Can I take money from my employee stock and put it towards another stock?
The question is for your HR department, or administrator of the plan. How long must you hold the employee shares before you are permitted to sell? Loyalty to your company is one thing, but after a time, you will be too heavily invested in one company, and you need to diversify out. One can cite any number they wish, 5%, 10%. All I know is that when Enron blew up, it only added insult to injury that not only did these people lose their job, they lost a huge chunk of their savings as well. Only if you sell the stock in question, and use the proceeds to buy other stock. (You should probably never feel bad about selling your company stock, even if it goes up a lot later, because from a risk-exposure basis you are already exposed to your company's performance through your career. Unless you have a lot of other savings, you should diversify.)
Stock options represent an option to buy a share at a given price.  What you have been offered is the option to buy the company share at a given price ($5) starting a given date (your golden handcuffs aka vesting schedule). If the company's value doubles in 1 year and the shares are liquid (i.e. you can sell them) then you've just made $125k of profit.  If the company's value has gone to zero in 1 year then you've lost nothing other than your hopes of getting rich. As others have mentioned, the mechanics of exercising the option and selling the shares can typically be accomplished without any cash involved.  The broker will do both in a single transaction and use the proceeds of the sale to pay the cost of buying the shares.  You should always at least cover the taxable portion of the transaction and typically the broker will withhold that tax anyways.  Otherwise you could find yourself in a position where you have actually lost money due to tax being owed while the shares decline in value below that tax.  You don't have to worry about that right now. Again as people have mentioned options will typically expire 10 years from vesting or 90 days from leaving your employment with the company.  I'm sure there are some variations on the theme.  Make sure you ask and all this should be part of some written contract.  I'm sure you can ask to see it if you wish.  Also typical is that stock option grants have to be approved by the board which is normally a technicality. Some general advice: I agree with the other comments that you should not buy/hold your company stock even if given at a discount. If equity is provided as part of the compensation package (Options/Restrictive Stock Units RSU)then this rule does not apply. As a matter of diversification, you should not have majority equity stake of other companies in the same sector (e.g. technology) as your employer. Asset allocation and diversification if done in the right way, takes care of the returns. Buying and selling on the same day is generally not allowed for ESPP. Taxation headaches. This is from personal experience (Cisco Systems). I had options issued in Sept 2008 at 18$ which vested regularly. I exited at various points - 19$,20$,21$,23$ My friend held on to all of it hoping for 30$ is stuck. Options expire if you leave your employment. ESPP shares though remain. "Hmm... Well there are several ways to do that: Go to any bank (or at the very least major ones). They can assist you with buying and/or selling stocks/shares of any company on the financial market. They keep your shares safe at the bank and take care of them. The downside is that they will calculate fees for every single thing they do with your money or shares or whatever. Go to any Financial broker/trader that deals with the stock market. Open an account and tell them to buy shares from company ""X"" and keep them. Meaning they won't trade with them if this is what you want. Do the same as point 2, but on your own. Find a suitable broker with decent transaction fees, open an account, find the company's stock code and purchase the stocks via the platform the broker uses." I think what you're asking is,  Can I buy 1000 shares of the stock at $1.  For $1000.   it goes up to $2, then sell 500 shares of the stock with proceeds of $1000, now   having my original $1000 out of it, and still owning 500 shares.    And that not create a taxable event. Since all I   did was take my cost basis back out, and didn't collect any gains.   And then I want to repeat that over and over. Nope, not in the USA anyway.   Each sale is a separate taxable event. The first sale will have proceeds of $1000 and a cost basis of $500, with $500 of capital gains, and taxes owed at the time of that sale. The remaining stock will have a cost basis of $500 and proceeds of whatever you sell it for in the future. The next batch of stock will have a cost basis of whatever you pay for it.   The only thing that works anything like the way you're thinking, is a Roth IRA...   You can put your cost basis in, pull it back out, and put it back in again, all tax free.   