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It’s a question many of us ponder as we transition into retirement: Beyond the financial aspects, what truly sticks with us from our working lives, and what do we find ourselves missing?
For me, like many others, it’s the daily banter and camaraderie with customers and colleagues. There’s a unique energy in those professional interactions—the quick jokes, shared challenges, and the general buzz of a workplace. It’s a specific kind of social connection that’s surprisingly hard to replicate.
I’ve found a great way to fill that void by increasing my participation in social sports like pickleball. It provides that regular, light-hearted interaction and a sense of shared activity that was so present in my working life.
I’m eager to hear from other HumbleDollar readers.
I’m with Richard H…I miss nothing. That’s not to say I didn’t enjoy my career (last 34 years with one company/ group) but when it was over at retirement the shift to not working was easy.
The social aspects and volunteering for my HOA and other organizations in retirement has been more than fulfilling in the transition . Also, spending more time with my family, especially my grandkids and being close to them as they grow up is awesome!
Mark, hope to see you on the Pickleball courts (I’m in North and central New Jersey)! 👍 We love the social aspects of this hobby.
Initially I realized I missed expertise – developing it and using it. But I replaced my technical expertise with travel knowledge – I planned my trips, mostly three to six months at a time, and then wrote about them. Initially I sent emails (using internet cafes!) and then I had a web site followed by a blog, plus from 2006 on I posted on the Fodors forums. Twenty-five years out, I wouldn’t say I miss anything. It was a long time ago!
My wife didn’t think I’d ever retire. I guess I didn’t either. It turns out that retirement has been quite satisfying. I play golf a few times a week and volunteer on several boards that advise on things ranging from F&B, golf course issues and the local Handicap Committee. I also volunteer for our local FD, as well as various fundraisers for local charities. And we travel a lot.
As I reflect on what I miss from my work life, the answer is nothing. I loved my jobs in Sales and Marketing Management, but I was more ready than I realized to enjoy the fruits of my labors. And I’ve kept in touch with three former colleagues through a book club we started and golf & fishing get togethers.
I’ve had few close friends over the years, but many acquaintances. I’ve held a number of leadership positions over the years. Corporate CEO, president and board member, Manager Systems Engineering, Scoutmaster, HOA Board Member and president, etc. They say it is lonely at the “top” and that is so. Politicking should be left to the politicians.
When I shifted to consulting one of my tasks was to evaluate and sometimes to fire other firms and consultants, or implement difficult or unpopular changes.
None of this required that I be popular or play favorites. There was one common trait. Failure was not acceptable. People’s livelihoods and well-being, jobs, and businesses were at stake.
As a volunteer, preparing boys to be men and going into the wilderness with them, sometimes many miles from “civilization” with no phone connections was not for the unskilled or undisciplined. Not all parents were aligned in this.
I became a board member of a large HOA in the aftermath of the banking crisis of 2008. The board was 50% social club and 50% disdainful of owners. It was a constant power struggle for them. Unit sales had plummeted; there were bankruptcies and foreclosures. Some on that board insisted to owners that if I were elected, I would raise fees above the customary, annual 5-10%. Nails were driven into the sidewalls of two of the tires of one of my automobiles. I persisted and desperate owners elected me, but it took some parliamentary maneuvering to get me on that board. The social clubbing was to end, and the board was to get down to work. I immediately took charge including expanding the monthly newsletter, preparing a reserve study, etc. It is said that everything can be accomplished in communications. I re-organized the board; under intense scrutiny and pressure some left. It was simple; be a fiduciary or leave. Some had made serious mistakes not consistent with their fiduciary duties; I used that to force change. Period.
It took me eight years to first stabilize and then transform that property, recruit a functional board, etc. Annual fee increases over that period fell to 0 to 3%. At the end of my tenure we had a 30 year viable reserve study, ample reserves, we’d caught up on all capital projects, etc. Property values were up and sales were hot (in the most recent two years selling prices are up 25%, and few units are available for sale).
In my endeavors I aways attempted to train others but good luck with that! It has been my operative philosophy that we are to be of service to others, in partnership. I practiced leadership by example. These are very difficult concepts for many to grasp and even fewer to master.
