r/retirement

Whoopsies - learnings from regrettable decisions in retirement

A good friend of mine has a retired sister who met someone on a trip, fell madly in love, got engaged, put her house on the market, and moved out of state to join her fiance in Colorado. A couple weeks later, she realized that Colorado was not for her, and that the two of them had a lot of baggage that would likely compromise a long-term relationship. And so she moved back. This wouldn't have been horrible, except that she's retired and this consumed a lot of emotional effort and money and damaged her optimism.

There are other tales of people moving into a 55+ community at age 59, finding themselves surrounded by people in their 70's and 80's, and deciding this is not what they wanted. Or moving to another state to follow a child and grandchildren, only to find that a new job made the young family move 2000 miles away again. Or selling their house, buying an RV with a plan to tour the country for a decade, deciding after nine months they didn't like the life or the endless stream of expenses, and selling the RV for a big loss. Or discovering that there were new major living expenses in retirement and that they'd retired prematurely.

The wisdom scars inflicted by the whip of the unexpected are worth sharing. What mistakes have you had to recover from in retirement? What we the recourses you had to take as a result? What advice would you give to help avoid a similar mistake?

reddit.com
u/Odd_Bodkin — 1 day ago

Any retirees who plan to be forever renters?

So much of the retirement advice I read or see on YT preaches the idea of paying off your home. The idea being that owning a paid-off home eliminates the largest non-discretionary expense in retirement.

However my spouse and I currently rent, and plan to continue renting in retirement (will be retiring within the next couple of years). We owned a home for many years before downsizing to an apartment, and we both enjoy the flexibility, location, and lack of maintenance and surprise costs that comes with renting.

I know there are pros to owning a home outright but I think some of the cons, especially as I get older, are often glossed over. Any other forever renters out there, and if so what have been the pros/cons in your experience so far?

reddit.com
▲ 168 r/retirement+1 crossposts

My cousin, he's RETIRED (and doesn't know what day it is)

I love being introduced like that. My cousin invites me out to a lot of outings. His wife and twin girls, super athletes...so proud of them.

"You remember, my cousin. He's retired now. Do you even know what today is, cuz?"

No. No, I don't know and don't care. I volunteer and other wise enjoy life with my wife. Just waiting for my grandkids...when God blesses. Going on a "glamping" trip in a few weeks and then I wait for CFB and follow my other cousin that coaches in MAC.

Love retirement.

reddit.com
u/MidAmericaMom — 2 days ago

Where do we live after retirement?

**Cross posted in another community**

My husband and I are in our 60’s. Both pretty healthy and looking forwards to finally getting to do stuff. We’ve been married 15 years.

We’ve been living in a little rental house for 15 years and really love the area and I’ve made such a love home for us. We’ve been really happy here.

MIL owns her home in the same area and also a condo in another state which is beautiful. She is quite old and as awful as it is we obviously haven’t moved bc we need to take care of her. We’ll be here until we are free to move on with our lives.

She has a grandson and her will has been split between my husband and his son. Both houses will be left to them but owned jointly. It makes things a bit confusing (we have an appointment to see a lawyer to try and tidy up our wills).

The plan was always to move to the condo but the more I think about it the more I don’t want to live in it. It’s sort of in the middle of no place and in a gated community on a very busy road.

My other reason for not wanting to live there is it’s MIL’s and I’d always feel I was living in her home.

I want to sell it and buy something cheaper and have some cash leftover. Obviously we’ll have to address that it is jointly owned by grandson.

Sorry this is so long. What would you do?

reddit.com
u/Honest-Register-5151 — 4 days ago
▲ 4.4k r/retirement+1 crossposts

"Can I spend the night?" What a seven-year-old taught me about retirement

I'm hanging out with my four-year-old grandson, he's on my lap talking away, but my mind was elsewhere. I was thinking about the future. I wasn't focused on him at all, but rather an important conversation I needed to have with another person the next day; an email I had to write; a phone call.

