Retiring Early and Often

Having the mindset of Retiring Early and Often and taking the leap was the best decision I have ever made. Setting out to live this lifestyle has enormous benefits. Anyone who has enough net-worth to fund their early retirement also has the awesome power of the retiring early and often lifestyle. A lifestyle that not only provides the freedom to pursue our desires and passions but also to increase wealth, donate to charity, or fund any worthy cause or hobby we choose to.

By having our retirement lifestyle fully funded we can be picky about working in retirement. Picky to only choose work that inspires us and only when we want to take on a new opportunity. Every penny we now make, including any new 401K opportunities can be saved and invested.

Retire Early and Often Lifestyle

Retiring Early and Often is like other common terms you may have heard and read about related to working in retirement:  Serial retirement, semi-retired, partial-retirement, para-retirement, encore career, second-act, mini-retirement, etc.

However those common working in retirement terms all have some specific definitions associated to them. As far as I am concerned retiring early and often is all-inclusive. Basically it starts when you have retired or withdrawn from your position or occupation to pursue a passion-driven freedom lifestyle.

It is a retirement lifestyle where you are free to choose any opportunity whether paying or not. Choosing only opportunities that meets your desires and fulfills your focus in life. Then if or when those desires are no longer met or your desires have changed, repeat the process and retire again.

I always liked the idea of being able to work in retirement doing something that truly interests me and then retire again. Taking what I tell everyone is just a personal sabbatical before looking for or accepting another project. I do love this freedom.

Retiring Early and Often – Is that really retirement?

For those who are thinking that working in retirement by starting a new job or business is neither retirement nor leisurely, I say consider this: As an early retired Leisure Freak, I will only consider opportunities that I have a desire to do, not have to do. I plan on constantly learning new and interesting things throughout my retirement and the rest of my life. Being paid to learn and do those things that interest me and I have a desire for is a huge bonus.

As I have said on other pages of this site, the absence of needing to work instead of the absence of work defines retirement.

Retirement isn’t limited to those who work until they are too old or too broken. People who retire early are an ambitious, motivated, and goal driven lot. All of that won’t just vanish from the “being productive scene” because they have saved enough to retire. Admitting to ourselves that we can be open to accepting paid opportunity of interest during our retired life is just being real with ourselves.

Early Retirement is possible

It all starts with choosing to embrace frugal living. That and setting your spending and savings plan into motion. This way you can have options available to you on how you want to live.

If your portfolio can’t produce the income level needed to fully fund your early retirement, then look at your early retirement funding as buckets. Buckets defined by periods of passion driven work and with possible savings support to fund your lifestyle. Then at some point funding relies on Social Security and your savings. Run the numbers and see if you do have the portfolio to start living your life this way now.

It’s not magic and still takes having saved enough to pull it off. But not nearly as much as you might think. Especially if you are successful with your reduced spending through frugal living and have a lower lifestyle cost to support.

Retiring Early and Often, a passion-driven lifestyle. Living the dreamIdentify your Passions and Positions that will appeal to you as an Early Retiree.

I had planned on retiring early and often for 11 years before my first early retirement. The whole point to this is to be free to pursue positions and opportunities that you as an early retiree want to experience. Otherwise what sense does it make? There is no reason to retire from one job to just take another you don’t want to be in.

Create A Bucket List

My bucket list has a column or section called “Jobs that I would like to do”. It isn’t precise. It shows what I would need to make a position attractive for me to target or accept to do.

For example:

  • I live in a small town and had to commute daily into the city for years so I listed – work close to home.
  • Having been an employee for what felt like forever, I also had on my list to be a consultant and try contracting.
  • I had worked for a large corporation so I wanted to work for a small company or start-up.
  • Having spent my entire career in Network Operations I now wanted to work in an IT environment.
  • I came from the telecom wireline world and wanted to try working in and learning about wireless networks.
Bucket List – What I WANT To Try Doing

There were a few entries on my bucket list. It isn’t a huge list under the “Jobs” section to knock out. The idea isn’t that all the items be checked off for any single opportunity. It is a list of what I WANT TO TRY DOING.

Nowhere on my bucket list under “Jobs” was anything associated to money. My expenses and freedom lifestyle are covered through my retirement funding plan. The list was about passions and experiences I wanted to pursue. If my life was only about money I could have easily just stayed in my stressful, time-consuming, soul sucking and unfulfilling job that I retired from.

If nothing else, finding a close to home, no (low) stress part-time position for some extra pocket-money and social interaction sounds a lot better than working 40 plus hours a week in a job that robs me of my time and isn’t aligned with my passions.

My passions and desires seem quite simple when it comes to jobs or work I wanted to try. I loved certain aspects of my past career and wanted to try doing them in a different environment and technology. I do have a detailed page along these lines – How To Choose Your Retirement Job that you may be interested in reading.

Retiring Early and Often – Cautions and Reality Checks

The number one Leisure Freak rule of retiring early and often is this: Do not voluntarily retire from your current long-held position if you have to find another job. The rules of the universe still apply – Life costs money. If you are short in your retirement funding and HAVE TO work, then do not retire early until you have found and secured your dream opportunity.

If you are close financially to being able to retire early without having to continue working right away, or your plan is to take some time off before pursuing or starting your passion-driven work, then just make sure you have a solid plan and the finances to back it up.

You are only in the position to consider retiring early because you have done many things responsibly to get here. But you must be aware of a couple of things.

