Early Retirement is a Mistake for Some People

But it doesn’t have to be terminal: What to lookout for.

Most people who retire early have their numbers figured out. But for some people their early retirement is a mistake. A mistake they will regret and claim they were seduced or duped by an early retirement illusion. Just because you can doesn’t mean you should retire early. At least not until you understand your own head and your early retirement “why”. People understand the importance of getting the early retirement math right. But many underestimate the mental side. Happiness happens between the ears.

A couple of recent conversations with early retirees claiming early retirement regret has reminded me of that. We have shared early retirement experiences but with different conclusions.

Even with all of my planning my early retirement messed with me a bit until I made the complete transition. But for others the transition doesn’t happen or happen fast enough because of what wasn’t seen as necessary to plan for.

Then there are those whose plan was spot-on but they didn’t see the signs of their pending problems. We have to recognize a problem before we can take positive corrective action.

Early Retirement is a Mistake If You Can’t Adjust Your Performance Driven Conditioning

Early Retirement is a Mistake for Some PeopleWe all begin our conditioning for performance and approval at a very young age. In school we push to get good grades. Then there is our decades in the rat race. Performance measurements, objectives, goals, etc. where we try to measure up and advance in some way. We compete with others whether we do so intentionally or not. Then we retire and it’s just us. All of our lifelong conditioning if left unrecognized, unchecked, or not planned for can turn anyone’s early retirement into a mistake.

For most of us this performance and approval based dynamic is the only life we have lived. Early retirees are usually very driven. It’s no wonder that retiring early before we are physically or mentally broken can lead to thinking our early retirement is a mistake. Our drive to succeed and perform doesn’t magically disappear when we walk off into the early retirement sunset. But it should change and we can change it.

How to Make Sure Early Retirement Won’t be a Regrettable Mistake

Some early retirees like the two I spoke with have feelings of dread that they made a big mistake. I admit that I felt a little of that too after the celebration of my early retirement faded. It only gets worse if not addressed. Going from being a hero to being a zero was how I felt it. For years I was the go-to guy for everything important. Then in a flash I was seen by the world as unemployed. I thought I had everything figured out and planned what I was retiring to.

My two pals claiming that their early retirement is a mistake also thought they covered everything. I feel that I was able to quickly make the transition. They are still trying to work things out.

Nobody wants to waste their priceless time on early retirement regret. There are things we can do so that retirement regret can be avoided, reversed, and/or managed.

Know Why You Want To Retire Early- What Are You Retiring To?

It’s something people forget to plan for. Retiring to something is overshadowed by what is being retired from. The celebration of ditching the rat race and everything that goes with decades of work obligation is wonderful. But the exuberance of a retirement based on what is being left behind is short-lived. Knowing what we are retiring to and identifying it as why we are retiring early is what helps us avoid early retirement regrets and feeling it was a mistake.

I have said it many times, nobody wants to or will enjoy retiring into a void. Leisure is great but our brains have been conditioned towards productivity. We have to replace the drudgery of unfulfilling work with things that we value to ensure long-term happiness.

First off make a plan to retire living a healthier and happier life and really think about what that means to you. Satisfy your brain’s conditioned need for goals and measurement with what it is that you want to do or accomplish. Is it a business venture? Maybe an encore career, stepped down job or volunteer work. Do you want to spend more time doing hobbies and activities that you enjoy?

I planned for what I was retiring to but there were some holes. My biggest miss was that I underestimated my social circle. I planned on having an active social life in my retirement. But after decades in a career I found that my circle of friends was exclusively work related. I felt it and then set upon a plan to meet new people. Recognize whatever it is that’s missing and plan to fix it. Don’t abandon early retirement and call it a mistake.

Recognize the Importance of Structure Your Brain Needs It

Our brain is conditioned to function under structure. It makes more sense to us when things start and finish at certain routine times. We should have planned scheduled timelines. They can be loose or rigid. It’s our call. But believe me, it is necessary. We feel better when in healthy and productive routines. Our routines then turn into healthy and productive habits.

