Reader Question:  Do You Harbor Any Regret About Retiring Early?  

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People on MMM board seem to battle the time glut they have on their hands.  My day-to-day grind has so much bullshit baked in that I can’t fathom missing it.  A few people, yes, the paycheck, sure, but not the life drain it has become.  Thanks for any thoughts. 

Future Early Retiree

That’s an interesting question.   The usual variation from the non-FIREy type would be “what are you going to do all day?”.   My brain immediately thinks “If sitting in this droning corporate meeting is the most exciting hobby you can imagine, I can’t help you”.

I’d rather be chasing these than sitting in a credit policy meeting

I can certainly relate to all the garbage baked into a job.   I would describe the final years of my job as 10% to 20% enjoyable and 80%+ time wasting corporate/political garbage that I will never miss.  So do I harbor any regret about leaving that?  Absolutely not.   In hindsight, I probably should have changed employers and have helped many coworkers do just that.   However, that probably would have increased the enjoyable parts to 40-50% while still dealing with garbage that comes with the industry. 

Here are some various issues I see and thoughts I have around this question:

Focus on the non-money stuff more than the money stuff.   As a long time contributor to the MMM forums, my observation is it’s a glut of people building up to or shortly after retiring early.  There’s not a ton of people who’ve been happily retired for years because they have migrated past thinking about early retirement and are now out enjoying life.  I post a lot less now.  I believe those forums have a disproportionate sample size of people that focus too much on the money and not enough on how to fill the time.  

Adjusting to Early Retirement:

Change In Routine:   Our entire life up until the point of FIRE involves ceding control of our time to another entity:  parents, school, college, and an employer.   These entities tell you where you have to be and when you have to be there.  If someone were 35 and taking a sabbatical for burnout, they are looking at 30 years of someone else controlling their schedule between school and work.   Adjusting to this takes time, especially after the first three months of waking up and pinching yourself thinking “this can’t be real”.

The Need to be Valued:   I think most people want to be valued for a contribution.  I wanted to be valued for my contribution.  Grades never really motivated me in school, but money became a good scorecard early in my career.  The paycheck was a good reward and showed I was valued.   As the career progressed, I felt value as being an expert to people.  Employees and coworkers would come to me for advice on transactions, clients would come to me for advice, figuring out how to get 

The Need to Feel Productive:  School and work programs what is and isn’t productivity.  Short duration tasks and projects are the norm.  Schoolwork and homework before a career and daily to-do lists in my career.   I always had to manage a combination of urgency and importance with a long list of tasks and responsibilities.   It was a bit of a shock when all of those disappeared.   It took time for me to figure out what the right amount of productivity is for the day.   I love not feeling rushed anymore.   

What advice do I have to people wrestling with these questions?

Commit to a certain amount of time off and tell your network.  

There’s no reason you have to declare you are never, ever, ever working again if you are exiting the workforce decades before others.  Tell people you’re taking a sabbatical.  I recommend eighteen months, it’s long enough for people to understand and respect your space by not bombarding you with job offers two weeks after you leave.   You were likely a solid and disciplined employee to get to FIRE and your skills aren’t going to have as quick of an expiration date as you think

Spend more time figuring out what an ideal day / week / month looks like to you.   

This is far more important than focusing on the money.   What do you want to do with your time?  What do you want to explore?   Early Retirement Dude had a similar corporate path as me and before I retired, he recommended I put together a long list of goals I wanted to accomplish in early retirement. Some things I haven’t done as much of (visit all the national parks, run a marathon), while others I’ve taken up and fallen in love with (surfing).    

It’s more than just about the hobbies though, it’s figuring out what an acceptable pace is for you.  It is rare that I feel rushed now.  That’s a complete shift from my working days, when everything was a rush.   I design my life around not being rushed. I wake up and take 1-2 hours drinking coffee, eating breakfast, and reading/writing/surfing the internet.  My wife and I walk our dog together twice a day.  There’s always 1-2 hours built in per day for exercise.  There are still life errands to get done.   That really cuts down the “free time” to a few hours per day that need to be filled.  Sometimes it’s filled with hobbies while other times I supplement it with some deal analysis I do for hobby work.    

This was an adjustment, but now my only real risk of boredom is when we get a multi-day stretch of bad weather that washes out my outdoor hobbies.  I live on the coast in the Southeast, that could look like a few stretches a year of cold and windy rain, or it could look like a stretch in the middle of the summer with high heat and flat surf.  Now that travel is more open than it was in 2020, I can predict those times a year and plan around it.

Find outlets to fill what work was filling:  

For me, I decided what was filling to me was having my opinion / knowledge valued.  I filled this gap in two ways:

Finance/Financial Independence:  I love answering questions related to finance, financial independence, and early retirement.  I absolutely see why some bloggers get accused of just having a full time job, because writing about this stuff does not feel like work.  It’s a hobby that can become self-sustaining if done for years with some monetization efforts.   Personally I spend far more time on Twitter and as a volunteer moderator for a large Facebook Group than I do on the blog, which I enjoy but it’ll keep the site from ever becoming a full time job or meaningful revenue source.   

Deal Evaluations:  I still enjoy providing an opinion on transactions.  The majority of these are real estate syndications that potential investors are looking at and want another opinion.  Sprinkle in some small business mergers / acquisitions / sales, and I can get some of what I enjoyed in my old profession without all the garbage.   I could pick up more of this work, but I balance this against my enjoyable and non rushed retirement status. I recently told a potential consulting client that short notice phone calls were a red line for me. If I wanted to tolerate the “get on the phone right away” moments, I could earn a lot more as an employee.

What’s my final answer?

Expect an adjustment period, then figure out what you valued / enjoyed from your job, and find outlets that fill those needs that come without all the other garbage.  In the meantime, plan what your post FI life looks like from a time perspective.  Expect an adjustment period, there’s a lot of deprogramming that will happen and the longer someone waits to retire, the tougher this deprogramming process might be.  I wouldn’t trade early retirement for any career, but that may not be the answer for everyone.   Financial Independence and a long enough separation from work will give you the time and space to figure out what’s right for you.

9 Replies to “Reader Question:  Do You Harbor Any Regret About Retiring Early?  ”

    1. The line that will cause me to bow out of any little consulting projects. A decade and a half of “OMG hair on fire (business) emergencies” gave me my fill for life.

  1. As someone on the cusp of FIREing (after almost 30 years in the legal industry), this was both a helpful and reassuring post to read. I’m anticipating and planning on an indefinite period of what you brilliantly call “deprogramming” (I’ve been referring to it as my “decompressing” period, but I like your term better). I’m actually curious how long “indefinite” ends up being for me. I’ve been thinking that when I’m “deprogrammed” I’ll know it. Curious if that was your experience.

  2. You’re right about an adjustment period. When I stepped away from my full-time job (not exactly early retirement… husband still works, but we’re close), there were a lot of days of being depressed and lonely. As much as the grind sucked, it did provide some structure and purpose. Of course, that didn’t make it worth it, and I wouldn’t trade this for the world, but it is something I wasn’t prepared for.

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