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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2 thoughts on “Retire Early and Often: A 7 Step Plan for Scoring a Successful Encore Career

  1. Great post Tommy. Lots of good insight and information. Very inspiring. If you keep your eyes open and put in a little bit of effort, there are always opportunities available that you can find. And if a job doesnt work out, no harm done. You made a few bucks and can look for the next one when you are ready.

    1. Thanks for the comment Arrgo. That is the great thing about FI and the willingness to look at opportunities as just that. An opportunity to do something I want to do and when I don’t as you say, no harm done. Just Chalk it up being another experience in the adventure of early retirement.

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