No, I don’t miss them, but for a very few with whom I was in partnership over the years.
I retired from an academic career. Strangely, perhaps, I missed the “deliverables” aspect of work, primarily that of writing reports and analyzing data — even of meeting deadlines. I subsequently filled the void on the board of a local non-profit. Turns out they always have documents to write or review along with numbers to crunch, and are grateful to have help.
I had similar feelings. Doing taxes with AARP, and being our HOA treasurer have replaced some of what I miss from work.
I rode the front of the tech wave from the pre-PC era to the dawn of free software to the birth of the online world (first job at CompuServe, also at AOL, Amazon), the Internet, Cyber security and AI. Mostly at the intersection of “IT” (no such word when I started doing it) and academia.
It was a fast ride that only accelerated as time went on. I miss being on the bleeding edge and being around the excitement of people who are creating the future and know it. But it was time to stop.
Per John Lennon, I think I’m content to be “just sitting here watching the wheels go round and round”. “All things must pass”
I’m not entirely qualified to answer this because I’m exactly 11 days from retirement, so I’ll answer with what I’m thinking now:
We’ll see in six months or a year or two if my thoughts have changed!
You’re right about COVID. It dehumanized work life. I spent the last 3 years working remote. I met my coworkers at a few on-sites, but in the end there were no lasting connections. There is something about meeting face to face.
Contrast that with 3 friends from early in my career who will be with me for the end of my Appalachian Trail section hike next month.
“Make new friends, but keep the old…”
We have a bi weekly breakfast club I call the Romeos … Retired Old Men Eating Out
Romeos 😂
The social aspect is very important to me, too. I have groups of friends from all over: former coworkers, neighbors, church, family, my time as a Scout leader, and “other”. If I’m not meeting someone(s) at least once a week then something’s wrong.
In my daily journal I have a section titled “out[ward looking]”. I list people, my planned interactions, what I’m doing for/with them, basically answering the questions “who cares what I’m doing today?/who am I helping today?”.
If that section ever starts getting small/empty, I’ve got to work on it
From two distinct occupations in my working years, the answer is the
same; It’s always the people. In retirement, I’ve kind of refused to let the people aspect go. It’s been 23 years since I left the beer business, I still meet up with a lot of those guys on a monthly basis. Family and friends now take more of my time, as well as some new faces in my life. A few solitary time wasters, gym workouts and hours spent in my vinyl resting place listening to music and posting with my friends from the HumbleDollar.
Dan – I listen to music all over the place. I have my stereo, iTunes Match on my computer, iTunes Match with airPods on my iPhone, and now I have a new car with all kinds of music sources (but not a CD player, dammit). Listening to music is my automatic pleasure mode whenever the opportunity arises.
The 90s called and want your CD player back 😉
That’s one for the tombstone: “my vinyl resting place,”
Yes, bury me with Diana Krall please…. but don’t tell Chrissy. Better yet, disregard this post…
Dan – going to see Ms.Krall July 2nd – sure she will be great as usual
I fall solidly on the “Or not” portion of this discussion.
I’ve always admitted I only worked as a way to earn enough money to pursue my hobbies on the weekends.
Now that I’m retired, I’m trying to turn my hobby into a ‘jobby’. Not particularly lucrative (yet), but very enjoyable.
My social circle has always been small–and I mean VERY small. But today I’m actually going to talk to three friends (one old one and two new ones). That’s more talking than I typically do in an entire month. I met all three of these friends through my love of dogs and dog training.
Kristine, your post made me remember the dog trainers I took my Irish Setter to 50 years ago. I can’t recall the trainers name but I remember their dog clearly. A giant schnauzer named Zoltan, who only recognized commands in Hungarian. A remarkably trained fearsome pooch if I ever saw one. He made my setter look like a real duffus, but I loved that goofy animal.
I think your dog training endeavor is going to yield solid dividends for you guys.
We taught each of our four dogs some of their commands in different languages. Even though I’m not fluent in any foreign language, I can say “Sit”, “Stay” and “Stand” in English, Czech, French and German.
I hope you have an enjoyable day… I was playing pickleball with a couple who had a dog at Crufts this year.
That’s awesome! Crufts is a big deal in the dog world!