Lets hear it from those who could retire comfortably but choose to work

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We have many threads on retiring and LOTS of people state how incredibly wonderful it is to not work anymore but I'm almost 65 and still work and am wondering about the others like me. I've owned my construction business for about 25 years and am having my best year ever and am planning on taking social security at 66 so I can continue to work and make money and not have that reduce my SS payments. I'm in good health and I lift weights and play about 6-8 hours of pickleball every week and go on lots of trips but sometimes things do get a little frustrating at work and I think about retiring. I have no debt except a little bit on a couple of rent houses, and I could live comfortably on my savings and SS but I couldn't blow money the way I do now. Plus things keep getting more expensive with no end in sight and assisted living can cost $6-7K/month which could go through the cash pretty quickly and I don't want run out and be a burden to my kids. I usually don't work as hard as I use to and can take off about any time I want, but sometimes things get really busy and I have to really crank out the production. I like feeling productive but I'm getting a little more tired than I use to and wondering about the future?
 
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I don't work at my previous career, which has become pretty much impossible due to change in the market, but I do work parts of the year. I've done all sorts of different jobs but when they start to seem like work I skedaddle. If I make my ammo money I'm good.

A word of advice: If you're thinking of selling your business then you need to sell when business is so good you don't want to. That's exactly the time a buyer will pay the most. They are easy to sell when things are hopping, and near impossible in a downturn. You can stay on at a salary for a while to help with the transition. That could go for two or three years. Think about it.
 
You’ve asked for thoughts and opinions, so I’ll share my current outlook on the matter. If need is not the reason, you really have to do what you personally feel is right for you. You will know and trust yourself and gut.

Personally, I have known too many people close to me that saved for retirement then retired and passed away within a year. Just life. Not from lack of working or having something to do, it was just their time and some of these never had a chance to enjoy the fruits of their labor. OTOH, I know people who didn’t take the future seriously and are now working at almost 80 part time because they can’t afford not to. With all things their must be a balance.
 
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I retired from my own business at 55, (15 years ago) and have been going non stop when it comes to helping friends, neighbors, relatives out with repairs and maintenance work on their homes, cars, motorcycles, etc.

I have made ZERO $$ becauseI have not charged them a penny! Some of my friends say I am foolish since I do what they tell me is superior work and people would be glad to pay me. That is probably true and in a monetary sense I guess I am foolish. Even my own wife tells me I should be charging at least a reasonable fee.

That said, we do get taken to many nice dinners, lunches, get thank you bottles of my favorite libation, etc. So am I being a fool?? Maybe, maybe not... who knows. Bottom line is that I truly enjoy it, keeps me very busy and I feel like my natural abilities are being put to use and are greatly appreciated. Could I make 6 figures a year doing this - absolutely. Am I a fool??
 
I retired from LE @ 51 but went to work at the Federal Gov’t for another ten years b/c I wasn’t ready for full retirement. Now, in my late 70s, I enjoy not having a schedule beyond what my wife sets for me.
 
Retired at 70 and don't regret it. I liked what I was doing and had the energy and commitment to do it. I decided that 70mwould be a good age to hang it up. I'm still relative healthy and enjoy my time in retirement. The sacrifices we made over the years means we can live a pretty decent life now. My wife and I planned a long time ago for this day and now life is good. Btw, we will be celebrating 52 years this summer.
 
When I turned 62 (3 yrs ago) I told all my.."less desireable" customers I was retiring and they would need to find other avenues of vehicle repair.

I enjoy working on machines but don't see eye to eye with many of their owners, especially living where I do.
Putting the NRA door knocker on the front door took care of many of them 15 years ago..but I thinned out the heard considerably since then,and now I flat out refuse to work on anything I don't want to. So sorry.

I won't close my business as it has a LOT of tax law and permit advantages and operating it on a part time basis has allowed me much more free time: the one thing money can't buy..
 
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I’ll be 62 in a week and have no idea what I’m going to do. I could take early SS and live fairly comfortably, but no extra money for the hobbies. I enjoy work and will have an opportunity to go into teaching with my company in a year or two, ostensibly at or near the same pay level, so I’m probably going to steer the same course for a few more years until I figure out what I want to do when I grow up.
 
The very first thing you have to come to grips with is what people tell you and the little white lies we tell ourselves about retirement.

Our generation might be wired just a little bit differently than those who have followed in our footsteps. I believe that later generations lack the work ethic that we have. On the other hand, they'll tell you "it's just a job".
That is probably a more healthy and rounded outlook.

Our generation is the bridge generation that has worked through the "big change" from benevolent family owned business to corporate mergers and acquisitions. We could talk to the boss, they talk to a lady from HR.

