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It is not healthy how much I’m thinking about retirement

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 7:49:55

Been watching a ton of financial planning and related YouTube videos, along with places to retire in Italy content. (I don’t think I’d want to move there full time, but real estate is so cheap I’d definitely consider a vacation place there.)

I’m probably spending 30+ minutes most days actively thinking about and looking forward to retirement. Which is not great since I’m 6 years away from being able to actually do it. I think it’s definitely sapping my motivation for my current job.

LAM having a 1) self employed 401k limit and 2) available 401k Roth is

Posted by gvibes <iframe src='https://mb.boardhost.com/TheDeuce/info/user=gvibes' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 21:00:36, in reply to "It is not healthy how much I’m thinking about retirement "

baller.

I didn’t realize the self employed limit had gotten so high. I thought it was in the 50s

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Trying to move up the date by selling LBK on all the things I'll do as her personal valet...

Posted by KingTalkyTiki <iframe src='https://mb.boardhost.com/TheDeuce/info/user=KingTalkyTiki' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 14:08:13, in reply to "It is not healthy how much I’m thinking about retirement "

...if I'm retired and she's still working.

Guessing it will probably still be 7 years-ish.

"You must own the honor of being the whitest, military vet, fat, multiple state property owner but most of all the one who hates their own country the most in our country."

I've never been eligible for Roth IRAs (LAM!) and can't do mega backdoor Roths. Anybody look into

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 7:31:06, in reply to "It is not healthy how much I’m thinking about retirement "

regular conversions right after retiring? This video got me thinking about it a few months ago....

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“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Everything you post is a LAM*

Posted by Stu <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Stu' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:02:26, in reply to "I've never been eligible for Roth IRAs (LAM!) and can't do mega backdoor Roths. Anybody look into"

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regular conversions right after retiring? This video got me thinking about it a few months ago....

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Chicken Little poster child

I guess if you're over 50 and a "high earner" your catch-up 401k has to go in...

Posted by shua <iframe src='https://mb.boardhost.com/TheDeuce/info/user=shua' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 7:58:33, in reply to "I've never been eligible for Roth IRAs (LAM!) and can't do mega backdoor Roths. Anybody look into"

an after-tax Roth. But that's really not a huge amount of contribution.

Yeah, and I addressed the Roth 401k thing below in the response to DT. So I will have *some*

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:51:40, in reply to "I guess if you're over 50 and a "high earner" your catch-up 401k has to go in..."

Roth money.

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an after-tax Roth. But that's really not a huge amount of contribution.

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Similar boat. I have roth IRAs from when I was way younger, but haven't been able to contribute in

Posted by illinibone <iframe src='https://mb.boardhost.com/TheDeuce/info/user=illinibone' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 15:31:53, in reply to "Yeah, and I addressed the Roth 401k thing below in the response to DT. So I will have *some*"

forever....

If the reason you can't do MBDRC is because your 401k admin is a doofus, then keep sitting on them. Ours didn't support it until 4? years ago, and they just didn't realize it was useful. With Fidelity, I don't even think there's a higher plan cost to it.

If it's because of your match, etc hitting the $72k annual max, then I can't help you.

Since I'm already paying tax on it, it's nice to have the extra in a tax sheltered account so I don't get double taxed on it later.

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Roth money.

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an after-tax Roth. But that's really not a huge amount of contribution.

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Yes, I plan to do this regularly since I’m trying to retire early.

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 7:55:19, in reply to "I've never been eligible for Roth IRAs (LAM!) and can't do mega backdoor Roths. Anybody look into"

I assume the video talks about converting a bunch of money while your income is low before social security and RMDs kick in?

I’ll read up on it more, but have to figure out how to do that while also taking capital gains at the 0% rate. Might take some finessing but I’m hoping to have a ton of years before hitting SS/RMDs so if I’ve got 20 years, might be able to get all capital gains at 0% and only pay 12% tax on my rollovers.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

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Ive started thinking about it and done some simple projections

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 7:52:53, in reply to "I've never been eligible for Roth IRAs (LAM!) and can't do mega backdoor Roths. Anybody look into"

I’ve got 100% of my retirement savings in pre-tax accounts, so Roth conversions definitely make sense for me, up to a point. But the big reason I am interested in them is the potential widow tax hit for me or my wife in our 80’s. And a secondary potential concern about a tax hit for my kids if we we die with a large taxable account balance, since they will have to take 10% out per year on top of their working income in their 50’s.

One contradiction I’ve seen in almost all financial planning discussions around Roth conversions is, on the one hand, they make a huge deal about the low income window right after you retire but before you start collecting SS. But on the other hand, the big pitch for retiring early is to have more “go go years” when you are healthy to enjoy your retirement. Which means front loading travel and other spending in those years. But you can’t have it both ways. You only have a low income window if you are going to be living on *less* than your SS benefit, which means extreme budgeting in the exact time that they say you should be living it up. Assuming a normal or higher than normal lifestyle from 60-67, my taxable income will be the same or higher than it will be once I start collecting SS.

The financial planners all scare-monger about RMDs and throw out huge tax savings numbers, but if you look into it, RMD percentages are pretty low until you get pretty old. They don’t get above 5% until you are 81, and don’t get above 6% until you are 85.

So the RMD risk is that you’ll live inter your 90’s with $2+ million in the bank. Which is, from any objective standpoint other than tax planning, an absolutely fantastic outcome. And yeah, paying a higher tax rate or IRMAA surcharge wouldn’t be great, but it’s also nothing that would make the slightest bit of difference from an actual lifestyle or happiness standpoint if it comes to that. So I’m not super concerned about it.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

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Yeah, your last two paragraphs sum up the kind of indescribable gut feeling I've had on the RMD

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:25:59, in reply to "Ive started thinking about it and done some simple projections"

discussion. And outside of the MBDRC, which I can't do, every time I bring up Roth conversions with my planner we end up thinking it makes no sense for me right now or at any time until I'm closer to 65-70. And even then, to your point, will I truly be "low income"?