He asked me, "Grandpa, can I spend the night?"

"Sorry, little buddy. Cannot do it. I have plans tomorrow."

This was three years ago.

Three years into retirement this week. I decided to take Social Security early because peace of mind has a value an online calculator cannot price. I was afraid, like many pre-retirees, that I wouldn't have enough. Three years in, spending has smoothed out and it's less than I thought. The life I was saving for turned out to be quieter than the one I had planned. We travel, we stay busy, but it's a funny thing about travel. No matter where I am, I can't wait to get back home.

Cut to this year. My grandson is visiting; we're hanging out together downstairs in the man cave. He falls asleep next to me. At that moment, a light switch turned on. After 45 years of being somewhere else, I'm finally here; I'm being present with my grandson. I don't have anywhere else to go. I'm not thinking about work tomorrow, the stressful presentation I have to give; no emails and phone calls. I'm with my grandson and that's all that matters in the world.

He wakes up. "Grandpa, can I spend the night?"

"Absolutely, little buddy! I will even make you breakfast and take you to school."

And so, the lesson I've learned in retirement so far? Going from a fragmented non-present corporate man to a man having realized what is important in life. That is, having the time to be present. For myself. For my family. For my grandson.

The next morning at breakfast, we're eating our cereal together. I watch him eat. Milk spilling over his chin. I realize: this is what I worked for my entire life; I just didn't know it.

reddit.com
u/MidAmericaMom — 5 days ago

American road trip: Three generations, two cars, 2,000 miles on Route 66

It was a once-in-a-lifetime opportunity to drive Route 66 from Chicago to Santa Monica, California, with my kids and my parents as part of USA TODAY's American Journeys series.

I was nervous about taking young kids on such a long trip, but everyone agreed that an article about the great American family road trip taken on the Mother Road's 100th anniversary had to include my family.

Then my father lost both of his siblings in eight months. The chance to deepen my relationship with my parents and theirs with their grandsons as we drove two-thirds of the country held new meaning.

Read about our family trip in USA TODAY:

https://www.usatoday.com/story/news/usa250/2026/05/17/route-66-anniversary-mother-road-family/89605580007/

u/Sarahdwire — 3 days ago

Stress levels around retirement

I know this topic has been asked about relentlessly but I was hoping for some more specific guidance.

I’m semi retired now, self employed and pulling the plug entirely by the end of the summer.

Stress levels the last couple of weeks have gone crazy. I’m not naturally or normally high strung but I’m waking up in the middle of the night, panic attacks beginning, it’s ludicrous.

As some background, money is not a concern. I’m 25% over my retirement money nest egg goal and living overseas with a 25% lower cost of living.

I also don’t have time for work as my hobbies can easily be ramped up and will be.

I think it’s the lack of control (I’m guessing though). Either it’s Lack of control of my finances or that I’m now a bystander to life.

Anybody else have similar experiences?

reddit.com
u/Isca64 — 4 days ago
▲ 75 r/retirement+1 crossposts

How am I doing on my way to retirement

In spite of two divorces, two bankruptcies, and one short sale, I have been able to somehow amass about $500,000. I am going to retire at the end of this year at 66. I already started taking SS, and have about $350,000 in a combination of taxable and cash. The rest is divided between my 401k and my IRA. I plan on using the cash first, about $60,000, and then withdraw from the taxable until I have to start taking RMDs. I plan on converting my 401k to my IRA and then converting to a Roth. My living expenses are modest( about $45,000 per year) and I am debt free.

Any advise, questions, comments, and concerns are welcome.

reddit.com
u/Cheap_paint_77 — 6 days ago

How was your retirement as you approached the 9 year milestone?

I (71m) ate lunch with my best friend, a retired veterinarian (71m). After speeding through the pleasantries, we crashed into the topic of what’s new? He replied, “I do pilates, jog on a treadmill 3x week, and yet, I feel occasional brain fog, need naps, and cannot workout everyday like I did 2 or 3 years ago."

