Four months! That’s how long it’s been since I transitioned to early retirement. I’ve been pretty quiet since then as I adjusted to the new reality. It’s been a great experience but it hasn’t all gone as expected.
I’ve always enjoyed reading others’ post- FI thoughts (it’s one reason I’m writing this). I try to be rigorously self-reflective. I thought I had a pretty good idea of how I’d feel after the FI race was over – but there have been a number of surprises so far. I’m sure there are more to come.
One thing that isn’t surprising? It was 100% the right decision. If you take nothing else from my ramblings here, know that my journey to financial independence and optional retirement was worth it. Yours will be too.
As for the rest, here we go:
Early Retirement Surprises
It Wasn’t A Bolt of Lightning
Some of my favorite content in the financial independence space are the posts (and Twitter threads) from peoples’ final days at a job. The countdowns, the day of conversations with coworkers, the freedom of walking out.
They all seem to experience a sudden and dramatic change in their lives. An instant sense of freedom. Early retirement is a clear break from one moment to the next.
It wasn’t that way for me. It was a slow roll into the moment, and since then it’s taken months for the reality to hit. It hasn’t really felt like a major change until the past few weeks.
Summer break is a different pace in the education profession. My partner and I have always worked hard in summer (and no teachers don’t get paid in the summer) but it’s still a different feel than the school year. Even as an administrator, things slow down quite a bit in July. (That wasn’t true in Covid-times, but then nothing was normal.)
Leaving my job on June 30, and going straight into local travel in July and August meant my first months of early retirement felt like an extended vacation rather than a lifestyle shift.
That all changed as school started again and for the first time in decades I didn’t have that combination of excitement/nerves/exhaustion/drive that always hits in late August and shifts quickly into frenzied problem-solving for the first two weeks of September.
As the weather shifted in October and the reality that I didn’t have a work schedule anymore started to set in, things changed.
Suddenly, I feel early-retired. It is a complex, but great, feeling.
But, it wasn’t a bolt of lightning.
I Rarely Think About Money
I’m going to say something very strange for a website that was founded on pursuing financial independence through personal finance – finances have been the least important part of the transition to early retirement.

Having struggled with feelings of financial insecurity for most of my life I harbored a secret fear that once I stepped into early retirement I’d end up a gibbering wreck in a corner rocking back and forth, going through spreadsheets.
While that was at the extreme end of expectations, I realistically thought I’d at least spend a lot more time in the first few months watching our expenditures, checking every dollar, and running more frequent than usual calculations.
None of that has happened. Instead, I’ve blissfully taken these early months off from paying much attention to personal finance. This was possible for several reasons:
We Already Did the Work
If you’ve followed our journey over the past 4 years, this is no surprise to you. If you haven’t, you can check out any of our financial goal and tracking posts in the Our Journey category.
Over the past five years we’ve slashed our expenses and created our ideal life for a reasonable cost. In the beginning, we did track our expenses closely, check our investments frequently, and obsess over every little move. Over time, the intensity dwindled and we focused on big things. We implemented a regular system of goals and financial checks and it shifted from being high effort to automated.
Now that it’s become part of how we live, rather than something we “work at”, the money part is second nature. It really is like working out – fitness is easier to maintain than build initially.
Thanks to our goals and actions over the years, we’ve saved more than enough. We built in several safety margins (remember that massive fear of financial insecurity) and planned diligently.
Sequence of Returns
One of the greater risks in early retirement is experiencing an unfavorable sequence of returns. In short, if your investments take a significant drop immediately after you stop earning new income, you are in danger of running out of money early.
I’ve spent a lot of time with Big Ern’s Safe Withdrawal Rate series which is a great guide for thinking about how to deal with sequence of returns risk. Our numbers plan for it and we’ve oversaved.
That said, had markets taken a dramatic drop in July or August, the chances of that gibbering husk in the corner would have gone up dramatically. Thankfully, it didn’t happen.
Now, we’re still early in the journey and this risk could still kick in – but it hasn’t yet. Each day that passes, it matters less and less.
Income
I’ve always believed that pursuing early retirement is more about pursuing the freedom to work or not, rather than not working entirely. I’ve also been financially transparent throughout the journey.
So, at the risk of bringing out those “you aren’t early retired at all!!!” comments, I’m clearly stating that we still have some income coming in.
You see, neither of us hated our profession. In fact, we love the mission of public education and have given the majority of our adult lives to it. That said, we were ready for changes and scaling back.
TFI is no longer a classroom teacher, but has taken a support role that she loves. I’ve taken a few small contracts for very limited hours. (More on this later…)
The best part? We aren’t earning because we have to. It comes as a side benefit from doing things we find interesting and want to do.
We still have money coming in. It looks like it will be less than 20% of our previous income. But, when you have already saved enough – that’s a pretty healthy safety margin.
Those three things together mean that my entry into early retirement has been remarkably stress free from a financial perspective.
The result? I didn’t need to spend any additional energy thinking about money. I knew we’d be okay.
My Mental Capacity Is Expanding
This has been the biggest surprise to me in early retirement. Largely because I didn’t realize what had happened to my brain.
