We Reached FI But Didn’t Plan for This: Emotions on the Road to Early Retirement

I had spent years preparing for early retirement. I modeled it. Stress-tested it. Spreadsheeted it within an inch of its life. I even built social connections outside of work so I wouldn’t wake up one morning retired and alone with my thoughts and too much free time. What I didn’t prepare for was the emotional ride, the months leading up to early retirement, and the strange in-between space that followed actually pulling the trigger.

Mrs. FI Designer gently suggested I document this season, not as a victory lap, but as a record of what it actually felt like to “land the plane” into our new Financial Independence, Retire Early (FIRE) lifestyle. The goal here is simple: to serve future readers better than I served myself.

If you’re on this path, I hope this helps you land a little softer.

Fear – The Thing I Expected to Feel but Didn’t
Of all the emotions I experienced leading up to early retirement, fear wasn’t one of them. I wasn’t afraid we were making the wrong decision. I wasn’t afraid the portfolio wouldn’t support our lifestyle.

From a numbers perspective, the probabilities were clear: there was virtually a 100% chance that this season of life with our kids would end… and close to a 0% chance that our invested assets wouldn’t support our current spending. In fact, I could already see it in our 11-year-old son. The window (the one where your kids want to travel with you, explore with you, and still think you’re interesting) was beginning to close. That realization was far scarier than sequence-of-returns risk.

Seven Years In – Still No Dimmer Switch
We had been intentionally pursuing Financial Independence for almost seven years. I worked full-time right up until my final day. If you know me, this won’t surprise you. I was born without a dimmer switch. I have two settings: on and off.

This is not the story of someone who gracefully phased into the “RE” part of FIRE. It’s the story of someone who probably could have done that part better.

If nothing else, learn from my hard landing.

T-Minus 11 Months – February 2025
Optimism, Stage Left
The market had just hit a new all-time high after a phenomenal run. Our assets were approaching 25× annual expenses, the classic “back-of-the-envelope” FI number tied to a 4% withdrawal rate. For the first time, it felt realistic that we might actually hit FI sometime in 2025.

T-Minus 10 Months – March 2025
Hello Anxiety, My Old Friend
Around this time, anxiety crept in, not about whether we could retire, but whether I had modeled it well enough. Suddenly, I felt compelled to master the Early Retirement Now Safe Withdrawal Toolbox and become proficient in tools like ProjectionLab or Boldin (formerly NewRetirement). Because obviously what I needed at this moment was more spreadsheets.

At the same time, the U.S. stock market slid into correction territory. Reaching our FI number by the end of 2025 no longer felt guaranteed.

That month, I attended the EconoMe Conference in Cincinnati. Somewhere between sessions, it clicked: I was far more afraid of missing this season with our kids than I was of running out of money. I resolved then and there to take a two-year sabbatical starting in 2026, whether or not we officially hit our FI number.

T-Minus 9 Months – April 2025
Red Numbers, Clearer Thinking
The market bottomed near bear territory. By this point, my wife and I had reframed our plan: 2026 and 2027 would be a sabbatical, not necessarily permanent retirement. That distinction mattered emotionally, even if the math didn’t care what we called it.

T-Minus 6 Months – July 2025
The Bounce
Markets rebounded hard. Our assets finally crossed 25× expenses. Suddenly, true financial independence in 2026 felt plausible, meaning I wouldn’t have to return to work unless I genuinely wanted to.

That optionality felt incredible.

T-Minus 5 Months – August 2025
Hedonism (Briefly, Responsibly)
This was a decidedly hedonistic month. I basked. I reflected. I celebrated.

I rewarded myself with a solo trip across a few states to attend an Electronic Dance Music festival near Minneapolis. It was loud, energizing, and exactly the mental reset I needed, a strange but perfect moment to reflect on how far we’d come and what lay ahead.

At the event I ended up talking with an attendee who had VOLUNTARILY ridden his bike nearly 100 miles from Minneapolis to get to this camping EDM festival. At that point, I felt morally obligated to ask the most predictable question possible: “So… have you heard of Mr. Money Mustache?” He had. And somehow, because the universe enjoys irony, he and his fiancée were also on the path to Financial Independence. Apparently the Venn diagram between extreme cycling, FIRE, and electronic music is not empty.

T-Minus 4 Months – September 2025
The Number That Wasn’t Anticlimactic
We reached our personal FI number: 26.3× annual expenses, equivalent to a 3.8% withdrawal rate.

I’d heard people say it would feel anticlimactic, just another number on a screen. For me, it wasn’t. It felt earned. It felt real. And it felt deeply satisfying.

T-Minus 2 Months – November 2025
Checklists and Gratitude
November was all about execution. Checklists. Dates. Decisions. We sharpened our pencil on ACA marketplace health insurance costs. I mapped out my notice timing. I built detailed, almost comically choreographed action plans to avoid gaps in coverage or awkward HR missteps.

This period felt surreal, like standing in the wings before a performance you’ve rehearsed for years. Gratitude ran high. The checklists helped keep anxiety in check.

Misfortune Strikes – The Deer (Or Was It?)
Just as we were feeling on top of the world, the rug was pulled out from under us. If you live in the Midwest, you know white-tailed deer are basically unguided missiles in November. Bucks, in particular, behave like high-school boys during mating season: impulsive, distracted, and absolutely convinced they’re invincible.

One evening at dusk, my wife was driving our daughter home on the interstate when a deer launched itself onto the hood of our white Pacifica minivan. Everyone was unharmed. The Pacifica was… not. Given the damage, and the suspicious lack of a deer body, I can’t completely rule out that Skynet sent a cybernetic deer back in time to terminate our minivan.

A Costly Reminder About Resilience
Financially, the damage was manageable. We lost about $2,000, our deductible. Psychologically, it felt heavier. We spent weeks negotiating with insurance and rushed to replace the vehicle. We ended up buying a used Sienna with comparable mileage, but two model years older. We felt swapping the Chrysler for a Toyota with similar mileage was worth going a few model years older.

We also paid cash using funds we’d been holding for early retirement, before insurance proceeds even arrived. It was a stark reminder that some things are outside our control, no matter how good the plan looks on paper.

A Family Lesson Worth Sharing
After the dust settled, we held a family meeting. I told our kids (then 8 and 11) that early retirement is like sailing across an uncharted ocean on a once-in-a-lifetime adventure. The van incident was a storm. It didn’t sink us, but our ship took on water.

Resilience kept us afloat. But resilience isn’t infinite. Too many storms, or reckless decisions, could still end the journey early. Everyone on the ship has a role to play like only taking reasonable risks.

They understood. And so did I.

T-Minus 0 Months – January 2026
Setting Sail
January was when everything became real. I used ChatGPT extensively to navigate my separation from work; drafting emails, planning timing, and ensuring I received my year-end bonus while leaving on good terms. Everything was deliberate, honest, and calm.

We sold our first shares from our taxable brokerage to fund the opening months of retirement. Markets were at all-time highs. It felt like setting sail with the wind at our backs.

My final paychecks were small, thanks to aggressive 401(k) deferrals, and we followed the checklist exactly, including securing ACA coverage with no lapse. On January 16, 2026, I was done.

Closing Thoughts (For Now)
This feels like a good place to pause. This post captures the emotions and experiences of the year leading up to early retirement, the part I didn’t adequately plan for.

What comes next, the beginning of early retirement, is already surfacing emotions I didn’t expect either. I’m working through those now. And when I’m ready, I’ll share that chapter too.

Picture Credit: My early retirement gift of a coffee mug with scenery augmented by ChatGPT.