FREE NEWSLETTER
Go to main Forum page »
I hear about this topic on YouTube retirement videos. It has also been a topic on HD from time to time. We all know about the process of preparing financially for retirement, but it seems that for many people facing a retirement lifestyle is equally challenging.
Honestly, I can’t relate. I never thought about what retirement living would be like. I had no expectations. Perhaps taking phased retirement for 18 months was a factor, but even when I decided on doing that it wasn’t with a plan to prepare for retirement, it was purely a financial move – collecting a pension, Social Security and half my pay simultaneously. Admittedly it gave me a taste of more free time and a loss of work related status.
It may be retiring at 67 was a factor as opposed to taking the leap at 55 or even 60, when the retirement years might be longer. Still, I have been fully retired over 15 years with no disappointments or regrets.
Why did I retire? I liked my job, that’s not it. I felt I had accomplished all I could. The senior leadership changed and in the process the company culture changed. At a meeting with the CEO about an incentive compensation issue he whipped out a flip chart and started writing formulas. It could have been Sudoku as far as I was concerned. That was it.
Perhaps I just have a dull personality. The older I get, the more mellow I seem to be. I am happy doing nothing if that happens. Connie maintains a pocket calendar with everything she (we) will be doing. There are two main activities. Family events and doctors visits. I write in “golf” twice a week. When there is a open date, I’m happy.
I’m equally happy traveling, even a road trip. I look forward to the five hour drive to Cape Cod, even driving to Florida in the winter.
SO, FOR THOSE RETIRED, how was the transition? Are you all settled into a comfortable retired life routine? Do you seriously miss any part of your pre-retirement life? FOR THOSE NOT YET RETIRED, what are your expectations?
I knew my retirement would be a paradigm shift. I was to simply walk away from an intense, rewarding business to a possible sedentary life. I had concerns. I did it gradually.
As an anecdote, I was once involved in a large and costly project that morphed into a financial disaster. I was 23 and in one of those “in the right place at the right time” situations I had uncovered the problem and made a detailed analysis and sent it to the executive VP of the firm. This was to have been a routine report, but what I did was beyond my scope at that firm.
I subsequently spent 11 months in a leadership position with a critical role in the resurrection of that project. It was ultimately a success. At the formal conclusion I was given a surprise by another of the firms involved. During a closure meeting I was gifted with gold Rolex, engraved with “To Norm, in Appreciation” with one additional cryptic word, of no meaning but to those involved at the time. Completely surprised I was asked how I felt about this. I stammered that “I guess I’m retired now”.
It took quite a few more years to actually retire and 44 years later I did it in steps. At the age of 67 I began reducing my hours and involvement. I had been doing a lot of volunteering, about 1,000 hours each year. I also began RVing part time with my spouse, began a YouTube channel and a blog to fill the spare time. (1347 posts created in two blogs). It took another nine years to retire completely, spending significant time each year in three areas of the country with travel in between. We were full-time RVers and I ran my business from various locations.
The blogs I created are journals and educational, some posts are 3,000 words or longer with photos, videos and embedded charts, etc. One was created in 2008, but most of the posts were created 2013 and later. Creating them and the 149 YouTube videos was a time filler and testimony to our travels and experiences. I learned a lot about videography and editing. I’ve reduced the frequency of publishing posts; the most recent was April 22, 2025. Using an alter-ego I’ve been writing and publishing on other matters since 2013.
I used the nine year period of partial retirement to plan and implement full retirement, structure my finances, extricate myself from my business and relocate in the U.S. It was good I completed this at the time I did because as I was completing these tasks I was diagnosed with an inoperable, rare and deadly stage IV cancer. From 2022 to the present dealing with that has been my primary challenge and occupation, with a few projects interspersed.
Today I prefer to avoid open-ended agreements. I’m currently completing a solar power upgrade to the RV which I originally installed in May 2022. I’m also upgrading the electrics in the golf cart.
When contemplating retirement I decided that I would prefer to be fully spent, burn out and be extinguished. It seems I may get that wish, but not yet.
“Are you all settled into a comfortable retired life routine?”
Since we’re international nomads, I wouldn’t say we’re “settled” in any way except we have no desire to change our life in the very near term.
As Kathy says well, we didn’t plan for our retirement, but we did save for it, and it has worked out well so far.
“How was the transition?”
Easy-peasy.
“Do you seriously miss any part of your pre-retirement life?”
Absolutely not.
More interesting than finance threads.
Not there yet but know I already have at least 2 years worth of projects including travel ready to kick off when it happens. Will be too busy to consider the work type replacement roles in the shorter term. Possibly more if I consider taking up pre college maths/science exam tutoring which seems to pay pretty handsomely given what people I know have been paying to help their teens over the line.
Go for the travel and leave any projects for later.
