I accidentally retired, and need tax advice

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Topic Author
Mattzees
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I accidentally retired, and need tax advice

Post by Mattzees »

I've got myself into a bit of a situation. It seems I've retired without meaning to. This isn't a bad thing, but it put me in sort of a feedback loop with my taxes.

I'm 49 years old. I have no IRA. I have a portfolio of 50/50 stock/bond funds. I own some real estate, and that's why the portfolio is a little heavy on the bonds.

My portfolio generates about $22K/year in ordinary dividends. Those are automatically reinvested, but obviously they count as income, and I have to pay taxes on them.

I have a couple of rental properties that gross $24K/year, which is the only cash I have coming in, and which also gets taxed.

So, I have a bunch of income, but very little actual cash flowing in. I'm dipping into my savings $10K to $15K per year just to live and pay taxes. I can probably do that for another five or ten years while the portfolio grows, then I would have to start drawing from it to live and pay taxes.

I wasn't prepared for this to happen now. I had planned on having more cash coming in for a few more years before I stopped working, but that's not how it went.

Should I invest my entire cash reserve into the portfolio right now and start drawing from the portfolio, or keep living off the cash reserve and let the portfolio grow more before drawing from it? Other options?
triggertreat
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Re: I accidentally retired, and need tax advice

Post by triggertreat »

Go back to work? What do you mean accidentally retired?
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BL
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Re: I accidentally retired, and need tax advice

Post by BL »

One possibility: don't reinvest dividends. Spend them for now.

Get a job, even low-pay part-time to lessen need for more cash.
Topic Author
Mattzees
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Re: I accidentally retired, and need tax advice

Post by Mattzees »

"Accidentally retired" means I closed up a tech business. Did some real estate. Planned on going back to work in tech, but after having spent a few years with real estate, I realized my skillset was badly dated and I'm about to turn fifty. I might buy and rehab another house at some point, but not now. Trying to make this work as-is. It seems some people can do it. I'm wondering how they structure their finances. I have no debt, and already live very frugally. It's the taxes that are getting me.
Last edited by Mattzees on Tue May 14, 2019 6:53 pm, edited 1 time in total.
IngognitoUSA
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Re: I accidentally retired, and need tax advice

Post by IngognitoUSA »

triggertreat wrote: Tue May 14, 2019 6:38 pm Go back to work? What do you mean accidentally retired?
I have heard of getting accidentally pregnant but not accidentally retired.
tesuzuki2002
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Re: I accidentally retired, and need tax advice

Post by tesuzuki2002 »

IngognitoUSA wrote: Tue May 14, 2019 6:49 pm
I have heard of getting accidentally pregnant but not accidentally retired.

:oops: :oops:
arf30
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Re: I accidentally retired, and need tax advice

Post by arf30 »

Would probably spend the dividends instead of reinvesting, possibly converting some savings to more bonds, and get some part time work to cover any shortfall. You should be in a low tax bracket and not too concerned about taxes unless you've left out some details.
Topic Author
Mattzees
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Re: I accidentally retired, and need tax advice

Post by Mattzees »

When you realize you haven't been working in your chosen field for a few years, you've accidentally retired. Never got anyone accidentally pregnant, but I accidentally retired. Whatever. I'm figuring on getting some part-time work, but would love to keep that to a minimum.

I guess my question is how do you structure your finances? You're working to pay taxes on the income generated by the investments? How do you feel about tax-exempt bond funds vs non-exempt in this situation?
Last edited by Mattzees on Tue May 14, 2019 9:07 pm, edited 1 time in total.
michaeljc70
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Re: I accidentally retired, and need tax advice

Post by michaeljc70 »

As another poster said, stop reinvesting the dividends.

You say the properties gross 24k and you pay taxes on that, but there has to be expenses.

I am not sure why owning real estate would encourage a 50/50 AA. I would consider the real estate closer to fixed income than equities.

If you are cutting it close (which it sounds like may be the case since this was accidental), a 50/50 AA is pretty conservative.

I am not sure what you mean by "cash reserves". Is this counted as part of the 50% fixed income?