Without this structure we can drift without accomplishment and our brain’s conditioning feels like we have wasted time. It can lead to things like anxiety, depression, and self destructive habits. All of which leads to classifying early retirement as a mistake.

I learned early on to introduce structure into my early retirement. I routinely exercise during certain daily timeframes, work on projects, socialize, etc. If I didn’t place some kind of timelines I would never routinely get to it. Not fulfilling what I wanted to retire to would be in the back of my mind always messing with my mellow.

Value Self-Approval : No Second Party Appraisal Rendered or Required

Some people’s brains value appraisal and feedback more than others but everyone understands when it’s missing. That pat on back for a job well done all ends with early retirement. It was a huge part of our conditioning from school grades to job performance reviews.

Understand the need to value self-approval for your early retirement. It starts with celebrating early retirement and continues with retiring well. Early retirement is a huge accomplishment in and of itself. Every month, fiscal quarter, and year of successfully living life on your terms in early retirement should be awarded with your own approval.  

After the first few months of early retirement I was aware that nobody but me really cared about my accomplishments. Everyone appreciates positive feedback. I soon learned that my happiness in early retirement is all the positive feedback that I need. When feeling other than happy then that is when self assessment is needed and corrective action taken.  

Last Words

There are many things from financial to the brain that can cause someone to claim their early retirement is a mistake. But it doesn’t have to stay or end that way.

One of the early retirees who claimed his early retirement was a mistake returned to the rat race at his old company. He is working 50 hours a week and is stressed out. But said the lack of forced structure in his retirement had him only looking forward to happy hour. He was drinking too much and over-eating. His Dr. told him he was headed for a heart attack. I am not sure jumping back into the performance driven stress-pool is the right answer. But I am certain he will retire again soon and make the necessary mental adjustments to feel good about his early retirement.

We can counter our lifetime of conditioning when it raises its ugly head. Another thing we can do to tame our brain’s performance driven conditioning in early retirement is recognize the important job we now have.

  • Portfolio Manager for the $XX-figure portfolio of a very important client.
  • Accounts Payable/Accounts Receivable Manager.
  • Leisure and Activity Program Director.
  • Project Manager.

The job is extremely flexible, fun, and rewarding. Best of all the boss is very appreciative.

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4 thoughts on “Early Retirement is a Mistake for Some People

  1. Awesome post!…I just took the plunge on Tuesday…and many of the things you talk about here are quite true and good things to think about and continue to be aware of. Thanks for posting…

    1. Thanks for the comment Dwayne.
      I am glad you liked the post and informative. There are a lot of little things that mess mentally mess with us when we retire early. Recognizing, understanding, and acting on them helps with the transition to early retirement freedom.

  2. I’ve never been able to relate to talk of retirement boredom, ennui or identity crisis.

    My career was incredibly important (more of a calling than mere livelihood), but never defined me. Only times I was bored were at school or work. Prior unemployment proved that I would enjoy retirement a lot. There are just so many interesting things to do that I’ll never run out of activities.

    My hiccup to retirement was involuntary dismissal before fully realizing I could retire (I knew I was close). So reluctant to detach from a profession I felt pushed out of. But unemployment is proving to be so sweet I think I can manage that last step!

    I’m also older (think millionaire next door), so not retiring that early. After 35 years in the rat race, most folks want to slow down. Yet I can easily see how younger retirees could get restless.

    1. Thanks for the comment Steve. I imagine being pushed out would make it different than a planned departure. I had planned for early retirement identity crisis. I still felt a little of it but I could easily see it and work through it. I just saw it as normal. I was 51. I did have a few job/careers I wanted to try and doing so was rewarding. But after they ran their course I retired again from that line of work. I resolved my curiosity and did what I wanted to do. My second early retirement at age 56 was much easier mentally. My motive to do these opportunities was different than those who feel that MUST stay in the rat race or be miserable feeling regret. Of which I think it is just part of the transition, withdrawal symptoms from the decades of worker-bee conditioning. I do believe as we age it does become easier.

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