Already Gone, Not Yet Gone: The Psychology of the Final Stretch
The bus dropped me at the corner and the door hissed shut behind me. A cold Washington DC wind found the gap between my collar and my neck. Somewhere on the block a wood stove was going, and under it, faintly, the smell of somebody's Christmas baking. Two weeks of nothing but friends, sports, games and presents stretched ahead of me. It was 1984. I was ten. And the last bell had finally rung.
On Christmas Eve my parents set up a folding card table in the formal living room, the same room where, decades later, they'd sit me down and finally talk to me about their money. We played Gin Rummy for an hour, maybe longer. I won more hands than I lost, which at ten felt like proof I was getting good at cards. I sat with my back to the dining room and the French doors past it, the ones that looked out on the backyard. My parents made it easy to stay where I was. Want another Coke? We'll get it. Need a break? Go on up to your room. My room faced the street. I didn't give any of it a second thought.
I was up before six on Christmas morning. I came down through the dark house to the den and counted shapes under the tree, and there were enough boxes for a good year. One thing was missing. Every Christmas there was a gift left unwrapped with nothing but a bow on it, and that morning I couldn't find it anywhere. I remember being confused for about ten seconds, deciding it didn't matter, and running back upstairs to wake my parents.
My dad was tired. My mom looked at him before she looked at me. I couldn't read the look and I didn't try.
They brewed coffee and put out coffee cake, and we spent an hour on the tree. Paper got shredded, bows went in a pile, clothes came out of boxes and got held up for pictures. I got the thing I'd asked for, a Daisy combination BB and pellet gun, wood stock and black barrel. My dad was a retired Marine and he handed it over with rules I had to agree to out loud: targets only, eye protection every time, and never in the yard without a parent. That gun was the first real freedom anyone ever handed me, and it led straight to the bottle rocket wars a few summers later.
I thought we were finished, and I was already thrilled with everything I'd gotten. I had a Hefty bag out and I was collecting wrapping paper, which is what you did before anybody recycled. My parents looked at each other again. My dad said, "I think it's time for the main event."
I checked under the tree and behind it and found nothing. He pulled on his coat, handed me my Redskins jacket, and told me this one was outside.
He led me through the kitchen and out the back door. Sixteen feet of trampoline stood in the middle of the yard, a blue pad wrapped around the frame, a black mat in the center, silver legs sunk into the cold grass, and a red bow taped and tied to the rail. I had never asked for one. I didn't know a single person who owned one.
I went out there in a winter coat, pajama bottoms and bare feet. The mat was stiff with frost and it burned the soles of my feet for the first few seconds. The springs shrieked with every landing. My breath came out in clouds. It was twenty-five degrees, and I was cold for about four minutes and then I was pouring sweat.
My parents stood on the back step in their robes and watched. Forty years later, the clearest thing I remember isn't the trampoline. It's the two of them enjoying my joy.
A crew from the sporting goods store had delivered it and built it the afternoon before, forty feet behind my back, while my parents kept me at that card table dealing another hand and getting me another Coke. I've wondered since whether I was actually winning or whether they were letting me. It doesn't matter much either way. I couldn't see what was happening behind me, and I couldn't have known to look.
I've thought about that trampoline a lot this year.
The Year at the Card Table
I'm in the last stretch before I downshift. The date is set, the plan is built, and almost nobody around me knows.
What I expected this season to feel like was restlessness, a countdown, one long exhale held for twelve months.
What it feels like instead is stranger and harder to name. I'm still at the table. I'm still playing the hand. And something is being built behind me that I mostly can't see.
Here's the feeling from inside of it, as honestly as I can put it.
My focus has narrowed hard onto the core of my job. Deliver the results. Be a good teammate and a good partner. Mentor the people coming up. Everything on the periphery has loosened its grip. The hundred-person call that's tangential to my role no longer requires my face in a box for ninety minutes. I'll take the recording, skip to the ten minutes that matter, and give that time back to something real. I'm not gaming the system. I'm just done pretending that attendance is the same thing as contribution.
Travel has changed in the same direction. I plan it down to the day now. What do I need to accomplish, what's the shortest honest path to accomplishing it well, and how quickly can I be home. I used to get there early for extra prep, building my career and my relationships, using the evenings to build trust with my team or with whichever executives in whatever city could help me on my way. There were more trips than I'd like to admit that ran a night or two longer than they needed to.
