Category Archives: Working In Retirement

Working In Retirement – Is It Worth It?


Once we retire, that’s it, right? You are finally able to give up your job and can leisurely sit back and relax. Or is it that simple?

Not all retirees want to give up their job once they hit retirement age. In fact, some even take up another job once they have retired from their regular one. Wondering why that is? Well, there are various reasons. For some folks retirement is the perfect time to pursue new opportunities of passion and interest. But the main reasons many retirees return to a paying job is they need the money or they just get bored with all the free time that retirement brings.

Thinking of calling it quits on your retirement and finding another job? Here are some reasons why it might be worth it.

Working In Retirement

The Benefits of Working In Retirement

Can Keep It Flexible

Lots of retirees enjoy the new lease of flexibility that it brings. They are no longer trapped by their nine-to-five. And it’s now possible to find a flexible job that they can do in their spare time. This is why there are a lot of retirees who are now becoming entrepreneurs and freelancers – the flexible way of working fits into their new lifestyle. You just need to remember to stay highly organized with your working schedule, paystub generator for your payroll, and filing your taxes. Being highly organized and having plenty of free time – they are the best things for helping your new flexible career become a success!

Provides You With A Regular Income

When some people hit retirement age, they are surprised to find that they haven’t saved up enough for their post-work life, despite all of their best efforts. If you find that you are in this situation, then you might be forced to go back to work. Don’t worry, though, even if your pension pot isn’t as big as you were expecting, it should make it possible to only go back to part-time work rather than a full-time job. Even taking on a full-time opportunity in retirement can be enjoyable. Especially if it’s aligned with what you are interested in doing or passionate about. Who knows, it could be the start of a rewarding encore career.

Working In Retirement has social benefits

Social and Personal Growth Benefits

Of course, it’s not just the monetary benefits that people get from going back to work. They also enjoy the social side of having a job as well! In fact, some retirees who feel quite lonely after leaving work choose to find a part-time job just so they have some regular contact with other folk. This is especially the case with retirees who live quite far away from their family.

Aside from this social benefit, working in retirement allows retirees the opportunity to learn new skills they have long admired. Personal growth is a rewarding self-investment that adds immense satisfaction.  

Delay Pension Withdrawals

If you do go back to work after retiring, you won’t have to begin your Government Pension (Social Security) or withdraw from your private pension (retirement accounts) as you will be living off your regular income. At the very least you will be able to withdraw far less. So, you will be leaving most of, if not all, of your pension for a later date, when you finally do retire for good. And, while your pension waits for you to fully begin withdrawing from it, it will be amassing more interest and will grow as a result. So, when you do decide to start making withdrawals, your pension pot will be larger than right at the start of your retirement!


Just because you are now at retirement age, it doesn’t mean that you absolutely have to retire. As you can see, there are a few different reasons why it might be worth returning to work!

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Create Your Own Phased Retirement

Just because your company doesn’t support phased retirements doesn’t mean you have to delay your retirement. Staying in their full-time rat race grind may be the only solution they offer. But it isn’t the only solution for anyone wishing to ease into retirement using a phased retirement approach.

Create Your Own Phased Retirement A recent study done by the Transamerica Center for Retirement Studies (TCRS) found that 77% of employers actually believe many of their employees plan to continue working after they retire. 47% of these employers also say many of their employees envision they’re using a phased retirement transition approach for their retirement.

Yet only 31% of the employers that Transamerica surveyed said they would let their employees shift from full-time to part-time employment. Not surprisingly, only 27% of employers said they would allow phased retirement seeking employees to move into less stressful or demanding positions.

Caution is Needed for Employer Allowed Phased Retirement

Retiring employees do need to be careful entering into a formal or informal phased retirement work arrangement with their employer.

Careful attention has to made into the impacts that a reduced schedule or a lower stress/lower paying position will have on any defined retirement benefits there may be. The defined benefit rules and the formulas they use are tough to get around. The last thing you want is for your phased retirement time dragging your retirement benefit amount down.

Other active employee benefits like medical insurance and paid-time-off/Vacation will also need to be carefully examined. Entering into a phased retirement arrangement will most likely impact them.

Signs to Look for Before Staying With Your Company in a Phased Retirement Agreement

Being able to have a phased retirement with one’s current employer is certainly the most comfortable way to go. We already understand the business, the work processes, and the culture. But based on my first career I believe caution is justified.

I think my corporate world experience isn’t unique and is a shared experience. Entering into a phased retirement agreement with one’s employer may not be the no-brainer decision you might think.

Think about the following:

Does your company have a habit of expecting employee loyalty but never reciprocates?

In other words, do they treat long-time loyal and dedicated employees as just a disposable number? Your phased retirement gig may be just short-term to ring out all they can before letting you leave on their terms, not necessarily yours. They will and do value younger employees who they think they can retain longer-term.

Do employees who have transferred to a new position or have been promoted get sucked back into their previous roles every time feces hits the fan?

Do you think your phased retirement agreement will stand if your company has a habit of doing that? Are you OK with a prolonged or indefinite return to your pre-retirement job obligations?

Has there been times when your company has backtracked away from promises made?

Think bonuses, raises, 401k match, pensions, health insurance, promotions, etc. When they do, did they include executives in the pain or did they state they decided not to include them in order to attract and retain the best for the company? Do you think they will honor your phased retirement agreement for as long as you want, need, or agreed to? If your company throws employees under the bus but never its executives then maybe you should think twice about extending your relationship with them.

Just take a moment and really think about your experience with the company.

If your career there has been nothing but a stellar experience then I think you are in the minority. If it’s that good I would also question why even consider a phased retirement. Just enjoy it until you can feel like fully retiring. If you have concerns now about the company then why enter into a phased retirement agreement and continue with any negative feelings in your life?

For my first early retirement I wasn’t thinking “phased retirement”.

