Tax Loss Harvesting

[stillers]

Well I made a huge mistake so thought I would share my misfortune and possibly prevent someone else making this mistake. I did tax loss harvesting in Vanguard after tax account of my trust and my wife's trust. My transactions did one at a time and went great. When doing the process for my wife it appeared COULD DO MULTIPLE TRANSACTIONS AT A TIME. I mistakenly did a 374,000 long term gain sale in 2018. This year will pay 20% plus 3.8% medicare tax because of my income. Called Vanguard and CPA and they say nothing to do about the blunder. Any suggestions or advice to make me feel less like an idiot appreciated.
STILLERS

[Hockey10]

I don't think that even livesoft will be able to help you out with this one. Look at the bright side, you had a very nice gain. Pay the taxes, learn from your mistake, and move on.

[H-Town]

It happened. Nothing you can do now. Just move on. Next time, triple check thing before hitting the Submit button.

[BoggledHead2]

You have a trust
Your wife has a trust
You’re upset about the fact you have to now pay tax on a large sum of money your investments earned.

You’re fine.

[TomatoTomahto]

For a number of reasons (profoundly uncooperative mortgage company, timing of employment, needing to buy before selling), we had to raise a large amount of cash in 2018. That resulted in a mid six digit LTCG, subject to taxes at the same rates as you. As you know, the market tanked later in the year, and we managed to TLH half of the LTCGs away. I'll leave it to you to decide whether that was good news or bad news

In any case, CG rates are lower than income rates. The glass is half full.

[stillers]

Well I am off the roof and having a beer. I of course do not like to pay more tax than needed but what a dumb mistake!!!
Thanks for the encouragement bogleheads.
Stillers

[bradpevans]

Well I made a huge mistake so thought I would share my misfortune and possibly prevent someone else making this mistake. I did tax loss harvesting in Vanguard after tax account of my trust and my wife's trust. My transactions did one at a time and went great. When doing the process for my wife it appeared COULD DO MULTIPLE TRANSACTIONS AT A TIME. I mistakenly did a 374,000 long term gain sale in 2018. This year will pay 20% plus 3.8% medicare tax because of my income. Called Vanguard and CPA and they say nothing to do about the blunder. Any suggestions or advice to make me feel less like an idiot appreciated.
STILLERS

Are you retired but pre-RMD.? That gain could fund a lot of Roth conversion if applicable ...

[libralibra]

I'm not sure how someone overlooks something like this. How do you know there wasn't a glitch? E.g. you thought you clicked on one lot but internally it selected a different lot? Did they have an intermediate confirmation page which you remember seeing what the sales and gain/loss was expected to be?

[TomatoTomahto]

I'm not sure how someone overlooks something like this. How do you know there wasn't a glitch? E.g. you thought you clicked on one lot but internally it selected a different lot? Did they have an intermediate confirmation page which you remember seeing what the sales and gain/loss was expected to be?

It happens. The other day, I sold a bunch of Treasury MM to buy . . . a bunch of Treasury MM. I had intended to move it to Muni MM. Sometimes the eye sees what it expects to see (eg., Invisible Gorilla http://www.theinvisiblegorilla.com/videos.html).

It pays to slow down. Not easy for some personality types to do.

[Longdog]

Well I made a huge mistake so thought I would share my misfortune and possibly prevent someone else making this mistake. I did tax loss harvesting in Vanguard after tax account of my trust and my wife's trust. My transactions did one at a time and went great. When doing the process for my wife it appeared COULD DO MULTIPLE TRANSACTIONS AT A TIME. I mistakenly did a 374,000 long term gain sale in 2018. This year will pay 20% plus 3.8% medicare tax because of my income. Called Vanguard and CPA and they say nothing to do about the blunder. Any suggestions or advice to make me feel less like an idiot appreciated.
STILLERS

What does doing MULTIPLE TRANSACTIONS AT A TIME have to do with mistakenly generating $374,000 in long term gains? What was the actual mistake (i.e., what did you intend to do and what did you do instead)? What will you do differently in the future? I cannot tell what lesson was learned.

[stillers]

Well I made a mistake and the lesson is to pay more attention , the why and where of this are not pertinent to this discussion but I accept the responsibility for this. The account is a after tax account and my question is any suggestion to soften the blow?
STILLERS

[TomatoTomahto]

Well I made a mistake and the lesson is to pay more attention , the why and where of this are not pertinent to this discussion but I accept the responsibility for this. The account is a after tax account and my question is any suggestion to soften the blow?
STILLERS

I apologize on behalf of some of the responders; apparently well-off people aren’t allowed to make mistakes like the rest of the world. BH are quick to jump into class warfare mode.

My suggestion to soften the blow is to reframe the mistake. In my case, how lucky to have enough not to be subject to a mortgage company’s quirks and to be able to reset our taxable basis. Still sucks, but it made me feel better. And then, at the end of 2018, how fortuitous to be able to TLH some of the LTCG away using STCL.

I don’t know any real way to soften the blow, but framing matters.

[libralibra]

I once had some lots reassigned weeks after settlement when I complained about a glitch. It was a tiny, trivial amount compared to your case though, so maybe not really precedent.

It sounds like you are saying it definitely wasn't a glitch and that you are sure you fat-fingered the trade. It doesn't help you now, but for future reference to others, you should be able to reassign lots up to settlement.

[stillers]

Thank you
Stillers

[fnhanks]

Well I made a huge mistake so thought I would share my misfortune and possibly prevent someone else making this mistake. I did tax loss harvesting in Vanguard after tax account of my trust and my wife's trust. My transactions did one at a time and went great. When doing the process for my wife it appeared COULD DO MULTIPLE TRANSACTIONS AT A TIME. I mistakenly did a 374,000 long term gain sale in 2018. This year will pay 20% plus 3.8% medicare tax because of my income. Called Vanguard and CPA and they say nothing to do about the blunder. Any suggestions or advice to make me feel less like an idiot appreciated.
STILLERS

What does doing MULTIPLE TRANSACTIONS AT A TIME have to do with mistakenly generating $374,000 in long term gains? What was the actual mistake (i.e., what did you intend to do and what did you do instead)? What will you do differently in the future? I cannot tell what lesson was learned.

Well I made a mistake and the lesson is to pay more attention , the why and where of this are not pertinent to this discussion but I accept the responsibility for this. The account is a after tax account and my question is any suggestion to soften the blow?
STILLERS

OP, Longdog wasn't calling you out in any way, they were genuinely trying to figure out what happened here. I admit I'm new to the game here and am in the same boat as them.

What did doing multiple transactions do here to trigger the large gain? Does doing the transactions independently do something different here that would've resulted in a smaller value? Can you please elaborate so I don't inadvertently make the same mistake when I eventually go down this path.

[stillers]

the mistake was doing multiple transaction on wife's account after showing my son how to on my account. I allowed him with me watching show me how to do multiple transactions rather than watch transaction individually. This was done with a house full of kids and many distractions and on 12/31/2018. As previously stated I made the mistake and doing multiple transactions added to the already confusing situation. Not sure this helps as this was a mistake of doing things at last moment, not concentrating and a hurried environment. The End