A bunch of my friends are retiring this year, all in their 50s and early 60s. They’ve enjoyed successful careers and are wrapping it up. But beyond the initial excitement of newly-discovered freedom, the threat of boredom looms. The prevailing conversation centers on defining the second act. What’s next? How should I rewire? What’s my passion? Paid or unpaid? Part-time or full-time?

I get it. I went through this transition several years ago when I retired from my consulting career and watched our youngest child head to college. Although I’ve discovered my second act, there isn’t a month that goes by that I don’t entertain the possibilities. And that’s okay. It’s called rewirement for good reason.

Rewirement offers an opportunity to look at our lives with intent and explore ways to learn new skills, challenge our minds, and gain new experiences. It’s not a one-shot, time-based deal. It’s a continual, exciting experience that enables us to live a fulfilling life not bound by time or societal boundaries, like mid-life and retirement.

Our fixation on the traditional age of 65 can get in the way of viewing our life as a continuum of experiences and roles, both paid and unpaid. Before the rise of company pension plans and the introduction of the Social Security Act in 1935, generations were not focused on a specific age. Today, age 65 has become synonymous with retirement, an age that was selected during a time when our life expectancies were much lower.

Fast forward to 2019, and there’s a lot of time between our 50s/60s and 80s/90s. We’re living longer and are healthier than ever before. Staying engaged and productive gives us a sense of purpose, and increases our happiness and well-being. But how do we figure out what our second (or third) act will be?

“Retirement is not my idea of living.”

Warren Buffett

Life is a Portfolio

Too often we think about our lives in black and white terms. Full-time career, not working. Stay-at-home parent, empty nest. Employed, retired. When we do this, we forget the greys and the variety of roles and possibilities that fill our lives to make them rich.

The concept of a portfolio life recognizes that our lives are a myriad of many things that provide fulfillment, breaking down the black and white barriers and paradigms that limit us. So, the first step is a conscious shift in our thinking, and an intentional focus on reframing this life stage from retirement to rewirement.

Lay the Foundation

Consider your goals. If you’re leaving your job, do you just want a break? Or, are you ready to jump into something else? Take the time to think through your goals, how you’d like to spend your time, and priorities for the next several years.

Think about your goals in three major buckets: your mind, your body and soul, and your relationships. Make your goals specific, with a specific action plan for each one. Your action plan describes how you will achieve your goal and the steps you will take to ensure success. (Read How to Set Real Goals and Action Plans (Not Weak Resolutions) to guide you.)

This goal-setting process lays the foundation for considering possible second acts. There’s no sense diving in to an encore career if it’s not consistent with your priorities and goals.


It’s important to assess your financial situation to determine whether or not you need to continue earning money for a secure future. Financial planners say that most people miscalculate how much money they will need for the rest of their lives, typically underestimating how long they’ll live and health care costs. Having ample savings provides greater flexibility when determining whether your second act requires the same income, less, or none at all.

Your fiscal health will likely impact the components of your portfolio life and whether your second act is full-time, part-time, or very part-time. Starting a business may not initially earn any money (and chew up savings), but may be what you’ve always dreamed of doing for your encore. Similarly, you may be drawn to volunteer roles, but need a monetary cushion to enable you to do this beyond part-time.

A Side Hustle

My kids call it a side hustle: starting a second act or passion while you’re working your main career. If you conclude you need to stay in your current job, dipping your toe into your passion or desirable second act may be the best way to transition.

My husband’s cousin is a perfect example. By day, Joe Galbato is the chief financial officer for Tennessee’s Department of Transportation. On nights and weekends, his passion is writing, arranging and recording with some of Nashville’s finest musicians. His band mates have toured with Billy Joel, Elton John, Brooks and Dunn, Clint Black, and others. Joe is back in the studio recording his third album of original tunes. (Check him out on Spotify.)

Love Your Current Field?

The career you’re leaving may, in fact, be your true calling. Your retirement may have more to do with wanting more free time and exploring other interests. If this is the case, explore ways to use apply your skills. Consider consulting in your field, working part-time, or using your skills in a different role.

Back to the Books

Assess your current expertise and talents, and identify the skills you’d like to attain. Try to differentiate what you should do from what you want to do. Pinpoint what drives you and gives you an instant high.

If there’s another profession or job you’d like to pursue (or maybe just explore), identify the requirements for this role and the best ways to gain these new skills. It’s never too late to go back to college or vocational school. There are also numerous online education sites that provide a tremendous opportunity to learn something new and build skills. Many of them are free or a nominal cost.

Jeanette Goldstein was 83 years old when she graduated from Syracuse University College of Law in 2004. Nola Ochs graduated from college at age 95 and went on to earn her masters degree at age 98 (she died at 105). Older students provide inspiring examples of how it’s never too late and that gaining an education is a lifelong endeavor.

Hobbies and Interests

What do you enjoy doing when you’re not working? Do you have a hobby or talent that you love? Maybe it’s a new interest you’d like to engage in, or an old passion that you’re excited to get back into.

A second act often builds on something you relish, an activity that provides a sense of meaning and joy. There are proven ways to monetize a hobby, including starting a small business, selling on Etsy, teaching others, or starting a podcast.

Keep Your Ego in Check

Second acts are great because they’re often chosen based on a passion or interest you’ve had for some time. Your goals for starting this encore may be different from when you started prior careers. Chances are your prior job may have paid more and you may have held a more senior position.

It’s a good idea to keep your ego in check as you open yourself up to new possibilities and experiences. Being more junior in your second career has the added benefit of less responsibility and, often, less stress.

Social Versus Solo Needs

Evaluate your activities and social needs. If your hobbies are things you do by yourself, you may want a job where you interact with people. Today, many jobs can be done virtually. But if your goal is social interaction, this may not be the choice for your second act. Finding the right balance will provide greater overall contentment.

Several months ago, I met Debbie at the local Whole Foods. She bags groceries with a smile and has a cheery disposition. Debbie is a retired schoolteacher who works part-time. She told me, “It’s not because I need the money, it’s because I’m happier when I’m around people and need to get out.”

Dive Deeper

Some people are fortunate and know exactly what their encore career will be. Some, however, aren’t so lucky. There are numerous self-help books that provide insights and guidance on selecting your career and making career changes.

Here are five books that are worthy of your time, all earning at least four stars on Amazon.

Designing Your Life: How to Build a Well-Lived, Joyful Life by Bill Burnett

Do What You Are: Discover the Perfect Career for You Throught the Secrets of Personality Type by Paul D. Tieger

What Color Is Your Parachute? A Practical Manual for Job-Hunters and Career-Changers by Richard N. Bolles

The Pathfinder: How to Choose or Change Your Career for a Lifetime of Satisfaction and Success by Nicholas Lore

Test-Drive Your Dream Job: A Step-by-Step Guide to Finding and Creating the Work You Love by Brian Kurth

Career coaching services offer a more personalized approach, but at a price. There are also online resources that provide meaningful guidance. The Good Life Project offers a Sparketype assessment that helps you discover the nature of the work you’re here to do, answering the question, “What am I actually doing with my life?”

A second act is your encore, your chance to keep your mind engaged and gain new experiences. It may be full-time, part-time, or very part-time, but it gives you a sense of purpose and provides greater balance during your rewirement. Embrace the opportunity.

For privacy reasons, only first names are used above to highlight individuals who have found their second acts. All of them are followers of North of 52. 

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1 Comment

  1. Great timing. I’m retiring this year and, other than some travel, haven’t a clue what I’m doing next. My wife is worried too!


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