Personally, the change was difficult. I saw all of the fringes melt away. Free health insurance, bonuses, and finally a company funded retirement become insolvent due to corporate raiders. I saw a company car with a gas card disappear only to be replaced with a mileage reimbursement that had to stand up to a sharp chisel wielded by an auditor with a map program who questioned every move of my vehicle. Every month was a battle.

I understand that as a business owner your tale might be a little different but maybe also the same in a lot of ways. However, the feeling of an ever tightening noose around your neck is something we are all feeling now.

I was raised in a family that were Carney folks. We traveled all summer with the carnival. I wouldn't have traded lessons learned for anything but I did go to work at about 9 years old. If we didn't work, we didn't eat. We all pitched in. Returning to school in the fall was a break.

After a lifetime in the harness, I was ready for a break. I had earned it. As my career came to a close I kept in contact with guys who I knew from my job early on. One day I got a call from a pal who filled me in on the details of how to collect on my long defunct company pension. Yeah, the Federal government picked it up and I could get a pension from you taxpayers. The money stolen by corporate raiders was going to be replaced and I could get about a grand a month...for the rest of my life. When I kick the bucket, my wife will collect until she goes home too. Thank you taxpayers!

If I needed a nudge, that was it. I'm outta here.
Well, my FIRST retirement lasted two months. I "didn't need to work" financially. But when you get up every morning and get in the harness it's very hard to just hang around the pad all day. I missed the interaction with the people I had worked with. It wasn't the finances, it was the whole social aspect. The gossip and back stabbing along with all the horseplay.

My wife....oh boy. A whole nother trip that I hadn't even thought of. Se was used to me being gone at dawn and returning after dusk everyday. It was almost like I had moved into her house. Under foot? Yeah, I was.

So, faced with being dealt this hand, I had to figure out how to play it and I had to do it fast. I did what I had always done, went back to work. Only when I did, it was with a modern attitude about my devotion to the "job". Now it was "just a job" and my tolerance for the "lady from HR" was going to be much different.

This time I was going to do what I wanted to do. A fun job. I went to work in a gun store. I was so fixed on taking this "dream job" that I overlooked a few details. It was full time and it was 30 miles away. Whoa, this dog won't hunt....so I retired again after a few months.

Now I'm going to go to work someplace in my own neighborhood. Someplace where I can work a couple days a week and wouldn't it be nice to "give something back"? How about doing something that I've always felt the need to do, helping people who are worthy.

I went to work at the local Habitat for Humanity ReStore. I can't tell you how working for a cause that's bigger than just me makes me feel. Helping people who need a hand up and not a hand out. All of the revenue we generate from selling donated building materials goes to building homes for hard working people who earn them.

Now I understand how Jimmy and Rosalynn Carter built homes well into their 80's.....and listen, I get back so much more than I give. I have found the purpose that I lost when I "retired" from my real job.

This is the lesson that I learned that only retirement can teach you. Experience is a cruel teacher because she only gives you the lesson AFTER you have failed the exam.

Never in a million would have thought that I'd be working into my 80's. I hit 70 years old this week and I'm proud to say it, It's taken me this long to find out where I really belong....and the couch ain't it.

Good luck with this.
It's going to happen whether you like it or not. You can't stop the clock.
 
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Throw me in the 'work if you can contrbute' column. I could have just sat down at 45 when I retired from policing, but have had two really challenging, interesting careers since. I tried retirement in late 2020, but by mid-'22 was ready to work. Found the best, most profitable, and most satifying position I've had, and it's leading to better ones. There are downsides, but the very day I decide that's a problem, I'll stay home.

Some of the happiest guys I know of my age (68) are working.
 
We have many threads on retiring and LOTS of people state how incredibly wonderful it is to not work anymore but I'm almost 65 and still work and am wondering about the others like me. I've owned my construction business for about 25 years and am having my best year ever and am planning on taking social security at 66 so I can continue to work and make money and not have that reduce my SS payments. I'm in good health and I lift weights and play about 6-8 hours of pickleball every week and go on lots of trips but sometimes things do get a little frustrating at work and I think about retiring. I have no debt except a little bit on a couple of rent houses, and I could live comfortably on my savings and SS but I couldn't blow money the way I do now. Plus things keep getting more expensive with no end in sight and assisted living can cost $6-7K/month which could go through the cash pretty quickly and I don't want run out and be a burden to my kids. I usually don't work as hard as I use to and can take off about any time I want, but sometimes things get really busy and I have to really crank out the production. I like feeling productive but I'm getting a little more tired than I use to and wondering about the future?

Actually, you're still limited to how much you can make in a year without having SS taken away. The amount for 2024 you can make without losing any SS is $59,520 if you're past your full benefit year. You lose $1 from SS for every $3 you are over that limit.

I'm 69 and took my SS at 65, my full benefit year was at 66. I get 97% of what my full benefit would have been, but I collected a year's worth of SS that I wouldn't have got if I'd waited another year, and it will take 18 years to make up the difference of getting 3% less each month if I'd waited another year.