I believe I also "accidentally" retired if that is any consolation. I actually think I retired 2.5 years ago and the 5 months I worked in that time was a fluke :shock: . Also in tech.
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segfault
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Re: I accidentally retired, and need tax advice

Post by segfault »

Second the idea to turn off dividend reinvestment.
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FIREchief
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Re: I accidentally retired, and need tax advice

Post by FIREchief »

There is a lot of honest work out there these days for somebody willing to work 40 hours per week to earn $25K per year. Perhaps that would allow you to continue to reinvest your dividends and maybe adopt a slightly more aggressive AA for an eventual "real" retirement.
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Katietsu
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Re: I accidentally retired, and need tax advice

Post by Katietsu »

You should only be in the 12% tax bracket based on what you posted. Therefore, tax exempt bond funds would net you less money and seems like a bad idea.

How much cash reserves do you have? Is this where the $10k to $15k is coming from?
Topic Author
Mattzees
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Re: I accidentally retired, and need tax advice

Post by Mattzees »

michaeljc70 wrote: Tue May 14, 2019 7:04 pm I believe I also "accidentally" retired if that is any consolation. I actually think I retired 2.5 years ago and the 5 months I worked in that time was a fluke :shock: . Also in tech.
Yeah, tech is crazy. I was freelance, and the time flew by. Not looking to learn the latest, newest, trendy things anymore. Don't want to upgrade my laptop every single year to look sharp in client meetings. :happy
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Mattzees
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Re: I accidentally retired, and need tax advice

Post by Mattzees »

Katietsu wrote: Tue May 14, 2019 7:11 pm How much cash reserves do you have? Is this where the $10k to $15k is coming from?
Yes. I have over $100K in cash. I've always kept a large reserve around for real estate purchases. Hadn't planned on living off it, but I guess that's why we have reserves.
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bampf
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Re: I accidentally retired, and need tax advice

Post by bampf »

What kind of tech? The whole world is moving cloudy, so the laptop thing is just a portal to get into the cloud. My Macbook Air circa 2013 is just fine. Understand not wanting to learn the latest and greatest. That being said, you can still do cobol and mainframes in the tech world. Its a big world. Can understand not wanting to work. Can understand not needing to work. Hard to understand being in tech and not being able to find anything. Sure, it depends on what you do, how you present yourself and where you are located, but, there are opportunities....
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lostdog
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Re: I accidentally retired, and need tax advice

Post by lostdog »

You can get an IT help desk job atleast. Maybe just some workstation support etc...
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GCD
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Re: I accidentally retired, and need tax advice

Post by GCD »

Congrats on your retirement. :beer
Jack FFR1846
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Re: I accidentally retired, and need tax advice

Post by Jack FFR1846 »

How about accidentally go into Home Depot and get a job?

Everyone's hiring. I walk at lunch. Only what I noticed today for help wanted signs....Marshalls, Stop & Shop, Papa Ginos, the car wash at Jiffy Lube.......
Last edited by Jack FFR1846 on Tue May 14, 2019 7:30 pm, edited 1 time in total.
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michaeljc70
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Re: I accidentally retired, and need tax advice

Post by michaeljc70 »

bampf wrote: Tue May 14, 2019 7:19 pm What kind of tech? The whole world is moving cloudy, so the laptop thing is just a portal to get into the cloud. My Macbook Air circa 2013 is just fine. Understand not wanting to learn the latest and greatest. That being said, you can still do cobol and mainframes in the tech world. Its a big world. Can understand not wanting to work. Can understand not needing to work. Hard to understand being in tech and not being able to find anything. Sure, it depends on what you do, how you present yourself and where you are located, but, there are opportunities....
Not the OP but in a similar situation. Of course I can find a job. Making what I made 20 years ago (I do freelance consulting). Not going to do it if I don't have to. I would have liked to work another 2 years or so. Companies are cutting costs and will hire someone with 5 years experience (vs. 20) and figure that is good enough (and pay accordingly). Frankly, maybe they are good enough. The focus is also on what technical "skills" you have and how current they are rather than if you can think, solve problems, understand the business, etc. That has always been the case. It is a place where projects are almost always late, over budget and under deliver. I am speaking about large company IT and not actual software companies.