Working from home for 3 years during Covid was a great way for me to transition into retirement. My husband had been retired for several years. When I retired 2 years ago, I was surprised that I didn’t miss work at all. I do miss several coworkers and stay in contact periodically via email or text. Unfortunately, my old company went bankrupt, so everyone is scattered across various companies now.
I completed a significant amount of prep work before retiring, which helped smooth the transition. We built a new home (downsized), included ‘aging in place’ features, researched Social Security options and Medicare supplement insurance options, and paid off our mortgage. I also had stopped my HSA contributions and transferred the account to Fidelity.
I haven’t settled into a routine yet. My purpose (little ‘p’) is discovering the little things I enjoy and doing more of that. We live a mile from a 2,600 acre park and take advantage of the trails for hiking and horseback riding. My husband golfs twice a week, while I enjoy biking. We’re putting in the vegetable/herb garden today. We see the kids and grandkids frequently, and I coordinate a lunch or dinner once a month with friends (12 couples) we’ve known for 30-40 years (on the 3rd Tuesday). The difficult thing I didn’t expect was losing 5 of our friends over the last few years. We traveled extensively over the last 25 years and now enjoy life at our lake home.
I will have been retired from full time work for twenty five years come October 1st, and part-time work a few years less. I retired at 53, and never regretted it, or missed work. I could have continued to work part-time for longer, but didn’t feel sufficiently enthusiastic about it. After fifteen years of extensive travel, I had some down time with ill-health and then Covid – I spent a couple of years home alone with a lot of books and my computer – but I am now staying very busy at my retirement community. I did not plan my retirement, although I saved for it, but it has worked out very well. So far.
I asked an AI tool about the retirement question. Here is the summary answer.
“While the ideal of a carefree and financially secure retirement is still prevalent, there’s a growing awareness of the potential challenges and the importance of proactive planning in all aspects of life to ensure a fulfilling and meaningful retirement. Individual views can vary significantly based on personal circumstances, financial situations, health, and social connections.”
I still see the key not as retirement planning, but life planning. In many ways the decisions we make in the decades leading to retirement may have subtle but profound impact on retirement living.
The transition was rough over ten years ago with the un anticipated release into the next phase of life. The structure, meetings, reports were all suddenly gone in the rear view mirror. Adjusting took some getting used to but now being experienced in this phase, the days have become busier than ever with travel, puttering and tinkering keeping up with technology changes. Projects around the house are gradual and eventually become completed. There is more time to visit the grocery store, enjoy a library book, and just relax.
The one thing I didn’t miss were the meetings — unless I was the one conducting the meeting of course 😎
“The days drift by, they don’t have names…” , lyrics from an old Jimmy Buffett song. That’s how I imagined retirement would be. But Jimmy was singing about his young self discovering a beach bum lifestyle in St Somewhere. In reality though, retirement requires a calendar. Things like doctor appointments, grandkids soccer/tennis schedules, the monthly meeting of my ElderBeerMen council of elders, (among other things, I’m a retired beer truck driver), and more.
Those are the things that give me purpose; I would not have it any other way, well, except maybe the doctor appointments.
I don’t usually know what day it is, except Sunday. Guess what it doesn’t matter and I don’t care.
I just got back from eye doctor and he said I was a delight to have a conversation with. He said the men my age he sees are mostly grumpy and slouching in the chair.
I’m more convinced than ever that attitude and out look play a big part in getting old gracefully. As a priest recently told me, some people go through through life as if they were baptized in pickle juice.
I totally agree. And that last sentence elicits a very funny visual.
I struggle with defining the moment when I retired. I stopped working full time for an employer 8 years ago. But I jumped into some significant consulting roles for the next 3-4 years. Covid slowed that down, but I still did a few gigs during the pandemic. I didn’t do any work in 2024, but turned down a short opportunity that conflicted with our family trip to the UK in March. This project will last years, so there will be more opportunities later this year. In fact I just completed the process to renew the clearances I need to participate.
What I miss about my working days is the people, the intellectual stimulation, the challenge, and the sene of being part of a team striving to accomplish something important. I’m finishing my first year as treasurer of our HOA. Our community is on a decommissioned Army Fort, We are in the process of transitioning from the legacy Army electrical distribution system to a modern system attached to our local provider. I am the lead for the community working with the design teams for the new distribution systems. I’ve had to learn a lot, but the process feels like old times. I’m also working with others to reconfigure some of the traffic patterns to make the community safer.
These are stressful efforts but I enjoy the intellectual stimulation. It’s also gratifying to realize that the skills I obtained during my career are applicable in other parts of life – solving problems, working with people with different points of view, managing challenging and conflicting requirements.
The best part of retirement is the opportunity to spend time with our family, and be involved in our grandsons’ lives. We experienced caring for our parents during our working years – it was stressful but rewarding. We have been able to travel, especially some big trips the past few years, as well as some road trips to see family and friends. We have more trips planned.
