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I’m 58 and my wife is 56. We’ve been planning our retirement with care and intention for years—no debt, solid retirement savings, a well-diversified portfolio, and a liability-matching plan (LMP) that covers us until Medicare kicks in. We’ve talked through our priorities, run the numbers, and built our plan together. The core approach to our plan was heavily influenced by Bill Bernstein and Wade Pfau’s writing and we are content with a good funded ratio.
One thing we agreed on early: when one of us loses or leaves work, we both retire.
Now, the time may be here. There’s a strong possibility I’ll lose my job in the next month or two, and while our Excel models say we’re ready, I’m realizing the emotional side of this transition is much harder than I expected. The idea of not working, shifting from saver to spender, and stepping into a whole new identity—it all feels very real now, and a little overwhelming.
We’re committed to retiring together, as we planned. But I’d love to hear from others who’ve walked this road:
I know we’ve done the work on the numbers. Now I’d love help making peace with the next step. Your insights would mean a lot.
I was booted out when the my boss retired and the CEO told me I had too many rough edges to take his job whatever that means. I did get a nice severance package. So, I decided to take a year off. Made absolutely no commitments to do or go anywhere I didn’t want to do or go. The year flew by. I did lots of projects around the house at my slow pace. The second year I started looking for something productive to do and started sub teaching (babysitting) at a private school. Loved it. Found an old guy coffee group. Read lots of books and went on several big trips out west.
Now I just found out I have aggressive prostate cancer. Bummer. Glad I didn’t plan too far ahead. I have a great wife who still works but may have to take time off to nurse me.
The moral of the story is don’t get to deed in the weeds planning every detail of retirement, cause life might throw you a curve ball. Good luck! and Enjoy the time you have!
Sorry to hear about your prostate cancer. I was diagnosed last year and my wife suggested a forum for information and support. You’re probably already aware of this avenue for support, but since I’ve found it helpful I decided to mention it just in case it hadn’t occurred to you yet. While I’m sure there’s several good ones out there, here’s one that’s pretty good to start with: Prostate Cancer: Discussions | Mayo Clinic Connect Note: you don’t have to be a Mayo patient to use their (free) blog, and in fact most of the guys in the prostate cancer section aren’t Mayo patients. Best wishes.
Wishing you well with your treatment.
Thank you for your advice. I am really sorry to hear about your cancer and I wish you the best as you tackle this malady.
Been there done that. I chose to ease into retirement. I just let my work time lesson and lesson over a 20 year period, and did not retire until 78. For you, if you are losing your job, get another one, even if it is only part time. If you can take the lower Social Security at 65, and the other person wait until maximum Social Security at 70. I would not retire at 58, to me that is just way too early. Invest in the low cost indexes, like S&P 500. I am confident you can make it work for your family and personality.
Regardless of other people’s retirement comments, each person situation is different and one must learn to assess their condition and plan accordingly. I retired at 74 (not by choice) in 2016 and my wife (now deceased) was totally disabled. We lived comfortably and quietly, traveled minimally because of her medical condition, but was comforting to have 51 years together. Our daughters say to me that my life revolved around my wife, although I never thought of it that way. But whatever it was, our life in retirement was what we made it. And I have no regrets on how we cared for each other — an important aspect of life.
Rembemer the old Nike slogan – JUST DO IT. You have a plan. you have assembled the resources. Everything is in place, so…
Taking a look only at the downside, while you could return to work and earn more money, you can’t earn more time. Only two years passed between when I retired and when my wife died. Those were the best of the 50 years we were together.
Time is rarely mentioned in retirement planning, and I believe that is wrong. JUST DO IT.
You want practical steps? When I took the leap from full time work to running my own business at age 58, I set up The Leap Fund at my brokerage. It’s cash – a lot of it from other accounts, from dividends, from my first new contracts – to see me through to stability. Think of it as Christine Benz’s Retirement Bucket # 1, even as I continue into self-employment. Peace of mind to cover bills or travel costs if I have a quiet month with the new gig.
Mark, I was struck by the fact that you both agreed to retire together. What is the motivation behind that decision? I will posit this. If you think that you both have to start this thing at the same time to maximize the experience, I would say it’s not necessarily so. You both need to find your groove independently. It’s less about vacations together and more about how you spend each day. She could reduce her hours, for instance. Shifting to deaccumulation is jarring at first. Some income can make the transition easier.