I've let my skills (at least in a work environment setting) degrade due to long term client needs.
Topic Author
Mattzees
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Re: I accidentally retired, and need tax advice

Post by Mattzees »

bampf wrote: Tue May 14, 2019 7:19 pm What kind of tech? The whole world is moving cloudy, so the laptop thing is just a portal to get into the cloud. My Macbook Air circa 2013 is just fine. Understand not wanting to learn the latest and greatest. That being said, you can still do cobol and mainframes in the tech world. Its a big world. Can understand not wanting to work. Can understand not needing to work. Hard to understand being in tech and not being able to find anything. Sure, it depends on what you do, how you present yourself and where you are located, but, there are opportunities....
Probably a separate convo, but I moved to a city where I'd get paid about 25% of what I used to get paid for the same work (small-med business tech support). Plus, there's not a lot of it here. There are well-paying corporate gigs, but I've never done corporate work in my life, and have no idea how to even talk to those people. During my time off, I've been coding and building my "moonshot" idea, but the reality is that it's a moonshot, it will probably never make any money, and so here I am asking how to minimize my tax burden, so I can continue working on moonshots.
staythecourse
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Re: I accidentally retired, and need tax advice

Post by staythecourse »

Mattzees wrote: Tue May 14, 2019 6:48 pm "Accidentally retired" means I closed up a tech business. Did some real estate. Planned on going back to work in tech, but after having spent a few years with real estate, I realized my skillset was badly dated and I'm about to turn fifty. I might buy and rehab another house at some point, but not now. Trying to make this work as-is. It seems some people can do it. I'm wondering how they structure their finances. I have no debt, and already live very frugally. It's the taxes that are getting me.
I think you need to find some work. How much in SS can you expect? How much premium are you going to pay for medicare when you are eligible? Can you free up the cash or even qualify for a mortgage without income for another rental?

Can you Uber for now until you find some/ any job?

Good luck.
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Kenkat
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Re: I accidentally retired, and need tax advice

Post by Kenkat »

Jack FFR1846 wrote: Tue May 14, 2019 7:28 pm How about accidentally go into Home Depot and get a job?

Everyone's hiring. I walk at lunch. Only what I noticed today for help wanted signs....Marshalls, Stop & Shop, Papa Ginos, the car wash at Jiffy Lube.......
I got a postcard in the mail saying the post office was hiring. After this week at work, I regret not applying. I need to accidentally retire somehow from my current job.
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Re: I accidentally retired, and need tax advice

Post by Dottie57 »

Mattzees wrote: Tue May 14, 2019 7:12 pm
michaeljc70 wrote: Tue May 14, 2019 7:04 pm I believe I also "accidentally" retired if that is any consolation. I actually think I retired 2.5 years ago and the 5 months I worked in that time was a fluke :shock: . Also in tech.
Yeah, tech is crazy. I was freelance, and the time flew by. Not looking to learn the latest, newest, trendy things anymore. Don't want to upgrade my laptop every single year to look sharp in client meetings. :happy
What tech do you know? Maybe others on the site can chime in on whether it is marketable at all.
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arcticpineapplecorp.
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Re: I accidentally retired, and need tax advice

Post by arcticpineapplecorp. »

pull a George Costanza (George go back to work and pretend he never quit):

https://www.youtube.com/watch?v=IW78swzn_Bs
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mhadden1
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Re: I accidentally retired, and need tax advice

Post by mhadden1 »

Mattzees wrote: Tue May 14, 2019 6:35 pm
My portfolio generates about $22K/year in ordinary dividends. Those are automatically reinvested, but obviously they count as income, and I have to pay taxes on them.

I have a couple of rental properties that gross $24K/year, which is the only cash I have coming in, and which also gets taxed.
With 24k in gross rents - there have to be some expenses. Property taxes? Insurance? Maintenance?

With 22k in dividends from the portfolio - aren't at least some qualified, and fitting in the 12% bracket, to be taxed at the 0% rate?
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rkhusky
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Re: I accidentally retired, and need tax advice

Post by rkhusky »

What is your total portfolio value? What are your yearly expenses?

If you are in the 12% tax bracket, long term cap gains and qualified stock dividends are taxed at 0%. Bond dividends, short term cap gains, and non-qualified stock dividends are taxed at 12%. Maximize the former and minimize the latter and your tax bill should be small.
Katietsu
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Re: I accidentally retired, and need tax advice

Post by Katietsu »

Is 24 k your gross rental income or the net that you pay tax on? With rental income the amount taxed is often quite a lot less than the rental payments.

And is the $22k of dividends just the ordinary dividends from the bond portion of your portfolio? Or does it include qualified dividends?