I've also stopped carrying my identity in the work, and I notice it most around money. I recently delivered a result that will pay me later this year. Two years ago I'd have been running that number against everything it could become: what it could buy, what it could fund, what we could give away, how much faster it moved the date. Now I think about it almost not at all. What I think about is that the thing we built will employ a lot of people and start a partnership that outlasts me. The Life Fund already covers the trip we want to take. The rest is liquidity for the back half of my departure year. There's no week at Disney with a young family attached to it and no worn-out couch getting replaced. It's a number adding to a number. After decades of saving, it's a rounding error.
I'll be honest about the part that isn't flattering. Some weeks I catch myself in survival mode, head down, running at the date instead of living the days between here and there. The whole structure of my profession is built to pull people into working at maximum intensity, because compensation is tied to outcomes and the outcomes never stop needing you. When you step partway out of that mentally while your body is still inside it, there's a tension to some days that I didn't anticipate and don't entirely like.
Intentionally Reactive
I've spent my career as a proactive person. When change came, I moved toward it. I built relationships with new leaders early, made myself useful, earned trusted advisor status, and made sure my teams were connected to the decisions being made about them.
For the past six months or so I've been intentionally reactive instead, and it's the strangest part of this whole season.
There's been reorganization above me. The version of me from two years ago would have triggered a specific set of moves. Reach out, offer help, provide continuity, build the relationship before anybody needs it. I'd have been on a plane.
I'm not doing any of that now. I'm still helpful where it touches my actual responsibilities. I'm just not building toward a future I don't intend to be part of.
The psychology underneath it is a little strange, and I'll name it plainly because I suspect some of you are living inside the same calculus. Either my results speak for themselves and I stay until the date I’ve chosen, or shifting structures catch me the way they’ve caught many good people before me. I’ve modeled both, and the plan holds either way.
Heads I win. Tails I win.
I recognize how fortunate that is, and I want to be careful not to sound cavalier about it. Plenty of people facing a reorg have no version of this available to them. That asymmetry is what financial independence actually buys, and it took thirty years of saving to build it. I wrote about what it feels like to have the door crack open in The Gilded Cage. This is what it feels like a few steps past that.
The one thing I do care about is finishing well. If a restructuring catches me, I don't want a single person able to say he was checked out or his performance slipped. That isn't about my career. As a person of faith, I want my work to reflect well on the One I'm actually working for. I've never thought of my direct boss as my ultimate boss. Working hard when nobody's watching isn't a productivity philosophy for me. It's a matter of who I think is watching.
What has genuinely changed is what I'm willing to chase. There's a large leadership conference this fall and I haven't seen an invitation yet. A year ago that would have occupied real space in my head, and I'd have read it as a signal about my standing. This year I followed up gently, and I found I meant it when I told myself I'd be fine either way. If the budget is tighter or the list is shorter, no hard feelings. What I'd want out of that week isn't the strategy sessions. It's drinks on the lawn with people I've worked alongside for years, while I still can.
Being intentionally reactive shows up in smaller ways too, in the things that used to cause me real anxiety. I took a week of vacation this summer. I took two days of leave to bury my mother. I'm taking three days of PTO to attend a personal finance conference. Three absences inside of a month.
The old version of me would have lost sleep over how that looked on a calendar. I'd have found a way to shave a day, or worked through the evenings to compensate, or answered emails and joined meetings from vacation. Instead I sent the calendar invite to my team and closed the laptop.
I should have stopped paying that price years earlier than I did. It feels good to be free of it.
Identity Preview Moments
If the last year has a gift in it, this is the gift. You get to meet the person you're becoming before you have to be him or her full-time.
Mine shows up on airplanes. In the season when I was leading a very large team and traveling constantly, my colleagues could tell when I was airborne, because that was when a hundred and fifty emails arrived from me at once. Flight time was the most productive block in my week and I used every minute of it.
Now I book the window seat on purpose. I watch cloud formations I wouldn't have looked up for. I think, and I pray, and on some flights I don't open the laptop at all. Same seat, same airline, same routes I've flown a hundred times, and a completely different man sitting in them.
It shows up in the early mornings too. Two decades of West Coast work trained me into waking at four or four thirty, and I still do, even on the mornings when nothing requires it. That used to be when I got ahead of the chaos. Now it's when I write. It's the quietest and most fully myself I feel all week, and it's the clearest evidence I have that the Next Endeavor is real rather than theoretical.
There's a countdown app on my phone now, which is not something I would have predicted about myself. I've always tried to live in the moment. I plan carefully, but I've been wary of putting too much hope into dates on a calendar, because calendars move and hope placed there tends to move with them.