Wow, is this timely. What makes it difficult for me is that I feel that I am being pushed out and the lack of respect is almost as difficult as the financial issue. I had planned on working until age 70 but my body and soul is begging to at least start transitioning from full-time to part-time. How did I get so tired at 68? Like Quan, the changes in caring for patients is soul-crushing. I spend more time documenting than seeing patients. I still fear that I will end up a homeless bag lady as irrational as that may seem. But I wanted to pay off my mortgage before retirment and it looks like that won’t happen. How have others dealt with the ageism in the workplace?
So who are you? A rude question, perhaps! And don’t answer me… answer yourself. For me, the loss of my professional identity before I was totally prepared to lose it was the hardest part, and I scrambled to assemble both interior and exterior personae. I’d advise doing that hard work first, in the months before you have to. Who are you in the work world? Who are you when you leave the office door? Is the non-work part as vivid and important to you as the work part? What would you like people to think of when they hear your name or see your face? Do that work well, and the rest is easy and fun!!
*If you CAN swing it financially, my knees (and other parts) are SCREAMING at you to do it at early as you can. The sheer bulk of the medications that keep me alive take up 1/3 of my full-time traveling suitcases (I’m 72 and didn’t retire until I was 67)
Get a set it and (largely) forget it financial plan you can manage with a sense of peace.
*AND the absolute best retirement advice I listened to? Do absolutely NOTHING for six months. No consulting gigs, no volunteer work. Take the red ball off your nose and put it in a corner. Let it deflate. Figure out the things YOU want to say YES to. I got a cottage by the water, took long walks WITHOUT my phone, made lists and wrote poetry, for goodness’ sakes. And we came up with slow travel for as long as we got the knees and minds to go it. But that’s us. You be YOU.
I read the book that concluded that happiness comes when we learn from the experience of others. READ about others have retired—successfully and not. Don’t make those mistakes. Don’t be one of those “touch the stove” retirement toddlers!
Yes. I’ve seen many in my family and friends just work throughout their lives and then descend into endless trips to medical care providers and hospitals. Thank you for that reminder.
Oh, a silver lining? Plenty of time for much more regular and inventive sex. Meds for his prostate cancer have slowed us down now but they HAVE kept him alive for 13 years of Stage 4 now so I can’t complain about the switch to heavy cuddling and ocassional voyeurism). TMI? The other great thing about retirement and old age? Perfecting the art of not caring about what other people think. I’m still mastering it.
Thanks for the smile! I hope to read more from you.
I love your comments. You sound awesome!
My husband and I have gone the opposite direction in our thinking. We always thought we’d retire at the same time or that if anyone retired first, it would be him.
But a funny thing happened. Last year it became clear to me that I was ready to be done with my job. My husband and I, who are both turning 65 this year, had been talking about 2025 or 2026 as an exit date. With a little over a year to go, I told him: “It needs to be 2025 for me. I can do one more year, but then I’m done.”
His reaction was “But…I’m not ready to be done.” He first tried to convince me to wait until 2026, but I was pretty adamant. It was a breakthrough for both of us when we realized that we didn’t, in fact, have to retire at the same moment. We could each do what was best of us.
It helps that because I’m a professor, I’ve had summers off and sabbaticals and a flexible schedule, so we can travel, go to concerts and sporting events, and otherwise spend time together even though we were both still working. We agreed years ago not to wait until retirement to start the fun/bucket list.
I think it will be really interesting to see how the next year or so goes—will he get envious seeing my free time and relative lack of stress? At this point, he’s talking about going until 70 and then retiring and filing for Social Security. I think we’ll see.
My husband retired due to a series of lay-off when he was 62, a full 12 years before I did. As my second marriage was to a happy person, he was a role model for retirement. As I struggled with my job and health (in my last years of working before I quit, largely due to regaining some control and self-respect in my life), he quietly waited, “Anytime you’re ready, I am,” he would smile as he patiently listened to the regular indignities and impossible situations I managed. My god, I even scheduled radiation for my breast cancer at 7 am a 1 hour’s drive away from my work so I could still put in a full day. In retrospect I was certifiable.