Over the past ten years, I’ve been taking on ever-increasing professional responsibility. From a single school to community-wide programs. I’ve built a larger network of administrators I support and built more ties to community organizations. All good things!
I felt like I was involved in so many things but was making sure things ran well. I was *good* at my job and felt on top of everything.
I feared losing that pace and sense of connection would be a problem. That my senses might dull or become unused. I suppose there is still time for that.
But you know what comes with all that responsibility and visibility? Constant connection. I received messages 24 hours a day. I hadn’t gone a single day, even on vacation, for at least 8 years where I didn’t have at least one minor problem to solve.
When I walked away, I knew it would feel strange. And it did.
But after a few weeks, I started to feel something else – an increased ability to pay deep attention to things. A restoration of a sharpness I didn’t realize I’d lost.
I’ve come to think of it like a cyclist who rides every day at a workout pace. No rest to allow muscles to recover. No slowing down to enjoy the sights. A slow draining of the body’s reserves. A few days of rest will do wonders and set up for better cycling down the road.
My brain is like that rested cyclist now. I didn’t fully understand how “at capacity” I was. How I was operating at a constantly fatigued level. Lifting that constant need to make decisions changed everything.
I’m enjoying learning for the sake of learning again. I can focus on things that aren’t immediately urgent and enjoy taking the time to understand them.
It’s great and I can’t wait to see how long this growth continues.
This was a totally unexpected result of the transition to early retirement. I’m loving it.
I’ve Lost My Ability to Be Still
Despite the positives in mental clarity and an increasing ability to focus, I’ve also realized that sometime in the last ten years I lost the ability to just be still.
Despite having a healthy bias for action, stillness used to be a strength of mine. I could split periods of activity with periods of calm. I could spend an entire day reading deeply and be satisfied. A moment with nothing to do was welcome and refreshing. That stillness was deeply satisfying.
Over the past ten years, when my work life was most intense, I thought I still had the ability because many vacations were just me doing nothing but reading or enjoying “relaxing.” I now understand it was just exhaustion and recovery.
Now that I control my time, it’s hard for me to go more than a few minutes without twitching for something to do. It’s mainly technology driven, but also tied closely to a work life of constant input and response.
I don’t have much more to say on this, as it’s an unfortunate recent realization. This is something I’m going to have to work on. I’ve always felt at my best when I can combine that ability for focused mental attention with an ability to be still. I’ll get it back.
Flickers of Identity Challenge
The challenge of shifting from a career-based identity is a pretty common topic in early retirement circles. It’s also one from which I expected to be immune.
I’m a self-confident person. I’ve been (mostly jokingly?!) accused of arrogance from time to time. A colleague once told me that I had an almost pathological absence of need for approval from others. I’ve mostly worked through my control issues, and long ago shed the requirement to climb any kind of prestige ladder.
So, I didn’t expect a change in my job status to matter at all. I was mostly right.
But not entirely.
I won’t pretend I was a major mover and shaker in my city. But, I was in enough spaces and conversations that I could make some things happen. Whether that was parents I knew through schools, community organizations I was part of, or the politicians that expected donations from me – I could at least have a conversation when I saw something in the community that needed to be changed.
Recently, I’ve noticed a few things in the community that I’d have mentioned and expected to at least be listened to. A small voice in my head said, “They don’t have to pretend to listen anymore.” It felt strange to not have those job-related connections just sitting there.
Of course, that’s not the way community problem-solving should work. Any citizen should have the opportunity. But is my word and reputation as valuable as it was when directly tied to my role? Do I still matter? An interesting question – and a flicker of identity challenge I didn’t expect.
Renewed Appreciation for my Work
I knew I still loved and believed in public education. That’s too deeply ingrained in my core to change. I thought I was forever burned out on education leadership, though.
I’ve now had the opportunity to talk with colleagues about leadership and their experiences and challenges without my mind being occupied by my own baggage and challenges.
It’s incredible! Absent the distractions and political realities that draw focus away from the important parts of the work, talking about goals and how to achieve them with others in leadership positions is so rewarding. I’ve also had the opportunity to spend time with those considering leadership and provide guidance and things for them to consider in the decision making.
It’s been invigorating enough that I’ve taken on some opportunities to provide leadership support. It’s even made me realize that at some point in the future I’d be willing to dive back into the career if the right opportunity presented itself. Not yet though.
I knew being able to choose what I spent my time on would be the best part of optional retirement.
I didn’t expect it would lead me to a new appreciation of the work I’d burned out on. It’s a pleasant surprise, and makes me glad I spent so many years doing the work.
Building New Routines is Hard
We need routines. I know this!
I went into retirement fully aware I’d need to build routines. I intentionally took some time away just to relax and live an unstructured life. I had plans for how I’d implement new routines and give myself the structure I need.
Those plans haven’t gone that well. I’ve always been a driven student, a successful Marine, and a great employee. Those things all provide an external structure to ground routines in. In the absence of that, I have to admit I’ve struggled.