I agreed. My fitness life - weights, running, and doubles tennis - now requires rest day(s) after a tough tennis match or an afternoon nap. Despite having a good results from my recent annual physical, I think this phenomenon of old age is the culprit.

I thought that I could combat this creeping fatique by giving up alcohol, going to bed at 9 p.m. and getting at least 8 hours of sleep, and eating clean (no alcohol, too), but I am not willing to give up my vices to win more tennis matches.

I find myself in the “adjustment phase,” where I accept double faulting more on the tennis court, waking up tired, and not feeling energetic most of the time when I was 65 years old. Would you share your stories of how you reconciled your decline?

reddit.com
u/kungfutrucker — 6 days ago

Conflicted about retiring soon at 75!

Female 74 years. Currently in terrific 12 year Exec Admin job that I love with no uncomfortable pressures or downsides. Married but only legally- no real partnership or companionship, but we do share finances. He has mental health issues and there is no plan for us to do things together in retirement. I'm planning to retire in October just prior to my 75th birthday, only because my body is starting to need more attention and care. I will miss the companionship of my many colleagues (large company) and the feelings of accomplishment and comraderie I get at work. As the time nears, I'm feeling anxious but (almost?) ready. I plan to stay in touch with a handful of friendly colleagues and hoping that helps with the transition. But they will still be working and I will not be. I need to remind myself that I really need to retire but part of me is resisting the change. This is not a change I've been *dreaming about*. My future is unclear. Ugh! I'm winging it. Money is not an issue as long as we are sharing.

reddit.com
u/ShoreGirl9999 — 7 days ago

How can I live half of the year in another place?

Should I just rent furnished places in both location for six months each? I don’t want to buy, leaving a property for six months at a time. I want to be in climate that allows me to be outside enjoying hiking, biking, etc. What would you do? Is there another option I should consider?

Background: I 62F sold my paid off house last year and I’m renting now (rent is about the same as property taxes were with house), and I invested that money, basically living on the interest, along with about $10k in part-time consulting work for my former employer. I’m not taking SS yet, and I have plenty of savings, investments, and retirement funds to support my lifestyle now and in the future.

reddit.com
u/moschocolate1 — 7 days ago

Sending out a goodbye email when it’s time to go…

What are your thoughts on these?

I’ve seen farewell emails from people I’ve worked with, some send them to one or two people, and bcc everyone else. Some send out an email, but everybody is in either in the To: section or they’re cc’d. What that happens, we’ll see the responses from many, many people.

I have mixed feelings about both of these, both receiving them, and whether I should send one out after 30 years.

Your thoughts?

reddit.com
u/nothingbutmistakes — 8 days ago

What was the best gift you received from a coworker?

Our Executive Director is set to retire next week, and I’m eager to find a thoughtful yet practical gift to convey my appreciation for her leadership and support. I’m particularly interested in suggestions that were well-received by others upon their retirement. Ideally, the gift should be compact and easy to ship, as she has already moved to another state. If you have any personal experiences or recommendations, I would love to hear them!

reddit.com
u/snarlywino — 7 days ago

Wife joining me in retirement in a month

I've been retired for 2 years as of June 1. My wife has decided to pull the trigger as of the end of June, with her last day (using vacation for the rest) on June 12.

We've been talking about the 'next phase' and we're both looking forward to it. The money 'should' work, there are adjustments we'll need to figure out, but we've made adjustments before.

What struck me was this basic thought: we've been married 46 years, and it's been over 40 years since we've been together--except for 1 or 2 week vacations--all day, every day. I worked, she worked, we had kids (who have turned out great). Now, suddenly, we will be sharing the space in ways we haven't for many years.

Meal prep, personal space vs shared space, chores, all of it will need to be figured out.

