Early Retirement: One More Year Revisited

*This post may contain affiliate links. Please see my disclosures.

In January of 2018, I posted my internal debate of working One More Year.   Financial independence was inevitable and I was faced with two choices:  Work through June or 2018 or retire in March of 2019 with a month-long notice.  More than three and a half years has passed since this post, so let’s look back at what I wrote and see how it all turned out:

Reasons I listed to go ahead and quit the full time job:

Achievement of a challenging goal:  100% still valid.  My old life looks foreign to me- wake up to an alarm clock, shower, put on a suit, commute to work, and let others mostly dictate my time with endless meetings.  The further I’m away, the more I realize how strange this entire concept is and that people do it for more than two decades simply to own bigger and bigger houses, fancy cars, and to experience restaurants just to have an army of peasants cook and serve them food.  There isn’t a day that goes by that I don’t appreciate achieving this goal.

Enjoying a weekday in January

Time:  Yes, this was a downside of working that additional nearly ten months.  I can’t get that time back.  I was always counting down the days and weeks until my next vacation.  That feeling only got worse as I approached the end date.  I didn’t like the idea of counting my life away.

Lack of (Work) Creativity:  Just looking back and reading what I wrote here makes me shudder.  “You are the execution team”.   This was basically leadership saying they don’t care about what we think and we are replaceable.   The extra ten months in this environment were not good for my mental health.  Life is too short to work for jerks or idiots.  The old employer knew how to balance having both.  This isn’t to say I’m incredibly creative today, in fact doing nothing is okay!

Vacation Time and Geographic Freedom:  Yes and yes.  It’s everything I thought it would be and then some.  I am pleased to see more and more people getting the geographic freedom I never could thanks to the increase in remote work.  I still don’t think that would have satisfied me long-term, 40-50 hours a week of redundancy was too much.  We now live within fifteen minutes of the beach and in a much better climate.   Our last vacation was nearly five weeks of travel; we simply moved our normal routine to a Hawaiian condo.

Enough is Enough:  I still struggle with this to an extent, more money is better than less money.  There’s always the financial boogeyman you can find on posts and forums justifying the need to work and save more (poor returns, health care, inflation ), instead I should have focused on what could go right.   Early Retirement Now did an analysis of my numbers around the time I was making this decision and it’s true that working 10 more months added 8-10% to our net worth in exchange for not that much time, but did we even need it?

Shorter Work Week:  I didn’t focus on this enough, how developing some part-time income would have helped me exit sooner.  I enjoy some of the mental stimulation of work, but a few hours a week is more my style compared to giving mental energy to it every day.

So what were my Justifications for Working One More Year?

Money:  I earned a decent amount of money, especially staying through a March 2019 round of equity that was issued at lower prices.  Thanks to the market returns over the past 2-3 years, this has been nice but not meaningful.  I never could navigate a severance package, you had to be a mediocre performer to get a lottery ticket at my old employer.

Capital for Private Investments:  I haven’t done as much of this as I thought I might.  Part of FIRE is understanding your risk tolerances and needs.  Why risk money we have and need for incremental returns we don’t?  I recently put 1% of our net worth in a private placement and might grow this some, but the statement written 3.5 years ago may have been more about ego than sound investment decisions.  To invest in a private deal today, I want a superior risk/return and will be picky.  Why take illiquidity risk for average returns?

Inability to Enter the Workforce at the same Level:  I laugh when I look back at this and can’t believe I ever wrote it.  This has been one of the more pleasant surprises, job opportunities are everywhere.  In June of 2021 I fielded two separate inquiries for comparable jobs to what I left.  One even offered a beach town in Florida as the destination.  The demographics are what they are in business and there are more people retiring than available to work.  

Inflation Diversity / Rental Properties:  I really messed this one up.  We moved to our new area in July of 2019 and didn’t buy a house similar to what we were renting right away.  We could have moved into the house and still had an asset with a 5-6% in leveraged yield,  eventually put a mortgage on it, then enjoy the 33% appreciation this market has seen in the last two years.   Ultimately we valued peace and simplicity and found a great landlord to rent from.  Turning over $40,000 to the realtor monopoly to get out of our old location also soured me on ownership for a while.  All the reasons I selected our current location resonated with the work from home crowd who flooded the area thanks to the pandemic.

