We Reached FI But Didn’t Plan for This: Part 2 – Emotions During the First Month of 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 whiplash, the identity shift, and the strange in-between space after pulling the trigger, but before fully arriving.

In Part 1, I walked through the year leading up to this moment, the spreadsheets, the milestones, and the confidence that we were ready. What I didn’t see coming was how different it would feel once the plan became reality.

Mrs. FI Designer gently suggested I document this season, not as a victory lap, but as a record of what it actually feels like to “land the plane” into early retirement. If you’re on this path, I hope this helps you land a little softer.

A Quick Disclaimer
Before going further, I want to acknowledge the obvious: This entire post falls squarely into the category of first-world problems.

I’m not writing this to complain. I’m writing it because this phase, unexpectedly, was one of the hardest parts of the journey. And if sharing it helps even one person navigate it better, it’s worth putting into words.

The Plan to Decompress (That Didn’t Quite Happen)
We kicked off early retirement with a mission: a 3-week road trip from Illinois to South Florida. Officially, it was a “test run” for a future multi-month National Park trip. Unofficially, it was also supposed to decompress me from a 23-year career in structural engineering.

A friend in the FI community (Kim), who had already gone through this transition herself, gave me this advice ahead of time:

This was excellent advice. But I give myself about a C-minus in the execution.

Old Habits Don’t Die, They Just Change Wardrobe
We had about three and a half weeks between my last day of work and the road trip. That time quickly filled with planning, packing, and preparing.

Looking back, I think I unintentionally replaced one “mission” with another. It gave me structure. It gave me purpose. It gave me something to optimize. All of those things felt familiar and comfortable. It also delayed the very decompression I needed.

Day 1 – I Think I’m Doing This Right
My first Monday of early retirement started off strong. I brewed coffee in my new stainless steel STANLEY French press and drank it from a custom mug sporting my new mantra: Believe in Yourself. (See featured image above) The coffee was objectively excellent. Possibly too excellent, but we’ll get to that.

I had a chiropractor appointment at 7:00 a.m., and for the first time, I flipped my normal routine. Instead of going to the gym before, I went after. That small change felt… significant.

At the gym, something clicked. For a brief moment, I felt like I had fully arrived. Not because I had earned an IFBB pro card, but because I finally had the freedom to treat my health as my life’s work.

In that moment, I joked to a FI friend in a text:

First day on my dream job – pro bodybuilder. Didn’t get my pro card, but I’m sponsored by the Designing FI Foundation. I know the asset manager. 😉

The Question I Wasn’t Ready For
Then something small, but important, happened. Someone at the gym noticed I was there later than usual and asked why.

Without thinking, I said: “I had a doctor’s appointment.” That answer surprised me because it wasn’t true. And more importantly, I didn’t feel ready to say the real answer, “I’m retired.” That felt… loaded.

Too many follow-up questions. Too much explaining. Too much potential judgment. Somewhere in the weeks leading up to retirement, a quiet thought had crept in: Who am I to be doing this?

Even with the math. Even with the plan. Even with the confidence. That thought stuck around longer than I expected.

Walking Around Without a Hall Pass
One thing I completely failed to plan for: What do you tell people when you’re not working… but clearly not on vacation?

I hadn’t even told my parents I was retired yet. So I defaulted to vague, socially acceptable answers:

• “I work from home and my schedule is flexible.”
• “I had an appointment today.”

Walking around town during normal business hours felt like skipping school. Like at any moment, someone might call my parents, or worse, send me back to work.

Day 2 – When It All Caught Up
My first Tuesday is when things unraveled. I showed up to the gym even later than the day before. That didn’t feel like freedom. It felt like I was slipping.

That afternoon, I found myself home alone. Quiet house. No structure. No urgency. What I expected to feel: peace. What I actually felt: anxiety.

My heart rate spiked. My thoughts spiraled. The lack of structure turned into a feedback loop of “I should be doing something” followed by “why am I not doing anything?”