I was fully in a “retire early and often” mindset. I have successfully done that with some rewarding and interesting post-retirement work. In hindsight some of the things I did while preparing for that included asking myself the above questions about my long-time employer.

Let’s just say that I have never worked for them again in post-retirement. I admit that there is some truth in the saying better the devil you know (than the devil you don’t)”. However I found entering into a new relationship to be in my favor when working in retirement.

I could work without a legacy of career obligation baggage to be dragged back into. I could create a retirement lifestyle where I would only seek opportunities aligned with my interests and passions. That includes only working under my terms for as long as I wanted to.

Not having to worry about upsetting or angering a long-time employer who may still have control over some of my retirement benefits, thus having control over me. That to me is a big deal.

Why Creating Your Own Phased Retirement May Be the Better Way

First off, understand what kind of phased retirement you really want. Even if your company does offer a phased retirement option it may not be aligned with what you envision.

  • Are you looking to go part-time?  
  • Change job duties to something with less stress and less responsibilities?
  • Wanting to only work certain parts of the year or specific seasons?  

Also try to figure out how long you want the arrangement to last. I think the fact anyone is willing to bring up phased retirement with their employer means they aren’t afraid to signal their retirement intentions. Hopefully this is done only after knowing one could actually retire because employers may sideswipe someone who have prematurely signaled their retirement intentions.

Rather than thinking only “phased retirement”, open up your options by thinking of retirement as the absence of needing to work. You can think of it as a phased retirement or as I had planned to do and have successfully done. That is retiring early and often.

If your plan is to go directly into your desired phased retirement position then begin finding, interviewing, and accepting a position before announcing your retirement. This will at least allow for you to explore your options over only attempting to stay at your existing company.

Here are some reasons supporting why you should create your own phased retirement:

Make a clean break from your employer. No worries of negatively impacting any retirement benefits through a reduced salary (less stress-pay/fewer hours) phased retirement agreement.

Free to choose opportunities aligned with your interests and passions. Not what your employer thinks is their best way to use you. It’s easier to limit your duties to agreed upon responsibilities and negotiate rather than be dictated when our role needs to be changed.

No previous legacy obligation of work to be dragged back into in any time of crisis, real or otherwise. That certainly could circumvent your phased retirement wants and needs.

New working environments offer new experiences. In people, work, education, and culture. It may not be as comfortable starting out but it makes up for that by being more exciting. We all stay in our ruts too long.

It’s easier to move on or as I call it “retire early again” when there are no long-term ties. Knowing that I can simply leave once a retirement job isn’t checking off all my boxes anymore makes working in retirement fun and not a dreaded burden.

Last Words on Creating Your Own Phased Retirement

The company I worked for over 3 decades did not offer any phased retirement options. It was “their way or the highway”. I waited some months after retiring early before I began looking for my first dream retirement job. It all worked out wonderfully. That doesn’t mean that it didn’t take some effort on my part.

I have several pages on this Leisure Freak site that might be of help:

Retiring Early and Often 

How to Choose Your Retirement Job 

How To Find Your Early Retirement Job 

Retire Early and Start Your Own Business 

Check under the Retiring Early and Often tab at the top of the page and there are pages on retiree resume  and interview  tips, handling the dreaded “overqualified issue, and even how you can increase your wealth by retiring early and often

Before I close out this post I would be remiss if I didn’t mention the fly in the ointment. It’s called health insurance. If you retire without a retirement medical benefit then health insurance must be considered. A phased retirement agreement at your employer that allows for employee group medical insurance does carry some weight.

When looking at creating your own phased retirement, include health insurance in your decision process. Look at staying with the same employer, looking for new opportunities that provide health care benefits, or buying health insurance in the single payer market.  

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Retire Early and Often: A 7 Step Plan for Scoring a Successful Encore Career

If I was able to retire early and have a successful encore career then you can too.

When I retired early from a long career at the age of 51 it was late 2009. Unemployment was high and the economy was low. It took having a plan of action for a successful encore career to happen for me.

People have many reasons for wanting a retirement job or starting an encore career. There are obvious social and financial benefits. For me there were some things I really wanted to learn more about and experience. Getting paid to do it was the frosting on the cake.

Successful Encore CareerI had always planned to retire early and often.   I needed to set aside my decades long engineer persona and all of its associated all-consuming obligation. My wish was to spend more of my time doing things closer aligned with my passions and interests.

I didn’t need to return to work. What I wanted to do was cherry-pick opportunities that concentrated on the skills I enjoyed using. I was and still am grateful for all that the earlier version of me and my career gave me. But I needed to move-on and reinvent myself  to living a more passion-driven lifestyle.

I’d like to share my seven-step strategy for landing a successful encore career.

Second Act, Here I Come

My 7 Step Plan for Scoring a Successful Encore Career

Phase one of my plan started with taking some time off to decompress and enjoy some alarm clock freedom. Phase one had it’s unique importance. It’s where I could mentally shed decades of institutional career-driven conditioning. That and embrace the new life to be lived on my terms. Phase two is where the 7 step encore career actions came into full play.

Step 1: It’s All About and Not About Money

Have Your Financial House in Order

Obviously my retiring early meant having a good handle on my finances and lifestyle cost. In my case my early retirement funding paid for my primary living expenses. This allowed me to remove money from the retirement job decision process. With money off the table I can ask myself whether I would really want to pursue an opportunity. That question is a tool I use in what I describe as “retiring well”. 

Even if lifestyle funding isn’t at 100% for the long-term, knowing where we are financially removes any job search desperation. I believe part of my encore career success was the lack of financial desperation in my opportunity selection process. I Chose well. It was at no time salary driven. I also believe having a lack of financial desperation helps in the interview process.

Encore career success isn’t just about money. It’s about scoring an opportunity aligned with our values, passions, and what we are interested in doing now.  What I did was focus on the opportunity first. I then only negotiated an appropriate salary after being offered the position.

Step 2: What Floats Your Boat?