Retiring Early and Often- What You Need To Know
  • There is age discrimination. If you are age 50 or over, and especially age 55 or older, it may not be easy finding that dream retirement job opportunity.
  • There is also discrimination against those who have not worked for a while. If you spend a long time enjoying your retirement before interviewing for that desired position, then you will need to be ready to answer questions in a positive way about your personal sabbatical.
  • If you have not had to search for a new job in a while, then you may be surprised that it may take a considerable amount of time to find and land a position. Many offered opportunities take in many applicants and drag their feet before making an offer.
  • Make sure that any retirement opportunity you decide to pursue and accept doesn’t end up costing you. Depending on your retirement funding, benefits, and from where it all comes from, don’t let taxes or breaking through other thresholds cause regret. Be aware and avoid retirement job mistakes.
You must also be realistic.

You can have all the passion in the world to do something. But if where you live, your health, physical fitness, education, or your skill-sets limits the chance of ever doing it, then you better make some plans to counter that. For example:

  • By moving to where the work is.
  • Getting the necessary education and/or expertise.
  • Finding or identifying a more realistic passion to pursue.

Whatever you choose to pursue, assess all of your lifetime experience and skills and match them to what you are passionate about doing.

Retirement is about retiring to something, not from something.

If you are miserable in your job and retire early then weigh that misery to the misery of retiring early without enough to fund your retirement. Especially if you are not able to find that extra required income if nobody will hire you.

To get to early retirement you are most likely acquainted with frugal living. But even if you are only a little short each month to cover your basic necessities and the things to make your life free it will be very stressful. It will leave you feeling like you are living a deprived life. Constantly worrying about money is no way to retire. I am trying to drive a point. Have a realistic plan and realistic bucket list.

Retiring Early and Often – Finding that next adventure.

My case after retirement finding a career

My first working in retirement opportunity came by way of Craigslist. I was focusing on technical jobs in my town with Craigslist and another sight I recommend, To my surprise there was an ad for a NOC Tech in a small wireless company less than 4 miles from my home.

The position paid a third of my earlier engineer salary. That wasn’t a detraction as I am retired through financial independence and money isn’t part of my decision. I am doing what I want to do. It was a Technician position where I had previously been a Lead Engineer. I knew the required stress and job expectations would be far less. A perfect early retirement gig for a freedom loving Leisure Freak.

It also checked off multiple items from my bucket list.

Work close to home, learn about wireless networks, a small company and a few more.

This company had a generous 401K match of which I took advantage of. I was also able to save and invest all of my take-home pay. All while fulfilling my desire to learn and work in the wireless industry.

I was happily there about a year and a half without really searching for another position. I was learning all that I could. Then my second opportunity presented itself by way of an email from a recruiter. They had found my profile on “LinkedIn”. LinkedIn is another site I recommend you should embrace and use.

This time it was for a consulting position at a large cable company. It also allowed me to check through several passion-bucket list items. As an added bonus the position paid even more than the Lead Engineer career I originally retired from. Of course now I am really saving and increasing my net-worth. This opportunity turned into what was a very rewarding encore career.

My Second Early Retirement

I was there enjoying the ride for about 3 years when I started to hear that little voice again. I then decided it was time to retire from what was a very lucrative and educational Video Systems Analyst contract position. It had simply gone as far as I wanted to go. I decided I had other things I wanted to now pursue with my Leisure Freak freedom lifestyle.

Now that I retired a second time at the age of 56 I have been warned that I may hit age hiring barriers. Barriers that will cause future difficulties in retiring often. But that is all part of this adventure and looking forward to what happens next. My next act may be a business venture or something that I have no idea of today. I only know that it will be of interest to me. My plans are to live, travel, and spend more time with my family for a while. However I will always stay open to interesting opportunities that are in my passion zone.


1/10/15. I have worked on a short-term side hustle with a salary bump for the same Cable Company. This time working in their voice telecommunications group. I call this gig my early retirement side hustle. It went for 6.5 months. Age did not hold me back as I was warned might happen.

As a note to my experiences above, none of these working in retirement opportunities happened overnight. The first took 4 months from application, interview, to start date. The second took 3 months from first interview to start date. You can see why you shouldn’t retire early if you have to work right away. I only reiterate this because if you are retiring from a position you have held for many years you may have forgotten how long it can take to be hired.


Here are a few Links that I have used for finding that next Adventure.

Perhaps you already know about some of these links below. If not, I hope these links help you find the perfect passion-driven early retirement job so you can live the retiring early and often lifestyle. If you have never used an online job search site before or unsure about them, then check out my How To Find A Retirement Job page.

Online Search Sites for listed positions:
  • monster   Monster is a well-known job posting and résumé posting site. This is the first site I used and is a favorite.
  • Snag-a-Job Lists jobs from many job sites in one convenient place. Large corporate full-time professional jobs to small company part-time temp positions. Create your user profile to set-up emailed job alerts and upload your résumé for simple job applications.
  • Indeed Lists jobs from many job sites in one convenient place. Large corporate full-time professional jobs to small company part-time temp positions. Post your résumé for recruiters to find in their searches.
  • craigslist  Lists jobs by the Craigslist area you are interested in. Great for local small company job searches.
  • linkedin  Establish your LinkedIn profile and start linking with your professional associates. Post your résumé for recruiters to find in their searches.
  • dice   Dice is a technical job site for job posting and résumé posting. I have used this site with good results.
  • Careerbuilder    Career Builder is another site for job posting and résumé posting.

Sites with work from home and freelance opportunities that look promising. I haven’t had personal experience with these but some people I worked with recommended them to me.

  • flexjobs   (Work from home/remote employee site)

Job listings and career advice for people over 50

Save pagePDF pageEmail pagePrint page