But every time your cost basis cycles in, that counts towed your contribution limits unless you do it fast enough to call it a rollover. "IANAL, but no, this is not sound legal advice. There are a few things that stick out to me as fishy. First off: you are calculating the 3% safe-harbor on the 2017 compensation limit of $270k, but limiting yourself to $53k in total contributions which is the 2016 limit. It's hard to tell what tax year you're working in here. If you're planning for 2017, fine, but if you're wrapping up 2016 then you need to use 2016 limits. Secondly (and this is something I think your counsel should know already): you don't take Employer contributions out of gross wages (box 1) on the W-2. They aren't even reported there in the first place! With your base scenario the 2 employees' W-2s would look like this: Employee A's W-2 Gross Wages (box 1) = 280,000 - 14,966.67 = 265,033.33 Employee B's W-2 Gross Wages (box 1) = 280,000 - 0 = 280,000 Elective deferrals are the only thing that should come out of wages. Not the SH 3% or Match. Thirdly: Retirement Plan expenses really aren't an ""above the line"" expense. They are not included in cost of goods sold. Even if you establish a ""pool"" for that expense, it's still not a direct cost attributable to the production of whatever your company sells. Also: Employee B should not have to contribute to the retirement account of Employee A! The only situation I can see where Employee A and B would be required to fund the match equally, were if Employee A & B are both 50% owners and the company has no funds of its own with which to fund the match. The company has obligated itself to fund the match, and if the company doesn't have any money then the money still has to come from somewhere (ie. the owners pony up more funds for the match they promised their employees, it just happens that the employees are also the owners). Even in this situation though, I still stand behind my first 3 points." Options granted by an employer to an employee are generally different that the standardized options that are traded on public stock option exchanges.  They may or may not have somewhat comparable terms, but generally the terms are fairly different. As a holder of an expiring employee option, you can only choose to exercise it by paying the specified price and receiving the shares, or not.  It is common that the exercise system will allow you to exercise all the shares and simultaneously sell enough of the acquired shares to cover the option cost of all the shares, thus leaving you owning some of the stock without having to spend any cash.  You will owe taxes on the gain on exercise, regardless of what you do with the stock. If you want to buy publicly-traded options, you should consider that completely separately from your employer options other than thinking about how much exposure you have to your company situation.  It is very common for employees to be imprudently overexposed to their company's stock (through direct ownership or options). Back in the late 80's I had a co-worked do exactly this. In those days you could only do things quarterly: change the percentage, change the investment mix, make a withdrawal.. There were no Roth 401K accounts, but contributions could be pre-tax or post-tax. Long term employees were matched 100% up to 8%, newer employees were only matched 50% up to 8% (resulting in 4% match). Every quarter this employee put in 8%, and then pulled out the previous quarters contribution. The company match continued to grow.  Was it smart? He still ended up with 8% going into the 401K. In those pre-Enron days the law allowed companies to limit the company match to 100% company stock which meant that employees retirement was at risk. Of course by the early 2000's the stock that was purchased for $6 a share was worth $80 a share... Now what about the IRS: Since I make designated Roth contributions from after-tax income, can I make tax-free withdrawals from my designated Roth account at any   time? No, the same restrictions on withdrawals that apply to pre-tax   elective contributions also apply to designated Roth contributions. If   your plan permits distributions from accounts because of hardship, you   may choose to receive a hardship distribution from your designated   Roth account. The hardship distribution will consist of a pro-rata   share of earnings and basis and the earnings portion will be included   in gross income unless you have had the designated Roth account for 5   years and are either disabled or over age 59 ½. Regarding getting just contributions: What happens if I take a distribution from my designated Roth account before the end of the 5-taxable-year period? If you take a distribution from your designated Roth account before   the end of the 5-taxable-year period, it is a nonqualified   distribution. You must include the earnings portion of the   nonqualified distribution in gross income. However, the basis (or   contributions) portion of the nonqualified distribution is not   included in gross income. The basis portion of the distribution is   determined by multiplying the amount of the nonqualified distribution   by the ratio of designated Roth contributions to the total designated   Roth account balance. For example, if a nonqualified distribution of   $5,000 is made from your designated Roth account when the account   consists of $9,400 of designated Roth contributions and $600 of   earnings, the distribution consists of $4,700 of designated Roth   contributions (that are not includible in your gross income) and $300   of earnings (that are includible in your gross income). See Q&As regarding Rollovers of Designated Roth Contributions, for   additional rules for rolling over both qualified and nonqualified   distributions from designated Roth accounts. You can't actually transfer shares directly unless they were obtained as part of an employee share scheme - see the answers to questions 19 and 20 on this page: http://www.hmrc.gov.uk/isa/faqs.htm#19 Q. Can I put shares from my employee share scheme into my ISA? A. You can transfer any shares you get from into a stocks and shares component of an ISA without having to pay   Capital Gains Tax - provided your ISA manager agrees to take them. The   value of the shares at the date of transfer counts towards the annual   limit. This means you can transfer up to £11,520 worth of shares in the tax   year 2013-14 (assuming that you make no other subscriptions to ISAs,   in those years). You must transfer the shares within 90 days from the day they cease to   be subject to the Plan, or (for approved SAYE share option schemes) 90   days of the exercise of option date. Your employer should be able to   tell you more. Q. Can I put windfall or inherited shares in my ISA? A. No. You can only transfer shares you own into an ISA if they have   come from an employee share scheme. Otherwise, the ISA manager must   purchase shares on the open market. The situation is the same if you have shares that you have inherited.   