Identify Your Passions and Interests

I asked myself, what do I want? The whole idea is picking the right encore career opportunity.  I began with a self-assessment of my passions and interests. There were specific industry and positions I wanted to pursue.

I then listed my relevant payable skills and divided them into 2 columns. Those I enjoy doing and those that I don’t. I only targeted opportunities that tilted heavily to the payable skills I enjoyed using. There will always be a need to do the things from the less desired payable skills column. The encore career idea I embraced was to limit my exposure to the non-enjoyed column skills as much as possible through purposeful opportunity targeting.

Step 3: What’s Your Story?

Be Able to Enthusiastically Answer the “Your Story” Question

The question can come in many forms. Tell me about yourself. Why did you retire? Why are you interested in doing XYZ? That’s when understanding my story became important. In my story I am the protagonist. I am more than a chronological list of my experiences. My resume certainly lays out that professional experience and accomplishments list. I didn’t want to just roll through that boring narrative when given the opportunity to tell my story.

Choosing an encore career path different from one’s first long career can be challenging. Instead of my early retirement and subsequent search for a new opportunity looking like I’m some kind of unpredictable, undependable flake. I wanted my story to be about coherent transition. My story is about all my experiences and discovering what I am really good at, love doing, and what I have passion for. It shows how I am pursuing opportunities that are on a logical path forward to grow and be productive in those areas. It’s why I should be seen as an asset and not someone making a nonsensical disconnected jump.

What I found necessary for encore career success is telling my story by adding emotion and interest to the chronological history. I used feelings to set myself apart by adding how I felt during certain milestones or personal discoveries. I also emphasized the impact it had on me, the business, and/or others. My belief in my story is projected out when telling it.

Step 4: Keep Growing

Add New Skills that are Aligned with Your Early Retirement and Encore Career Goals

I am very curious and that is a big part of my early retirement. I’m always exploring new concepts and adding new skills. I had many interests that went in different directions when I was looking at opportunities. Even though I was targeting opportunities based on what I loved doing, the job ads listed things I had never done or wasn’t as proficient at doing.

I took free classes that were offered at my library. It was a gardening class and had nothing to do with my eventual encore career. It was about other encore avenues I was exploring. I also did volunteer work in what was another path unrelated to my eventual encore career. Although they did not result in an encore career the experience was still rewarding and helped me in other ways.

I did sit for a few sessions with a friend of mine who was an Excel and SQL-pro. He tutored me on advanced spreadsheet and database query skills. They were skills aligned with my targeted technical encore interests. Those skill learning sessions were directly related to my eventual coveted retirement job. There are many ways to learn new skills.   

When we keep growing in areas of our interest and passions it makes our early retirement fuller and only improves our chances for starting a successful encore career.

Step 5: Practice Makes Perfect

Test the Waters and Yourself

I actually started interviewing a year before I retired from my first career. At that time (2008) job opportunities were limited due to the deepening recession. Doing it gave me practice. Job interviewing is like a game or dance. The better we are the more likely we are to stand out. It’s something we get better at the more we do it. Our resume facts are the same. But it’s all about feeling and acting more natural and comfortable in the role of self-promotion and being judged.

I also did some volunteer work and a side hustle. The volunteer work was very physical and allowed me to test my interest and passion for the outdoor recreation industry. For the side hustle I was a private consultant. It was a contract related to telecom litigation and paid extremely well. I was able to explore my self-employment path in an area I thought I enjoyed from my long career. In both of these examples I decided the experience showed me that they weren’t exactly what I wanted to do in my retirement.

The volunteer work was too physical for my 50ish old body and I couldn’t easily keep up with my younger team members. I had to set aside that targeted path and honor my limitations. The other was too close to my first career. Requiring heavy use of skills I preferred to limit using going forward regardless of how much it paid. However it did bring to view how much I really loved some of the other skills I had to use. The experiences fine-tuned and narrowed my focus to the space where my eventual encore career lived.

Step 6: Get Off Your Island

Stay Connected To and Keep Expanding Your Network

After retiring it’s easy to withdraw from our professional connections. Our focus happily changes and the last thing we want is to stay connected to anything associated to the past grind. That withdrawal is what I allowed during my first phase of my early retirement (career mindset decompression). It was a time I concentrated on building my social circle. I began reconnecting to my professional circle in phase 2. I did this by email. No big drawn out dialog. Just reconnecting and reminding them of my retire early and often plans that many thought was crazy or funny when I mentioned it during my pre-retirement years.

I also expanded my network using LinkedIn. There were many people who had left my orbit over the years that I had worked with and respected. I reconnected and mentioned my intentions when appropriate. What all of this did was lock-in what I was going to do. It gets the word out but more than that it made me accountable to myself. I then started mentioning to my social circle that I was always open to the right opportunity. Retiring early and often became a great conversation topic at social events when others discussed work matters.

My successful encore career came out of LinkedIn. An email came to me asking if I would be interested in talking about an opportunity. Using social networks like LinkedIn is a necessary tool but it is important to go beyond them. Through face to face social conversation I met executives and other key connections to add to my network. Just by talking about what I did and what I wanted to now do.

Step 7: Throw Your Name Into the Hat

Post Your Resume Online and Talk to Everyone

I did what everyone does. I started searching for opportunities that were posted online or in the newspaper. Unfortunately applying for those openings and getting a call back during those times had a very low success rate. Hopefully things are better for that now. I did successfully get a lot of contact from simply having my resume posted online and viewable to recruiters. I have used Snag-A-Job, Monster, CareerBuilder, Dice and InDeed.

Obviously not all targeted jobs use recruiters to fill positions. If you have no network connections for a foot in the door, then the good old-fashioned way of going on site or to their online portal and applying is the only way to get your resume in front of someone. My stepped down retirement jobs came that way. The resume posting sites I mentioned above allow you to directly apply your posted resume to job listings. 

