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Semi-Retirement: Benefits of Working “Retirement Jobs”


While the concept of a retirement job may sound paradoxical, I think it’s totally reasonable. Plenty of people retire from a career to later work all sorts of odd jobs, and there are plenty of reasons to do so beyond the money one can earn.

A normal retirement can easily last a couple of decades, and an early retirement could lead to half-a-lifetime remaining once some leaves their primary vocation. You can fill that time with travel, volunteerism, hobbies, family obligations, etc… and some people choose to work a little bit here and there or even start an encore career.

The Leisure Freak clearly covets his leisure time, but he did work numerous jobs after leaving his career job. He describes those jobs and motivation for seeking them out below. As I’ve said before, I like to think of the word “retire” as a verb, and it’s something that some people do again and again. I see nothing wrong with that.

This Friday Feature was originally published on Leisure Freak.




Looking back over my early retirement, there was a lot to love about my scaled-down retirement jobs. Right from the start of my journey to FIRE, my plan was to be open to paid work in early retirement.

What some people refer to as semi-retirement, I happily called what I was going to do “retiring early and often.”

For me, it was all about being able to pursue interests. Interests that my long career wouldn’t allow me to do. That and shedding some of the stuff I didn’t like doing.

I looked forward to accepting opportunities for just as long as I wanted to do it. That, and also gain the life flexibility I had sacrificed over the decades while serving the corporate world system. Basically, my paid work in retirement will be a rewarding adventure or it isn’t going to happen or continue. Here’s some of what I loved during my retirement work experiences.



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The Best Parts About Working Scaled-Down Retirement Jobs


Done right, being open to taking on scaled-down retirement jobs has only upsides. Everyone will have to decide what “done right” looks like for them.

I set my own working in retirement guidelines and stuck to them to leverage the work experience in my favor. Aside from getting to meet and work with some awesome people, here’s what I loved most:


Money wasn’t my motivation; it was learning and doing something I had interest in

I had established my retirement funding to cover things regardless of my working. Anything I earned would be added to our overall net worth, not increasing our budget or spending. It freed me to purposely target opportunities based solely on interest.

I could ask myself, if money was removed from accepting this position, would I still want to do it? There are some things, like herding cats (project management) that no amount of money could get me to do.

This mindset also made it easy to decide when it was time to end the job experience. I retired early again without hesitation from an encore career that paid more than my first long career. This mindset provides empowerment. No longer shackled to unrewarding work, unreasonable management, or a toxic work environment because of the need for a paycheck.

It allowed me to experience work in a different way as a paid observer. I was only there to perform my duties and absorb all I could without the pressure of attempting advancement for monetary reasons. I was able to learn, experience different interests, be rightfully paid, and simply move on once the itch was scratched.


The ability to leave it at the end of the day and not take it home

My long telecom engineer career included 24×7 on-call. But worse than that was having to continually think about it to stay ahead of problems or plan ahead for the next day.

What I enjoyed most about my scaled-down retirement jobs was being able to leave it all there at work. It was no longer my job to take care of the world. That was left for the career driven go-getters who still needed to.


The pleasure of having absolutely no pressure to over perform

During my old career we had monthly accomplishment meetings with management. Where it was all about the question, how have you performed over the past 30 days? We had to prove our worth to keep our job and add to or subtract from our annual appraisal metrics for salary treatment.

Make a measurable mistake or underperform in the last month of the year and they gladly erased all previous accomplishments that year. In fact, any poor performance month was used as a reason to withhold a raise. There was none of that pressure in my scaled-down retirement jobs. If there was, I wouldn’t have accepted the position.

I vowed to be reliable, do my job, and learn all I could from the experience. No more sacrificing my personal life or covering for incompetence, outdated and overworked software/hardware/machinery, or doing more than I really wanted to do.

When I did go above and beyond it was because I really wanted to help out. Not out of some obligation to do it or an attempt to avoid feeling the sting of management’s retribution.


Being able to refuse accepting the thieves of personal life: On-call and overtime

Turning down every offer of taking an on-call duty, working a nonscheduled weekend or holiday, and any overtime was a whole different feeling of freedom.

This also endeared me to my coworkers who were hungry to earn extra money and saw me as someone not competing against them for that.