The app has our thirtieth anniversary on it, a big trip we've been planning, Christmas, my birthday, and the last spring break ski trip with our son. And yes, my notice date and my planned last day.
I don't check it daily. Every few weeks, maybe. What surprises me is that the anniversary and the trip generate as much anticipation as the last day does, which tells me something good about where this is heading.
I do have to remember to close it before I set my phone down on a conference table. A notification reading Last Day would end the secret in about four seconds.
The strangest preview came at the dentist. I finished a routine visit a few weeks ago and they scheduled the next one for March, which is right around when I plan to give notice.
I stood at that counter holding an appointment card and realized I'd be handing in my resignation before my next cleaning. A date that had felt permanently far away turned into a thing on a calendar between now and Christmas. It felt closer than I was ready for. It also felt wonderful.
The Social Complexity of Holding a Secret
I'm fifty-two, and if the plan holds I'll be fifty-three when I downshift. I planned for most of my adult life to work into my sixties. I don't know a single person at my company who has left this early, and I hold a role that people spend entire careers trying to reach. Walking away from it voluntarily is going to surprise people.
Nobody there knows. A couple of colleagues and I have talked in general terms over the years about what a nest egg would need to look like, and that's the extent of it. A few close friends read this blog. None of them work with me.
I'm not naturally good at holding something like this, so I'm careful. The conversations that require the most care are the ordinary ones. A colleague asked me recently where I see myself in five years. I said something true about the work in front of me and changed the subject.
Most of the questions are small. Where do you want to take your career? Don't you want to be at that industry conference next spring? The honest answer to the last one is not really, and the honest answer to the first is a story I'm not ready to tell yet. So I answer at the level of the work in front of me, which is true, and I let the rest sit.
What I keep coming back to is that the discomfort is small and temporary, and the alternative is worse. Announcing early would change every conversation I have for the next six months, and it would put me at risk. I'd rather do good work as myself for as long as I can, and tell the story once, cleanly, when it's time.
The Empty Wednesday
Here's where I'll be least tidy with you, because this is the piece I haven't fully solved.
I've journaled in real detail about what a Tuesday looks like on the other side. I know the shape of the Next Endeavor. I've written about the five paths worth exploring and I know which ones are mine. In a recent Desert FI subscriber survey, the most common struggle among readers at or near financial independence wasn't the money. It was purpose and identity, and the empty calendar behind them. The solved math and the unsolved meaning.
I'm not immune to it, and it would be dishonest to write this post as though I were.
Some self-doubt has crept in recently. What if I finish the Next Endeavor work faster than I expect and find myself with thirty unstructured hours a week? What if I don't have the nerve to take the hike alone? What if the guys aren't free for kayaking, or I get bored with pickleball sooner than I think?
I have evidence on my side. I get up before my family on weekends to hike, and I know without question that I love it. On a weekday I should be able to go whenever I want. The trails will be emptier on a Wednesday morning than a Saturday, which is mostly a gift and partly a planning problem. Hiking alone means a walking stick, a first aid kit, and somebody who knows where I went.
And there are Saturdays in the Arizona summer when I wake up early with every intention of getting out, step outside into heat that never broke overnight, and say no thanks. That's fine in August. It's a warning about who I might become if I let it turn into a pattern. The pull of the couch is not how I want to spend the healthiest years I have left.
One thing helps more than I expected, and it's smaller and more social than you'd think. Having a good answer to what do you do.
There's real awkwardness in telling people you're retired at fifty-three. There's none at all in saying I downshifted from a corporate career and now run a growing community for people thinking about money, early retirement and midlife reinvention. Or in saying you spent twenty-five years in a classroom and now you tutor and coach kids through their college applications. Or that you ran restaurants for thirty years and now you help other people open theirs.
The Next Endeavor gives you a sentence. That sentence carries a lot of weight in a room.
What I'd Tell You If You're Twelve Months Out
Build the plan, then have somebody check it. Get the financial side genuinely solid before you set a date. Build your own model if you're inclined, then pay a fee-only CFP to build one independently. You want to know whether your plan holds up, not whether you like the answer.
Describe the life, not just the number. Journal about it. Talk it through with your spouse and with the friends who'll tell you the truth. Most of the people who struggle after leaving are the ones who assumed the free time would sort itself out. If you can't describe an ordinary Tuesday in detail, that's the work, and it's more urgent than another round of Monte Carlo runs.
Start living pieces of it now. You think you want pickleball. Go find out. A lot of rec centers and indoor clubs run free intro classes, and a friend who already plays will teach you faster than a video will. The same goes for the park you keep meaning to visit and the hobby you keep meaning to pick back up. Two months of trying is worth two years of assuming.