Family / Charitable Support:  Fortunately we haven’t had too many monetary family needs come up.  I did have to front some money and give up months of my time when my dad passed away unexpectedly and left a messy family and financial situation to figure out.   We’ve done some for charity, but have a bit of a resistance in making major gifts until our housing is settled.  With the rate of housing inflation, this is such an unknown.

Ease of the Job:  I regret ever writing this line.  Shortly after I posted this I had one employee take an internal promotion and another leave file a better opportunity.  One of the two replacements turned out to be the worst hiring decision I’ve ever made, a person with a pretty resume but a professional at getting fired and filing baseless wrongful termination lawsuits.  My last fifteen months on the job were miserable, so much so that I navigated an internal transfer out of that role three months before I quit.

Mathematical/Market Variables:  We know how this worked out, but couldn’t have predicted it at the time.   The portfolio is up 33% even though we have a conservative allocation and have been withdrawing money.

Health Insurance:  We paid about $425/mo for crummy insurance through my employer and now pay $675 for similarly crummy insurance.  When I wrote this, we were in the second half of working on a medical issue for Mrs. Shirts and hadn’t quite figured everything out.  The unknowns here kept me working, but it may have been better if I could have given more attention to care and recovery and gotten us moved for a better lifestyle.   Now we pay for both a concierge style relationship with the right specialist along with carrying traditional insurance.  Access and how healthcare is paid for with an aging population will likely be an issue for our entire life.  We weren’t going to let this force us to work forever.

Compensation Gains and Pension Variables:  When I wrote this, I was due for an in-role promotion in my current job.  It may have been worth $10k-$20k annually, which in hindsight was really meaningless in the scheme of things.  My boss at the time was inept at his job, preventing this from ever happening.  Instead, I collected some equity due and made a slight improvement to my pension calculations by replacing my 2014 compensation with 2019.

The Pain of Moving:  Update – moving still sucks.  In an ideal world, we would have known our location and bought a new home as a 2nd home prior to me quitting a big W2 job.  Unfortunately we looked in four other areas before finding our current location.  That and the burnout from the job made me use the few vacation days I had just to get away.  Moving is always going to be a pain, but it is a pain that can be made easier with both time and money.  Fortunately we did find a good landlord in our moving process and will pay for more of a full service move in the future.

Work Friendships:  This is just funny to look back on.  95% of the work friendships were built on a common bond (work, idiocy of a large company), remove that common bond and you find most other things aren’t relatable.  I made an effort to stay in touch with many of the people I worked with, but only a few of those people remain close.  This was inevitable and a crazy reason to delay in hindsight.

Expensive Travel Year:  Yeah that never happened…

So what can others take away from my rambling about what if’s?

  • Life is too short not to like or love where you live.   I’m unsure looking back why I ever agreed to move to places we wouldn’t love, especially after saving the first $500,000. We knew we didn’t enjoy DFW yet stayed for an extra ten months.  I could have taken a small compensation cut and moved to the beach or the western mountains for the same type of career “reset” the internal promotions were costing me between 2013 and 2015.
  • Know how you’re wired:  I still make a little money.  I specifically told everyone I was taking at least 18 months off and now I find it easy to make $1,000 – $2,00/mo on various projects that require minimal hours.  Most early retirees will still earn something, so why work extra time when “cushion funds” are inevitable?
  • If you’re kicking the can down the road, retiring doesn’t change that:  For me whether it was owning rental property, charitable giving, or buying the next house, it was still possible to kick those down the road after the excuse of work ended.
  • Prioritize Happiness.   The undertone of this writing when I look back included “I’ll be happy when” and focused on money, but we had already won the game.  It was always about the next forward milestone instead of considering what we had achieved.  We were financially independent with enough financial runway to absorb a decade or more of issues.  The extra money is nice, but not at the cost of that extra ten months of stress and burn-out.

We will never know when the perfect time is to retire early. It’s easy to know if you’re way short of a goal, but tougher to pick that exact moment. Given 12+ year bull market (with only a couple brief interruptions), most early retirees out there “worked too long”. Personal finance is personal and we all must decide what’s the right fit for us individually.  I hope by sharing my story over the last nearly four years including looking back at these thoughts I wrote three and a half years ago help others as they debate their decision.