One thing I have done is started moving my contributions this year (normal - not catch up) to Roth 401k contributions, so I do have something in my Roth bucket when I get older.

And I am building up my taxable account as fast as I can too. To be able to take money out as LTKG earlier on, rather than ordinary income.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

?si=KV4fuNF36yK9hfFv

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Can you withdraw from a Roth ages 60->70 but then convert too?

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 9:21:55, in reply to "Yeah, your last two paragraphs sum up the kind of indescribable gut feeling I've had on the RMD "

Because this would be a way that you could get the income necessary to live how you want while having a low tax bracket to do your conversions.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

?si=KV4fuNF36yK9hfFv

Does that actually make a difference?

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 9:33:49, in reply to "Can you withdraw from a Roth ages 60->70 but then convert too?"

Say you have $60k in Social Security and want $130k in income.

Option 1: withdraw the $70k from a pre-tax account, pay taxes on that amount. Roth balance unchanged.

Option 2: withdraw whatever the after tax equivalent of $70k is from the Roth to get the same after tax income as Option 1. This then leaves extra head room for a Roth conversion which you can use by withdrawing $70k from your pre-tax account, paying taxes on it and depositing that into your Roth.

At the end of the year, the two options are identical. Am I missing something? (And I think the same logic applies to using Roth balances early in retirement to allow for more aggressive conversions of pre-tax accounts. It works out exactly the same as leaving the money in your Roth and just withdrawing from the pre-tax account to cover living expenses.

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Because this would be a way that you could get the income necessary to live how you want while having a low tax bracket to do your conversions.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

?si=KV4fuNF36yK9hfFv

Admittedly, this is a strategy I’ve thought about from 50-59, not 60+

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 13:58:28, in reply to "Does that actually make a difference?"

So yeah, doesn’t map to 60+ as well.

Can’t touch IRA/401K for withdrawals under 59.5 or whatever (unless rule of 55) but you can 1) withdraw Roth CONTRIBUTIONS and 2) convert IRA.

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Because this would be a way that you could get the income necessary to live how you want while having a low tax bracket to do your conversions.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

?si=KV4fuNF36yK9hfFv

I think so. But obviously you need a Roth account funded during working years to do so.*

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 9:22:55, in reply to "Can you withdraw from a Roth ages 60->70 but then convert too?"

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Because this would be a way that you could get the income necessary to live how you want while having a low tax bracket to do your conversions.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

?si=KV4fuNF36yK9hfFv

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

And actually you can start this before 60 on contributions to Roth*

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 9:22:21, in reply to "Can you withdraw from a Roth ages 60->70 but then convert too?"

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Because this would be a way that you could get the income necessary to live how you want while having a low tax bracket to do your conversions.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

?si=KV4fuNF36yK9hfFv

There’s a bit of bait and switch aspect to the argument

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:44:25, in reply to "Yeah, your last two paragraphs sum up the kind of indescribable gut feeling I've had on the RMD "

I’m reading Thinking, Fast and Slow right now, which is all about ways the mind and decision making actually work, and how that departs from strict logic and rationality. This doesn’t exactly track with anything in the book (at least not in the part I’ve read so far), but is in a similar vein.

The argument that’s made for Roth conversions is around lifetime tax savings, and that number is quoted up front. And then psychologically, you look at that amount and think about it in today dollars, and the impact that losing that amount of money would have on your retirement savings and security.

But the actual cost is incurred 20+ years in the future, and even more importantly, the marginal utility or happiness impact is even lower than you’d get just by considering some time discounting. Because RMDs will only impact anything if they are forcing you to withdraw more than you otherwise would. So they cannot possibly impact your basic retirement standard of living.

That doesn’t mean they are pointless. If you can do some simple things to lower your tax bill, then that makes sense. But the discussion around it is way too breathless and extreme.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

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I think that as with a lot of things, the mental overhead of actually nerding out and optimizing it

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:53:17, in reply to "There’s a bit of bait and switch aspect to the argument "

could be significantly more costly than the marginal tax cost (discounted as you say). In other words, the juice may not be worth the squeeze if it you have to do so much work to get it right.

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regular conversions right after retiring? This video got me thinking about it a few months ago....

?si=KV4fuNF36yK9hfFv

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

I’m on the 65-67 trajectory. 3 kids going to college soon is expensive. We also made a conscious

Posted by voiceofreason <iframe src='https://mb.boardhost.com/TheDeuce/info/user=voiceofreason' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 7:27:20, in reply to "It is not healthy how much I’m thinking about retirement "

decision to spend more on family vacations, etc each year. Not above our means by any measure, but it is money we could have been putting away.

Decided it was better to see/do stuff while we were in better shape/health than in our late 50s, early 60s. And to spend quality time with the kids and have them see things in the world.

Looking back, I’d make the same decision again. I’ll be a little jealous of you early retirees, but I’m good with what we’ve been able to see/do.

My biggest fear is how I’ll end up having to pay for all of the single income families in my neighborhood that somehow can afford to drive $100,000+ SUVs and go on $20,000 vacations. At some point, that shit is going to end up costing all of the responsible folks. I hope I’m wrong,

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I’m with you VoR, though hopefully on closer to the 62-65 timeline than the 65-67 one.

Posted by DocWalk20 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DocWalk20' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 13:54:23, in reply to "I’m on the 65-67 trajectory. 3 kids going to college soon is expensive. We also made a conscious "

We too have done bigger, slightly spendier family vacations as our kids got older and into college even. Still planning one more to Europe hopefully next year that got pushed back by an unplanned but ultimately good job change / move this year.

Also needing to purchase a new home still and fully contemplating the wide range of price options and what they can and can’t get us. As much as I like the concept of keeping housing costs (much?) lower than we can afford, we want to enjoy the time we do spend at home which includes some working from home time as well.