Free from legacy obligations

Being new on a job means everything now touched is fresh and new too. In my long career, there were a lot of things touched and worked on.

Management created a fix-it-fast culture where they didn’t care who was really responsible. That meant anything worked on over the decades that broke, even when it was outside current job responsibilities, it still ended up in your lap because nobody wanted to take the time to learn or own it.

Losing and no longer bogged down with legacy work history was a refreshing aspect to my scaled-down retirement jobs.


It wasn’t about money, but I still loved padding net worth while enjoying a retirement job –

Who wouldn’t love adding money to their portfolio while having fun working on their terms? Even my lowest paying retirement gig went towards our overall net worth.

I had retired early with a modest mortgage that we had refinanced to get the lowest budget-friendly payment possible. I was able to pay that off from my earnings over an 18 month retirement job stretch.

During one short contract, I was able to divert almost all of my earnings to the 401k to approach that year’s federal maximum contribution allowance. It deferred taxes, reducing it to near zero on earnings other than Social Security/Medicare withholding during that earnings stretch.


It Wasn’t All Smooth Sailing, There Were Some Challenges To Retirement Job Bliss


Time off and vacation time offered, but with a catch –

After spending decades at the same company in my first career I was caught off guard by how my scaled-down retirement jobs managed employee time off.

They didn’t.

For all my corporate-based retirement gigs it was put on the employee to make sure either the shift was covered or have a full backup person cover you. Difficult to do when everyone is already stretched to their limits with work.

We still traveled and vacationed while on these retirement gigs. I found it an intimidation strategy to get career driven employees to not take their vacation benefits.

Getting time off under their rules was a challenge. I admit that because of my retirement work mindset where there was no financial fear of dismissal that I may have circumvented their time-off process a few times.


Scheduled to work weekends and holidays –

I accepted that I may have to work weekends and holidays as long as it was fairly assigned. It was tough to be unavailable to be with family when they were off work whenever I was stuck fulfilling my duties.

I did experience having to work an early morning Christmas shift for the first time in my life. It went by fast and I kind of enjoyed the quiet day. We had already planned Christmas with our kids and grandkids later that day anyway.

Unfortunately, that Christmas the entire next shift of 2 called in sick (they weren’t) and I refused to work a double on Christmas. Somehow I was in more trouble than those fibbing illness.

Turns out it disturbed my manager’s holiday. It was nice having that conversation with my boss the following day. Reminding him that I did my job duties and it wasn’t my job to make it easier for him to manage his people and the business. The joys of financial independence in all its full glory.


Income taxes were a handful

To fund my early retirement in my pre age 59 ½ days I was living off of Sepp 72t IRA distributions, something that I couldn’t turn off without IRS hassles. I then banked all work earnings, taking advantage of 401K opportunities when offered, use of IRAs, CDs, and a savings account.

I had 10% federal taxes withheld from the 72t payments and I claimed Zero at the single higher rate on my work W4. With all of that I would still owe a big chunk at tax filing each year.


The longer on the scaled-down retirement job, unwanted legacy work obligations creep in

The longer I worked a retirement gig, its own legacy work obligations that I had gladly moved beyond from began to show up again. There will always be some undesirable work that people will drag their feet doing. If you have proven success with it then management will pile it on you to make their life easier. It’s the nature of most jobs where excrement rolls downhill. It’s one of the reasons that added to my decision to end what I call my encore career. I wanted to learn and experience my interests, not carry operational BS because new or full-time people didn’t want to do it and management just wanted it done without disturbing their own bliss.


Management trying to add unwanted scope

When I was hired for my scaled-down retirement jobs it was well detailed what I used to do. They even mentioned the “overqualified” issue. I selected opportunities based on what I wanted to experience. I made it clear what I was there to do because I wanted to do it. My retirement jobs were perfectly scoped based on my being rationally unreasonable about that. But they can’t help themselves but to try and change the scope or rules. Sadly that doesn’t work for them once you are happy to call the relationship over if pressured to accept it. I did have a 4 month stretch until my contract ended where a new manager was unable to accept this dynamic and created a slightly hostile environment.