A key tip is to talk to everyone you can. Even when they are calling or emailing about a position that you know upfront you wouldn’t be interested in. Don’t just ignore them. Have fun and learn what’s going on. It is easier talking with them when you don’t want the job. I would return their calls/emails and ask for more details. After listening to their pitch I then would explain why I didn’t feel it was a good fit and what it was I was looking for. I would be totally honest. I would also share the name and contact details of anyone else I knew that was looking for an opportunity in that field. What this did was create a certain rapport and a new professional connection. I still get contacted from many of them even after removing my online resume over 5 years ago.

In Closing

I believe that retirement is the absence of NEEDING to work, not the absence of working. That doesn’t mean I will always do paid work or even look for new opportunities. But when I do it is something I really WANT to do. Parts of all seven of these steps came fully into play for me to score my encore career. They will again if I choose to do another opportunity.

Now that I’m in my second early retirement I look back at all of my retirement work opportunities far more fondly than my first career. I believe that’s because they were all on my terms and aligned with what I valued doing. Doing what I wanted to do for as long as I wanted them in my life.  

There is nothing special about me. We all have our own unique skill-sets and experiences. I hope by sharing my approach for scoring a successful encore career that it inspires you to see a way to set your own retirement job strategy into motion.

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Retiring Well: Looking Beyond Finances

Retirement brings freedom and options. With that comes many choices that retirees must make. Obviously having our finances in order is a key to retiring well but that alone is no guarantee. There are two questions I always ask myself as a guide for keeping me on my retirement well-being track. Two questions that I believe can help anyone avoid doing something that will mess with successfully retiring well.

Having enough money available to live the retirement lifestyle you want and can enjoy is primary to retiring well. There are many online retiring well financially geared articles and plenty here on this Leisure Freak site.

Of course there should always first be financial analysis. Deciding whether we can afford to do something or how our spending, portfolio strategy, budget, saving, etc. will impact our long-term retirement funding. After that is settled comes the two questions to make sure we truly retire well.

Retiring well means retiring without regret or unnecessary backtracking to repair a bad decision.

Believe me, retirement and its freedom brings a lot of options and decisions to make. Retiring well means living life on your terms and doing so purposely. Retiring well means retiring to something, not just from something. Nobody plans on retiring into a void. That isn’t retiring well. Neither is retiring and taking on bad projects, strangling obligations, putting up with difficult people, being unnecessarily idle, or accepting a unfulfilling retirement job.

Retiring WellRetirement is much more than our finances that support it. There is the living part of retirement that must be addressed so that we can retire well.

Retiring well must include our avoiding making any bad move that strays from what it is we really want in our retired life. We get to call our own shots and everyone makes mistakes. But I use these two questions to make sure I am truly on track to a no retirement regret decision.

Two Questions To Ask Yourself To Help Ensure Retiring Well

Question #1- If money was removed from my decision, would I still do this?

By answering this question we force ourselves to focus on the importance of the decision. Its importance as it relates to what we truly value in our retirement.

I definitely used this question in my decision to retire early the first time.

It was the end of 2009 during the recession. My portfolio was significantly down but the retirement calculator numbers still came up with favorable but tight results. When asking myself this question the answer was YES. A financial only mindset would have probably caused more retirement delay even though I was truly ready to move on to my freedom. Answering this question gave me the push to clear all the economic uncertainty. There will always be less than perfect financial conditions.

I have also used this question when presented with a paid opportunity.

I focus on skills and experiences of interest and passion when it comes to working in retirement. Sometimes the salary can have me momentarily stray from my planned path. In those cases the answer to this question is NO. But for one stepped down lower paying gig the answer came up as YES. It checked off all of my interest and passion boxes and I enjoyed every minute of it.

This question was also prominent in our retirement decision to not move to a less expensive and snow-less location. Although our financial analysis showed we could improve our finances by making the move. It also showed we could stay put without negative financial issues. But by answering this question we were able to focus on what we really valued. That is, being close to our children and grandchildren. So the answer was NO.

There have been times when our financial analysis showed that we best decide against something.

But by asking this question we gauge the importance to what we value in our retirement. In some cases we really did want to move forward and answered YES. We then made necessary budgetary and income adjustments to counter the financial negatives.

Question #2- If I knew I only had 10 years left to live, would I still do this?

This question is the ultimate ego tamer when it comes to work, activities, and relationships. It forces us to remember an undeniable truth that we are finite and puts our mortality into the equation. It has us prioritize what is most important to us.

When it comes to work opportunities it counters heavy financial justifications and our ego.

In the case of relationships it has the power to force us to focus on where we are and where we really want to be.

How we want to really handle a bad relationship, what to do about grudges we may have, or close the distance between friends and loved ones that we want in our lives.

It has us look differently at social activities that we may not feel like participating in.

It does so by adding, do I really want to miss this opportunity to be with those I care about? Answering this question can change our focus because there is no guaranty of tomorrow.

This question comes up for me with work opportunities.

They checked off all of my interests and passion boxes after passing the first question that removes money from the decision. But I have answered NO for this question because the commitment was too long. Other times the project looked and sounded perfect but I had no respect for the company or its leadership and policies. One in particular opportunity had very tight deadlines covering many months. It would have made taking time-off for family trips or vacations too difficult to fit in.

Sometimes I need this question to silence my ego when it pushes me to investigate or do things that are not aligned with my retirement values.

It allows me to stop wasting my time on things I do not value. There can be many reasons why I wouldn’t want to waste any of my finite time. I then answer NO to this question.

This question has me prioritize relationships that I truly value so I can strengthen them.

I also use the question in how I view and limit relationships with people I really don’t care for but still have because of business or other connections.

In Closing

Retiring well does need having our finances in order. But there is the living part of retirement that counts just as much. The freedom that retirement provides also brings many options and decisions to make. But decisions dictated by a singular financial mindset may cause a retirement of regrets.

I use the above two questions to enhance my retiring well decision process. I am sure there are many others that can be used to keep us on the path to enrich our retirement with what we truly value. For instance questions about our health which is also important to retiring well.