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Yeah—it’s all a balance, and the goal is to have the happiest and most fulfilling life

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:06:38, in reply to "I’m on the 65-67 trajectory. 3 kids going to college soon is expensive. We also made a conscious "

As mentioned below, you could live an incredibly simple life to maximize savings and retire earlier. But I think most people would enjoy their life more if they balance saving for the future with spending on things you enjoy today. And exactly where that balance is will depend on a bunch of factors thst are different for everyone. There’s no one right answer.

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As Ive said previously, my kids’ college set me back $500,000*

Posted by Stu <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Stu' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:02:07, in reply to "I’m on the 65-67 trajectory. 3 kids going to college soon is expensive. We also made a conscious "

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Chicken Little poster child

Same. I can retire at 55 so I have 3 years. I will have to do something part time

Posted by Tbag <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Tbag' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 14:00:19, in reply to "It is not healthy how much I’m thinking about retirement "

would not be a full retirement. Wife is a year younger than me so she has 4 years we work at the same company. I feel the clock ticking in my head every day

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Just turned 55.

Posted by KingTalkyTiki <iframe src='https://mb.boardhost.com/TheDeuce/info/user=KingTalkyTiki' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 14:09:47, in reply to "Same. I can retire at 55 so I have 3 years. I will have to do something part time"

I am not retired. *kicks rock*

"You must own the honor of being the whitest, military vet, fat, multiple state property owner but most of all the one who hates their own country the most in our country."

Same boat here*

Posted by Chilango <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Chilango' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 6:47:30, in reply to "Same. I can retire at 55 so I have 3 years. I will have to do something part time"

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would not be a full retirement. Wife is a year younger than me so she has 4 years we work at the same company. I feel the clock ticking in my head every day

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same. i play out several scenarios far too frequently vs what is realistic with the ages of my kids

Posted by lcubed <iframe src='https://mb.boardhost.com/TheDeuce/info/user=lcubed' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:59:19, in reply to "It is not healthy how much I’m thinking about retirement "

scenario 1 is the ability to buy about 3 years of time at about $20k, then i have 1 year of sick time that would count, so i could theoretically retire in 6 years at age 51 with 30 years credit. my oldest would be 20 and youngest would be 12

scenario 2 is not buying the time so having to extend the 6 years to 9.

scenario 3 is working until my youngest is 22 so another 16 years. that would give me 37 years into the system which i think is what is needed to max out my pension but that's a really tough thought to have to work 16 more years at least doing what i'm doing now/have been doing my entire career

i find myself landing in maybe the 10-ish range, retiring and then maybe doing something else that would hopefully be less stressful until my youngest would be about 22

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I am mostly just fixated on the fact that like half my net worth is in real estate.

Posted by gvibes <iframe src='https://mb.boardhost.com/TheDeuce/info/user=gvibes' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:49:29, in reply to "It is not healthy how much I’m thinking about retirement "

That seems really dumb but I either would need to sell the LAKE HOUSE or borrow against them, but I don't want to do the former and the latter seems dumb at current rates.

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I mean, like 80% of my net worth is in my retirement accounts*

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 13:27:17, in reply to "I am mostly just fixated on the fact that like half my net worth is in real estate."

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That seems really dumb but I either would need to sell the LAKE HOUSE or borrow against them, but I don't want to do the former and the latter seems dumb at current rates.

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“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Thinking about it stresses me out way too much.

Posted by OB25 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=OB25' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:44:31, in reply to "It is not healthy how much I’m thinking about retirement "

I end up going back and forth between two negative thoughts:

1) I am not doing enough to save money in the most effective way now and will regret it later.

2) I’m going to end up dead before I even get to take advantage of these savings and I should have done more to enjoy life in my younger/middle-aged years rather than saving money that I may never get to use.

Eat at Arby’s.

When something is happening, young people like to say it’s “lit.”

I just put in my 4 year retirement notice to my school, so my clock is ticking. Met w/my financial

Posted by OWWDig <iframe src='https://mb.boardhost.com/TheDeuce/info/user=OWWDig' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:43:18, in reply to "It is not healthy how much I’m thinking about retirement "

advisor yesterday and he says my plan is in a good place. It's going to be hard to not think about it over the next 4 years.

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If we stop moving states all the time like idiots, my wife’s teacher pension will be a big key

Posted by snipes824 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=snipes824' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 12:07:59, in reply to "I just put in my 4 year retirement notice to my school, so my clock is ticking. Met w/my financial"

to retiring well.

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advisor yesterday and he says my plan is in a good place. It's going to be hard to not think about it over the next 4 years.

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Yea. Definitely was a perk that drew me to the profession *

Posted by OWWDig <iframe src='https://mb.boardhost.com/TheDeuce/info/user=OWWDig' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 12:09:31, in reply to "If we stop moving states all the time like idiots, my wife’s teacher pension will be a big key"

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to retiring well.

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advisor yesterday and he says my plan is in a good place. It's going to be hard to not think about it over the next 4 years.

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I've just been thinking about where to live once we retire

Posted by ISeeDeadHawkeyes <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ISeeDeadHawkeyes' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:21:04, in reply to "It is not healthy how much I’m thinking about retirement "

Once kid is out of the house and done with college and we retire, the plan is to take all of the equity in the house and try to cash it out to outright buy a house somewhere.

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Our family owns two houses next door to each other on our block...

Posted by haighter <iframe src='https://mb.boardhost.com/TheDeuce/info/user=haighter' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:40:04, in reply to "I've just been thinking about where to live once we retire"

Our idea is to keep them both forever an eventually give one to one kid (the one we live in) and the other, larger, one to the other kid.

But the retirement plan isn't to fully move, but spend a month here or there in longer term rentals. Spend a month in NYC, a month in Mexico, a month in London, etc.

Just kinda bounce around without actually needing to maintain a secondary house somewhere...we already have a home in Tahoe that will require our maintenance and attention.

