Author Topic: Tax Loss Harvesting: When is it enough?  (Read 1019 times)

dragoncar

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Tax Loss Harvesting: When is it enough?
« on: May 20, 2020, 11:37:43 PM »
At this point I probably have like $60k in carry-forward capital losses.  Up until now I've been happy to take the $3k annual deduction against regular income but that's not going to last another 20 years.  I have the opportunity to take another $10k in losses right now, but... I'm not sure it's going to get me much.  Some day it's just going to be offsetting long term capital gains, in which case it's basically a wash, or very low-bracket regular income.

At what point do you say enough is enough and quit playing the TLH game?  Am I missing something that makes it a bigger win?

terran

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Re: Tax Loss Harvesting: When is it enough?
« Reply #1 on: May 21, 2020, 05:56:19 AM »
I don't think there's much disadvantage. Like you say, the worst case is that it offsets gains that would have been smaller if you hadn't harvested the loss in the first place. Even then, at least it gives you some flexibility to realize gains from the sale of whatever you want (not just those particular shares). I could be missing something though.

dragoncar

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Re: Tax Loss Harvesting: When is it enough?
« Reply #2 on: May 21, 2020, 03:45:06 PM »
I don't think there's much disadvantage. Like you say, the worst case is that it offsets gains that would have been smaller if you hadn't harvested the loss in the first place. Even then, at least it gives you some flexibility to realize gains from the sale of whatever you want (not just those particular shares). I could be missing something though.

To me the biggest disadvantage is that it forces you to take an annual $3000 deduction that you might prefer not to take.  Say you have no income one year... that -$3k evaporates.  Although I guess I have to look into whether you can opt out of this deduction.... I’ve never seen the option in any consumer tax software so I’d have to look more closely at the form

terran

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Re: Tax Loss Harvesting: When is it enough?
« Reply #3 on: May 21, 2020, 04:04:20 PM »
Couldn't you just Roth convert enough every year so you always at least use up the loss and the standard deduction? Seems like you'd want to do that anyway to take advantage of the 0% tax on that amount.

You can't opt out of taking it, but I wouldn't be surprised if you can continue to carry it over if you truly have no income to offset. I haven't found anything to that effect after a quick perusal though, so i'm not sure.

Edit: Looks like you can carry over the full amount if you don't have enough taxable income to owe tax without the loss deduction: https://fairmark.com/investment-taxation/capital-gain/capital-losses/capital-loss-with-little-or-no-income/
« Last Edit: May 21, 2020, 04:07:11 PM by terran »

MDM

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Re: Tax Loss Harvesting: When is it enough?
« Reply #4 on: May 21, 2020, 05:17:03 PM »
To me the biggest disadvantage is that it forces you to take an annual $3000 deduction that you might prefer not to take.  Say you have no income one year... that -$3k evaporates.  Although I guess I have to look into whether you can opt out of this deduction.... I’ve never seen the option in any consumer tax software so I’d have to look more closely at the form
It's not "consumer" (i.e., for profit) software, but apparently a timely update a couple of weeks ago: Added the Capital Loss Carryover worksheet for the next year's return.

dragoncar

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Re: Tax Loss Harvesting: When is it enough?
« Reply #5 on: May 21, 2020, 11:41:20 PM »
Couldn't you just Roth convert enough every year so you always at least use up the loss and the standard deduction? Seems like you'd want to do that anyway to take advantage of the 0% tax on that amount.

You can't opt out of taking it, but I wouldn't be surprised if you can continue to carry it over if you truly have no income to offset. I haven't found anything to that effect after a quick perusal though, so i'm not sure.

Edit: Looks like you can carry over the full amount if you don't have enough taxable income to owe tax without the loss deduction: https://fairmark.com/investment-taxation/capital-gain/capital-losses/capital-loss-with-little-or-no-income/

Good point.  I screwed the pooch last year when we had very low income in 2018 and I failed to think about a roth conversion.  My failing will be that I won't look at my tax bracket until the new year... but I really should make it a habit to follow a year-end task list.  Maybe there's a thread around here for what might go on that list.

seattlecyclone

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Re: Tax Loss Harvesting: When is it enough?
« Reply #6 on: May 22, 2020, 12:41:10 PM »
I think it all depends. Your $60k of existing losses are enough to last for 20 years of not selling anything for a gain. If you plan to be retired to a low tax bracket before then, and you don't plan to liquidate a bunch of stock at some point prior to retirement to buy a house or something of that nature, you're right that harvesting more losses probably won't be a major win.

Let's look at an example. You say you have $60k of existing losses, and could harvest $10k more. Let's say that $10k unrealized loss comes from stock you paid $100k for. It's worth $90k now. Let's suppose you want to start selling that stock in a decade. It appreciates to $200k by then, and you want to withdraw $50k per year. For the sake of easier calculations let's suppose the market stays flat for a few years after that: you withdraw $50k for four years and that uses up this lot of shares. In the ten years between now and then you are able to use $3k of your existing loss per year to offset other income, leaving you with $30k carried forward in a decade.

Scenario 1: You don't harvest your $10k loss now.
Year 1 of withdrawals: $3,000 net capital loss. You start with $200k of stock, $100k cost basis. You sell $50k, realizing a $25k gain. Your existing $30k loss carryover wipes out this gain and you're able to claim an additional $3k against regular income (Roth conversions, perhaps?).
Year 2 of withdrawals: $23,000 net capital gain. You start with $150k of stock, $75k cost basis. You sell $50k, $25k gain. Subtract your $2,000 of loss carried forward, and that leaves you with a $23k gain and nothing to carry forward.
Years 3-4: $25,000 net capital gain.

Scenario 2: You harvest the $10k loss now.
Year 1: $3,000 net capital loss. You start with $200k of stock, $90k cost basis, $40k loss carryover. You sell $50k, for a $27.5k capital gain. Your carried-forward losses erase this gain plus $3,000, leaving $9,500 of losses to carry forward.
Year 2: $18,000 net capital gain. $27,500 gain minus $9,500 carry-forward. Nothing to carry forward to the next year.
Years 3-4: $27,500 net capital gain.

Not a huge difference here. By harvesting $10k of losses now you have $5,000 less capital gains income in year 2, at the expense of $5,000 more capital gains income spread evenly across years 3-4. What this would do is give you a bit more flexibility on the timing of your income. If you really wanted to keep that capital gains income lower in years 1-2 you'd be able to follow the withdrawal schedule I outlined above for Scenario 2. If you wanted to smooth out your income a bit more (for ACA purposes or something else) there's nothing stopping you from harvesting some gains in Years 1-2 to let you have lower gains in years 3-4. With a smaller amount of carried-forward loss you lose a bit of this flexibility, but it likely won't make a huge difference either way.

blackletterlaw

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Re: Tax Loss Harvesting: When is it enough?
« Reply #7 on: May 23, 2020, 05:34:18 AM »
Another thing to think about, is whether Congress every decides to increase the yearly carry forward loss amount for individuals.
Could happen given how bad this year will be boomers, and they will be upset. And it is an election year.