I am considered a Serial Retiree. I write this post just after finishing an early retirement side hustle. Looking back at it I have to say that it went very well. Now the entire ride was not as perfect as it started out but I have to take some blame for that. There was some frustration and conflict but I made some concessions and stuck it out.

That said, I have some Confessions of a Serial Retiree to offer after successfully retiring early twice now. First from a long telecom engineering career and then starting and retiring from an encore career in the cable video IT realm. With this last 6.5 month early retirement side gig under my belt it is evident that I should reveal a few things. It’s an entirely different working dynamic shift.

I have expressed how wonderful and awesome it is to have the financial independence to be able to pursue opportunities of interest and passion. How living a “retire early and often” lifestyle is both personally and financially rewarding. However there is the flip side to of all of this. A side that is a bit more dark and less than inspirational or motivating that I must confess.

You see, I am all about pursuing opportunities that I am interested in doing. Where I work at the things I find rewarding and have a passion for. There are things I want to learn. All of that is what makes living this way great. But I do concede that doesn’t always work out so nice for those I am working for or working with.

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So IF I was to look at my passion-driven lifestyle as a coin toss where “Heads” I win. Win because this side of the coin represents what is awesome and perfect for me as a serial retiree living the retire early and often life.

THEN that means “Tails” you lose because this side of the coin means someone isn’t very happy about it. I do confess that in this coin toss I always win.

Confessions of a Serial Retiree. Blame it on the Corporate World.

It is not my fault. The fault lies in the way the corporate world operates.

When I do the résumé and interview dance I don’t mention my financial independence, early retirement, or my retire early and often philosophy. I go in based on the job description and how it measured up to my interests and passions. Then it’s all about matching skills and experience to get the position.

The company doesn’t necessarily list any of the mundane and bad parts of the position either. Those are not discussed and come only after you have accepted an offer and start working there. That has worked for decades. All because standard corporate policy is to dump stuff on people and if they don’t accept it then threaten to terminate them. Or later rate them badly in their performance review thus financially hitting them. That policy works for the multitude of desperate employees that these companies rely on.

But it doesn’t work for me. If the mundane and unpleasant isn’t fairly distributed then this opportunity isn’t to my satisfaction. I am only too happy to return to retirement leisure. The problem is the employer doesn’t know that until they need to know that. You see, I have been in the corporate world a long time. It seems there is always those who are politically connected and/or inept who escape having to do the unpleasant and mundane activities of any corporate operation.

To get the others to carry the load there is a kind of acceptable corporate bully culture that is allowed. That crap doesn’t fly with Leisure Freak Tommy any more.

Confession #1-

Heads: It is about chasing rainbows and finding the pot of gold.

During my first long career while on my FI journey there were aspects of the job that I loved and those that I didn’t. Now I only want to do those things I love to do. I have no interest in performing all the mundane repetitive operational and production related tasks.

I prefer working on the product creation side of things. Being project oriented instead of the reactive problem resolution and tracking side.

Tails: You might not like it:

When I say I will work for you doing certain kinds of work and I have no interest in doing the other types of tasks then believe me. I won’t be helping you out with that crap-work if the pain isn’t fairly shared.

I am only trading my time for money doing what I have interest in doing and learning. Otherwise we need to part ways. This isn’t about some generational inflexibility. This about someone who is financially independent and doesn’t have to put up with BS anymore.

Confession #2-

Heads: Flexibility goes all ways.

In my first career there was always talk of a balanced work and personal life. But they picked and chose who got to have that. For me it was required I be there at my desk for the day. Now I love to take advantage of any flex work benefits offered. From scheduled work hours, flexible start time to home office.

Tails: Look who is balancing their personal and work life.

Now when a company offers flexibility to some employees on the team and not to others, like flex-time work schedules and work from home, all or partial days. I am not going to ask or say anything. I will just participate in the same benefit as long as it fits my work needs and job completion requirements.