But pic a spot or two a year to try out.

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Once kid is out of the house and done with college and we retire, the plan is to take all of the equity in the house and try to cash it out to outright buy a house somewhere.

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There are days where I feel like i'm way ahead of target and peers by age 40

Posted by John Coctostan <iframe src='https://mb.boardhost.com/TheDeuce/info/user=John+Coctostan' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:40:58, in reply to "It is not healthy how much I’m thinking about retirement "

there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

I was the idiot who didn’t start putting away into a 401k until age 29, so my compounding is behind

Posted by snipes824 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=snipes824' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:41:32, in reply to "There are days where I feel like i'm way ahead of target and peers by age 40"

55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

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there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

29 is still pretty early. My employer didn't even offer a 401k until I was 27 and didn't match until

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 13:26:33, in reply to "I was the idiot who didn’t start putting away into a 401k until age 29, so my compounding is behind"

I was probably 29.

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55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

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there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Still annoyed that my employer of the previous 10+ years cut its match soon after I started working

Posted by DocWalk20 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DocWalk20' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 13:39:27, in reply to "29 is still pretty early. My employer didn't even offer a 401k until I was 27 and didn't match until"

there. As of February I’m finally back with an employer that does match. #freemoney is good

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I was probably 29.

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55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

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there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

Both my current and previous employer have pretty generous matches plus a profit share kicker.

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 13:56:15, in reply to "Still annoyed that my employer of the previous 10+ years cut its match soon after I started working "

They match up to 4 or 5% of my income plus the 5% profit share. That's a lot of #freemoney.

And I've had HSAs for the last 10-15 years too. So I've built up pretty good reserves there too. AND I save my medical receipts for future withdrawals from the HSA, which is a bit of a PITA but doable with smartphones and programs like Evernote.

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there. As of February I’m finally back with an employer that does match. #freemoney is good

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I was probably 29.

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55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

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there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

The HSA receipt thing is one thing I don't do that I'm just never going to.

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 14:07:21, in reply to "Both my current and previous employer have pretty generous matches plus a profit share kicker."

Keeping receipts for a long period of time and then going back in and actually having the discipline to enter them just has too high of a risk of me just never doing it.

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there. As of February I’m finally back with an employer that does match. #freemoney is good

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I was probably 29.

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55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

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there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

I figure I can just use it to pay my old age medical expenses and not have to worry about it now*

Posted by illinibone <iframe src='https://mb.boardhost.com/TheDeuce/info/user=illinibone' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 19:27:28, in reply to "The HSA receipt thing is one thing I don't do that I'm just never going to."

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Keeping receipts for a long period of time and then going back in and actually having the discipline to enter them just has too high of a risk of me just never doing it.

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there. As of February I’m finally back with an employer that does match. #freemoney is good

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I was probably 29.

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55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

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there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

Step 1 - install tampermonkey: https://www.tampermonkey.net/index.php
Step 2 - install this script: https://greasyfork.org/en/scripts/577609-boardhost-idiot-hider
Step 3 - Add/modify user list

You can but you can also use it to pay for all expenses tax free if you account for your medical

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 7:27:31, in reply to "I figure I can just use it to pay my old age medical expenses and not have to worry about it now*"

expenses now and apply future disbursements to them.

Basically it's a way to get free money before you tap into your actual retirement accounts or regular accounts.

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Keeping receipts for a long period of time and then going back in and actually having the discipline to enter them just has too high of a risk of me just never doing it.

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there. As of February I’m finally back with an employer that does match. #freemoney is good

Previous Message

I was probably 29.

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55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

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there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Yes, I'm just planning that when I'm old and in memory care, my HSA still won't cover the

Posted by illinibone <iframe src='https://mb.boardhost.com/TheDeuce/info/user=illinibone' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 15:21:59, in reply to "You can but you can also use it to pay for all expenses tax free if you account for your medical "

$12k/month or whatever at 2026 prices.

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expenses now and apply future disbursements to them.

Basically it's a way to get free money before you tap into your actual retirement accounts or regular accounts.

Previous Message

Keeping receipts for a long period of time and then going back in and actually having the discipline to enter them just has too high of a risk of me just never doing it.

Previous Message

there. As of February I’m finally back with an employer that does match. #freemoney is good

Previous Message

I was probably 29.

Previous Message

55 is way off the table for me. 60 *maybe*, but I’m probably on the 65 trajectory.

Previous Message

there are others where i feel like i'm incredibly far away from being to a point where i'd be comfortable to retire at 55.

Step 1 - install tampermonkey: https://www.tampermonkey.net/index.php
Step 2 - install this script: https://greasyfork.org/en/scripts/577609-boardhost-idiot-hider
Step 3 - Add/modify user list

yeah i did that from day 1 at my job, so since 22. Makes a big difference

Posted by John Coctostan <iframe src='https://mb.boardhost.com/TheDeuce/info/user=John+Coctostan' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:59:00, in reply to "I was the idiot who didn’t start putting away into a 401k until age 29, so my compounding is behind"

by the numbers, i'm ahead of schedule

but then i see people around my age that are spending lavishly, much nicer houses, much nicer vacations, etc. and wonder if i'm somehow way behind. Or if instead, those people just spend 95 cents of every dollar they bring in every month and have nothing really saved up

Probably the latter + potential inheritance.

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 12:05:03, in reply to "yeah i did that from day 1 at my job, so since 22. Makes a big difference"

I have a good buddy that lives like that and is approximately 40. Hadn't really pried on his financials, but was wondering what was the case.

We were riding together on the golf course a few weeks ago and he goes "So tell me about 401ks. Should I be contributing to these?"

I didn't even know how to respond. Turns out after I asked some follow ups, he and his wife have no savings and are tens of thousands of dollars in debt.

People that you might think are successful/smart/appear happy may not be financially literate enough to know they're fucked.

