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Retirement, any regrets

Was not an easy transition for me. First time I retired I got bored and slightly depressed. Missed the sense or purpose, solving problems, missed co-workers too, even though the job was frustrating half the time. Called manager said I might be interested in coming back, he said tell me what you want. Gave me all I asked for and more. Felt better, more engaged etc.

Second time I retired effects were less. It’s been two years now. I’m still restless but have accepted it much better. Still, the thought of some “mad money” is appealing. Hmm… I could buy more gear without dipping into savings or retirement money.

I’ll probably find a volunteer opportunity soon. Miss collaborating with others.

Talking it over with my wife also helped.

Good luck.
My dad has retired several times.....well he retired then occasionally picks up a job here or there in his field and he's old enough that it doesn't affect his social security or other retirement benefits. He says its nice being at work knowing you can just punch out an any moment with little to no downside.
 
Health insurance was a big issue. Private insurance Blue Cross was $1100/mo with $25k deductible. Started Medicare at 65, but delayed and went on SocSec at 66 and 4 months to get the "big bump" - whatever that is [not a money guy at all]. And we are both on SS now. Have an IRA I guess I'll need to start drawing from at 72.

This is a huge thing, even for those of us decades away from retirement. My wife and I have employer-sponsored health insurance and we flat-out could not afford health insurance on either the marketplace or privately if one of us was to become unemployed and lose it. No matter how the pie is sliced, health insurance *individually* would cost each of us more than our mortgage payment each month. We would have to go without it, period. Scary to think about.
 
I'll be retiring in the next 12 months! I've spent 30 plus years working as a I.T. recruiter. I have worked for some of the largest staffing firms in the world, with the last 14 years working for my self from home. My wife, a school Principal retired three years ago.
We have been watching the housing market in "cottage country" for the last year, we both have a burning desire to get out of the city, there are just too many people here (7.1 mill) in the GTA! Our house was paid off three years ago.
I have always wanted a place on a lake, my boat tied up on my dock, waiting for me to go out fishing! My wife shares my dream of a quieter existence.
We just need to cut the cord and get our kids settled and out of the house! That plan is in motion.
Fishheadjoe
 
This is a huge thing, even for those of us decades away from retirement. My wife and I have employer-sponsored health insurance and we flat-out could not afford health insurance on either the marketplace or privately if one of us was to become unemployed and lose it. No matter how the pie is sliced, health insurance *individually* would cost each of us more than our mortgage payment each month. We would have to go without it, period. Scary to think about.

Health insurance cost is one of the big barriers to "retiring early" that I think about. I sometimes think about retiring from my career job, but picking up another hobby job to get benefits. I also wonder if it would be good for my mental health to leave the thing I've been doing my entire working life and explore something new, even at a pay cut. Maybe someday I'll work as a barista or a salesman at a music shop.
 
Health insurance cost is one of the big barriers to "retiring early" that I think about.
This is an important consideration. I retired at 62 but won't qualify for Medicare until I'm 65. So I've been buying private health insurance through the ACA exchange, which costs me about $350.00 a month. The cost of private health insurance is expected to increase dramatically in 2026.
 
I retired almost 14 years ago. No regrets, except for one. My pension from my old job is set. Never to be increased. What I'm getting now is exactly what I was getting on "day one".

Issue. Inflation. My set in stone pension has lost at least 35% or more buying power because of 2%, 3% etc inflation every year.

I never thought about this when I signed on the dotted line for retirement. I probably should have worked another 3 to 5 more years.

Oh well. The wife and I are getting by and eating soup beans for supper everyday ain't too bad! Wink, wink.

View attachment 7314521
I took my pension in a lump sum and invested it. I was offered to either take monthly payments or a lump sum and the way I figured it out was the lump was equivalent to 19 years of monthly payments.

So I consulted with my account, Steve Miller, and he advised me to "take the money and run."
 
I plan on retiring early next year at 65. I see no real benefit to waiting as continuing to work full time for much longer isn't going to increase my SS payments by very much. I do plan on continuing working part time (like 3 days a week only).

I retired from being a professional artist, musician, writer and life coach about 10 years ago, so I gave up all the "self-employed" interests that I used to make money at. Currently I manage a picture framing department for a regular paycheck and insurance. I can easily do that a few days a week to supplement my income.

But I know that when I retire I can get back to painting, writing and music, but it will finally be on my terms not my clients needs/wants because I won't need to do any of it for the money, but rather for the love of it (money will just be a bonus).

My wife has a very good paying job and recently got a promotion and is now the "boss" where she works. She's ten years younger than me and feels her job is very fulfilling. So she will work full time for at least another ten years, which will give me many days all to myself.

A couple of years ago we decided to get rid of everything we didn't really need and made a conscious effort to simplify our lives now that all our kids are out of the "nest". I purposely decided to slow down and get off the treadmill. I love living a casual life and watching the rest of the world run around like crazy squirrels.

I love people. I just don't like them. :laugh: I prefer living a quiet, peaceful and mostly solitary existence.

So I'm really looking forward to retiring. With a passion for art, writing, music and my love for astronomy I couldn't be bored if I tried to. In retirement I can do those things because I want to instead of out of necessity.
 