Our transition was unplanned and best understood in retrospect. But we are doing well, navigating the changes and challenges that life throws at you. We have lots of blessings. And I’ll repeat something I’ve written before – getting involved with the HumbleDollar community has been an unexpected blessing and pleasure. Thanks Jonathan and everyone.
Are you talking about Ft Monmouth?
Always appreciate your perspective Rick.
Love your viewpoints Rick. You are a welcomed contributor to HD.
After working for so many years and having my life dictated by my job the past five years of retirement have been about not having any regular commitments. I like finally being able to do what I want when I want to do it.
A perfect example is in just the past week on Saturday I drove from NH to Connecticut for my sister in law’s memorial, traveled back to NH on Sunday. Then on Monday helped set up, and attend my mother in law’s memorial service. Then the next day was a trip to Boston with my wife and daughter for lunch and to drop her off at the airport to return home. Wednesday was a recharge day, then yesterday it was four hours edging my driveway in preparation for an overcoat of asphalt, then two hours cutting the lawn (my neighbor had to cut his lawn in the rain, nearly a daily event this month here, after work). Today another recharge day. Tomorrow who knows what it will bring.
The best part of summer is on the weekends looking at the upcoming weekday’s weather and picking the best day to head to the beach to avoid the crowds.
Agreed My one expectation in retirement was too have autonomy over my time. It’s not complete autonomy, but it’s pretty good.
That’s it. No regular commitments is a good way of putting it. That what i enjoy as well. The thing is i still wake up around 5 am as i did while working. Just can’t break that habit.
I have some specific things I know I’ll be doing (or still doing) once I retire in July. Like luvtoride, I’m on our condo community’s HOA board, have some specific church activities that I’ll keep doing, and spend a lot of time with our Peloton machines and the Pilates studio I recently joined. I also have a book contract that will occupy some time during my first year, and we have some trips planned.
But that won’t fill all my time. I expect to be really, really happy to have less responsibility and more freedom to do/not do what I like/don’t like. For my last few years, really since we went back to campus after COVID, my favorite days are weekends and breaks between quarters. I’m weary and ready to lay it all down. I expect to be very happy about this.
The part that’s fuzzy to me is how I keep from filling up my free time so that I’m not too busy. I know that’s a danger for me; I’m just wired that way.
I’m staying very busy since I moved to my retirement community, but I block Sundays as “introvert recharge day”. I believe another poster here, in a similar situation, also blocks Wednesdays. I do go out to exercise, but otherwise I’m home alone. Maybe, in your case, reserving a couple of afternoons a week would help.
Yep, here at my CCRC I help solve residents’ tech problems four afternoons a week. I keep the Ws to myself (Wednesdays and weekends), along with all mornings and evenings. And I’ve so far avoided joining any group that meets more than once a month. 🙂
Great suggestion!
Dick, I am so glad you asked this question. We are in the second year of retirement. So far it has not gone at all like I expected. I thought we would be able to travel and do fun things. It has not been that way. We are smack dab in the sandwich generation time: helping with our kids and young grandkids, elderly parents who are needy and live 4 hours away from us, and the last year of Spouse’s brother’s life and his recent death from ALS. We are still playing catch up at home. I can’t imagine either of us working through all of this. It has been HARD. Our finances are ok, we are settling into our retirment income. I am grateful for that. Just this morning we sat down with the calendar and planned a few weeks where we could either get away, visit our parents, or do a staycation. The summer is already busy with watching our grandchildren some days, the garden, house stuff and the upcoming move of our daughter’s family to a house on the next street over. So some good things to look forward to also. Retirement so far is nothing like the ads try to tell you on TV. LOL! Chris
I wish you the best for a future retirement. I’m sure things will settle down in time. We never experienced the sandwich issue as my parent were gone before we retired and they lived with my sister or visa versa.
Getting rid of a house and lots of stairs was a big relief for us. Not being able to travel any longer as we used to is a downer, but to be expected for 80+ year olds. As long as i can still drive a golf ball, I’m happy.
Dick, thank you for the encouragement, it is much appreciated. Chris
Interesting question you pose and I’m sure there will be many varied responses. I have been retired for almost 2 years from a long career in the insurance industry, and with one company for the final 34 years. I did do consulting for them on a part time basis for several months following my retirement, but that ended about a year ago. For me (and my wife) the transition has been successful and very busy. I’ve filled my free time with various activities including:
I’ve had no shortage of things to fill my former work time, including the hours commuting to and from NYC where we were required to come Back to the Office after Covid.
Quinn, I’m younger than you, but my wife and I keep our calendars on our iPhones under a shared calendar color so that we both know when we have time for individual pursuits. I haven’t even had time to play golf!
So far, so good and better than I expected!
I admire people who can be so involved. I can’t do that. I recently joined our HOA finance committee, but now find it’s not for. Perhaps 50 years of meetings and committees and managing budgets was enough.