🌵 I'm Not Leaving Yet — And Here's Why You Might Not Want to Either
I'm FI. I could leave tomorrow. I'm not.
And that's not a failure of nerve.
Growing up, my family made summer pilgrimages to Lake Geneva, Wisconsin. It's a small town built around a clear, cool lake — emerald water, old wooden boathouses, Chris-Craft runabouts cutting slow wakes through the morning calm. One of its more unique traditions is that mail is still delivered to lakefront homes by boat. Not dropped at a dock — delivered. A college student stands on the bow of a moving vessel, waits for the right moment, leaps to the dock, runs to the mailbox, drops off the day's mail and picks up anything going out, then sprints back and jumps onto the boat — which never stops moving — before it passes.
The whole thing happens in seconds.
Leave too early and you land cold and wet, watching the boat pull away.
Leave too late and you've missed your ride home entirely.
The jump has to happen at exactly the right moment — enough speed to make the dock, enough margin to run both ways, and enough trust that the boat will be there when you turn to come back.
I've been thinking about that mail carrier a lot lately. Because the exit from a long career works the same way.
Leave too early — without adequate cash liquidity and the right allocation in place — and you may find yourself selling assets at a steep discount just to fund ordinary life, precisely when the market has decided to test your conviction. The silence arrives before you know what to do with it. The freedom feels like falling rather than flying.
Leave too late — and you give away years that don't roll over. The years when your health is good and your energy is high. The window to travel slowly, on your own schedule, in the off-season when the crowds are gone and the prices are honest. The season when your kids — whether they're still in school, freshly launched, or somewhere in between — could benefit from a parent with time and presence rather than a packed calendar. The years with aging parents while they still have their health. The version of the exit that happens on your terms rather than your employer's.
The mail boat doesn't wait.
And neither does your life.
When my son finished his senior year of high school, I remember that last summer vividly. There was an ache in it — the familiar rhythms winding down, the realization that the house was about to get quieter in a way that wouldn't reverse.
But when August came and we dropped him at college, we cried less than we expected.
Because it was right. He was heading somewhere that fit who he was becoming. Holding on would have been about us, not him.
So it is with the season of work eventually coming to a close. Staying past the right moment — out of a false sense of loyalty, or the quiet fear that things will fall apart without you — isn't really about their outcomes. It's about yours. The boat is approaching the dock. The question isn't whether to jump. It's when, and how — and whether you've done the preparation to land well.
You may be in this same season — career winding down, identity shifting. If so, you're not alone on this trail.
Why People Stay — And Which Version You're In
The OMYS Trap.
One More Year Syndrome is seductive because each individual year seems reasonable. The income is real. The health insurance is comprehensive. The kids have one more tuition payment. The market is down and it feels like a bad time to leave. Each reason is defensible in isolation. It's only in aggregate that the cost becomes visible — and by then the currency has already been spent. The version of the exit that happens not on your terms but on your employer's — a layoff, a health event, a reorg — happens to people who wait too long more often than they expect.
If you're financially independent — if you've been thinking about leaving for a while, if it never quite seems like the right time — ask yourself honestly: if not now, when? And what are you leaving on the table? The joy. The time with family. The freedom to actually enjoy what you worked and saved so hard to build. The future is not guaranteed. Nobody reaches the end of their life wishing for one more day of work. At some point it's time to get about the business of really living.
Not judgment. Recognition. The trap isn't obvious from inside it. But if you can see it, you can decide what to do about it.
If this description felt uncomfortable to read, that discomfort might be the most useful thing in this post.
Inertia.
The work is acceptable, the income is real, and the friction of actually leaving feels higher than the discomfort of staying. Nobody names this one. It just continues — quietly, year after year — until one day you look up and realize the exit has been theoretically possible for a long time and you still haven't made it real. This version is probably the most common one in rooms full of high-achieving, financially capable people. It doesn't feel like a trap. It just feels like next year.
If this one lands closer to home, the sections below are for you.
Intention.
A defined window. A clear exit date. Something concrete to walk toward. Not escape — completion. This version is rare. It's the one I'm in. I have a date. It's less than a year away. I know what I'll say and when I'll say it.
Whatever your timeline, the preparation work below applies regardless of which exit you're building toward.
The goal isn't to escape. It's to arrive somewhere worth the jump.
What Intentional Staying Actually Looks Like
Something has shifted in how I experience the work — and it's not what I expected.