Hopefully these two questions has you thinking about questions that go beyond finances that you can use as guidance toward your retiring well.

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A Fun Retirement Job Starts With Your Motivation

I have had a few working opportunities since my first early retirement. I can tell you that a Fun Retirement Job Starts With Your Motivation. Work and Fun together in the same sentence seems to be the ultimate oxymoron. But the reality is that working for the right reasons in retirement can be fun. I love the definition of retirement as the absence of NEEDING to work. Basically we are still retired if we choose to work for reasons other than our financial survival. Being forced back to work for a paycheck just to make it is unfortunately another flavor of the rat race.

More and more people plan on working in retirement. There are many reasons why retirees choose to work. Motivators include:

  • Working in a Field of Interest and Passion
  • Being Social
  • Brain Stimulation
  • Staying Active
  • Learning New Things
  • etc.

For some retirees the motivation to work in retirement is for a financial boost or extra play-money. For a fun retirement job money can’t stand alone and shouldn’t be the only motivator.

No matter what our reason is for starting a new retirement gig, having a fun retirement job starts with our motivation. Then using our motivation to pick the right job that checks off all of our motivation boxes.

My Fun Retirement Job Experiences

I had always planned on retiring early and often. Since my first early retirement as an engineer from a long telecom career I have had some amazing retirement jobs. I call these fun retirement jobs my passion driven opportunities.

Wireless Telecommunications NOC Tech

A stepped down responsibility position from my land-line engineer career where I was able to learn everything I could about wireless networks.

Cable Video on Demand Systems Analyst

This was my encore career. It was a nice transition into IT away from my earlier life in network operations. I was able to use a lot of my passion focused skills to learn and work in the video world.

Cable Telecommunications Billing Systems Analyst

This was a 7 month early retirement side hustle. It started as the most perfect and fun consulting gig I have ever done. I was able to use the skills that I like doing from my first and second career together.

Craft Beer Bartender

This was a part-time gig of passion. I love a good beer and the craft beer movement. It’s a totally new working experience and it gave a huge boost to my social circle.

Not a bad run of opportunities since first retiring in December 2009. These passion driven opportunities were all fun retirement jobs for me. It was my motivation that made them that way. Many of my coworkers in these gigs were not having fun. That is because they HAD to work there. They were motivated by career driven money reasons and their financial survival.

What was their rat race existence was my learning, social outlet, rewarding (financially and otherwise), passion driven and fun experience.

Having the Right Motivation: The Key to a Fun Retirement Job

We have all been there. Having a job to pay the bills and enduring the crappy commute. We lived for payday and the weekends. If we were lucky we had some fun doing what we did for money.

Working in retirement has the same challenges. There is still usually a commute and a work schedule which obligates our time to be committed to the employer.

The difference that makes a fun retirement job is we only work in retirement because we want to. The key is tying anything we do to our passions and interests. Otherwise we trade one rat race lifestyle for another.

Work is work but if we choose our retirement job correctly, the Fun comes when everything is aligned perfectly.

My motivation has always been to try and learn new things. I also focused on skills I enjoyed using and steered clear of skills that I had and didn’t enjoy doing. My passion driven opportunities were for reasons other than money.  That is what made them fun. Money was just the frosting on the cake. I targeted areas of high interest and passions. How could I not enjoy doing them? It also doesn’t hurt knowing that leaving a job is always an option.

Sometimes it doesn’t Work Out or Last

We will never know until we know. As we grow and move forward some of our passions and interest can change. That is when a passion driven retirement opportunity can stop being fun. The money side of the brain can take over and convince us to stick it out. But that isn’t what working a fun retirement job is about.

When the fun ends then that is when it’s time to move on. Life is short. That is the “retire often” part I love. When I hear that little voice that I have all I wanted from the opportunity and it loses its fun-factor it is time for me to go.

Sometimes the opportunity is still something I have interest in or passion for but other elements have made it lose its luster and fun.

  • Difficult Coworkers and/or Managers
  • Difficult Clients
  • Change in Work Scope
  • Commuting Changes
  • Health and Wellness Issues

There can be a number of reasons that can make what was a fun retirement job turn into dreaded unsatisfying work. Once our motivation is no longer being met then it becomes another obligation slog. Just like any pre-retirement job. It is then time to move on to the next fun retirement adventure.

In Closing

a Fun Retirement Job Starts With Your MotivationI just ended a short 3 month run as a Craft Beer Bartender. It was a blast and totally outside of anything I have done before. The people were great, the PUB was awesome, it was close to home and I learned a lot.

However my old back injury was aggravated by all the standing on hard surfaces and the constant bending over for low stored items / low dish sink. I have had to limit a lot of things I used to do because of my back issue. So I had to resign and return to loyal customer status.

I only worked part-time a couple of shifts a week. It was still a scheduled obligation and if it wasn’t fun it would feel like an unwanted obligation. Looking forward to going in for a shift was exactly what a fun retirement job is about.

On my last shift which was this past Saturday I felt more sadness about leaving coworkers and the business than I did in my first 2 early retirements. It was hard to quit something I was enjoying doing and being a part of. Sometimes things just don’t work out but we gain great things in the experience.

Who knows what or when the next passion driven opportunity will come along. Early retirement is an adventure. My primary motivator is to strive to keep it fun and rewarding.

Are you open to considering working a fun retirement job?

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Retired Multimillionaire Busboy Dishwasher

This weekend I saw a Retired Multimillionaire Busboy Dishwasher. I know many early retired folks who since retiring have either happily started their own businesses, began their dream encore career, or simply have taken on part-time work for a scaled down approach to working. All of them doing what interests them and doing what is aligned with their values and passions. They don’t need to work but they want to. After all, that is what retiring early and often is all about. However this guy is someone I would not have expected to see with an apron on and taking on the cleanup role at a grand opening for a new (craft beer) micro-brewery.

He happens to be the only Multimillionaire that I know.