I’m doing it – just much more slowly. Following the principles in books like Atomic Habits helps, and each time I build one the next one becomes easier.
I’ll get there, but it’s more work than I expected.
Related to my routines…
Goals Matter…
I’ve always been driven by goals. What is the next thing I need to accomplish?
Second to my fear of being in the corner rocking over financial worries, was dread that one of two things would happen after I walked away from my career:
- I’d feel totally lost and listless
- To avoid feeling listless, I’d go overboard and set a bunch of goals, replicating my frenzied work state
Fortunately, neither really happened. I know I need goals.
…But I’ve Got Time
I’ve been surprised at my ability to coast a little bit, and start slowly setting new goals. I’ve done a few home improvement projects, but not nearly as many as I expected. I have a good project plan that stretches out over time instead of keeping me busy constantly.
Similarly, I’ve made good progress on my physical health – which I anticipated. But, I haven’t yet decided to do an iron man or some other crazy endurance event.
Those things may come, but one real benefit of not being consumed by work is that I actually feel like I have time. Perhaps I should have expected that, but I didn’t.
Summary
Achieving FIOR (financial independence optional retirement) has been as good as expected. Yet, despite reading countless posts on post-FI and doing my usual deep level of reflection and planning, I’ve had some real surprises. Fortunately, most fall on the positive side of the ledger.
Just like we all have different reasons for wanting to take control of our financial lives, we’ll all have different reactions when we finally reach it. It’s not a cookie cutter journey, so the finish line won’t be the same for anyone.
Some may not even like it when they get there. Yet, we all benefit from having control of such a significant part of our lives.
Despite my surprises, financial independence is worth it. I can’t wait for you to experience your own surprises at the finish line!
This is very insightful and I appreciated your thoroughness. It seems to me that it would be very natural that after a career relying on hyper-vigilance, it would take a significant amount of time to find your groove in retirement. It sounds like you are giving it that air to breathe and I wish you very well in that endeavor…
I’m an upper elementary teacher myself and I do not envy the role of administrators in my school. I am also anecdotally noticing a very high rate of administrator turnover in our districts and others nearby. Given what I observe the job to be, it doesn’t shock me at all. You alluded to the taxing nature of it in your “thought I was forever burned out on education leadership” comment. I’ll be interested in exploring more of that on your site (I’m new to it).
Personally, I ended up taking a year of leave from teaching for some of the reasons you referenced (mostly the stressful and unrelenting nature of the job). In this year I have been able to find small windows to slow down, but based on your post, I’m going to keep working on it (which seems silly to write but, as you know, that pace just stays with you. )
At the same time I took the leave of absence, I found FI. This catapulted me so deeply into that rabbit hole that I am just now finding daylight. And truthfully, it has given me a lot of hope for my career. The idea of the conventional 30 year pension was untenable, but now I hope to have the option to retire (I like the FIOR acronym btw) in 5 years.
Excuse my life story in the comments! As I said, it’s all new to me… Thanks for the insight and I look forward to diving into your past posts and following you moving forward!
Most people think that they could not be busy in retirement but there are always things to do.
Ditto here on your mental capacity point, which surprised me too. I’ve found creativity to be a big part of that, like I finally have enough free brain cycles to be more creative (and creativity was part of my job, though not the largest part). It’s exciting!
On routines, what helped me was to experiment with a bunch of different versions of possible schedules, to see what felt easier or better. It took quite a while (> 6 months) to find a schedule that felt right, and I’m still tweaking it.
That 6 month time frame is great to hear, and does feel like the right range for my routines to start settling. Thanks for sharing!
I love these kinds of posts! I’m a few years ahead of you on the journey, but remember similar feelings to you at the 4 month mark. Enjoy the continual evolution of retirement, I’ve found it to be one of the more fascinating aspects of the journey.
Thanks! It’s such a strange feeling – GREAT but I’m still adjusting to that continual evolution part without work / need to earn defining any of the boundaries.
Thanks for sharing these surprises.
What is your net worth and annual spend in retirement?
It would help to have some numbers.
New here! Congrats on no I want to think about money anymore. It is pretty amazing, because I started watching much more closely my money when I left in 2012 at age 34. How old are you?
I went through a series of negative emotions and uncertainty for the first 6 to 12 months. So again, kudos to you for being able to becalm and collected during this period.
I wonder if it is partly to do with how much money you left behind? The more you leave behind, the more doubts you might have and vice versa. Leaving behind a banking job that paid well was really tough to do. But I went for it anyway due to a negotiating a severance.
I also worried about whether I’d be able to afford kids one day if I retired early. Do you guys have kids? Now that I am a father of two, I feel like retired early or making enough passive investment income to cover your own living expenses is kind of like a walk in the park compared to trying to be financially independent with kids in a big city!
Sam
I left enough money on the table for it to matter, but made a major shift in how I think about time vs. money in the past few years and (thankfully) that held on my entrance to early retirement.
We’re a little later in life and did not end up having kids, so it’s definitely a factor for us. I know anything I have left will go to nieces and nephews, but don’t have to think directly about our own children’s future. It certainly would have been a different journey!