I used to be online before the sun came up. Now it's more like 7:00 or 7:30. Several days a week I'm working out — like I used to — but on the other mornings something has changed. On those days, before I open a single work tab, I spend time in prayer — asking for wisdom, for God's leading, for the clarity to know the difference between my plans and His. A man's heart plans his way, but the Lord determines his steps. I hold my plans loosely enough to mean that. Then I'm planning, testing, dreaming with specificity. This week, for example, I made a list of every place I still want to see — in the US and around the world. Got it all down, then started sorting: which destinations are easy with our dog, which ones are better suited to longer international treks without her. If our son is settled in a few years and works from home, the longer trips come sooner. If not, we'll get to them in our 60s. Either path works. There are dozens of great places in between that don't require either condition.
When a reorg gets announced — and in large organizations they always get announced — I find myself less rattled than I used to be. This too shall pass. The momentary turbulences now read as exactly what they are: momentary. The 2030 roadmap is genuinely less interesting to me than what I'm building and who I'm becoming. That's not checked out — it's reoriented.
I should be honest: not every day is serene. There are long meetings with unclear agendas, and it's harder than it used to be to stay fully engaged. Some days it's difficult to locate the motivation that used to feel effortless. I'm doing my best to show up well — and I am — but the fire that drove me for years now requires more intention to access. I'm watching my timeline closely for exactly that reason.
I still care deeply about delivering great outcomes. That hasn't changed. What's changed is that I worry less about being seen away from a screen for an hour or two. I measure my worth in results, with less energy spent on optics. I'm comfortable in my own skin. Playing the game doesn't feel as essential as it once did.
If you're in a similar season — giving your best while quietly building your exit — you know exactly what this feels like.
What I'm Building While the Clock Is Still Running
The year before a significant transition is not a year to coast. It's one of the most strategically important years available to you.
Testing the Next Endeavor from inside the constraints.
There's something genuinely powerful about proving to yourself that you can build what you're dreaming about while still carrying the full weight of a demanding career. For me it's Desert FI — writing, coaching families through financial decisions at my church, testing whether the work I want to do actually resonates and helps people. Every week something works — a post that lands, a conversation that starts, a subscriber who says it arrived at exactly the right moment. That's not proof of arrival. It's evidence worth building on before staking my retirement purpose on it.
For you it might look completely different: a jewelry business you've been sketching in spare moments, a consulting practice built on decades of specialized knowledge, a non-profit board that needs exactly what you have, a creative practice that has been waiting patiently, a foster program for animals that brings genuine joy on an afternoon when you're the one setting the agenda. The specifics don't matter nearly as much as the act of starting before you need to — while the stakes are low enough to experiment freely.
Whatever your version is, start before you leave. The evidence you build now is worth more than the confidence you hope to find afterward.
Preparing the financial infrastructure for a clean launch.
The plan isn't just "I have enough." It's written, stress-tested, and specific. It has scenarios, levers, and honest answers to hard questions — including ones I hoped I wouldn't have to face.
I've worked through these questions with trusted friends who know my full situation and will tell me the truth, with confidential FI communities that have seen versions of this before, with outside financial counsel when I needed a perspective I couldn't generate myself, and yes — even AI tools that can run scenarios and pressure-test assumptions faster than any spreadsheet I could build manually.
Beyond a traditional three-bucket retirement strategy, I've set aside what I call a Life Fund — roughly 60% of one year's expenses, sitting in a separate account, available regardless of what markets are doing. It's not part of my annual spending projection and it's not part of my investment math. It exists for travel, for a meaningful gift to my wife, for helping a family that hits a hard season unexpectedly, for a broken HVAC when the Arizona heat doesn't negotiate.
I remember the Great Recession clearly. Travel deals appeared that were genuinely extraordinary — destinations I had only dreamed of, at prices that reflected a world trying to fill its planes and hotels. I was underemployed and scraping, and I watched those deals disappear. I made a quiet promise to myself then: someday I'd create the margin to say yes to moments like that. The Life Fund is part of keeping that promise — a moat of margin that doesn't get touched by market conditions or annual budget decisions.
I'm also intentionally building liquidity in my taxable brokerage — holding more cash than strict optimization would suggest, not because I distrust the long run but because I want the optionality. The margin to act when something unexpected and good appears.
Your version of this infrastructure will look different. But the principle is the same: build the moat before you need to swim across it.
Simplifying before the launch.
One thing I didn't anticipate spending time on: decluttering. Not just physically — though I'm working through a storage unit of accumulated life, separating what's worth keeping from what was worth having at some point and isn't anymore. Also financially. I'm consolidating brokerage firms, closing bank accounts that served a purpose in an earlier season, reducing the number of statements, passwords, and decisions the financial life requires. The goal is to arrive at the transition with a financial life as clean and navigable as the portfolio math itself.