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That's always my assumption too

Posted by John Coctostan <iframe src='https://mb.boardhost.com/TheDeuce/info/user=John+Coctostan' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 12:09:54, in reply to "Probably the latter + potential inheritance."

I have several acquaintances/friends that I know for a fact don't make nearly what we do. and they're building lake houses, private schools for kids, 10 day vacations to disney, etc etc. I don't know how that's at all possible if unless you're basically saving $0

And/or not paying off credit card balances.

Posted by DocWalk20 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DocWalk20' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 13:42:59, in reply to "That's always my assumption too"

The number of people with well paying jobs who accrue credit card interest each month well into their 30s, 40s, and beyond boggles my mind.

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It’s very healthy how much we’re enjoying retirement*

Posted by TarheelIllini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=TarheelIllini' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:17:29, in reply to "It is not healthy how much I’m thinking about retirement "

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Recrudescence

Been reading up on Bogleheads and FIRE (and derivatives)

Posted by Dilbert <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Dilbert' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:16:15, in reply to "It is not healthy how much I’m thinking about retirement "

But that is a ways off for the moment.

FIRE seems to require to much asceticism to be very realistic for me. Both before and in retirement.

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:32:01, in reply to "Been reading up on Bogleheads and FIRE (and derivatives)"

I'd rather live a more normal life, ride the VOO snake, and retire around 60. I feel like I'll have more money built up in the nest egg.

“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

I have a couple of FIRE friends

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:23:36, in reply to "FIRE seems to require to much asceticism to be very realistic for me. Both before and in retirement."

they travel a lot, but their frugalness seems miserable to me.

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I'd rather live a more normal life, ride the VOO snake, and retire around 60. I feel like I'll have more money built up in the nest egg.

That’s basically the conclusion I came to WRT FIRE. To each his or her own though.*

Posted by DocWalk20 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DocWalk20' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:21:29, in reply to "FIRE seems to require to much asceticism to be very realistic for me. Both before and in retirement."

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I'd rather live a more normal life, ride the VOO snake, and retire around 60. I feel like I'll have more money built up in the nest egg.

I love what I do, so I'd probably be doing it in retirement without pay -- so why retire?*

Posted by Quiz <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Quiz' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:09:29, in reply to "It is not healthy how much I’m thinking about retirement "

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Some random stuff I learned that may help people here

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:47:06, in reply to "It is not healthy how much I’m thinking about retirement "

I consider myself pretty on top of personal finance things, but these had slipped past me.

1. Max out your HSA. It can be turned into an IRA when you're old enough. Order should be 1. Get full company match 2. Full HSA contribution 3. Anything else you want to put into IRA/401k.

2. Always donate appreciated stocks before donating cash. Gets you out of capital gains taxes, charity doesn't have to pay them, etc.

3. You actually don't have to pay capital gains taxes if your income is low enough. Something to consider should you retire early and not have normal income.

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2a. consider if a donor advised fund makes sense for charitable giving

Posted by illinibone <iframe src='https://mb.boardhost.com/TheDeuce/info/user=illinibone' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 19:23:32, in reply to "Some random stuff I learned that may help people here"

we double up in even years, take the standard deduction in odd years, and use the DAF to evenly spread our donations across those two years while still seeing growth in them.

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Step 1 - install tampermonkey: https://www.tampermonkey.net/index.php
Step 2 - install this script: https://greasyfork.org/en/scripts/577609-boardhost-idiot-hider
Step 3 - Add/modify user list

Oh and 1a, if your 401k (and your income) supports it, mega backdoor roth*

Posted by illinibone <iframe src='https://mb.boardhost.com/TheDeuce/info/user=illinibone' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 19:25:24, in reply to "2a. consider if a donor advised fund makes sense for charitable giving"

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we double up in even years, take the standard deduction in odd years, and use the DAF to evenly spread our donations across those two years while still seeing growth in them.

Previous Message

Step 1 - install tampermonkey: https://www.tampermonkey.net/index.php
Step 2 - install this script: https://greasyfork.org/en/scripts/577609-boardhost-idiot-hider
Step 3 - Add/modify user list

How does something like Mega Backdoor Roth sit vs saving on 529?

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:17:37, in reply to "Oh and 1a, if your 401k (and your income) supports it, mega backdoor roth*"

Right now our order is:

1. Company Match
2. HSA max
3. Max 401ks
4. 529s

I’ve always assumed 529s before Mega Backdoor Roth (plus it’s just easier) but haven’t really done the due diligence on it. If I’m thinking about it right, both contribution are after tax and both let you withdraw gains tax free. But 529s also give you a state tax break on the front end, so as long as you feel confident you’ll need it for college, 529 should be the way to go?

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we double up in even years, take the standard deduction in odd years, and use the DAF to evenly spread our donations across those two years while still seeing growth in them.

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I live in an income tax free-ish state(*), so 529s are less interesting.

Posted by illinibone <iframe src='https://mb.boardhost.com/TheDeuce/info/user=illinibone' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 15:20:50, in reply to "How does something like Mega Backdoor Roth sit vs saving on 529?"

* - Cap gains >250k are taxed at 10% with no offset for loss, and income >1M is set to be taxed at 10% in 2028 (and if they're cap gains, you're effectively double taxed).

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we double up in even years, take the standard deduction in odd years, and use the DAF to evenly spread our donations across those two years while still seeing growth in them.

Previous Message

Step 1 - install tampermonkey: https://www.tampermonkey.net/index.php
Step 2 - install this script: https://greasyfork.org/en/scripts/577609-boardhost-idiot-hider
Step 3 - Add/modify user list

Late night, come home, work sucks, I know*

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:41:52, in reply to "It is not healthy how much I’m thinking about retirement "

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I think about it all day every day*

Posted by Stu <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Stu' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:57:43, in reply to "It is not healthy how much I’m thinking about retirement "

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Chicken Little poster child

ADIDAR*

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:25:17, in reply to "I think about it all day every day*"

[Stu] no idea [/Stu]

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

No idea. NIKER? NEW BALANCER?

