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eastsideTim PowerDork
9/17/21 7:53 a.m.

I just recently turned 46, and while I'm not in a position to retire immediately, I've been saving enough that I think retirement in my 50's is an option.  If anyone here has retired between the ages of 50-60, I'd love to hear your experiences/opinions, and thoughts on advantages and pitfalls of it.  I take pride in my work, but I am more of a "work to live" than "live to work" type.  I think as long as I had enough money to survive, and indulge my interests, I could keep busy.

Anyway, two possible paths I am considering right now:

  1. Try to stick to the current career until age 55, then flat out retire.  My wife is planning on working into her early 60's, but I've seen so many stories where that plan goes to E36 M3 once the working spouse gets jealous of the retired spouse's lifestyle, and decides they want to retire, too.  At 55, we could likely both retire, but just more modestly than if she continued working for 5-10 more years.
  2. At around 50, try to switch to seasonal work until I am 60, preferably working for someone else, but maybe going the independent contractor route if need be.  Work maybe 6-8 months a year, then spend the remaining time traveling, and doing whatever I feel like.  The danger in this one is if I find I don't like this lifestyle, I am low enough in the IT world, that a gap in employment will hurt my chances of getting back in at anywhere near my current salary, so if I do this, I pretty much have to commit.  That said, right now, if I could somehow work half a year for half my current salary, I'd take that deal now, and not even wait until I'm 50.


So, thoughts on your own retirement experiences, and on my loose plans above?  I'll try to do a bit more of a brain dump later in this thread, but for now, I'd really like to learn from others.

Fueled by Caffeine
Fueled by Caffeine MegaDork
9/17/21 8:01 a.m.

Following. I'm 42. If I keep saving at the same rate I can retire from 60-62 with enough for full salary replacement at the 4% rule. If I live modestly I could go earlier.  

It's not been easy with 10 years of a single income and my wife now making less than an associate in a Walmart warehouse ( teaching is a scam).  Ohh and three kids. 

Back to Tim and his question. I met a guy who was about in his late 40's early 50's and he just blended his lifestyle with work to give him happiness.  He works for a cloud provider in sales or account management.  He can work from anywhere.  He lives in a downtown apartment in minnespolis in the summer and spends his spare time at the lake or mountain biking. In the winter he lives in Florida and hangs out fishing or on the beach.   Seemed pretty happy with it. 

docwyte PowerDork
9/17/21 8:05 a.m.

I'm hoping to retire age 57 or so.  Most of my hobbies are physical and I want to be able to still do them.  My wife and I both own our businesses and the buildings they're in.  I'll have my Air Force pension when I turn 60.  She's likely going to work longer than me as she's only owned her business for 3 years.  So between her income, the sale of my business and monthly rent from my building, along with my Air Force pension I think we're going to be ok. 

While you can always earn more money, its hard to get the time back...

STM317 UberDork
9/17/21 8:31 a.m.

With average market returns, I should hit my number around age 50. I'll have to see what life is like at that time to determine if I actually pull the trigger or not. 

Some general things to think about/plan for:

You can't access most retirement funds until age 59.5 without penalty, so you'll need to have money set aside to get you from whatever time you retire until age 59.5. A Roth IRA is probably the most common vehicle for this. If you don't have one, get one. If you do have one, stack it up there (possibly doing Roth conversions/Roth ladder with funds from traditional retirement accounts).

Healthcare seems the biggest wildcard to me. Rates on the ACA marketplace can be expensive. Or not. And they change frequently, so good luck guessing what they might be 5-10 years from now. Make sure there's a plan for this though. And do as much as you can to stay healthy.

Sequence of returns risk is another concern. Basically, if the value of your nest egg drops a lot very early in your retirement it can cause failure later in life. So limit spending in these cases, have enough cash available to get by without touching your investments, get a part time gig to have extra income coming in, etc.


JesseWolfe Reader
9/17/21 8:34 a.m.