Am I worrying too much?

reddit.com
u/MiserableCancel8749 — 8 days ago

Search strategies for mid-term winter stays in Florida?

Hello everyone,
I am a recent retiree looking to tap into the wealth of experience in this subreddit. My wife and I are planning a trip down to Florida for a two-month stay (possibly longer) in the Port St. Lucie area, and we are looking for some guidance on how to find affordable rental options.
We have used Airbnb in the past, but between the standard rates and the mounting fees, it is becoming incredibly expensive for a mid-term stay.
We’d love to know what alternative platforms, local resources, or strategies you all have used to secure reasonable monthly or multi-month rentals.
Are there specific regional websites or snowbird-focused platforms you trust?

Is it worth trying to connect with local property management companies directly in the area?

For those who do this annually, how far in advance do you typically need to lock a place in to get a fair rate?

There is so much practical wisdom in this community, and we would truly appreciate any advice, tips, or platform recommendations you can share to help us navigate this next chapter.
Thank you so much in advance

reddit.com
u/Paula_56 — 6 days ago

Financial reviews in retirement

Switching from saving to withdrawing has been harder than we expected. We finally hit our number and retired, but now I’m unsure what kind of monthly or yearly reviews I should be doing. We’re already handling things like Roth conversions and keeping a healthy amount of cash or cash‑equivalents, but I’m used to the structure of quarterly business reviews to make sure everything stayed on track.

What should a solid retirement portfolio review actually look like? I’m hoping for something mostly automated and not too time‑consuming.

reddit.com
u/Pleasant_Ad_9259 — 8 days ago

Using up PTO days vs getting them paid out.

The place I work allows you to accumulate your vacation time up to what you earn for two years. In other words, if you get 24 days a year, you can accumulate 50. Many soon-to-be retirees here will use them up in their last couple of months.

The two biggest benefits are, you still accumulate even more PTO during that time, plus you’re not getting hit with the taxes from a big lump sum.

Any sick time you accumulate, you can only get paid out for half of that.

In my opinion, the only negative to taking all the time off is, the place I work cannot even start the replacement process until after you’ve actually reached your official last day. But that’s on them.

Anyone have something similar in their place?

reddit.com
u/nothingbutmistakes — 9 days ago

I pulled the trigger, July 3rd will be my last day.

I just informed my manager that I'll be retiring July 3rd. Pretty exciting. The plan has been afoot for a while now, but I needed to let them know. I've tested the numbers, I've created my fund for the rest of the year. I have a plan for health insurance, and a 30 year budget that has weathered many ups and downs and continues to work.

Now the interesting question is, will they just fire me? In my business that is pretty common. I'm prepared for that possibility. I did wait until I was on a project that would take me through the end, and one that required a government clearance, making it much harder for them to just fire me, but you just can't trust any employer at this point so I'd put the odds at 50/50 that they cut me loose. In 50 years of working I've never been fired from a job, it would be quite ironic to be fired from the LAST job, just because I quit.

but who is counting?

reddit.com
u/TheFreeMan64 — 10 days ago

Summer contract work could improve my finances substantially

I don't really want to go back to work yet. But there is a contractual position - if I take it and succeed for 3 to 6 months, we can boost our retirement finances substantially. However, I have anxiety and stress disorders, I don't know if I want to get back into the ring so to speak. I am 63 1/2 now, this temp job could allow us to leave our Social Security and retirement accounts untouched until we are 65.

reddit.com
u/Mediocre_Insect_1008 — 8 days ago

Pension payments or lump sum.....

I have enough money in my retirement accounts and 401ks I think for the rest of my life. My question is this should I take the lump sum for the pension or monthly payments. There is no Cola. My inclination is to take the lump sum and invest it whether it's stocks or bonds or whatever I think I could make at least 4% in a tax-free account. Probably could make six which would be the same as the monthly payment and not have to pay taxes on. What are your thoughts thank you

reddit.com
u/Busy_Conversation537 — 11 days ago