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I am currently contributing 15% of my paycheck to it
This seems too high. And are you putting 15% of your paycheck to your 401k too?
I've heard some say that post-Enron, post-Worldcom, post-Sunbeam you shouldn't put more than 2% of your paycheck toward your employers stock, but the average employee stock holding in their employer in a 401k is at 16%, down from 19%. Note that is in a retirement account.
Just because you can buy a max of $21,250 every year in the ESPP doesn't mean that you necessarily should. Not sure about CVS 401k matching but this may be a source of confusion. ESPP gives a 10% built in return. 401k matching gives a 100% built in return. If CVS says they match 401k contribtions up to $X, that gives you 100% built in return on you first $X amount of dollars. Basically don't even think about ESPP until you're set to reach their 401k match minimum. Hopefully you're at the 401k maximum and the ESPP is just a way for investing 'fun money' instead of an ordinary brokerage account, though being locked in for 2 years is less fun.
Wow, looks like you and @Dr Wario have great long running strategies for capturing gains and reducing risk.thanks for the concern
I have been maxing the ESPP for 5 years now but have always sold the instant that I could and reinvested the money, this has netted me a very nice profit without taking on the risk of having significant investments in your place of employment.
I think it's a horrible investment IMHO and they are the last stock I would invest in at this time. Learn stocks my friend, much more lucrative way to invest your money.
Do you sell as soon as you can regardless of a qualifying vs. disqualifying position?
I have been maxing the ESPP for 5 years now but have always sold the instant that I could and reinvested the money, this has netted me a very nice profit without taking on the risk of having significant investments in your place of employment.
I typically sell before it becomes a qualifying dispensation, the tax difference has not been that great due to the stock's movement pattern and I like moving the money into my real estate.
TurboTax should have a part to guide you through it. They even have a webpage explaining it:How do you file taxes if you sell as a disqualifying dispensation? Is it reported as regular income? Is it easy to do with a program like TurboTax?
^ good summary. I would add that the effective tax rate for most pharmacists is 20% and capital gain tax is 15% so therefore the difference is just 5% in taxes.
TurboTax should have a part to guide you through it. They even have a webpage explaining it:
https://turbotax.intuit.com/tax-too...s/Employee-Stock-Purchase-Plans/INF12047.html
Note that regardless of whether you do a qualifying or disqualifying disposition, part of it will still be taxed as regular income. For example:
The price on the first day of the window 7/1/14 was $76.04 and the last day 12/31/14 was $96.31. On 12/31/14 you get to purchase at 15% off the lower of the two, so $64.634 and say you buy 100 shares = $6,463.40.
If you sell now in Jan 2016 for $95, it is a disqualifying disposition because it hasn't been 2 years from the offering date 7/1/14 yet. So CVS will put on your W-2:
$96.31 - $64.634 = $31.676 x 100 = $3,167.60
which will be taxed as regular income.
Now if the cost basis at your broker only shows $6,463.40 then you must adjust it by the $3,167.60 to make sure you don't get taxed twice on this amount. So the adjusted cost basis is $9,631.
Now you will actually take a small long-term capital loss because:
$9,500 (sale proceeds) - $9,631 = -$131
Summary:
$3,167.60 regular income
-$131 long-term capital loss
=======
$3,036.60
---------------
If you sell after 7/1/16 so that it is a qualifying disposition, the taxation will be different. The amount taxed as ordinary income will be the price at the beginning of the offering period minus your purchase price:
$76.04 - $64.634 = $11.406 x 100 = $1,140.60
Once again, this amount will be put on your W-2 and you will have to adjust your cost basis:
$6,463.40 + $1,140.60 = $7,604
Now say you sell for the same $95, but after 7/1/16:
$9,500 - $7,604 = $1,896
This will be taxed as a long-term capital gain.
Summary:
$1,140.60 regular income
$1,896 long-term capital gain
=======
$3,036.60 (same for both scenarios)
However, the qualifying disposition will be taxed about $250 less because the long-term capital gain is taxed at 15%. So you should work it out using your particular stock prices and decide if it is worth it to wait for a qualifying disposition or not.
Thanks so much, pezdispenser! Even with your explanation, I find it confusing. I should put this into a spreadsheet.
TurboTax should have a part to guide you through it. They even have a webpage explaining it:
https://turbotax.intuit.com/tax-too...s/Employee-Stock-Purchase-Plans/INF12047.html
Note that regardless of whether you do a qualifying or disqualifying disposition, part of it will still be taxed as regular income. For example:
The price on the first day of the window 7/1/14 was $76.04 and the last day 12/31/14 was $96.31. On 12/31/14 you get to purchase at 15% off the lower of the two, so $64.634 and say you buy 100 shares = $6,463.40.
If you sell now in Jan 2016 for $95, it is a disqualifying disposition because it hasn't been 2 years from the offering date 7/1/14 yet. So CVS will put on your W-2:
$96.31 - $64.634 = $31.676 x 100 = $3,167.60
which will be taxed as regular income.