We met years ago through our shared automotive hobby interests and through some of my volunteer work. That said I won’t be specific with his name or the establishment for privacy reasons. He is a good guy, very down to earth, and active in the community. His is a story that illustrates that working in retirement doing what you want to do and enjoy doing is the new retirement model to strive for. It also illustrates how those who do retire early don’t lose all ambition and never work again. We the early retired just never trade our time for meaningless work anymore.

His story is common for many Multimillionaires. He started a business, grew it to great success, and he and his partners sold it years later to a larger corporation for a massive amount of money. He took some time off and could have just taken another corporate executive position but instead wanted to stay in town and make a difference locally. He saw an opportunity to buy an automotive repair shop in town where he shows up daily and promotes the business and stays active in the automotive enthusiast – hobby world. His manager and mechanics do the day-to-day grind. Not a bad gig for him. I am sure even he wouldn’t have thought a few years ago that he would be a Retired Multimillionaire Busboy Dishwasher but that is what makes the early retirement adventure so interesting. You don’t know what your next opportunity or passion driven endeavor will be.

Why Be a Retired Multimillionaire Busboy Dishwasher?

Retired Multimillionaire Busboy DishwasherThe simple answer is he is a part-owner of the new craft beer micro-brewery. He invested in this new business as something of interest and passion. He also knows the mastermind behind the operation. The primary has owned and operated the Home Micro-Brew supply store in town for years.

You may be saying, “Man I knew it. It’s his joint. No wonder he was busing tables and washing dishes.” Sure, that is normal for business owners but not so much for Multimillionaires. He could just have easily hung out, shook-hands and back-slapped all day long. Nope, you see those who worked hard, made wise financial decisions, and lived within their means to get to early retirement are driven, motivated and not the type to be sitting around just counting their money or worrying about looking like a rich jack-hole who is above any menial work.

Are You Thinking You Might Join the Retire Early and Often lifestyle?
  • Have all the necessary financial and non-financial early retirement boxes checked.
  • Always keep an open mind.
  • When something interests you dig into it and find out everything you can.
  • Always stay curious because you can never know enough about anything.
  • Figure out what you would love to do.
  • Understand the necessary skills.
  • Assess your skills against the required skills.
  • Close any required skill gaps.
  • Learn all you can even if it means working somewhere starting at the bottom to get it.
  • If later you find you no longer enjoy what you are doing in retirement then retire again.
  • Don’t lock yourself into something you don’t love doing anymore.
Final Comments

So I saw a Retired Multimillionaire Busboy Dishwasher this past weekend and I wasn’t really all that surprised. I know the dude enough to get what makes him tick. His early retirement has him still active in the local small business world and he is having a ball. They guy is always smiling living life on his terms even when getting down and dirty.

For those of us who have reached early retirement and have been open to pursuits of passion and interest it truly is worth all the hard work, spending discipline, and saving to get here. For those on the path toward financial independence this kind of life is a worthy goal to strive for even for us non-Multimillionaires.

If you were a Multimillionaire could you see yourself busing tables and washing dishes?

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Never Say Never Just Say No Thank You

I was just reminded of my diplomacy mantra “Never Say Never Just Say No Thank You” when I need to reject an opportunity. I also use it on myself to quell ego and greed. Two insidious human conditions that are counter to the way I want live now. You see, sometimes when you least expect it and are least prepared an opportunity can present itself. After the initial surprise my best instinct is to follow my gut. But then my brain kicks in. You may think that is how things are supposed to work. But my making a shift to a passion driven mindset means thinking beyond money when living my retire early and often lifestyle.

Never Say Never Just Say No Thank YouMy brain is very good about identifying financial benefits.

Especially after all the exercise it got during the long trek to financial independence. My brain can’t help itself, running the numbers starts-up immediately. However my being open to opportunity in my early retirement does come with important limits. After all it is my finite time I am trading for money when I CHOOSE to accept paid work. In this case the opportunity was aligned with what I have previously identified as work I enjoy doing and have interest in. It even matches up with my last early retirement side hustle but this time my gut immediately said something else to me. It said, “Hell no, not again”.

Passions Can Change so Never Say Never Just Say No Thank You

Sometimes I see or hear about opportunities that look interesting because I have done them before and I am very good at doing it. My ego then will have me consider stretching the work interest and passion limits that I have set. My brain runs the numbers and lets greed chime in to make its case.

But my gut is the gate-keeper trying to calmly keep things balanced and aligned with the passion driven way I have chosen to live. This time with this latest opportunity offer my gut had something important to say.

  • Perhaps it was how my last side hustle turned into an extension and didn’t go as promised.
  • Perhaps the corporate world is just more than Leisure Freak Tommy wants to deal with anymore.
  • Perhaps I am just having too much fun now not doing paid work and not ready for any paid work.
  • Perhaps I just have too much planned now. Projects, travel, celebrations, and whatever I want to do.
  • Perhaps my passions and interests have changed as it just doesn’t fit well with me anymore.
Putting Trust In My Gut

There was no “perhaps” about it. After some self-assessment of what my hesitation and gut was telling me it was all the above.

I hadn’t given it much thought until now so I am surprised with the results of my honest self-assessment which put money totally aside. I really don’t want to engage in Tech anymore. Not as a telecom engineer or technician. Not working in IT and being a business, data, or systems analyst. I am no longer interested in any of it and have scratched those skills and work from my passions list. At least for now. They served me well with my first career, my encore career, and even my early retirement side hustle but I want to move on. I checked off some bucket-list items doing it and now it is time for new adventures when I am ready to begin another.

So to this opportunity I simply said to myself Never Say Never Just Say No Thank You. To the consulting company I replied No thank you, due to current obligations I am unable to accept the opportunity at this time.

It is a truthful response.