Posted by Stu <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Stu' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:27:13, in reply to "ADIDAR*"

HOKAR?

Chicken Little poster child

I'm trying to not allow myself to do that.

Posted by EffinIllini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=EffinIllini' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:33:13, in reply to "It is not healthy how much I’m thinking about retirement "

While we're in a decent financial position, we don't make big money nor have pensions. I can't see retiring for at least another 10 years, probably a dozen or more until I'm into my mid-60's.

It's all just a bit depressing.

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same - trying to make it another 10 years myself.....*

Posted by bulldogmba <iframe src='https://mb.boardhost.com/TheDeuce/info/user=bulldogmba' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:23:07, in reply to "I'm trying to not allow myself to do that."

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Yep, same here as well. MrsHarb can retire now but will probably teach two more years. *

Posted by harb <iframe src='https://mb.boardhost.com/TheDeuce/info/user=harb' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:41:21, in reply to "same - trying to make it another 10 years myself.....*"

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[Assassin] Harb is the epitome of a Goldfish Troll.
[Opey] Assholes gonna asshole
[tiki] #### all the way off with that, you bloodthirsty hilljack.

I put everything into SPCX, so I'm sure i'll be able to retire soon. I haven't checked it lately,

Posted by doubledown <iframe src='https://mb.boardhost.com/TheDeuce/info/user=doubledown' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:32:13, in reply to "It is not healthy how much I’m thinking about retirement "

but I'm sure it's going to the moon as we speak.

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30 minutes doing that is much healthier than 30 minutes of doomscrolling. *

Posted by ghost_of_clt <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ghost_of_clt' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:32:09, in reply to "It is not healthy how much I’m thinking about retirement "

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N U D E S I N B I O

It is not healthy how much I’m thinking about a life of crime.

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:16:35, in reply to "It is not healthy how much I’m thinking about retirement "

I made the mistake of reading a reddit thread about job seeking last night. I'm probably as secure in my current position as anyone could be, which means it's 50/50 whether I still have a job in a year. I have no idea what I would do if I did get let go, but there's a good chance it wouldn't be legal.

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

This is interesting. Do you have an example?*

Posted by Warrin'_Illini $<iframe src='https://mb.boardhost.com/TheDeuce/info/user=Warrin\'_Illini' width='330' height='300' border=0 style='border:none;'>$ on June 23, 2026, 9:45:56, in reply to "It is not healthy how much I’m thinking about a life of crime."

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You cannot lose games in the NFL and still win.

Ideally, I would take shit from those who wouldn't miss it.

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:08:32, in reply to "This is interesting. Do you have an example?*"

Wealth redistribution on a nano level.

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

I'm literally not sure if you're being serious

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:24:47, in reply to "Ideally, I would take shit from those who wouldn't miss it."

or just referencing the plotline of Your Friends & Neighbors.

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Wealth redistribution on a nano level.

mostly the latter

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:38:30, in reply to "I'm literally not sure if you're being serious"

if I ever tried to pull a Coop, I'd be in prison within a week

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

It's a good show

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 13:27:07, in reply to "mostly the latter"

but the idea that none of these rich people have cameras is pretty ridiculous.

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if I ever tried to pull a Coop, I'd be in prison within a week

Imma start doing that I think.*

Posted by Warrin'_Illini $<iframe src='https://mb.boardhost.com/TheDeuce/info/user=Warrin\'_Illini' width='330' height='300' border=0 style='border:none;'>$ on June 23, 2026, 10:29:50, in reply to "Ideally, I would take shit from those who wouldn't miss it."

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Wealth redistribution on a nano level.

You cannot lose games in the NFL and still win.

Have you seen Your Friends and Meighbors?*

Posted by Sounder <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sounder' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:59:22, in reply to "It is not healthy how much I’m thinking about a life of crime."

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one of my faves

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:24:38, in reply to "Have you seen Your Friends and Meighbors?*"

Apple TV's really on a heater

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

skateboarding is not a crime sammich*

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:31:43, in reply to "It is not healthy how much I’m thinking about a life of crime."

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“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

Selling swatches of reflecting pool detritis on eBay? *

Posted by doubledown <iframe src='https://mb.boardhost.com/TheDeuce/info/user=doubledown' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:20:30, in reply to "It is not healthy how much I’m thinking about a life of crime."

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Soon I'll be selling whatever I can spare on ebay

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:27:11, in reply to "Selling swatches of reflecting pool detritis on eBay? *"

because my collection of gig jobs won't quite make ends meet.

I'll take a shift on Rover to watch my friend's pets while they're out driving for Uber. Then I'll order some Doordash so I can talk to my other friend, but not for too long. They've got three more deliveries in their car, and if they don't get 5 stars they might as well get 0.

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

I feel you. I have about the same amount of time left and think about it every day.

Posted by PapaDels <iframe src='https://mb.boardhost.com/TheDeuce/info/user=PapaDels' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:14:57, in reply to "It is not healthy how much I’m thinking about retirement "

It isn’t helping that two good friends are retiring this year and another just moved to where I plan to retire. I’m very happy for them, and I’m also envious.

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I have schweppervessence and wessonality.
Too sweet to be sour, too nice to be mean.

same, but I've got 20+ years to go

Posted by IlliniSax05 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=IlliniSax05' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:07:07, in reply to "It is not healthy how much I’m thinking about retirement "

i often find myself looking at retirement account calculators to have an idea of how much I might have when the time comes, how much income that might generate, etc.

I just don't want to have to work

Why do you hate me, Sammich?

