researching volunteer opportunities that happen during weekday hours, something I've never been free to do. And I want to check out the weekday pickleball scene, mornings or midday rather than the after-work games I've played for years. That’s next on my experimentation list for a slow workday lunch.
None of it is built. All of it is worth building.
The Boxes in My Closet
There's one more thing the gap surfaced, and it’s one I’ve been ignoring for several years.
A few boxes of my late father's possessions are sitting in my home office closet and in corners of the house. Old photographs that need sorting and scanning. Keepsakes that could be framed. Some items that could be donated and be a blessing to a new owner. Between the emotions of working through grief and being perpetually busy and then recovering from the busy and the travel, it has been easier to push them off until there's time. With my mom passing this year, there are more items to sort.
Now there's some time. Soon there will be more.
Those boxes are the most honest version of the thing this whole season is about. The important work that isn't urgent, the kind that waits until you have margin, and then waits some more. I don't want to be the person who still hasn't opened them a year from now.
What Surprised Me Most
It wasn't the gym or the missing Bible study.
On Tuesday, the day after the gym experiment, I had a rare open morning and used it for focused, heads-down work. No calls. No meetings. No context switching. I had the most energy and creativity I'd had at work in months.
I wrote in Cutting the Ankle Weights about shedding the hidden costs of a career that looks impressive from the outside. I wonder sometimes if the pace and the stress are the ankle weights, and without them I'd be a better, more creative version of myself. Not less engaged. Sharper.
That isn't an argument for checking out. It's an observation that the margin made me better at the thing I'm still doing. And if that's true now, in a gap between projects with one foot still in the machine, I want to know what it looks like on the other side.
Where I Am
Six months out, I'm about 85% excited and 15% nervous. Excited about the life I keep getting glimpses of. Nervous about whether I'll fly, whether I'll find a rhythm, whether I'll make the most of the gift of time or let it pass me by. Nervous, if I'm honest, about whether I'll rebuild the Gilded Cage in a different form.
All change is felt as loss, even the change you chose. But I have more evidence now than I did a month ago. The gym is crowded at ten. The trails are empty in September. The men's study I assumed would be waiting doesn't exist yet. And I sleep better when my mind has room for bigger things.
Some of the life I've been dreaming about is already out there, running every weekday morning while I sit in meetings. Some of it I'll have to build. Both are worth knowing now.
The coffee shop is still there. The journal is still open. The mountains are different now, but they're just as visible. And this time, when I walk in, I won't have to leave.
Landing the Series
This month's series set out to cover three things: timing your exit, protecting your income, and landing safely. Landing the Plane, Part 1 built the drawdown framework. Part 2 handled the timing. She Could Have Asked Me to Keep Working was about landing smoothly with the person you're on the journey with. Already Gone, Not Yet Gone was about what the final stretch feels like from the inside.
The landing itself is the part I can't write until I get there. So this was the rehearsal.
Three questions to close out the month:
If you're within a year or two of your own exit, what's one piece of the next chapter you could test this week?
If you've already made the leap, what surprised you about the weekday world?
And wherever you are on the trail, who are the four or five people you'd call on a Wednesday afternoon, and do they know it?
Tell me what you think in the comments below. A question you're stuck on, something here you think I got wrong, or what you found when you tried it yourself. I read every one and I answer every one.
Let's make wise choices and live a great life together.
🌵 Desert FI
Want to go deeper?
Become a Desert FI Insider. Testing the life before you leave goes better with company. Insiders get Weekend Reflections every Sunday morning plus free Insider-only resources like a reflection guide for your downshift, and access to live conversations like our recent subscriber-only Zoom call. If you’re not on the trail with us yet, join at DesertFI.org/join.
Already an Insider? Here are three posts worth exploring:
Already Gone, Not Yet Gone: The Psychology of the Final Stretch: on the inner shift that comes before the exit
She Could Have Asked Me to Keep Working: on the conversation with my wife that had little to do with money
Taste It Before You Can Afford It: on dreaming vividly and tasting the life before you can fully fund it