I also retired at 65, and with my pension and SS, plus some investments and income on a rental property, and my wife's salary, we live okay without me having to work. She is 65, but enjoys her work, is healthy and wants to continue to her full benefit year which for her is 67 and a couple of months.

I do still work, but it is more for pleasure and to stay in shape, the money is nice, but is really inconsequential because I don't make that much. I was in health care for 37 years, and am doing landscaping work now with a friend the same age as me. We do a lot of different things (no mowing) and it's outdoor work, so is weather dependent. I usually work about 18-20 hrs a week and enjoy it a lot. I get what you're saying about assisted living or skilled nursing as you get older. I take care of my almost-97 year old Mom and do her finances, and am always scrambling for ways to cut expenditures and stretch her money. I care for her in her home, paying private sitters and doing a couple of nights a week myself.

Luckily, I got into an annuity a few years ago that has a long-term care provision and is guaranteed for the remainder of my life if I have to go to a facility. I have two grown daughters and I do not want them to have the experience of caring for an elderly parent like I am doing. I hope my wife's health holds out, as I was not able to get her the same deal I got (done through my financial advisor).

Good luck in your reclining years, may you be hale and hearty past 100.
 
I took SS at 66+2mos. but continued to work to keep my wife covered by my employer’s hospitalization. She’s younger than me and not eligible for Medicare plus she cares for her 92 YO mother.
My pay plus my SS allows us to splurge some.
I’d like to be able to retire but I don’t think it will happen.
 
I retired 7 years ago at age 64 1/2. 19 years in a private trial practice followed by another 21 years on the bench was enough. Plus, my term ended and it was easy not to stand for retention again. I found, though, that I wasn't particularly good at retirement so after about two months I resumed mediating/settling civil litigation. I had done a lot of that while I was on the court so it was an easy segway to private work. It keeps me as busy as I want to be, keeps me in touch with the outside world, helps me feel like I'm still accomplishing something and it's lucrative. I'll continue with it for the foreseeable future and, while I don't really need the money, it's nice to have too. So, that's what works for me. But you have to decide what you like to do, or not, and act accordingly. Each person is different.
 
Just turned 59. Retired as California chief of police at 50, college president at 53. Working as a VP for an international firearms/ammo manufacturer and international security consultant, concurrently. I’ll continue working until it’s no longer enjoyable.
 
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Retired 4 years ago and spent the first two years remodeling homes to sell.

For the past two years, I have been bored stiff. Just not enough to do.

A company that has been trying to hire me for 4 years, finally asked what it would take. I told them I wanted a salary and commision, and I would work 20 hrs per week. They said ok. I start next week.

Robert
 
I'll put in my 2 cents. Yes, I have been retired for almost 8 years and it's been great. No more commuting 90 miles a day, and my life is my own. I have medical opinion that retiring when I did may have saved my life.

Before I retired I happened to have an appointment with my old cardiologist. I told him I was thinking about retirement, and he told me to make sure that I had something going on to keep my mind active. He described some people he knew who retired and had no outside interests, and ended up suffering significant cognitive decline. Luckily I was already acting on his advice since I had been working as a volunteer on the borough planning commission and made my way up to being its secretary. After I retired I just kept doing doing that.

I end up doing about 6-7 hours of work in any month the planning commission has a meeting, between preparing for the meeting, attending the meeting, drafting the meeting minutes and submitting them to the Borough Secretary. I do my best to create a complete and accurate record of the proceedings at each meeting. The town officials appreciate my work. I don't make a dime doing it this work, but it does give me a regular source of mental activity and a sense that I'm giving back to the community in which I have chosen to reside.

And just for the record, at my next appointment the cardiologist asked me what I was doing since I retired. I was able to reel off enough activities to convince him I was OK.
 
I retired from my own business at 55, (15 years ago) and have been going non stop when it comes to helping friends, neighbors, relatives out with repairs and maintenance work on their homes, cars, motorcycles, etc.

I have made ZERO $$ becauseI have not charged them a penny! Some of my friends say I am foolish since I do what they tell me is superior work and people would be glad to pay me. That is probably true and in a monetary sense I guess I am foolish. Even my own wife tells me I should be charging at least a reasonable fee.

That said, we do get taken to many nice dinners, lunches, get thank you bottles of my favorite libation, etc. So am I being a fool?? Maybe, maybe not... who knows. Bottom line is that I truly enjoy it, keeps me very busy and I feel like my natural abilities are being put to use and are greatly appreciated. Could I make 6 figures a year doing this - absolutely. Am I a fool??
I don't think you're being a fool at all. When you start charging, it becomes a business and the self-satisfaction slowly goes away. Helping others is American. We need more like you.
 
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