Take real steps toward the Next Endeavor before you need it to work. You don't want to arrive at your last day and discover the thing you planned to do doesn't suit you. Building it while employed costs you sleep, and it buys you evidence, which is the only thing that actually settles the question. Think out the life as carefully as you think out the money.
Learn from people who've studied this. Wes Moss surveyed more than two thousand retirees to find out what separated the happy ones from the miserable ones, and the answers had less to do with money than you'd expect. Start with his Retire Sooner podcast or What the Happiest Retirees Know.
Enjoy the journey. That one is advice to myself as much as to you. The final stretch is a season you only get once, and running at the date is a way of missing it.
What Surprised Me
Peace, mostly, and more of it than I expected.
I did the work earlier this year to build a real plan, and then I asked a longtime friend who's a CFP to build one independently with his own software and his own judgment, so I'd know whether mine held up. It did. Our money is already deployed as though I've downshifted. If a layoff comes tomorrow, I'm about as ready as a person can be.
The peace isn't total. In my less settled moments, what gets to me is the market. I follow it more closely than I used to, because how it performs matters more to my peace of mind now than the number of days on that app does. A 20 to 30% drop before my notice date would force a real decision, and I've thought about it enough to know I'd have options without having settled on one. I can't picture having the energy to keep working at this pace for another two years waiting out a recovery. I can picture negotiating something part-time, or taking a lower-pressure and lower-paying role and riding it out.
There's a reasonable case that retiring after a decline beats retiring at a peak, since sequence risk is front-loaded into the first few years. That's the whole argument of The Sequence That Determines Whether Your Retirement Lasts. Knowing it helps. It doesn't entirely quiet the part of me that checks.
The second surprise is that I'm busier than I would be if I'd chosen a clean retirement. Building a Next Endeavor while working a demanding job means early mornings, late nights and weekends. Fritz Gilbert built The Retirement Manifesto over three years while he was still working, and Bill Yount is still working now while Catching Up to FI keeps growing. I've signed up for a compressed version of the same thing, with the added complexity of writing anonymously, and there are weeks when I feel it.
I'd do it again. The evidence I'm gathering about myself is worth more than the sleep.
There's an idea in my faith about the tension between the already and the not yet. Already loved, already redeemed, already being changed. Not yet fully what we'll be. This year feels exactly like that. Already gone in most of the ways that matter. Not yet gone in any of the ways that show.
The Main Event
I got the BB gun that Christmas. It was the thing I asked for, it was a good gift, and my dad taught me to shoot with it in the backyard exactly the way he said he would.
I couldn't tell you what happened to it.
The trampoline is the one I still think about forty years later. It became the hangout spot, and friends came over for a week straight that Christmas. We worked out in real time what happens when two people land at once, which is how I went over the side and into the chain link fence at the back of the yard, bleeding a little and not caring at all. In high school we'd jump until our lungs ached and then lie flat on our backs on that mat in the dark, talking about our lives and everything we were going to do with them.
I never asked for it. I didn't know it existed. It was the best gift I ever got.
My parents had a knack I didn't appreciate until much later. They'd give me the thing I asked for, and then they'd find the one gift I never would have thought to want.
That's the part I keep coming back to this year. Financial independence is the BB gun. It's the thing you asked for, and you should absolutely ask for it, and it's worth every year you spent getting it. But it isn't the main event.
The main event is whatever you build with the freedom, and there's a decent chance you haven't thought to ask for it yet.
Two questions before you go:
If you're inside your own final stretch, what have you stopped caring about lately, and what does that tell you about who you're turning into?
And if you're still years out, what's being assembled behind your back right now that you can't see from where you're sitting?
I'll be out in the desert in the cooler months, on an empty Wednesday trail, looking for the version of me who's already out there. And if I ever find myself near a trampoline again, I intend to lie flat on my back on it and talk about the future with people I love, the way I did when I was sixteen and the future was still entirely theoretical.
I've waited a long time for the main event. I think it's going to be worth it.
Tell me what you think in the comments below. A question you're stuck on, a number you'd run differently, something here you think I got wrong. I read every one and I answer every one.
Let's make wise choices and live a great life together.
🌵 Desert FI
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Already an Insider? Here are three posts worth exploring:
The Weekday World I Never Saw: on testing the life you’re planning before you leave
She Could Have Asked Me to Keep Working: on the conversation with my wife that had little to do with money
I’m Not Leaving Yet, and Here’s Why You Might Not Want to Either: on choosing the timing of your exit
