Tag Archives: tax loss harvesting

Offsetting Capital Gains with Tax Loss Harvesting

This year in order to afford a few items, such as my used car purchase, I sold a bit of stock. What I Wasn’t considering at the time was the amount of capital gains tax I’d have to pay come April. So now I’m trying to quickly offset my capital gains with losses (which for better or worse are starting to appear in my portfolio due to the stock market pullback as of late.)

At the moment I have $3792.71 in long term gains and $256.95 in capital losses. (This doesn’t include dividends which are starting to add up, and I really need some advice on dividend strategy since I’m might — if i’m lucky — hit Obamacare fines in 2015 (if I make $200k, which is possible due to my bonus structure, we’ll see… still a stretch goal but more possible then ever before.)

Therefore I need to offset 3535.05 in capital gains or I’ll have to pay approximately $883 in tax come April. That’s a bit of a pain because I know I have a pending loss of a whole chunk of money in my former employer that will likely go under in the next few years, but I can’t sell that stock as a loss yet. So I’m left with $3535 to deal with or else I have to pay an extra $900 in April.

I guess you can say that it is silly to *try* to find $3535 in losses to offset a $900 tax. However if the losses exist anyway it makes sense to take them (i.e. sell the stocks) and then immediately reinvest them in a potentially better performing alternative.

It’s also not so silly because I happen to live in the second highest place in the WORLD for capital gains taxes. That’s right, California has the highest U.S. capital gains rate and the second highest internationally, with a top rate of 37.1%

Since selling anything from my Sharebuilder account costs $8 per fund, I started clearing out in my Vanguard fund, which allows free trades between funds.

Thus, the other day I took a $419.08 capital loss on two funds that had shot down due to the stock market corrections…

That leaves me with $3116 (or $779 in tax) to deal with in the next two months.

I think I may have some rollover capital losses that I need to deal with from 2012 and 2013… but that would only be at max $1000… still need to find $2000 in losses to tax harvest these gains away.

While my IRA accounts are performing poorly that doesn’t help. My Sharebuilder individual taxed stocks and ETFs are actually doing fairly well. Boeing (BA) is down a bit so I might sell that, but waiting on it to either go down enough where it seems to make sense to just sell it for the loss (i.e. $200 loss or $50 savings doesn’t seem to make sense, though I would just have to sell it and wait a month to buy the same stock back so I could take the loss, not a big deal. The question is will the stock go up more than $50 in a month to make the point of selling it moot. Who knows, but $50 isn’t much in terms of the market so I’ll prob just continue to hold. In reality I should probably buy more now, not sell it.

Ok, so it looks like I’ll probably just have to deal with paying an extra $900 in taxes this year. At least I’m not dealing with AMT in 2014 and taxed an extra 5% on my capital gains. Next year I just need to remind myself not to sell any of my investments in case I happen to hit AMT and the Obamacare tax. I can sell my stocks when I’m retired. Only PITA side of the equation is that since all my money is tied up in stocks I won’t ever have a downpayment for a house. Kind of sucks but at least I should be ok in retirement.

Anyway, it’s been a rough money financially. Just due to stock market plus not having job I’m down about $20k. I still have high hopes for hitting my $300k goal this year but the stretch goal of $325k is probably not going to happen. If the stock market keeps kicking my ass I may be able to save $900 in capital gains tax but I won’t get to $300k, which would make me sad. That said, I’m fixated on breaking $400k by 2016 (and the big $500k by 2017) so… I’ve got a lot of work cut out for me. If the markets don’t cooperate then I guess… no matter how much work I cut I won’t actually hit my goals.