Are you paying taxes on capital gain distributions?

Do you have any money in IRA’s or other tax advantaged accounts?

It doesn’t seem like taxes should be a big concern. But, also, you have not provided enough details to get good advice about any tweaks that could help.
ohai
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Re: I accidentally retired, and need tax advice

Post by ohai »

OP, I am surprised to hear that you are paying taxes on your rental income. I am so used to coastal real estate where almost all show a depreciation or other operational loss that offsets income.
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Watty
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Re: I accidentally retired, and need tax advice

Post by Watty »

One thing you might do as a second career to bring in some income is to manage rental properties for other people. It sounds like you already know how to do that.

A possible downside is that if your are getting your health insurance with an ACA subsidy then you would need to watch your income so that you did not lose the subsidy.

You did not say what your housing situation is or if there are mortgages on the rental property. If you have a mortage then one option would be to pay it off if possible to help improve your cash flow.
Mattzees wrote: Tue May 14, 2019 6:48 pm I'm wondering how they structure their finances.
There are details to work out but when you are running your own business you can put over $50K a year into retirement plans.

It is oversimplified but it sounds like you have taxable accounts so you could spend $50K from that in to live on. If you also ran a business that generated $50K in earnings then you could put that into a retirement plan. Your taxable income would be around zero and your net worth would stay the same too.

The downside is that the taxes are just deferred so you will have to pay them eventually when you withdraw them from your retirement account.
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FIREchief
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Re: I accidentally retired, and need tax advice

Post by FIREchief »

Jack FFR1846 wrote: Tue May 14, 2019 7:28 pm How about accidentally go into Home Depot and get a job?

Everyone's hiring. I walk at lunch. Only what I noticed today for help wanted signs....Marshalls, Stop & Shop, Papa Ginos, the car wash at Jiffy Lube.......
Yeah, this. I'm just not seeing the issue here. Most of us living in the real world who found ourselves unemployed (accidentally, deserved, expected, unexpected, etc.) just went out and found another job. I only had to do it once, but that doesn't change the equation. It's really about more than taxes. It's about generating income until you don't need any more. :moneybag
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retire2022
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Re: I accidentally retired, and need tax advice

Post by retire2022 »

Op

Are you money mustache person?

49-67=18 years until FRA Social Security

One needs 40 credits of SS in order to be eligible

Like others suggested go back to work.

I would suggest a second career something which will fill your soul and make work more passionate.

Good luck
niceguy7376
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Re: I accidentally retired, and need tax advice

Post by niceguy7376 »

Before the thread goes out of control on how OP needs to get back to work (that is an entirely different post), OP needs to provide more info that is clear so as to get advice to their original question.

If OP could provide the info in the layout of my signature, it will help posters to understand and customize the ideas.
It is not clear as to what is the income and tax bracket and how much the OP has or expects to have from SS.
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Re: I accidentally retired, and need tax advice

Post by Longdog »

IngognitoUSA wrote: Tue May 14, 2019 6:49 pm
triggertreat wrote: Tue May 14, 2019 6:38 pm Go back to work? What do you mean accidentally retired?
I have heard of getting accidentally pregnant but not accidentally retired.
It's a slightly different process... :happy
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Re: I accidentally retired, and need tax advice

Post by Longdog »

I think you really need to have a good handle on your expenses to make the best decision for yourself on what to do next, how to allocate your portfolio, whether to get another job, etc.
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rai
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Re: I accidentally retired, and need tax advice

Post by rai »

From the movie The Big Lebowski:

“My advice is to do what your parents did; get a job.”

Seems like the job market is not difficult. My 18 year old daughter with no skills got a job in no time flat at $12/hr would figure out to $2k a month.
"Life is what happens to you while you're busy making other plans" - John Lennon. | | "You say that money, isn't everything | But I'd like to see you live without it." - Silverchair
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beyou
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Re: I accidentally retired, and need tax advice

Post by beyou »

In a taxable account you should not reinvest dividends anyway. Creates opportunity for accidental wash sales if you sell after a "buy"
in the form of a div reinvestment. Pain for bookkeeping.

Added benefit is having the cash to pay bills, including taxes.

