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Defining Your Post-Career Purpose

Greener pastures toward finding your post-career or retirement purpose.Retirement is a fuzzy line these days. It seems increasingly rare for older people to cross the threshold from career worker to retiree on a single day and remain retired indefinitely.

My Dad did that. So did a few of my extended family members and former coworkers.

But when I ask retirement-aged people about their stop-working plan, they answer like this:

“Well, maybe next year if the market doesn’t crash.” 

“After this project, we’ll see what happens.”

“I might come back part-time.”

“My spouse wants me to keep working. I don’t.”

“I’ll get bored in retirement. I need something to keep me on my toes.”

“Yeah, I could sell my business. But I’m in a comfortable situation right now. Maybe when I’m 75.”

“I regret selling my business (at age 76). Now I don’t have anything to do.”

“I’ll keep working for as long as my body allows.”

If you love what you do professionally, why stop based on some arbitrary age or number? Why retire at the top of your game if you’re healthy and want to continue?

But many of us don’t love our careers and stay anyway.

Several factors can influence the decision to stay — ongoing expenses, status, lifestyle, family needs, professional connections, or having nothing else to do. 

We need a plan and motivation beyond disliking our careers to build the confidence to live our best lives. 


Just this week, I came across two articles about retirement and rejecting retirement. 

Michael Amoroso wrote an eye-opening piece for the HumbleDollar about the three stages of retirement — the honeymoon, the letdown, and the redefinition. He should know; he retired 26 years ago.

Unless you develop a solid plan for how to enjoy your newly available time, life after retirement can be filled with bouts of boredom, anxiety, and even depression.

Amoroso says redefinition is about building a new identity, developing new habits, and being active. Redefinition is the most challenging part of retiring from a lifelong career. 

Our happiness after retirement hinges on our pursuits. And the more pursuits we have, and the more diverse they are, the happier we’ll be. The worst part of retirement is losing our identity. The best part is finding a new one. 

It’s the letdown phase that can lead to unretirement — going back to work after retiring.

The unretirement phenomenon has always perplexed me because my retirement bucket list is already vast.

But only some have developed that clarity before they retire. That may be okay.

Marc Fisher from The Washington Post wrote that older Americans are dominating like never before.

The story highlighted a palliative care physician who unretired at 70 because she had too much free time and felt the “most competent and proficient that I’ve ever felt in my life.”

Fisher points to several “geriatric elites” thriving in politics and business. Octogenarian Hollywood royalty still attracts large audiences.

When older workers maintain enjoyment, fulfillment, a manageable workload, and professional aptitude, staying actively employed makes sense.

But if you don’t enjoy your profession or can no longer tolerate the workload, define and prioritize what’s essential and prepare to eliminate what is not.

Post-Career Purpose

I defined what I thought would be my retirement purpose at age 27. Seems silly looking back. 

Solo backpacking was my passion in my 20s, so I assumed it would be again after a long career and raising a family. 

But so much has happened in the last 20 years.

I’m a husband, Dad of three, son to aging parents, neighbor, community volunteer, avid swimmer, family traveler, and professional blogger.

The relationships and activities I’ve prioritized over the past two decades are my purpose today.

I avoid the phrase retirement purpose because I’m not retired

Our post-career purpose is the diverse collection of relationships and activities that keep us happy to be alive.

That can include more paid work. But it cannot include a career we’ve outgrown.

My IT career was never important to me. It was a job that paid well but never a calling or passion.

I spent a disproportionate amount of time on it, often ten or more hours daily. Worse, the work consumed my premium brain power, leaving my second-best for everything else.  

I miss parts of that career — the daily human interactions, steady income, office culture, and a company that had my back. 

But I left to live my ideal life full of what I care about most. Decades of saving, investing, and building a side business made it possible.

Remove the unimportant to prioritize the essential. 

Deriving Purpose from Work

Undoubtedly, some of us can work hard for a paycheck from college graduation until retirement.

We all share the basic human satisfaction of getting paid for a hard day’s work.

Our feelings toward our careers reside somewhere on a spectrum from despicable to loveable. In the middle is a big area called tolerable.

Most people I know fall in the tolerable zone. I was there for many years. 

When I started my first IT consulting job, I didn’t think I could find a career where purpose and prosperity could coexist.

Work was the place to make money. Life’s pleasures, enjoyment, and fulfillment were outside of work.

So, I followed the money for over a decade instead of digging deeper for something more meaningful. 

My interests and need for a creative outlet led me to start a blog. I realized it could be another path forward when I started earning money — around 2015. 

Discovering a job, profession, or business that makes us excited to wake up and work every morning is an incredible feeling that I suspect many never find.

We can use our less-than-perfect careers to build wealth, but not happiness. Seek purpose from your relationships and what you’ve already prioritized outside of work.

If you desire to continue earning beyond your career, look for opportunities where your interests, relationships, and capabilities overlap. 

A second act should be fun and fulfilling. Retirement — or whatever is next — is not just about leaving a job; it’s about finding a new identity and embracing diverse pursuits that make you happy to be alive.

Photo by Sean Robertson on Unsplash

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  1. “My spouse wants me to keep working, but I don’t” What kind of relationship is that?? As long as the numbers work out, should be an agreeable decision.

    Would love to know what businesses these people have that don’t want to step away, or regret doing so. It seems self-employed folks are more reluctant to retire, which tells me there is something they knew that employees don’t.

    1. Ha ha, that’s not a direct quote, but I remember someone joking about it. Maybe that was his awkward way of saying he can’t afford it.

      I can say now that I’m self-employed, I’m much less interested in retiring. But we’ll see if my tone changes in 7 years.

  2. I like to think of the time spent in endeavors, whether money producing or not, as “occupations”. There are so many ways we can use each precious day we get. From occupations that produce money and other rewards to those that produce creativity, joy and satisfaction without a financial yield, our time and energy are sacred gifts to others and ourselves. Retirement changes much, but our gifts and talents can be cultivated across entire lifetimes. Many just need to relearn how to structure a non-workplace day full of blissful, blessed time!

  3. I am enjoying the new newsletter format. I wasn’t reading articles w/ the links…this has me engaging the content again. Great post. The sentiment about planning your retirement in your 20’s is spot on…so much about who we are and what we value changes over the decades. I’m still working full time as an employee but am finding a better work/life balance that makes working longer more likely. [Peru/Bolivia last year…Italy/Dolomites this year.] I appreciate the reinvention/retirement takes work thread and will spend some time thinking through that for clarity in this season and what’s to come. Keep it up Craig.

    1. Hi Eddie,
      Yeah, the new email format a crowd-pleaser. Looking to further improve it every email. Thanks for the thoughtful comment.

  4. Steven from Shareholder Vote Exchange says:

    I enjoy the new email format.