The benefits of working in retirement are many, from financial to social. I retired early at the age of 51 and planned on pursuing certain paid opportunities that I was interested in learning and doing. I was excited about the prospects of experiencing second act retirement jobs that I had passion for. A passion and excitement that was lost after decades of doing mostly the same thing with a lot of stress and legacy baggage attached to it.

I did find success in my second act efforts and can truthfully say it exceeded my expectations. There were a couple of jobs, a side hustle, and even a 4 year encore career that I enjoyed before I retired early again. Although I can look back at my second act experiences with pride and label it all a great success, there were certainly some things that worked and some things I tried to do that didn’t work as well.

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My Second Act Retirement Jobs Adventure

Knowing What I Wanted For My Second Act Retirement Job

I wanted to choose the right retirement job, not simply jumping back into the unfulfilling rat race. The first thing I did was identify my payable skills and experiences. I then split them between the skills that I enjoyed using and the ones I didn’t enjoy doing. On the ‘didn’t enjoy’ list I also identified those skills I wish to never do again. The idea was to target positions that were heavy on the ‘enjoy using’ side of my skills ledger. In no way did I want a second act retirement job heavily weighted toward doing things I didn’t enjoy.

Next I listed what jobs and industries I wanted to experience. I had some technical opportunities I wanted to pursue that were aligned with my first career, others were not. There were some non-technical opportunities I really wanted to experience. I also listed other desired second act attributes I was looking for, like commute limitations, avoiding the corporate world, flexibility, etc. This gave me an expanded retirement job target zone.

Then there was the early retired side of me. In my first career I was a lead engineer and I no longer wished to have the stress of a high professional position. At least not right out of the retirement gate. I wanted to look for lower level opportunities that would be less stressful.

This worked!

This was an important aspect of my successful second act adventure. I accomplished knowing what I wanted for my second act retirement job and then eagerly went after it. It set realistic goals based on the payable skills I had and enjoyed using. 

A Lower Stress Stepped Down Position

None of my second act plans revolved around making the big bucks so scoring a lower stress position was tops on my list. This turned out to be a lot harder than I thought it would be. Even though there were many aspects of my technical career I still enjoyed doing, I prioritized finding a non-technical opportunity.

I carefully applied and interviewed for positions I really wanted to do. Even though I had some desired cross-over skills, the fact that I had no real documented experience in these fields held me back. I noticed a common issue during interviews. Because of my previous high technical past, the interviewers in one way or another had concerns about boredom doing nontechnical work. In their minds I was only applying for the position because I was bored or they were concerned I would soon become bored if hired. No matter how I tried to counter this issue I failed.

I shifted my strategy to pursue a lower level technical position that aligned more with my first career. I didn’t have to deal with the boredom issue but instead the overqualified kiss of retirement job death. But I countered honestly by telling them why I wanted the position and found success.

First attempts failed but strategy shift worked.

Seeking stepped down opportunities outside of my long career failed. I should have either attempted to work part-time in these fields of interest before I retired or signed up at a temp agency to work in those industries to get experience. That may have been enough proof that I had real interest in them regardless of my long career. However, after finding success with my strategy shift, I must say that my first retirement job was a fun and rewarding experience. Even though my initial desire to attempt staying out of tech failed, I have no regrets about how my second act journey played out. I stayed just short of 2 years with this first opportunity before accepting what would become my encore career.

Being Honest and Setting Boundaries

For my second act I was looking for something more rewarding. I was honest about my experience and skills. I didn’t want to fake my way into a job that I wouldn’t enjoy doing or putting myself in a position where I couldn’t meet their expectations. But I also set some boundaries. If during an interview things came up that were skills I never wanted to do again I would honestly explain my position and bow out. I feel this worked well for me.

I had no issues in my first stepped down position but I did experience push back in my encore career and even more so during what I call my short-term early retirement side hustle. The longer I worked for them, the more they pushed to expand my responsibilities into my no-fly skills zone. I was mostly successful in maintaining the boundaries set when I was hired on during my encore career stint. There was honest discussion that resulted in agreeable compromise. I retired early again and I still look back more favorably on that experience than my first long career.

My short-term side hustle experience within a different business segment of that same company was another story. I accepted the short-term gig after honestly defining the scope of my work. It was probably the best work arrangement of my life. But after a couple of months when the first phase of the project was completed, the pressure started again to push me into doing things beyond the scope of our agreement and what I found acceptable for my second act.  

I successfully maintained my boundaries but there were repercussions.

Sometimes honesty isn’t acceptable, especially when management just wants conformity and silent obedience to authority. I saw that everyone was being pushed to expand roles and responsibilities. I simply and honestly said that maybe it’s best we call this good and part ways. Management doesn’t always seem to like that kind of honest conversation. The situation resulted in my staying on for the last 4 months of the agreed upon contract but there was obvious hostility from my manager. I can’t call this short-term side hustle a second act retirement job win. If ever in this kind of situation again I would now just resign and happily return to retirement.

Being A Competent Overachiever In A Stepped Down Retirement Job

For my first retirement job I wanted a less stressful lower responsibility opportunity. Having been an engineer and becoming a technician in a similar field was exactly that. I was doing very well in the position and I found myself applying some of my previous self, like documenting training for new techs that went beyond my role. It was appreciated and I had a very good relationship with my coworkers and manager. That was the upside. But I did experience something I hadn’t planned for.

An opportunity to move into a different job within the company became open that I really wanted. It was a slight promotion but still within my stepped down lower stress retirement job parameters. My manager was for it and the hiring manager was ready to offer me the position. But my director had different ideas. Two things were on his mind. I was in my fifties where everyone else was 25-35 and I was basically too good to let go. He went to the VP and the offer was killed. My background and early retirement status was well-known. I was seen as a flight risk. Better to continue using me where I am already productive for as long as they can. 

I felt the sting because I forgot how business works.

I somehow let myself fall into a youthful exuberance of being in a company I liked, doing something I had passion for. All said, the director was absolutely right. I had no real intentions of staying for a long time.

It wasn’t a major setback in how I grade this second act experience. But I felt a mental sting and call this a great lesson in handling stepped down retirement jobs. My lack of life drama made me dependable. I was reliable and capable. My lesson learned- Being good at your retirement job can’t counter the realities of how management thinks. At the same time understand and remember my goals. If I really want to make a long commitment then communicate that. Voluntarily go above and beyond but don’t lose sight of my defined second act employment parameters. I have to remember that as a retiree willing to take on retirement jobs that I will always be a flight risk. Throttle expectations to that truth.

Financial Blessings

I was prepared to live off of my portfolio when I retired early, but I always planned on living a retire early and often lifestyle. This allowed me to have the courage to retire with less than a million dollar portfolio. I enjoyed second act retirement jobs for just short of 6 years and earned a little over $350,000. It’s amazing how different work can be when you do something you enjoy learning and doing. I accepted opportunities that I had interest and passion for and was paid for doing so.

This is a total win!

Money wasn’t my primary motivation to pursue the opportunities I took on. But I knew that earning even a little money in retirement makes a huge difference in portfolio longevity.

I always say that retirement should be redefined as the absence of needing to work, not the absence of working. I went into retirement with that definition and my experience was better than expected. Some things I did worked, others didn’t or at least only partially worked.

From education to careers, so much of our life’s employment decisions are career minded and money centric. My second acts were more about working in areas of interest, passions, and doing it on my terms. Nothing much that we do goes off without a hitch. However, by having goals we tilt the odds in our favor.