8 Replies to “Early Retirement: One More Year Revisited”

  1. I think the decision has a lot to do with how you feel about your job. Its that knowing how you are wired thing you mentioned. I drew a lot of satisfaction from my career and from achieving the work goals I had set for myself. I also enjoyed being the guy that ran the company I started working at as a summer intern. I saw our products as being vital to everyone’s daily life and felt good about providing good jobs with good pay for my seven hundred coworkers. I eventually was ready to retire, but only slightly early. That was five years ago and I have no regrets about waiting as long as I did. And zero regrets about not staying longer. It was perfect timing for me. And like you also said, the job offers do keep coming. I really didn’t expect that but it is kind of fun to turn them down.

  2. I’m getting more and more interested in these stories.

    I got all hot and bothered about FI when I was frustrated by my job and thought I was tired of the field. I got a new job and now four years later I’m FI and I’m contemplating the role that work plays in my life satisfaction. During covid lockdowns I was able to realize that having work is important to me. With WFH I have enough flexibility to go surfing midday, I lost my long commute, I work for a small company that I like, and I like being able to keep my mind engaged. I’m considering that quitting my job would lead to lots of time on the couch getting depressed. Of course I’m not about to give up my financial independence either!

    Ok, now getting back to this blog – Mr. Shirts, if you could rewind to age 18 what would you do differently? Compared to DFW you I have it great: a fun gig, life in coastal CA. No shirts to iron. Do you wish you had gone into a different field? Different city? Different priorities? Seems that you’re quite good at making decent money without anywhere near 40 hours a week, should you have downshifted earlier?

    The recent livingafi post combined with some decided depressed-sounding FI blogs has really been making me think that FI is great but RE might be a mistake for a lot of people. At this point I’m waiting for the current gig to sour at which point I might take a sabbatical but I think I’ll miss productivity after a bit.

    As usual, thanks for sharing! Much nicer to read content from people who are FI than people who hope to be someday.

    1. Bill,

      I love the questions and your comments.

      I’ve followed the personal finance space for years and many people blog or post on message boards about their journey to financial independence, then stop once they’re past FI/RE and go off doing something else. The planning was even a distraction from work. I think most go on to live productive life on their terms, almost all of which is productive and some of it involving paid work. It sounds like you have a great gig!

      The “what if” questions. I gave this interview about eighteen months ago when I was pondering that question one year out of the workforce: https://thefioneers.com/coast-fi-financial-independence/

      I loved the business puzzle aspect of my job and I enjoyed it even more when I really became an expert and could dissect deals on the fly for a team of people I was working for. I still love that, but am finding outlets where I can do it on my own time without the restrictions of a large financial institution. The pay differential was too big to do that prior to being financially independent though.

      I do think different priorities / maturing earlier would have helped. I had a big ego and wanted the next job up, which came at the expense of moving away from an area I liked and staying with a company that was losing what made it a good place to work. If I could have done it over, I either would have stayed in a similar role to what I had from 2007-2013 and pursued a better lifestyle, or made a lateral move in that position to the beach. I actually tried to do that in early 2013 and was not hired for an internal role in Tampa/St Pete and that was kind of a bummer. I needed the bigger city for skill development, but should have either created lifestyle in the Atlanta based job or made sure my next lateral was for quality of life, either in the institution, the location, or both. Otherwise the only real “what would I have done different” is to have taken some risks with leveraged real estate in my 20s when there’s decades to make back the money if it went wrong.

      My current advice to any early retiree is announce you’re taking an eighteen month sabbatical to figure out what you want work to look like in your future life. It’s long enough for people to respect your space but not so long you’re completely discounted out of the workforce. I still receive job inquiries today.

      Love the surfing midday comment, we may finally get a real swell on Friday thanks to some storms.


  3. Hi,

    Thanks for sharing your insights which are very beneficial.

    I opine that it makes more sense for one to take the shot as long as one has assessed that the generated dividend from the investment portfolio is able to cover the annual expense. Action speaks the loudest of all.


  4. I think about this occasionally and know that in hindsight I probably worked one year too many. But I wouldn’t have quit any earlier given my portfolio size and spending needs at the time! Ahhh the benefit of hindsight.

Leave a Reply