Looking back, a few things were working against me:

• Productivity Withdrawal – I had spent decades tying my sense of progress to output. Remove the output… and suddenly the signal disappears.
• Too Much “Freedom” Too Fast – No structure sounds great, until you’re dropped into it cold.
• Caffeine… A Lot of Caffeine – That French press coffee? Let’s just say I accidentally created something closer to rocket fuel. By day two, even my wife had opted out of what I proudly called “Kick-Ass Coffee.” 🤣

In Part 1, I had spent months worrying about sequence of returns risk and withdrawal strategies. Ironically, none of those were the source of stress that day.

Day 3 – A Small Reset
The next day wasn’t dramatic, but it mattered. We replaced our water heater. A known expense that we had planned for, but still a reminder that life keeps happening, even when you stop working.

That night, I met up with a close friend who’s also on the path to early retirement. That conversation helped more than anything else that week. It grounded me. It reminded me that:

• We had planned this carefully
• We were incredibly fortunate
• And even if things didn’t go perfectly… we’d be fine

Sometimes you don’t need a new plan. You just need perspective.

Week 2 – Finding a Rhythm
By week two, things started to improve. Not dramatically, but noticeably. I added a few small anchors to my day:

• 20 minutes of morning meditation
• A weekly midday yoga class (with the retired crowd I now realized I had officially joined)
• Slightly less aggressive coffee

None of these things were revolutionary. But together, they created just enough structure to steady things. That was the surprising part: It took effort to relax.

Still Not Saying It Out Loud
Even two weeks in, we still hadn’t told most people. One exception was our neighbor, who found out the way these things often do, through our kids. He was very close to our family and had practically adopted our kids as his own grandchildren. So if anyone was going to know early, it was him.

We told him I was on a sabbatical. At the time, that felt like the most honest answer I was emotionally ready to give. Not because it was technically more accurate than “retired,” but because it required less explanation and carried less weight.

We also reassured him that we had planned this carefully. That we had savings, health insurance, and that our family (and his surrogate grandkids) were safe.

Looking back, I think “sabbatical” wasn’t just a description, it was a bridge. A way to ease both other people and myself into this new identity. There was also a practical side to that choice. Calling it a sabbatical gave me space, both psychologically and professionally, to return to engineering someday if I felt the pull to design again. It kept the door open without needing to define anything too permanently.

If you’re approaching early retirement, it might be worth thinking about this ahead of time: not just what you’ll say, but what you’ll feel comfortable saying. Because even when the math is solid, the words don’t always come as easily.

Week 3 – Back to “Mission Mode”
Week three shifted back into preparation mode for our road trip. Planning. Packing. Coordinating. Familiar territory.

Around this time, I also updated my LinkedIn profile to reflect my separation from my previous employer. I landed on: “Currently on a planned professional sabbatical while remaining active in structural engineering through leadership and research in a professional society.” That wasn’t just strategic, it was truthful.

One title I briefly considered was “Consultant.” It felt simple. Clean. Socially acceptable. But after looking into it further, I realized that, especially as a licensed engineer, that label carries real implications. Calling yourself a consultant suggests you’re actively taking on work, which may require professional liability insurance and comes with expectations tied to the profession.

If I wasn’t actually doing that, it wouldn’t just be a semantic shortcut, it could be misleading and potentially damage my professional reputation. So I stuck with “sabbatical.”

Looking back, this was another small but important realization: Even after leaving your job, how you describe what you do still matters. Not just for others, but for maintaining alignment with your own values and professional identity.

Week 4 – A Glimpse of What This Could Be
By week four, something finally shifted. Not completely, but enough to notice. One morning, I had about an hour to kill before picking up our National Parks pass for the trip. So I went for a walk.

It was a cold, clear morning. Blue skies. Quiet park. And for the first time since leaving work, everything felt… still. No urgency. No pressure. No mental checklist running in the background. Just presence.

I texted a FI friend that morning:

Week 4 of early retirement. Picking up our national park pass… took a walk in the park full of gratitude and reflection. 🙏

That moment didn’t solve everything. But it showed me what was possible.

Closing Thoughts
If the first post was about preparing to leave work… This one is about what happens when you actually do.

What surprised me most wasn’t the logistics. It was how long it took for my mind to catch up with my reality. Early retirement didn’t feel like freedom right away. It felt unfamiliar. Unstructured. At times, even uncomfortable.

But slowly (very slowly) it started to feel like something else. Not an escape from work. But a transition into something I’m still learning how to define.

And that’s where I’ll pick up next time.

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