If you have financial complexity that's been sitting unaddressed, this season is the right time to simplify it.
Maximizing what only this season can provide.
Healthcare coverage, full retirement account contributions, any incentive compensation that vests before the exit date — these don't replicate after you leave. Add vision care to the list: updated prescriptions and new frames while comprehensive coverage still exists is simply good planning. Whatever your employment provides that has a hard stop date, capturing it fully while the clock is still running is good stewardship.
Make a list of what your employer provides that ends when you do. Then maximize every item on it.
Dreaming with specificity.
Most people have a vague sense of what the next chapter will feel like. Fewer have mapped it concretely. I now have a plan — not a wishlist but an actual sequence, with seasons and costs and tradeoffs considered. I've imagined what a good weekday looks like in Year 1 — when the people around me are working and I'm the one choosing how the hours unfold. I've pictured it clearly enough that it's become a destination rather than a wish.
That specificity is doing something important. It's replacing the abstract anxiety of will this be enough? with a concrete image of the life the plan is building toward. The two questions require different answers — and only one of them gets answered by running more Monte Carlo scenarios.
Start mapping your version. Not someday. Now.
What a Well-Timed Jump Actually Requires
The question most people ask is: when will I have enough?
The better question is: what does a well-timed exit actually require?
Four things need to be in place before you leave the boat.
Adequate cash liquidity and the right allocation to weather a bad first year. For many people that means two to three years of living expenses in cash or short-term bonds — enough to fund life without touching equities through a significant downturn. In a strong year, draw from portfolio growth. In a flat year, draw from a mix. In a down year, draw entirely from cash and let the equities recover. The goal isn't to optimize returns. It's to never be forced to sell at the wrong moment. Sequence of returns risk is the single greatest threat to a long retirement, and the antidote is a written playbook for how you'll respond at specific thresholds — before you need it.
A clear sense of what you're walking toward. Not "I'll figure it out." A direction. A vision for what a good weekday looks like when nobody else is setting the agenda. People who arrive at FI or full retirement with a calling already underway experience the transition as spacious. People who arrive without one experience it as an echo chamber. Both outcomes trace back to the years before the exit.
A written plan you've tested under real pressure. Scenarios. Levers. Honest answers to the hard questions before someone else forces you to answer them. If you've already worked through the worst-case scenarios with people who will tell you the truth, you're probably ready. If you haven't, that's the next thing to do. I've defined specific levers I'll pull at different thresholds — market declines, underperformance of supplemental income, unexpected expenses. Having the playbook written means the decision is already made before the emotion arrives.
A graceful, decisive departure. Know your date. Know what you'll say. The cleanest exits are the ones where the decision is firm before it's announced, the notice is professional and generous, and the departure is completed with the same excellence the career deserved. Consider booking the first trip of your new season before you've given notice. Having something on the calendar you're walking toward makes the exit feel like a beginning rather than an end.
Reading those four is easy. Answering them honestly is the hard part. So I built a one-page companion — The Well-Timed Exit Checklist — with the questions worth sitting with, the thresholds worth setting now, and a quick way to score where you stand.
If You Can See the Trap, You Can Choose
I'm not writing this for people who are genuinely miserable in their work. If the work is damaging your health, your relationships, or your sense of who you are — leave. The math can be worked out. The years cannot be recovered.
I'm writing this for the person who is FI or approaching it. Who could leave. Who is wondering whether staying a little longer is wisdom or cowardice.
If you read the OMYS Trap section and felt something uncomfortable stir — that discomfort is probably the most useful thing in this post. The trap isn't obvious from inside it. But if you can see it, you can decide what to do about it.
Here's what I've found: when the cage door is open and you're choosing to finish what you started, the work tastes completely different. The same desk. The same inbox. The same meetings. But you're not trapped — you're wrapping up. There's real dignity in that.
The season is shifting. The boat is approaching the dock.
Don't leave before you've picked up the outgoing mail.
Don't wait until the boat is already past.
Time the jump.
Let's walk with wisdom together.
🌵Desert FI
New here? A few good places to start:
The Moment I Realized the Life I Built Wasn't the Life I Wanted— where this journey began
The Three Paths Out of Midlife Stagnation— on choosing your path with intention
The Gilded Cage— on the life that looks right from the outside but has stopped fitting on the inside
Not yet on the trail? Join Weekend Reflections below — a personal letter every Sunday morning on money, meaning, and the courage to build a life that finally feels like your own.