Yesterday, after I posted this, my husband snuck away from his desk for a Friday afternoon round of golf with a neighbor. Came home frustrated and annoyed because so many things came up at work that he had to go right back to his desk to deal with emails and calls for another hour or two before dinner. There were a couple of pointed “I have a job—you don’t” comments. (I said that I do still have a job—I haven’t turned in my spring quarter grades and technically don’t go off the payroll until the end of the month!)
I just feel like it might not be long before this starts to get on his nerves. I’m fine either way. I can keep myself occupied, and as I said, we get plenty of time together (he works 100% from home, too).
Maybe soon your husband will realize a bad day at the golf course may be better than a good day at work. 🙂
I retired in 2018 around the same time as Fritz Gilbert at the Retirement Manifesto. He has a lot of great stuff on the questions you are asking-and a lot more. The Retirement Manifesto Blog What I think helped us my wife and I being on the same page and having a high level plan. We took a very nice trip after I retired. I encountered a big surprise-I found I missed the part of my job I enjoyed so I have been doing that part time. Good luck.
A big thing is what will you do after breakfast every day. That is a serious question. Many people do not think through how they will spend their time in retirement. Volunteering, part time work, hobbies and socializing are important things for retirees. Hopefully, you have thought about that aspect of retirement and have a plan.
This may sound silly to some, but many of us are not wired to watch TV and surf the internet all day. We want to do things, and most of all we want our life to still have a purpose.
Best wishes in your retirement.
If you volunteered or had a hobby before you retired you may enjoy more time for those activities after retirement, but just because a person retires does not mean suddenly they will enjoy them.
We may have more free time, but we are the same person. I think it’s a mistake to try and plan daily life in retirement. That is stressful and may lead to disappointment. In addition, how you approach each day changes over time.
Another major factor can be family. Our retirement has been driven in large part by family events and activities, but others may not experience that.
I think one big issue is finding meaning in life after retirement if our job contributed to that. And doing things that we find challenging that we also enjoy as that adds to our feelings of accomplishment and self worth. The problem again is if our job was part of that finding other things that can fulfill that aspect of our lives. If our work friends were a large part of our life due to interactions at work, finding others we interact with frequently to fulfill that need as work friends start to vanish also matters. These things can take some thought and planning.
No doubt for many people you are right, but I never experienced it myself. I had a job I very much enjoyed, that consumed 60 plus hours a week. But after nearly 50 years, I went on phased retirement for 18 months cutting back hours and then walked away.
I’ve never been bored unless I want to be. I started a blog just before I retired and still have one. But that’s about it. Gradually by chance acquired new friends, traveled quite a bit, spend time with grandchildren and most of the year play golf twice a week. Go to Florida part of the winter.
Life just happens with no need for much planning. Now, after being retired 15 years I look forward to a day with no place to go and nothing to do.
I agree with you to a point, Richard, certainly about being the same person and having flexibility. In retirement, I keep a calendar and write to-do lists, both of which help me to maintain my sense of purpose. I’m still working on accepting unanticipated changes to those though. As a retiree, the expectation is that one is ready for unplanned activities, I think, more at the drop of the hat.
Good questions. I was going to retire in 2020, but COVID hit and my company required us to work from home. It was such a joy to work from home, I worked another 3 years. We had paid off our mortgage prior to 2020, so I was able to save a significant amount in addition to my 401(k) and Roth IRA. Here’s our pre-retirement checklist:
https://humbledollar.com/forum/pre-retirement-list/
Looking back, I think those extra three years helped prepare me for retirement. To my surprise, I didn’t miss the work at all, though I did miss several of my co-workers. The first few months were busy as I needed to apply for Medicare Part B, purchase a Medicare supplement and dental insurance, and apply for Social Security. These are important to get right so it pays to talk to one or more experts. In addition, I went to doctor, dental, and vision appointments under my company medical plan before I left.
My sister-in-law used to say, “I don’t know how I had time to work”. It’s so true – I’m always busy and have more time to help the kids/grandkids. I was pleasantly surprised how much time my husband and I spend doing things together. He had been retired for several years and I expected he would continue with his routine. 🙂 We bike or hike almost every day and go out with friends twice a week. We also get together with 10 couples (whoever can make it) once a month.
I would have liked to have done larger Roth conversions, but that would have pushed us into the next tax bracket. Spent more time than I needed on our withdrawal plan, but in the end I learned a lot.
Thank you for the link to the checklist!