Now if the cost basis at your broker only shows $6,463.40 then you must adjust it by the $3,167.60 to make sure you don't get taxed twice on this amount. So the adjusted cost basis is $9,631.
Now you will actually take a small long-term capital loss because:
$9,500 (sale proceeds) - $9,631 = -$131
Summary:
$3,167.60 regular income
-$131 long-term capital loss
=======
$3,036.60
---------------
If you sell after 7/1/16 so that it is a qualifying disposition, the taxation will be different. The amount taxed as ordinary income will be the price at the beginning of the offering period minus your purchase price:
$76.04 - $64.634 = $11.406 x 100 = $1,140.60
Once again, this amount will be put on your W-2 and you will have to adjust your cost basis:
$6,463.40 + $1,140.60 = $7,604
Now say you sell for the same $95, but after 7/1/16:
$9,500 - $7,604 = $1,896
This will be taxed as a long-term capital gain.
Summary:
$1,140.60 regular income
$1,896 long-term capital gain
=======
$3,036.60 (same for both scenarios)
However, the qualifying disposition will be taxed about $250 less because the long-term capital gain is taxed at 15%. So you should work it out using your particular stock prices and decide if it is worth it to wait for a qualifying disposition or not.
Yes, that's the horribly confusing part, but it's crucial that you do it correctly otherwise you will get taxed twice on the same gain! Yes, it is because part of the gain is reported on your W-2 to get taxed as regular income (exactly how much depends on whether you made a qualifying or disqualifying disposition as shown in the example). But your broker doesn't take this into account. They only report the cost basis as the discounted amount that you paid. So you have to increase your cost basis by the amount on your W-2 to take it out of the capital gains tax calculation.Why would you have to adjust your cost basis to an amount greater than what you pay? Is this simply because it is reported on your W2?
I have a different ESPP with ComputerShare and I think they charge $35 to sell through them, and $50 to transfer to another broker. So I will just go with the cheaper option and sell through ComputerShare when the time comes.I have about 95 shares available to sell now. If you don't plan on selling, do you guys keep it in Computershare? Is there any advantage of the two transfer options, Transfer to Broker or Issue Shares?
I have a different ESPP with ComputerShare and I think they charge $35 to sell through them, and $50 to transfer to another broker. So I will just go with the cheaper option and sell through ComputerShare when the time comes.
I believe Issue Shares means they will send you the share certificates, and there is probably a fee for this as well. It's very old fashioned and will cause you more problems when you want to sell your certificates so I wouldn't do this.
Yep, that is the advantage of a "Qualified Section 423 ESPP" like CVS's and Walgreen's. You don't pay any taxes until you sell. If it were a non-qualified plan, then you would pay taxes on the discount portion when you buy the shares.Thanks, I'll keep it in ComputerShare. I won't have to do anything fancy with taxes until I sell, right?
If we ever leave CVS, would we still have access to ComputerShare?
Note: you do need to pay taxes on the dividend income. The IRS let me know that recently...Yep, that is the advantage of a "Qualified Section 423 ESPP" like CVS's and Walgreen's. You don't pay any taxes until you sell. If it were a non-qualified plan, then you would pay taxes on the discount portion when you buy the shares.
Yes, you will still have access to ComputerShare after you leave, and the shares are still yours to keep.
CP 2000 notice? LolNote: you do need to pay taxes on the dividend income. The IRS let me know that recently...
That's the one.CP 2000 notice? Lol
Yes, it is just a straight long-term capital loss, which you can deduct up to $3,000 from your income, or carry over the rest for future years. This is because it is a qualifying disposition (more than 2 years from offering date 1/1/2015, and more than 1 year from purchase date 6/30/2015).What happens if you sell at a loss? You don't pay any taxes right? And carry over the capital loss to the next year?
I believe the 1/15-6/15 offering period was bought around $83/share which is a little above the current share price. I was thinking of selling at a small loss to use towards a down payment for a home.
Unfortunately CVS stock went down today, so you're probably at a loss again. But if you were to take a small profit, yes, you would have to take the difference between your sale price and the purchase price as ordinary income, add that to your cost basis, then I guess you'll have a small capital loss equal to your brokerage fees.I just looked and the 6/30/15 purchase date was for 80.835/share. So it would be a tiny profit if sold today. A lot of paperwork for nothing.
Bump:
You know, when they granted stock options and a 15% discount on ESPPs, the stock was going up. Some were making close to $10,000 from the combination of both. Now employees are actually losing! Literally losing money for the latter holding periods (around mid 2015). If you max out the ESPP purchase, you're really gambling out an average of $20,000 of after tax money that you can't cash out for a year to year and half. Coupled with the fact that the discount was reduced to 10%, the risk of losing money and time value of money, I am not sure if it is worth it anymore.