How to Walk Away from the Money

  • Ask yourself, if money was no object, would you want to do this work?
  • Set Retire Early and Often (working in retirement) limits tied to and aligned with your interests and passions.
  • Live by the interest and passion limits you set so you won’t dread any paid work you accept.
  • Remember your mortality. I see the government actuary tables  show my life expectancy to be 84. Simply do the math. No sense wasting any of it in misery for money.
  • Remind yourself that your health is best now while younger and don’t put off doing what you want to do until later when older age physical conditions will change.
  • Trust your gut. If it doesn’t feel right it probably isn’t regardless of how much money it pays.
In Closing

I use saying to myself Never Say Never Just Say No Thank You to cope with the fact that my passions and interests can and will change. For all I know someday I may have a change of heart and would enjoy doing tech work again. So I leave myself open to that fact this way.

Life and early retirement is an adventure. You never know what you will find along the way.

How about you. Can you see how your passions and interests can change but see the benefit of saying never say never?

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High Encore Career Success Rate

I was reading the results of a recent study that destroys the biggest argument from my naysayers about being able to start an encore career living the Retire Early and Often lifestyle. They insist that finding a new meaningful and rewarding career is impossible due to age discrimination. They insist that anyone’s encore career success is due to luck.

This survey just came out from the American Institute for Economic Research (AIER). Their study results clearly show a High Encore Career Success Rate for those 45 and older making a sought-after career change in their later life. Success at a far better rate than people would expect.

Surprisingly the results go against most published articles on the matter. As the majority of respondents not only found and started new careers that provided them greater satisfaction. But also received higher pay than the career they left.

Of the survey respondents: Eighty-two percent reported they successfully transitioned to a new career after age 45. The key was having and using their transferable skills that they gained from their earlier career.

Not only did they find themselves being happier in their new pursuits but also receiving higher pay to do it. Some said they did initially start their new career at a lower salary. But they worked hard and climbed the income ladder to be paid higher than their first career paid.

My Experience Matches the Study Results.

This is certainly what I experienced. My first retirement was from an Engineering career working in telecommunications network operations. After some time off I started to pursue opportunities of interest in the wireless industry. I focused on skills that I liked doing. I did land a sweet position in a wireless company’s network operations and was enjoying it when I made another move. This time pursuing interest in the video (cable) industry working in IT as a Systems Analyst.

Again I was using my transferable skills to win the position. My wireless experience did pay less than my first career but that job was a lower stress and lower expectation job. The video position was in a new industry and career segment for me (IT instead of network operations). It paid around 13% higher than my first career. I retired from that IT career after a few years and later returned for a little early retirement side hustle in their telecom IT unit.

It seems that success can be found pursuing opportunities when using your first career and for myself even my second career gained skills and education despite everything we hear to the contrary that most people can’t find meaningful work in their later years.

Results Show a High Encore Career Success Rate but not 100%.

Although there was a high second career success rate from the respondents. There were still those who were unable to make a career change. The study results explained it came down to being short of the necessary education or skills required. The study found that for those who failed to connect to their dream position. They only had two of the required attributes being looked for.

From this we can see the importance of planning ahead and getting the necessary education and skills needed to improve our odds of making a later life career change. Respondents did go out and did exactly that in many cases. Although it would seem through the high success rate that age discrimination wasn’t a brick wall to overcome. There is no way to know how prevalent it was as a factor among respondent’s pursuits.


The study was actually called “New Careers for Older Workers”. But all the findings would fully relate to those who retire early and often by seeking their desired encore career. Because starting a new career in later life is exactly what starting an encore career is about.

If you want to see more about the study you can download the PDF from the American Institute for Economic Research site using the following link: Just find the “download report” button. Your email is required.

The download even includes the survey questions so that you can evaluate how the survey was done and the depth of the questioning asked to come up with their results.

Have you found success pursuing an encore career?

Do you plan on retiring early from your current career and then seeking a new encore career?

Do you find the High Encore Career Success Rate surprising?

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How My Big Mistake Saved My Financial Keister

Sometimes you make a mistake and you just have to suck it up and soldier through it. If I was to put a chapter title to the first 3 months of Leisure Freak Tommy’s book of 2015. I would title it Sadness, Frustration and Budget Hits. How my big mistake saved my financial keister.

My Big Mistake

If you have read some of my earlier posts you may recall I took on a little early retirement side hustle last October. It was funded for a sweet two and half month gig that went to the end of year. It was the best gig I have ever had. When they asked if I would consider accepting an extension I laid down my boundaries by being rationally unreasonable. They accepted my conditions and made me an offer to stay into this year until mid-May. Of which I accepted.

It all started wonderfully but slowly as the weeks went by the corporate behemoth I am consulting for started pushing past the agreed upon boundaries. Pushed to the point where now they don’t recall anything about said boundaries.

My big mistake is I allowed them to do this and I didn’t just say that it is time for me to move on.

I get it. They have business needs and after losing some staff the work needs to still be done. I am just a softy and decided to be nice instead of being right. It isn’t the end of the world but it does add some frustration. That’s because I prefer to spend my time doing the things I am interested in doing. Not the boring meaningless stuff of everyday production problems.

It makes me feel a bit of a fraud because for me it’s all about being passionate about what I am doing. I am not to the point where I hear that little voice saying there is more to life than this. But I do think that if I didn’t know I was returning to retirement soon that voice may just be singing to me now.

That said I am honoring my end of the deal until mid-May. I do take solace in knowing that I held up my end of the bargain and maybe that is my passion connection. Living honestly with integrity.

I am looking forward to returning to early retirement in a few weeks. I am being well paid which is what has saved my financial keister. For the most part this early retirement side hustle has been very rewarding.

How My Big Mistake Saved My Financial Keister – My Three Pay-Offs

Mistake Pay Off #1-

I had posted about recovering from the blown budget blues in January where I explained how our long time beloved pet, our fury family member was diagnosed with terminal heart disease. I am sorry to announce that he passed away a couple of weeks ago. From his first symptoms through all the tests and medications we did spend $2800. We spent that to make his last months as comfortable as possible. The money from the side hustle certainly spared taking this money from my emergency fund.