Look, I do get-it. The only way you can allow some people to not be there is because you have other people’s cheeks-in-seats to carry the office presence load, clear ticket queues and answer the phones. As far as I am concerned flexible benefits are going to be shared. If you don’t like it then let us have that awkward conversation.

Confession #3-

Heads: Encore Careers are most likely short careers.

My encore career in the cable-video world lasted less than four years. I have always found that after a couple of years you have learned as much as you can or want to and then master the position. After that you just get sucked into all the operational and production related minutia. Once my interest wanes or passion leaves its time to retire again. If I start another encore career I go in with no time-frame limits so who knows, I may prove this confession false someday.

Tails: You feel like you made an investment in me and just as it pays off I leave.

I understand that you feel like you are now just benefiting the most from my employment but this is about me now. It’s time for corporate policy to get use to the idea that it isn’t just a company perk to be able to dismiss someone when they want to. Now some of us are dismissing our employer when we feel the time is right.

Confession #4-

Heads: Keep it realistic. I don’t care about doing the impossible to climb the ladder, I only care about my work.

With my first career I gave heart and soul to the company and my organization. It was expected. Loyalty is not reciprocated in the corporate world now. I lived and died with results. I “Leaned-In” and worked whatever hours it took to get the job done no matter how stupid the timelines or expectations were. Now I only care about doing my part or task the best I can within a manageable and reasonable timeline. I know what it’s like to be top-dog from my first career and now I am out of the competition and will happily let others chase that false dream.

Tails: You have no idea what to do with someone purposely and obviously “Leaning Out”.

It seems there is always a crisis or all hands on deck situation. I am happy to help but burning through a night and day and do it for FREE, no thank you. If I am on a 40 hour a week paid contract to provide you work based on all of my years of experience and skills, then you can have me paint houses or dig ditches for 40 hours (for as long as I will put up with it). You are paying for the time but I won’t be that go-getter that is willing to do anything to please the corporate masters hoping for special recognition and advancement. Been there and done that. I leave that now to those who feel they need to taste it for themselves.

Confession #5-

Heads: I can happily walk away at any time.

The beauty of living this lifestyle is NOT NEEDING to work. I only do it when it aligns with what I want to do for as long as it stays aligned with what I want to do. This is total freedom to live life on my terms.

Tails: I am not afraid to tell you that I am willing to or going to walk. Best of all I get to pick when.

Maybe I get pushed too far, maybe being falsely reprimanded in front of the team because you are having a bad day with those above you, or maybe things have just run its course and I am ready to move on. I did give a months’ notice when I retired from my video encore career.

I came close to giving a negative couple of hours during my most recent side gig. You know, leave your lap top and badge in the desk cabinet, go to lunch and then call your contracting company to let them know that it isn’t working out anymore and have them call the client and tell them that I am already gone. I fantasized about it but after hearing positive input from my team members who matter more to me than the disconnected management I cooled down and stuck it out. That experience is one of the reasons for this post.

My final thoughts on the Confessions of a Serial Retiree.

I prefer to just think about the “Heads” side of the coin where I go in and do my thing for as long as it is beneficial to us both and when it’s time to move on I just give reasonable notice and retire again.

As for the “Tails” side of the coin, none of that stuff really came up during my encore career. My encore career just ran its course and I was ready to go.

However the side hustle through the 2015 extension period did touch on most of the darker side of the coin. Same company as the encore career but a totally different team and focus. It had me utilizing skills and experience from both my first and second career doing work in their voice telecommunications group. I made some compromises. Not for the company or the management but for some of my team mates. The company went against our agreement but I am just a softy and can’t stand it when someone is getting unfairly dumped on.

I hope that reading through my Confessions of a Serial Retiree you don’t think I am just a jack-wagon and you can instead focus on the “Heads” side of this coin. The side where there is an agreement about what I will work on and everyone plays nice. However I will tell you that reaching financial independence and retiring early and often is like being able to give the corporate world’s unfair work policies your middle finger by living life and working on your terms.

Do you have a confession to make?