As far as tech, I am too in 50s and facing leaving the business. Not sure if I want to work anyway.
Prefer to harvest my years of savings now....
ad2007
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Re: I accidentally retired, and need tax advice

Post by ad2007 »

Have you plug in your moving forward numbers into a tax calculator? H&R Block and Intuit free tax calculator are pretty good. Gives you a ball park or your tax liability. Doesn't sound like you'll pay that much taxes on your qualified div and rental income (assuming you're still have depreciation on the properties).

Your possible bigger costs will be health care / insurance premiums.

Can you un-retire on purpose?
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Re: I accidentally retired, and need tax advice

Post by AerialWombat »

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Last edited by AerialWombat on Fri Feb 04, 2022 7:36 pm, edited 1 time in total.
This post is a work of fiction. Any similarity to real financial advice is purely coincidental.
Thesaints
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Re: I accidentally retired, and need tax advice

Post by Thesaints »

"accidentally retired" = "unemployed" ?
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celia
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Re: I accidentally retired, and need tax advice

Post by celia »

ad2007 wrote: Wed May 15, 2019 4:08 pm Have you plug in your moving forward numbers into a tax calculator? H&R Block and Intuit free tax calculator are pretty good. Gives you a ball park or your tax liability. Doesn't sound like you'll pay that much taxes on your qualified div and rental income (assuming you're still have depreciation on the properties).
+1 Start with a tax calculator or 2018 tax software. Input your expected incomes for this year to see what your taxes would be. If your income is lower now, your taxes will be lower, too. You might not even have to pay any taxes on your LTC gains and Qualified Dividends if you end up in the 12% tax bracket.

Then, to enable us to analyze your portfolio and to make proper suggestions, share your data in this format: Asking Portfolio Questions. You don't have to give us exact numbers, but just an estimate with all your holdings adding up to 100%.

We also need to know your yearly living expenses so we can figure out if you have enough assets to support your current retirement or not. And what are you doing for health insurance?
inbox788
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Re: I accidentally retired, and need tax advice

Post by inbox788 »

niceguy7376 wrote: Wed May 15, 2019 2:48 pm Before the thread goes out of control on how OP needs to get back to work (that is an entirely different post), OP needs to provide more info that is clear so as to get advice to their original question.

If OP could provide the info in the layout of my signature, it will help posters to understand and customize the ideas.
It is not clear as to what is the income and tax bracket and how much the OP has or expects to have from SS.
Yes, need more information about current situation to figure out whether retirement at this stage is a reasonable option, or if retirement is forced (as in unemployment or disability), how to best manage the next 50 years. Or is this tax advice for a transient period that's going to generate income and revenue (from say real estate business) in the near future for a decade or two?

When you're asking for directions, you have to know where you are and where you're going.
Mattzees wrote: Tue May 14, 2019 6:35 pmMy portfolio generates about $22K/year in ordinary dividends. Those are automatically reinvested, but obviously they count as income, and I have to pay taxes on them.

I have a couple of rental properties that gross $24K/year, which is the only cash I have coming in, and which also gets taxed.

So, I have a bunch of income, but very little actual cash flowing in. I'm dipping into my savings $10K to $15K per year just to live and pay taxes. I can probably do that for another five or ten years while the portfolio grows, then I would have to start drawing from it to live and pay taxes.
It's not clear if you're positive or negative cash flow. If you're spending 22k dividends & 24k rental income & $15k savings, you're probably not going to make it, even if there is some SS and other (pension) income in the future. But if the dividends are being invested, and you're only drawing 15k out of 22k, then there's a chance the investments can grow to meet your minimum expenses.

You can try to tax optimize, but you need to look at the grander picture.
Last edited by inbox788 on Wed May 15, 2019 5:00 pm, edited 1 time in total.
Cody6136
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Re: I accidentally retired, and need tax advice

Post by Cody6136 »

Thesaints wrote: Wed May 15, 2019 4:21 pm "accidentally retired" = "unemployed" ?
+1.

If I say that I'm unintentionally single, everyone knows I'm looking. Far better to let everyone know that I'm LOOKING. :beer
joelly
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Re: I accidentally retired, and need tax advice

Post by joelly »

IngognitoUSA wrote: Tue May 14, 2019 6:49 pm
triggertreat wrote: Tue May 14, 2019 6:38 pm Go back to work? What do you mean accidentally retired?
I have heard of getting accidentally pregnant but not accidentally retired.
:D Best laugh I have in months :sharebeer
michaeljc70
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Re: I accidentally retired, and need tax advice

Post by michaeljc70 »

As others have said, we need more info. One thing I didn't see mentioned that we need is the basis of your portfolio. Taxes are calculated off that. The holding period matters too as LT gains are taxed more favorably.