Mistake Pay Off #2-

My mother could no longer climb the stairs from her basement apartment at my sister’s home. She was basically trapped because she would restrict climbing the stairs due to pain and the length of time to get through the ordeal.

After speaking with my sister the logical decision was to find one of those stairway chair-elevators. My sister hasn’t the money. Even though Medicare will help pay for a Jazzy-Chair to zip around the neighborhood. They do not pay for a way to get up and down stairs in your old age.

So as I am on this side hustle I happily purchased said chair elevator system for $4900. Once again the money from the side hustle certainly spared taking this money from my emergency fund. Because even if I wasn’t still working this side hustle I would have done this anyway. I love my mom.

Mistake Pay Off #3-

Last week totally out of the blue my father-in-law passed away. As the family is trying to recover from the shock we will be traveling out-of-state to the funeral. We will also be pitching in money for the wake and obituary.

As this trip is coming in the next couple of days I don’t know the total we will be spending. But the money from the side hustle certainly spared taking this money from my emergency fund. Or at the very least from our travel and vacation fund for this year. It sucks to deal with a death in the family at a personal level. But I feel badly for anyone who has to also suffer through financial pressure too.

In Closing.

Things happen in life that you can’t budget for. Having an emergency fund is very important. I have also been thinking a lot about how my early retirement side hustle was extended. How it has turned out with me sticking to my end of the bargain by staying on even though they broke my rules for being there.

I certainly could have walked off the job anytime I wanted to. I can’t help but think about the old saying that things happen for a reason. With all that has happened through March I hope that my life quiets down, my contract comes to a quiet but exciting (for me) end, and I return to my early retirement life living totally on my terms.

Have you ever had a run of bad financial hits within a short time period?

Have you had a business deal go sideways but you still held up your end?

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Are You Ready to Retire Early and Often

Are you ready to retire early and often? I had asked myself this same question many times before I pulled the plug on my 31 year telecommunications career as a lead engineer. Then becoming Leisure Freak Tommy. Living my retire early and often dream lifestyle. What I am wanting to do with this post is walk through a self-assessment. That way you can see how to answer this very important life changing question. Are you ready to retire early and often?

Are you ready to retire early and often- Passion filled lifeAre you still passionate and interested in your current long-time career job?

Before I start going through all the other early retirement assessment questions. This one is key and if you can answer YES to this question, then don’t retire early. Are you doing what you want to be doing? There is something to be said about this well-known quote from Confucius

“Choose a job you love, and you will never have to work a day in your life.”

If you can answer YES to the above question and “love” your job. Then you are set and living your version of a dream. There is no need to continue with the assessment. I would consider you already retired. As you are no longer “working” as the quote states.

However, if your answer is NO. Then you might want to continue with the self-assessment as I did.

Can you retire early and have enough to pay for your living and other retirement costs?

This is a big question and unless you are just super fortunate and everything has fallen perfectly into place for you. You probably have planned for early retirement a long time now.


To answer YES to this question most likely means you have no debt. Except maybe a low-interest mortgage. You have lived below your means and saved for retirement. You possibly have reached a point in your career where you are pension eligible based on your age and years of service. People with pensions are far and few between. But I bring it up because many early retirees are people who did choose a career where they traded a larger salary for a lower salary with a pension benefit. Answering YES to this question means you continue with the assessment.


If you have answered NO, all is not lost. You need to figure out what it will take to be able to say yes to this question. Or decide how close you are. If its debt, then pay it off first. If its savings then you need to ramp up your savings rate. If it is making the numbers to become pension eligible then you need to stay and meet those qualifications.

There isn’t anything you can do about the pension eligibility unless you are far too many years away to make it worth sticking it out in a job you now despise. If you answered NO and are close to being able to retire then you can retire from your career. But should do so only after you have found that perfect fit of an opportunity that you have looked for. Do not give up your seniority and salary until you have the new one locked in.

You will hear that you are just changing jobs and not really retiring. However, you are retiring from a career you are no longer passionate about or in love with for one that you are. If you happen to also have a pension then you can put that to work for you rather than your company by saving and investing your pension while taking the new opportunity of your dreams which will really ramp up your finances.

Are you a go-getter who knows what they want in retirement and know what they are passionate about?

Perhaps you are looking for a less stressful career or less hours. Maybe you have a new business that you want to start. What I had was a couple of career paths I wanted to explore and learn about. You have to have reasonable expectations and goals but if you do this right you will have an awesome lifestyle. One where you enjoy what you are doing and passionate about it.

If you were one of those people everyone considered retired-in-place at your old career, then you should know that today’s workplace is super competitive and you need to be a sharp go-getter to start a new career. If you live somewhere with limited opportunity, then you have to be realistic. What I am saying is if you have to work, don’t give up your senior position and income for a dream that isn’t based on reality.

Are you ready to retire early and often? Then the perfect situation to be in is:

  • You can fund your retirement without having to work again. Retire on your own terms and you get to decide what you will do in it. You can enjoy your early retirement whether spending the days doing whatever you feel or being engaged in rewarding and productive endeavors that you can be passionate about.
  • You know what you want to retire to and where your passions and interests are so you can be picky about what opportunities you would come out of retirement for. Retire to something, not just from something.
  • You have realistic expectations about opportunities based on where you live, your background, skills, education, ability, and energy. You can have all the passion in the world but if you are not up to the task or you live somewhere where opportunities related to your passions are not available, then that is not going to work for you very well.
  • Once you find that new career or opportunity, ride it out as long as you can still be passionate about what you are doing. Beware of the “retire early and often trap” where you stay too long for various reasons and it becomes what you retired from the first time. Learn to hear and listen to that inner voice and just retire again so you always live a life on your terms where you are happiest and living your dream life.

So after doing a little self-assessment, are you ready to retire early and often?

Let me know your thoughts and comments on this subject.

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