I'm 41YO, can retire when I'm 57YO, so 16 more years at this job before I can pension out.  My wife has 17 more years before she can.  Our "plan" is to move somewhere even more quiet where we can work part time at jobs we love, rather then sticking our current well paying jobs even longer, to have even better pensions that allow more flexibility in retirement.  


My experiences with coworkers that have pensioned out and retired in their early 50's, is that they still got part time jobs, like working in public schools to have better insurance and more play money, but they won't actually quit working for 10 years after leaving.

preach (fs)
preach (fs) GRM+ Memberand Dork
9/17/21 8:38 a.m.

I'm 51. Current plan is rolling hard until 60 then retiring. Seems like a bunch of us are in the same boat.

I will retire with 22 years of .gov. 401k, pension, SS (maybe), small personal stock portfolio, and a probable side gig for kicks. 

My wife is 12 years younger than me and can telework for the rest of here career (so far).

We are planning a move to a much lesser cost of living, new house paid off+ than the current one. All I want to do is farm for us (and maybe some close family) and berkeley off in my garage with 10+ cars in various states of repair.

I look forward to the experienced fellas replying.

mtn MegaDork
9/17/21 8:42 a.m.


I'm 31. I was on a path for retirement around age 50, but then life happened in a terrible way, my wife was out of work for 6 months, worked for 3 months, then was out of work again for 3 months before going back part time. 6 months later, Covid happened, my wife was out of work for over a year, and my side gig evaporated.  All of that added up to our retirement contributions being significantly cut. Now my wife is back full time, and once kiddo gets vaccinated, I can go back to my side gig, but it will be a while before we can get back to where we were, and I think the new retirement goal will be 59. My plan at that point would be to referee hockey, as long as I'm still able, and possibly another flexible side gig.


My wife used to say she'd never retire. I'm pretty sure she is changing her tune on that pretty quickly.

pres589 (djronnebaum)
pres589 (djronnebaum) UltimaDork
9/17/21 8:49 a.m.

Following.  43, hoping to stay fully employed for another decade or less, then go semi-retired and have something I can do mostly from home and work about half time.  One more reason I'm trying to get more into photography is to have a hobby where I can make some money (like $5k a year, not much expected), stay busy, and not just 'sit to death'.  I think a little structure does me good and I can start working less with more years of ability to enjoy it.  

trigun7469 SuperDork
9/17/21 8:55 a.m.

I can't imagine retiring without the first number of my age being 7X to my name lolz. What are your guys plans for healthcare since you won't be eligible for medicate/Medicare?

Apis Mellifera
Apis Mellifera Dork
9/17/21 8:57 a.m.

My Dad retired three times, beginning in his middle 40s.  The last one finally took, but he still works.  He was always successful and financially secure.  He's is wired for 110v, but runs on 220v.  Always has been and at 73, he still can't sit down and do nothing.  He just loves to work and accomplish goals.  His latest retirement hobby has been raising organic beef.  I could retire at 56, but not only did I not inherit the ability to fall backward into a pile of cash, the 9-5 of my job is an excellent excuse for not finishing the 4 or 5 car projects I've got going.  If you're the type that enjoys being active and seeing the tangible fruits of a day's labor, consider the non-financial aspects of early retirement.

jharry3 GRM+ Memberand Dork
9/17/21 8:58 a.m.
trigun7469 said:

I can't imagine retiring without at the start of 7X to my name lolz. What are your guys plans for healthcare since you won't be eligible for medicate/Medicare?

You had to pop the balloon!

SkinnyG (Forum Supporter)
SkinnyG (Forum Supporter) UberDork
9/17/21 9:00 a.m.

I'll retire at 58, with what was an "unreduced" pension (the pension plan changed and 58 is now "reduced," but the money will be the same).  I will have taught for 32 years by then. I have single digits remaining.

You will always live within your means.  Whether it's grey poupon and cavair, or sucking ketchup packets at the food court, you will always live within your means. You will adjust your life accordingly.  You always have.