MAJOR UPDATE: "Maybe you're not such a bad egg, Lisle-y"
-Sammich, 1/15/2011

Oof, that’s rough. I’d never really thought about it until recently

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:20:09, in reply to "same, but I've got 20+ years to go"

The whole DOGE experience kind of broke me. First by making me leave the career where I had deep roots and a strong sense of purpose. My new job is good but I’m just not as connected with it, so I’m psychologically much more viewing it just as a way to pay the bills as opposed to a career or a calling.

And on top of that, I had to look at the possibility of losing my job which made me realize I was a lot closer to being able to retire than I’d thought. Really just need to get Sprout through college and then financially it will be doable. But have another couple of years to be able to access my retirement accounts without penalty, which will probably be the limiting factor, unless there’s a real Great Depression level market meltdown.

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I assume you're aware of the Rule of 55?

Posted by Tortillini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Tortillini' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:26:54, in reply to "Oof, that’s rough. I’d never really thought about it until recently "

https://smartasset.com/retirement/401k-55-rule

Yeah, but unfortunately that doesn’t help me since I just started a new job

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:04:17, in reply to "I assume you're aware of the Rule of 55?"

No retirement savings in my current gig.

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https://smartasset.com/retirement/401k-55-rule

Ah, that's right. Boo-urns.*

Posted by Tortillini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Tortillini' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:14:21, in reply to "Yeah, but unfortunately that doesn’t help me since I just started a new job"

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No retirement savings in my current gig.

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https://smartasset.com/retirement/401k-55-rule

I'm in the same boat but a few years further off.

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 7:52:55, in reply to "It is not healthy how much I’m thinking about retirement "

Lately I've been coming across people my parent's age that are still working and say they can't imagine what they'd do if they retired. Just can not even comprehend that mentality. My poor in-laws haven't taken vacations in years because my father in law needs to "watch the markets". Guy trades a couple dozen shares a day and bullshits with his friends all day on the phone.

Anything in particular out there content wise that's caught your eye?

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Agree that I just don’t get that mentality

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:14:19, in reply to "I'm in the same boat but a few years further off."

I can understand that it’s a big transition and you need to be mentally prepared and able to find things that you think are meaningful to occupy your time, as opposed to just sitting around doing nothing. But I think I’ll be able to do that, and don’t define myself by my job.

The best financial planning/retirement presenter I’ve found is Erin Talks Money. She is really good at explaining content clearly and isn’t trying to scare you or drum up investment business, and is much less click-bait than most, although there’s a bit of that.

https://m.youtube.com/@ErinTalksMoney?ra=m

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Every now and then I'll start to think about "What if we just pulled the trigger now and moved to Thailand... we could find some good schools for the kids... right?"

Which is completely impractical for a huge number of reasons but I still think about it. Lately I've been coming across people my parent's age that are still working and say they can't imagine what they'd do if they retired. Just can not even comprehend that mentality. My poor in-laws haven't taken vacations in years because my father in law needs to "watch the markets". Guy trades a couple dozen shares a day and bullshits with his friends all day on the phone.

Anything in particular out there content wise that's caught your eye?

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I like her content. I also like The Money Guys, who are kinda geared towards 30 and 40 year olds

Posted by ATL <iframe src='https://mb.boardhost.com/TheDeuce/info/user=ATL' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:39:26, in reply to "Agree that I just don’t get that mentality "

but they offer very grounded, sensible advice on how to get rich slowly.

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“We are old and tired and just want to be taken care of.” - Republican voter, Dec. 2024.

I don't know how I found them, but I've listened to quite a bit of the Retirement Nerds podcast

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:48:07, in reply to "Agree that I just don’t get that mentality "

Which is a little weird because the sidekick guy sounds EXACTLY like Ryan Reynolds.

Any good retirement PLACE content you've seen? Right now that's mostly just House Hunters International TV shows and the like and international living website. Tort and I are on the "hey, let's do a bunch of this retirement abroad" kick, so welcome to the club!

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As far as place content, there’s a ton of AI generated stuff

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 7:19:53, in reply to "I don't know how I found them, but I've listened to quite a bit of the Retirement Nerds podcast"

Videos where it’s obvious someone just prompted a model to score places on 4 or 5 metrics then summarize the top 5 or 10 in a video. Thise aren’t bad but have the methodology weaknesses of those sorts of top 10 cities type rankings that you see, plus I don’t completely trust that the scoring is actually valid.

As far as real human content, I like this guys videos about Italy:

https://m.youtube.com/@ANewLifeinItaly?ra=m

The production value varies from cheesy to non-existent, he looks like a slob just recording under a bare bulb in his kitchen or something, but the actual information content is good, and highlights places that aren’t in everyone else’s lists. I’ve also seen a guy that goes around to off the beaten path places, tours a for sale property or two, and eats at a local restaurant. If you like house hunters I could track him down—it’s more in that vein.

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Cool thanks. I’ll take a look. And yeah the AI generated stuff is the stuff I’m trying to weed out*

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:13:27, in reply to "As far as place content, there’s a ton of AI generated stuff"

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This is the houses and food guy

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 24, 2026, 8:17:05, in reply to "Cool thanks. I’ll take a look. And yeah the AI generated stuff is the stuff I’m trying to weed out*"

https://m.youtube.com/@Justdreamitaly?ra=m

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With the curbs on Golden Visas and tax headaches and whatnot I'm leaning heavily towards slow travel

Posted by Tortillini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Tortillini' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:56:47, in reply to "I don't know how I found them, but I've listened to quite a bit of the Retirement Nerds podcast"

rather than buying a place overseas (for either full or part-time living).

But I absolutely do still check out real estate listings abroad from time to time.

My wife will hopefully be getting Italian citizenship later this year which will open options

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 9:26:18, in reply to "With the curbs on Golden Visas and tax headaches and whatnot I'm leaning heavily towards slow travel"

But I don’t think I’d want to live permanently in a place where English wasn’t the local language. I feel like that would just add too much friction and close off a lot of interaction and social channels. Yeah, I could learn enough Italian to get by, but that’s very different than really being able to communicate interact in a substantive way with people.