People are saying to get a job, etc. which is premature since we know practically nothing (what are his expenses? what equity is in the rentals? does he own a home? how big is the portfolio? sounds like there are savings outside the portfolio??)
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Re: I accidentally retired, and need tax advice

Post by willthrill81 »

FIREchief wrote: Wed May 15, 2019 1:43 am
Jack FFR1846 wrote: Tue May 14, 2019 7:28 pm How about accidentally go into Home Depot and get a job?

Everyone's hiring. I walk at lunch. Only what I noticed today for help wanted signs....Marshalls, Stop & Shop, Papa Ginos, the car wash at Jiffy Lube.......
Yeah, this. I'm just not seeing the issue here. Most of us living in the real world who found ourselves unemployed (accidentally, deserved, expected, unexpected, etc.) just went out and found another job. I only had to do it once, but that doesn't change the equation. It's really about more than taxes. It's about generating income until you don't need any more. :moneybag
I second your motion. The answer to an accidental retirement (which I still frankly don't get because if you leave your primary career, you know that you're leaving it) is to return to the workforce. It's not really a problem for a 50 year old to get a job these days in most areas, certainly not where we are. The problem is that a 50 year old is unlikely to make as much after returning to the workforce as they did when they left it if they were earning at least a fairly high income before. But that seems to be the OP's best move from where I'm sitting.
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Mattzees
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Re: I accidentally retired, and need tax advice

Post by Mattzees »

I got a lot of good perspective here, and thanks for the advice.

It turns out that an error was made in the tax projection that prompted me to ask for help in this forum. Some capital gains from the previous year were not removed, but were instead doubled. I thought my tax liability was going to be over $22K. When this error was corrected, that number looks more like $2800.

That's more like what I was planning for.

Obviously, some freelance work is in my future, which is fine, but I wanted to avoid a full-time commitment to someone else's company, especially at a much-reduced pay rate.

Thanks for the comments.
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Re: I accidentally retired, and need tax advice

Post by LadyGeek »

FYI - The OP is requesting assistance here: Criticism of my portfolio, please?
Wiki To some, the glass is half full. To others, the glass is half empty. To an engineer, it's twice the size it needs to be.
SoAnyway
Posts: 422
Joined: Tue Jul 31, 2018 11:49 pm

Re: I accidentally retired, and need tax advice

Post by SoAnyway »

Mattzees wrote: Wed May 15, 2019 6:31 pm It turns out that an error was made in the tax projection that prompted me to ask for help in this forum. Some capital gains from the previous year were not removed, but were instead doubled. I thought my tax liability was going to be over $22K. When this error was corrected, that number looks more like $2800. That's more like what I was planning for.
OP, fwiw others asked a bunch of good questions/sought more info re. your actual numbers. As others indicated, there are several reasons your post didn't quite make sense as far as the tax rules go, and you may be overlooking some opportunities. (Based on the info you gave, turning off auto-reinvest seemed like a no-brainer to me but there may be other better options....) If you're interested, feel free to post the info and you'll get much better guidance on your tax question.

As for increasing cash flow via full-time/part-time/consulting/what-have-you, obviously you've got marketable skills of various types/earning levels, and have considered various options. It's entirely up to you how you choose to spend your time and you're owning the consequences, so choose according to what suits you. (Not judging!) Incidentally, I did notice this bit in your other thread that LadyGeek pointed out:
Tax filing status: currently single, but may get married in the next couple of years
If the prospective spouse brings in income, obviously that's another avenue for upping the cash flow that hadn't been previously suggested....
One caution, though: If either you or said individual is female just don't get "accidentally pregnant"... ; )
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Topic Author
Mattzees
Posts: 22
Joined: Thu Jan 25, 2018 9:37 pm

Re: I accidentally retired, and need tax advice

Post by Mattzees »

AerialWombat wrote: Wed May 15, 2019 4:18 pm
3). Continue working on your moonshots. I, for one, will highly encourage such behavior. Most Bogleheads will not.
Thanks for that. :happy
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