Turning down extra shifts, overtime, etc., on occasion caused some conflict with management

Most of the time there was a ready supply of work go-getters willing to snap up any opportunity to make more cash. But when there wasn’t, my response of “no thanks” to their requests was less than acceptable. I hate to admit it, but they paid the price for my pre-retirement decades of work abuse and my unrelenting desire for a balanced working-in-retirement lifestyle. My refusals were always done with a smile and soft tone.


My Retirement Gigs Didn’t Last Forever, Nor Meant To

The list of my paid retirement work isn’t vast. I retired early at the age of 51 from a traditional and ravaged Bell System company as a lead engineer.

I took some months off and my desire to learn wireless technology guided me to a Wireless (Cellular) company Network Operations Technician position.

My interests in cable technology and past experience led me to an opportunity to become a Video on Demand Systems Analyst. It’s what became what I consider my encore career. Even though it was going very well and paid more in salary than my first long engineering career I got all I wanted out of the experience and then retired again.

Months later I accepted a short Cable Telecom Systems Analyst contract. The recruitment came from some people I enjoyed working with before. It started as the best contract experience of my life. Once that project ended after 2 short months I was extended 4 more months for another project. It was a lesser experience but tolerable due to my set retirement job boundaries.

Then one summer I worked as a Craft Beer bartender to help out in a small local coffee shop/Pub that I frequent. I worked during busy weekends and events. That was by far the most fun I have ever had while getting paid.

There were also some super short contracts that were more like paid tasks than anything else through the 11 years of my early retirement.


Going forward?


I have no idea what I may try to do next or when I will do it. I’ve become extremely picky about work now that I have met my jobs bucket list goals. Maybe never, it doesn’t matter. But I do know I will frame any opportunity I do accept to be aligned exactly with what I want to do under the retirement freedom rules I created.

I don’t consider what I do as semi-retirement. I believe that retirement is the absence of NEEDING to work, not the absence of working. What I consider “scaled-down retirement jobs” goes beyond having lesser responsibilities or salary. What it means to me is having a different mindset about it. Working on my terms, doing what I agreed and accepted that I would do, for as long as I want to without financial fear of losing the job or being forced into unrewarding situations.

I’ve had some fantastic and rewarding scaled-down retirement jobs over the years. They’re awesome because I set my own rules and I can leave before it can become a bad experience.

Because of this freedom to live this way, I’ve been simply retired since the first day I walked away from my long demanding career and during every one of my paid retirement opportunities since.


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8 thoughts on “Semi-Retirement: Benefits of Working “Retirement Jobs””

  1. I qm 64 and I read the full article. I have had numerous jobs all my life. But like in Article you can pick and leave whenever you want. My mind is different now. You had alot of good points. I’m thinking qlot different today. Thank you.

  2. Subscribe to get more great content like this, an awesome spreadsheet, and more!
  3. Thank you and all the replies. 55, Special Ed teacher for 30 years- just retired in Feb. 2022.
    It took me all of about 10 min. to get used to!
    Still thinking, peacefully for the first time 4 children, 2 still at home, for a new hobby that pays. Thanks for the encouraging thread. .
    Marilyn – Michigan

  4. I “retired” from my medical career in January and immediately embarked on a new path working for an insurance company. It is full time but considerably less stressful than working as a physician and less mentally taxing, too. The days go by quickly, and I learn new things about medicine everyday. I earn about half of what a full time radiologist does, but it is a much easier job and can be done from anywhere. So far, I am enjoying my retirement job quite a bit.

    • Hi. I am interested in learning what sort of work you do for the insurance company? Sounds fantastic. I am thinking of doing the same.

        • YES! YES! YES!
          JUST WHAT I NEEDED TO HEAR!! I am 64. Working EVERY DAY since I was 9 (seriously). My job of 32 years as an Administrative IT support is wearing on me somewhat and I desire MORE control of WHAT I WANT TO DO AND HOW…moving forward. GREAT ARTICLE. Just the MOTIVATION I needed!!!!

  5. I had a similar retirement path and one day a week of consulting paid all the bills the first five years I was retired. I stopped that a couple of months ago and only do non paid volunteer work now. Not to say I wouldn’t consult again, but only if the work was very tempting. I do think it makes a nice off ramp from full time work, especially demanding careers where you are on call all the time, as you and I were.


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