Plus permanent residence would subject us to Euro tax rates, which are way higher than US rates and more than offset any cost of living savings.

But I’d definitely be interested in long travel or getting an apartment to use as a vacation home and base to travel around Europe. One hurdle there would be pets—we’ve always had dogs and that seems like it would make extended travel impossible.

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rather than buying a place overseas (for either full or part-time living).

But I absolutely do still check out real estate listings abroad from time to time.

The pet thing is definitely an obstacle.*

Posted by Tortillini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Tortillini' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:38:43, in reply to "My wife will hopefully be getting Italian citizenship later this year which will open options"

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rather than buying a place overseas (for either full or part-time living).

But I absolutely do still check out real estate listings abroad from time to time.

Yep same.*

Posted by Carl Spackler <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Carl+Spackler' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:58:25, in reply to "With the curbs on Golden Visas and tax headaches and whatnot I'm leaning heavily towards slow travel"

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rather than buying a place overseas (for either full or part-time living).

But I absolutely do still check out real estate listings abroad from time to time.

My dad is 80…has been semi-retired for 15 or so years (with a part time job)…

Posted by haighter <iframe src='https://mb.boardhost.com/TheDeuce/info/user=haighter' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:40:44, in reply to "Agree that I just don’t get that mentality "

Recently fully retired and is going downhill quick.

It’s a real chicken or the egg situation.

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Conversely...

Posted by EffinIllini <iframe src='https://mb.boardhost.com/TheDeuce/info/user=EffinIllini' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:48:52, in reply to "My dad is 80…has been semi-retired for 15 or so years (with a part time job)…"

but first - Sorry about your Dad, haighter. I know it does go that way sometimes.

Maybe we've just been lucky, but my Dad took an early retirement at age 51 worked part time refueling outages for contractors at the nuke plant (60 hours for 4 weeks every 9 months) and then maybe 15-20 hours a week at the golf course for the next 10-15 years. Probably fully retired for the last 10-15 years. Now 81 and doing great (outside of his treatable afib). Planning another RV trip west this fall.

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Recently fully retired and is going downhill quick.

It’s a real chicken or the egg situation.

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I've been thinking about semi-retirement a lot. Unfortunately I don't think there

Posted by Warrin'_Illini $<iframe src='https://mb.boardhost.com/TheDeuce/info/user=Warrin\'_Illini' width='330' height='300' border=0 style='border:none;'>$ on June 23, 2026, 8:43:07, in reply to "My dad is 80…has been semi-retired for 15 or so years (with a part time job)…"

are many part-time jobs that give you health insurance.

Kevin Spacey seemed pretty damn happy when he quit his white collar job and started flipping burgers in American Beauty. Color me intrigued.

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Recently fully retired and is going downhill quick.

It’s a real chicken or the egg situation.

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You cannot lose games in the NFL and still win.

If I can figure out health insurance in "early" retirement, I'd be content with working...

Posted by haighter <iframe src='https://mb.boardhost.com/TheDeuce/info/user=haighter' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 13:24:47, in reply to "I've been thinking about semi-retirement a lot. Unfortunately I don't think there"

...at a record shop. Just listent to music and alphabatize records all day long.

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are many part-time jobs that give you health insurance.

Kevin Spacey seemed pretty damn happy when he quit his white collar job and started flipping burgers in American Beauty. Color me intrigued.

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Recently fully retired and is going downhill quick.

It’s a real chicken or the egg situation.

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Yeah—a phased retirement with a part time gig would be pretty ideal

Posted by DT <iframe src='https://mb.boardhost.com/TheDeuce/info/user=DT' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 10:01:33, in reply to "I've been thinking about semi-retirement a lot. Unfortunately I don't think there"

But I have no idea whether I could find a part time gig that was anything I actually wanted to do. I’d be doing that less for the money and more to stay mentally engaged and have an opportunity to do something interesting but without the stress or responsibility.

Depending on the remainder of my full time career, I might be able to get a think tank gig, which would be sweet. Not sure what other options there might be.

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are many part-time jobs that give you health insurance.

Kevin Spacey seemed pretty damn happy when he quit his white collar job and started flipping burgers in American Beauty. Color me intrigued.

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Recently fully retired and is going downhill quick.

It’s a real chicken or the egg situation.

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I like to think that when I retire I'll get a part time gig at a lego store

Posted by IlliniSax05 <iframe src='https://mb.boardhost.com/TheDeuce/info/user=IlliniSax05' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:44:47, in reply to "Yeah—a phased retirement with a part time gig would be pretty ideal"

mostly for the discounts

Why do you hate me, Sammich?

MAJOR UPDATE: "Maybe you're not such a bad egg, Lisle-y"
-Sammich, 1/15/2011

I could do the part time thing if I moved somewhere that I really wanted to live

Posted by IlliniOllie <iframe src='https://mb.boardhost.com/TheDeuce/info/user=IlliniOllie' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 11:05:41, in reply to "Yeah—a phased retirement with a part time gig would be pretty ideal"

find something to do in some mountain town in Colorado, and go home to that every night? Fine by me.

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are many part-time jobs that give you health insurance.

Kevin Spacey seemed pretty damn happy when he quit his white collar job and started flipping burgers in American Beauty. Color me intrigued.

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Recently fully retired and is going downhill quick.

It’s a real chicken or the egg situation.

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Don't forget to extort your boss for two years' severance.

Posted by Sammich <iframe src='https://mb.boardhost.com/TheDeuce/info/user=Sammich' width='330' height='300' border=0 style='border:none;'> on June 23, 2026, 8:50:36, in reply to "I've been thinking about semi-retirement a lot. Unfortunately I don't think there"

IIRC, his salary in that movie was something like $60K, which seemed like a lot at the time.

And stay the fuck away from your closeted neighbor!

I want to break it up
I want to smash it up
I want to #### it up
I want to watch it come down

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