Congrats on being close to retirement. I’m in a very similar situation — I’m 58 and my wife is 56. We stopped full-time work 4 months ago. It has been amazing!
Few practical steps that helped me:
Finally, I’ve worked since 12 years old. Did the full corporate ladder. Traveled 2+ million miles. Did too many 6 a.m. and 10 p.m. meetings. I was considered a guru in my area and well compensated. Yet … It is great being free from the meetings, emails, project due dates. It has been 5x better than expected. You’ll love it!
As a good friend told me last year “Come to the other side! It is amazing!” I now know what he’s talking about.
Best of luck!
Thank you for sharing your thoughts and the note about Transitions! I’ll definitely add it to my read list!
You are in a wonderful place. I agree that the emotional side of this transition can be much harder than expected. The shift to spender was difficult for me. There are ways to manage that.
I decided to re-evaluate and viewed retirement as an opportunity. Why had my spouse and I been saving so diligently? We decided to travel, at times with family. I resumed volunteering. I decided I’d miss the structure of work and so after travelling for a bit, I then resumed working part time. I’d designed a “phased”, flexible retirement. I didn’t miss my work because I knew I could go back to it and did after a short sabbatical. That knowledge made the transition easier.
For eight years I worked part-time and we travelled, etc. using the time that was freed-up. I eventually said my good-bye’s to customers and disconnected the business cell phone to stop the work. I did continue a few hours of work intermittently for another six years before ceasing entirely.
Financially I could have stopped earlier than I did. The market was unusually robust, so I took advantage of that. I used the opportunity to continue contributions to my Roth-IRA and the income paid for all of the travel. Over that 14 year period my net worth increased substantially, even with reduced income, travel expense, purchasing a 3rd RV, etc. We’ll also be able to gift more than we had planned.
The financial aspect of my retirement is different than most so I won’t go into that, but emotionally I was no different. I was going from a high place in a company where I worked nearly 50 years to – well, just another retiree. I didn’t think about it.
I decided to retire in March 2008 and began phased retirement in July that year and fully retired in January 2010.
Two weeks after I “retired” in July we took off on a three week trip to Russia and kept traveling twice a year or so until three years ago.
To my surprise, I didn’t miss work, each day in retirement just fills itself. I began playing golf more, we did more with family and still do. Now after fifteen years I welcome a day with no plans.
I very much enjoyed my job and was in a unique position in the corporation, but it was time. I never regretted my decision and within a year or so even the thought of going to work was unwelcome.
The difference with me was I was nearly 67 when I finally retired.
You have planned well, you are prepared, you know what’s coming. Don’t let overthinking life in retirement spoil those days. It will all come together if you let it.
Plan a grand adventure for shortly after you retire. Start your new life with a bang and don’t look back.
I’ll follow this with interest as while not in an identical position very much deep into the personal territory of Just do it vs Prevarication/What if.
I think what I’ve learnt from the many sources and resources I’ve accessed is that there is no perfect way of being entirely at ease with such a major life step. We are emotional beings after all and “grief”/regret is part of any major change.
But no one who has taken the plunge seems to say in hindsight that they regretted it. Survivor bias has to be taken into account here, of course. Those that loudly proclaim “Retired” and then slink back to employment within a year tend not to broadcast if they got the numbers wrong and will more likely position it under some sort of fulfilment banner.
But if your numbers aren’t wrong, or at least if they are they won’t be shown up until 10+ years when X+1 unforseeable things have happened, then I suspect you should back yourself.
In a way you have the perfect set up- you’ve predefined the condition and if you are made redundant then the trigger is someone else’s so you don’t have to agonise about your decision. I suspect as the process goes you should ask yourself often – how will I feel if they don’t let me go? A frequent check on that will tell you whether you’re already emotionally checked out and therefore on to the next phase already.
The TLDR version. I suspect you’ll never be entirely comfortable until you leap. Then within a short time that water that looked cold will be a wonderful ambient temperature.
I don’t fully fit your model, as I’m 63 and my wife almost 60 and I’ve backed-off to a little more than half-time, but I’ll offer a couple of thoughts.
First, congratulations! You’re ahead of the game at an early age. I suspect it’s taken a lot of discipline to get there. I’d also suggest you don’t let that discipline work against you by getting locked into a decision early on.. I think Rick Conner’s advice to stay flexible is wise.