I loved my job, but we ALL hated the company.. I dont miss the toxic environment they seemed to work so hard creating.. At all…One thing Ive considered doing is applying for jobs with companies i despise, getting a pair of those specs that record stuff, and then filming myself being the worst employee they have ever hired. I would set new standards for incompetence, then put the filmed results out there on the innerweb, kinda like one of them “influencers”, whatever they are. I’d start with Amazon. Drive that forklift off the loading dock right down the road until the battery died. Tell them i misunderstood and thought i was supposed to deliver the package. I could see myself as a WalMart greeter, doling out unsolicited advice-“You have to be smarter than the shopping cart”…When asked where a particular product might be-“ask somebody who really gives a damn”…Stuff like that.
 
I retired almost 14 years ago. No regrets, except for one. My pension from my old job is set. Never to be increased. What I'm getting now is exactly what I was getting on "day one".

Issue. Inflation. My set in stone pension has lost at least 35% or more buying power because of 2%, 3% etc inflation every year.

I never thought about this when I signed on the dotted line for retirement. I probably should have worked another 3 to 5 more years.

Oh well. The wife and I are getting by and eating soup beans for supper everyday ain't too bad! Wink, wink.

View attachment 7314521
That looks like some mighty fine beans!
 
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I work in computer technical support. There is no way on this Earth that I will regret retiring. Never never never. I may regret missing the money but getting my life back minus the inanity. People suck.

Edit: all about the $$$
I hear you. I worked in tech as a software engineer and in managment for 36 years. The constant stress takes a toll on you and it's sneaky. It slowly effects you and the funny thing is that you don't realize how much you're impacted until you get away from it. I left the profession at the end of 2017 and have taught at a local college since. I'm getting ready to hang it up for good within the next year or so. Basically a timing thing with healthcare, etc.
 
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Very apropos discussion. After 40+ years in IT, I will be retiring at the end of this month. I turn 65 in a couple of weeks, going on Medicare - lots of changes on the horizon, but I'm ready. Can't say I don't have some anxiety with all the change, but at this point I feel I have plenty of things that will keep me busy for years to come. Definitely plan to invest more time in my various hobbies including bass playing.
yes, I had a 36 year career in tech. I can say, there are times when I miss being in the middle of it all. But, then there are times when I realize the stress took it's toll and i'm much better of. I'm turning 65 in November, and will be stepping into retirement permanently (currenty teaching at a local College) soon. My wife is a couple of years behind me, so it's a timing thing at this point.
 
This is a huge thing, even for those of us decades away from retirement. My wife and I have employer-sponsored health insurance and we flat-out could not afford health insurance on either the marketplace or privately if one of us was to become unemployed and lose it. No matter how the pie is sliced, health insurance *individually* would cost each of us more than our mortgage payment each month. We would have to go without it, period. Scary to think about.
Yes, and that's why I'm in a timing thing at the moment. My wife is a couple of years younger than me (I turn 65 in November). Back in '17 when I "retired" from the tech industry, I was extended an offer to teach at a College. The best thing about it is the healthcare (Blue cross) is cheaper through me than my wife's company (small company so they don't have the buying power). I've filed for medicare "A" as required, but will likely be teaching for another year or so just to get the timing right.
 
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So Anyway, I'm assuming the OP was retiring from a day job and not from music. Retirement should be enjoyed.

I can only speak from my own local experience, but of all the people I've played gigs with over 50 years:
  • I can count a handful of them who willingly 'retired' from music.
  • Of those who don't play anymore, very few of them quit a working band and said no to every musical offer.
  • Most guys who said they've retired from music just had the phone stop ringing or their band fell apart. If an offer came, there's a good chance they'd be back in it....and I've seen this several times.
The same goes with bands on their 3rd or 4th 'final tour'. :laugh:

When I retired from my day job, I was able to say 'Yes' to a lot of things that I didn't have time for as a Full Time Employee. A short time after I retired, I was working or subbing in 4 different bands. I did that for a few years not for the money, but because I enjoyed being busy with music. And it fed my ego and identity as a 'musician'.
But that's just me.
I retired from music a couple years ago, and I have no plans to ever do it again. There's no offer that would make me get back in. I sold all my gear except for 1 bass that has sentimental value.
Nobody says “I wish I had worked more” when they’re on their death bed.
I have a friend who will probably say this. He seems to be obsessed with it. All to make someone else wealthy? No thanks.
 
I hear you. I worked in tech as a software engineer and in managment for 36 years. The constant stress takes a toll on you and it's sneaky. It slowly effects you and the funny thing is that you don't realize how much you're impacted until you get away from it. I left the profession at the end of 2017 and have taught at a local college since. I'm getting ready to hang it up for good within the next year or so. Basically a timing thing with healthcare, etc.
Coming on year 29 in the industry. From my seat it appears that humankind went off the rails in 2020 and humans have not recovered their sense of grace and dignity ever since. The rudeness is off the chart to me and I have had to fire two clients already because of that.
 
Send me your recipe and I'll send you mine.
Bellissimo!
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I work in computer technical support. There is no way on this Earth that I will regret retiring. Never never never. I may regret missing the money but getting my life back minus the inanity. People suck.

Edit: all about the $$$
Haa! I do IT work in a hospital. I got cha! Plus I commute about 1 hr 15 min each way! I am. Counting down just to quit at 65! I will have to work part time for $$ to make ends meet. But it will be close to home!
 
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