I believe THIS is IMPORTANT: You should be developing a hobby in your working years that you can transition to when you retire.  Whether it brings in money or not doesn't matter (live within your means), it needs to occupy you, and put wind in your sails. As you get closer to retirement, the work/hobby balance needs to begin sliding away from work, and towards hobby. My mind has begun tilting the scale over to hobby quicker than my allotted time, which is surprising me.

You have NO idea what your health is going to do (and MANY people who work longer, die sooner), so if you can get out and enjoy some life while you still have energy and health to do so, DO IT.

You can't take it with you.

Relationships and family are far more important than the money (except my extended family; they suck).

JesseWolfe Reader
9/17/21 9:01 a.m.

In reply to trigun7469 :

My dad didn't retire until he was 73YO, it was a bit forced at that too.  His dementia and Parkinson's was getting too bad for him to drive anymore.  Had that not happened, I'm sure he'd still be working at 82.  As much as I idolize him, being my hero and role model for work ethics, I don't want that to be me.

Streetwiseguy MegaDork
9/17/21 9:03 a.m.

Retire to what?  Are you a gardening enthusiast?  Do you enjoy driving seniors to appointments?  Calligraphy?  Taking up professional funny car racing?

Not wishing to sound snarky, but if i didn't have a reason to leave the house every morning,  I would sit down in my recliner until my butt bonded to the fake leather, then I would die. Retirement is not a thing for me, I don't think.

Duke MegaDork
9/17/21 9:15 a.m.

In reply to Streetwiseguy :

My first year, I plan to clean the garage.

My second year, the basement, and my third year, the attic.

By that time I'm sure I'll have figured something out for after that.

I'm 56.  DW just turned 58.  We had sort of planned for her to get out at the end of this year, but for a variety of reasons (only tangentially financial), that may be next year.  I'll probably get out the year after that, also at 58.  I can't wait.  I need to get off my ass and do some of the renovations we have planned, in order to make DW comfortable getting out of the rat race.

We'll need to bridge the health insurance gap until 62, but we should have everything covered.  We've got enough socked away to live like we are now until 90 and still leave some to the DDs.


bmw88rider GRM+ Memberand UltraDork
9/17/21 9:18 a.m.

I am in the exact same boat. 46 and zero liabilities. Just got the deed to the house. Car is paid for and only has 13K miles on it. My 2 project cars are not sucking major money either. Well funded 401K and saving about 5-6K a month between all of the sources depending on the size of my commissions check. 

Honestly, my biggest concern is healthcare. I've been maxing my HSA for 5 years now and with investments, that will be of a decent size. There are some rules where you can pay cobra with it but that won't be enough to make it to medicare time. I don't see myself retiring in the US though. All of the family I'm close to have passed or will pass in the next 10 years. 


Skinny, I totally agree with what you said there. My dad had that situation where he didn't have that for many years and he had a lot of issues with that. It wasn't until he got involved with the Shriners and a couple other groups that things went ok for him. 


I don't see myself retiring so much as taking a job where I don't care what the salary is. A passion position vs. a need to pay the bills position. 

alfadriver MegaDork
9/17/21 9:30 a.m.

I'm 54, and am planning on retiring next may when my wife hits 30 years. I'll have 30 and 2 months. 

Plans?  Travel for now. Thanks to COVID, we added camping to our travel plans, which saves a lot over cruising and going to Europe. 

in terms of what else to do?  I have some thoughts, like volunteer at a local distillery. Or at least more of that for the university. 

BTW, you can't access a 401k until 59.5 without penalty, which one of us hits next year...

For the youngsters, start now. We have planned this since before we were married, and have been maxing out contributions since then. 

9/17/21 9:39 a.m.


Living the life as we speak.

If you are a money worrier, or you carry a lot of overhead, retirement will drive you nuts. There is a lot at stake and a lot of uncertainty in the tea leaves. If you live in the USA, a medical event can wipe you out financially in no time no matter how much you saved. 

Life should be about expanding the circle of experiences, easy to go the other way and contract your circle when you retire; either out of laziness or financial fear or personality. Everyone thought I was a workaholic, I knew that at my core I can be lazier than a pet raccoon, and I am loving the life.