Dan Smith’s suggestion to find structure is also valuable. I work three days per week, with an earlier quitting time. So, on my off days and my extra hours in the afternoon, I schedule my time to stay useful. That useful time may be having fun with my wife, but we’re trying to reclaim some balance.
The Smith structure keeps us sane, while the Conner flexibility should help us more nimbly navigate the opportunities that arise. I wish you the best as you move into unknown territory.
You are in an enviable position in terms of number. Congratulations. With regards to making peace with the future, I would recommend treating yourself to a journey inwards to find your true identity or life meanings. We humans are meaning seeking creatures afterall.
I too was well prepared financially to retire early and was unwilling to give up my identity as a physician responsible for people’s health needs for over 20 years. My wholehearted effort to hang on was crushed by the COVID pandemics, the demand by the US healthcare system that consumed my attention far more than patient’s needs – I quit at 63 yo, out of frustration and exhaustion. My physical endurance was reduced from brisk walking 2 miles a day to dragging my feet less than a hundred yards with severe shortness of breath, yet my family doctor and cardiologist could not find any evidence of infection, or coronary artery disease. The Japanese knew well similar cases, named it Takotsubo syndrome, or broken-heart syndrome, a form of stress-induced cardiomyopathy. It took 2 years for me to recover my physical and mental health, while I devoted to a spiritual journey, shaking off my clinging to a socially approved identity, a self-centered world view that is in constant conflict with true well-being.
There is no point of looking back or second guess myself. When life was good or easy, it was simply not possible to choose a different life, making different choices until life forced us to confront our suffering.
Financial security definitely eased the suffering, but it did not bring life’s satisfaction. Personal relationships do and they are priceless. I have become far happier a person being present and attentive to my roles as a retiree, a son, a husband, a father, a brother, an friend available to many. It feels great to be a nobody, free to love everything to my heart’s content.
Thank you for sharing your journey into retirement. While it was initially stressful, you are now at a place where you realized the true value of personal relationships and the happiness one derives from them,
I am looking to reduce my role in a couple years as I hit Coast FI and the emotions are wild. I can only imagine the emotions are even more so jumping straight into retirement. Congrats to you both for having the numbers ready and the financial means to do so.
I do agree with the structure comment.
Also, if travel is part of your retirement, time to plan that trip so when you jump both feet in you all will be ready to have an epic time!
Thank you for your encouraging comments. Travel seems divine as a way to manage the emotional roller coaster!
Mark, congratulations on putting yourselves in a sound financial position. I faced the end of my job in 2017, at 59 1/2. I have 2 thoughts. First, if your job does end, don’t panic and jump into something too soon. Think about what you want to do. I took a few months to consider my next move, which turned out to be consulting. Second, don’t set limits on yourself, or let anyone else set limits. You and your wife are very young and have a lot of time and a lot to offer. You never know what opportunities will be presented. Having the done the hard work of preparing for retirement, you have the opportunity to take your time and decide what’s next.
I will say that the loss of a paycheck was a bit of a psychological blow for me, even though I started my pension. Moving into a consulting role was good for me, financially and mentally.
Take your time, be open to life, and make decisions that are right for you and your wife.
Good points. It is tempting to go back to what is familiar, but keeping an open mind and being deliberate is the best approach.
Mark,
It’s fantastic that you guys are of one mind about retiring at the same time, and impressive that you are financially prepared at such a young age.
My insight, in a word; structure.
We have an idea of things we’d like to get done every day, but we don’t knock ourselves out getting to them. Coffee and morning news, a chore or two, lunch with old friends, a good book, the gym, maybe even a nap. Eventually and unfortunately doctors appointments will creep into your structure.
I enjoy reconnecting with old friends, and I lunch with or talk to them often. We are not avid travelers like some, but if that’s your thing, and it fits in your budget, by all means go for it.
Best wishes for you guys. Dan
Thank you! Structure with the ability to pivot without remorse is definitely an idyllic retirement!
I, personally am a bit wary of those that seem to smother themselves in too much structure from day 1. Feels to me that they risk engineering an environment with just as much “time stress” as work.
Better to use structure to hold yourself accountable to not wasting or killing time. Noodling around a hobby or diving into a research hole is fine. Mindless scrolling of Youtube/Tiktok etc because of general boredom not so good.