You are not able to transfer them into an ISA. "Price is current price per share, but you can buy fractional shares. Minimal investment is how later the first purchase of shares must be to make it worth their efforts to set up the account for you. How you manage it is up to you. You can buy or sell shares at any time, pretty much, though it may take a few days for the transaction to ""settle"" and take effect. You can do this via checks, or you can give the broker (or the investment house, if you are dealing directly with them as I do) permission to take money from or put money to your bank account when you tell them you want to buy or sell shares. You may be able to set up direct deposit; talk to your employer about that. Or you may be able to have your bank make a periodic transfer/purchase for you." Your gain is $1408. The difference between 32% of your gain and 15% of your gain is $236.36 or $1.60 per share. If you sell now, you have $3957.44 after taxes.  Forget about the ESPP for a moment. Are you be willing to wager $4000 on the proposition that your company's stock price won't go down more than $1.60 or so over the next 18 months? I've never felt it was worth it. Also, I never thought it made much sense to own any of my employer's stock. If their business does poorly, I'd prefer not to have both my job and my money at risk. If you sell now: Now assuming you hold for 18 months, pay 15% capital gains tax, and the stock price drops by $1.60 to $23.40: This is an old question that has an accepted answer, but it has gotten bumped due to an edit and the answers given are incorrect. I am assuming this means that every other Friday, the company is going into the open public market, buying those shares and then giving it out to the employees. No. Companies will internally hold shares that it intends to offer employees as additional compensation. There are no open market transactions, so the market price of the stock does not change (at least not due to buying pressure).  The only net effect is an equivalent expense for the compensation, but that should already be accounted for in the share price as normal operating expenses. These share may come through an initial buyback from the market, but more common is that when companies issue new shares they keep some internally for exactly this situation.  If they issued new shares every pay period, it would dilute the existing shares several times a quarter which would be difficult to account for. I would pass on their deal if they will only match if you invest in their stock.  Think about when/if the company falls on bad times. What happens to the stock of a company when bad times come? The board of directors will reduce or eliminate the dividend payout.  Current and potential investors will take notice. Current owners of the stock will sell. Potential investors will avoid buying. The price of the stock with go down. And, quite likely, the company will lay off workers.  If/when that happens you would find yourself without a job and holding (almost) worthless stock as your savings. That would be quite a bad situation to be in. You can probably roll it over into the new company's 401k too, so just talk to your HR rep there.  I set up a separate Vangard IRA so when I changejobs or anything, I just dump my investments into that account and don't have to worry about keep track of them all over the place. "You sold $10,000 worth of stock so that money is essentially yours.  However, you sold this stock without actually owning any which means that you, through your broker, are currently borrowing shares amounting to (at the time of your sale) $10,000 from someone who actually owns this stock. You will be paying this person interest for the privilege of borrowing their shares, the exact amount charged varies wildly and depends on factors such as short interest in the stock (loads of people want to go short = shareholders can charge high interest) etc. If I remember correctly hovering over the ""position"" column in your portfolio in the IB Workstation should give you information about the interest rate charged.  You will have to buy back these shares from the lender at some point which is why the $10k isn't just ""free money."" If the stock has gone up in price in the meantime you are going to be paying more than the $10k you got for the same amount of shares and vice versa." If your employer does not offer contribution matching, and you don't like the range of investment options provided by the company 401k, then you probably are better off investing in your own IRA instead.  In an IRA held at a bank or brokerage, you can invest in multiple stocks or funds and move money around within the IRA pretty freely in most cases. If your company is doing well and is actually sharing profit into the 401k, you might consider leaving your 5% contribution to the 401k where it is and put the other 5% you are planning to contribute into a new IRA of your own.  This straddles the risk of you losing money if your company 401k tanks (or profit sharing dries up) and your missing out on profit sharing if it continues to pay well.