If your workmates were a significant part of your social life, it gets weird. 

Spouse wont be far behind if you retire early. 

You can always go back to some kind of work, you might be surprised how little you spend and even a trickle of an income can be a bonus. You dont have to actually pretend to care about your employer anymore!


Datsun310Guy MegaDork
9/17/21 9:54 a.m.

Guy at work retired at 55 - his wife is a VP something and still works carrying their insurance.  

He has a classic car and attends local car shows 6-7 nights a week.

After a few years he got bored and delivers car parts for a store part time.   

Fueled by Caffeine
Fueled by Caffeine MegaDork
9/17/21 10:01 a.m.

Here are my thoughts on my retirement jobs. 

1). Teaching English abroad 

2) college professor / lecturer 

3) Xmas tree farm 

4) something agricultural  

5) own a franchise or three?


but you guys are right. We need to do something or we just die. 

z31maniac MegaDork
9/17/21 10:04 a.m.

I'm 39 and due to indiscriminate spending on cars, modifications, and motorcycles when I was younger, plus giving up a house in a divorce.........and a serious hospital stay when I was younger, I suspect I'll die before I can retire. I know that sounds a bit morbid, but it's just realistic. 

I'm just hoping to be able to pass on enough to the better half that she can live out her last years in the same comfort I've made her accustomed to.

bmw88rider GRM+ Memberand UltraDork
9/17/21 10:11 a.m.

In reply to alfadriver :

I know on the 401K. I max it out every year and then put the rest into a conventional brokerage account. Right now, it's about 1/3 IRA/401K and 2/3 conventional brokerage. I just need to quit looking at it and thinking mmmm that could be a 911. haha.  

ProDarwin MegaDork
9/17/21 10:14 a.m.

I'm 38.  Targeting a semi-retirement in mid 40s.  Not lavish, but there will be enough with the 4% rule to cover my needs for sure.  My accounts are all funded, but I can transition to something that interests me more, gets me health insurance, and allows for more time off, etc.  I'm currently looking at some investments to start building a secondary income to allow for that.  If that fails, I'm looking at age 50 probably.

So I guess my plan aligns more with your option #2.


mtn MegaDork
9/17/21 10:22 a.m.

jharry3 said:

trigun7469 said:

I can't imagine retiring without at the start of 7X to my name lolz. What are your guys plans for healthcare since you won't be eligible for medicate/Medicare?

You had to pop the balloon!


TBD. I have 20 years minimum in a best case scenario, and 30-35 years in a realistic scenario to figure that out. Honestly, I think something drastic is going to happen to Medicare/health insurance in that time. From a wanna be actuarial standpoint, I don't see how the current path is sustainable, especially with what I think Covid has done to overall healthcare costs. 

But if it doesn't, and we can't afford it, we'll figure something out with continued employment. 

Streetwiseguy said:

Retire to what?  Are you a gardening enthusiast?  Do you enjoy driving seniors to appointments?  Calligraphy?  Taking up professional funny car racing?

I'm going to guess that your job is something you legitimately enjoy, and you're one of the lucky ones who is able to make a living doing what you love (or at least like). Many, if not most of us are not that lucky. 

I've never understood this point, honestly. What do you do in your free time now? Don't you have any hobbies? I don't have enough free time. I want to work out more, play more hockey, ref more hockey, go fishing a lot more, play a lot more golf, bike Ragbrai, cook more of my own food, play a lot more music...

ProDarwin MegaDork
9/17/21 10:27 a.m.
mtn said:

I've never understood this point, honestly. What do you do in your free time now? Don't you have any hobbies? I don't have enough free time. I want to work out more, play more hockey, ref more hockey, go fishing a lot more, play a lot more golf, bike Ragbrai, cook more of my own food, play a lot more music...

Agreed.  I've never reached the end of the weekend and thought "I really want to have to go back to work"  And I enjoy my job.

I could dedicate 10x the amount of time I do now to my hobbies and it still wouldn't be enough/I would just acquire more hobbies.

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