Is it possible to allocate pre-tax money to a specific stock?
Whether an investment is pre-tax is determined by the type of account (i.e., tax-advantaged vs ordinary taxable account), but whether you can invest in individual stocks is determined by the provider (i.e., the particular bank where you have the account).  These are orthogonal choices.  If you want to invest in individual stocks, you need to look for a bank that offers an IRA/401k/other tax-advantaged account and allows you to invest in individual stocks with it.  For example, this page suggests that Fidelity would let you do that.  Obviously you should look into various providers yourself to find one that offers the mix of features you want.
"I know your ""pain"".  But don't worry about investing the money right now -- leave it uninvested in the short term.  You have other stuff you need to school up on.  Investment will come, and it's not that hard.  In the short term, focus on taxes.  Do some ""mock"" run-throughs of your expected end-of-year taxes (use last year's forms if this year's aren't available yet).  Must you pay estimated tax periodically throughout the year?  The tax authorities charge hefty penalties for ""forgetting"" to do it or ""not knowing you have to"".  Keep an eye out for any other government gotchas.   Do not overlook this!  This is the best investment you could possibly make.  Max out your government sanctioned retirement funds - in the US we have employer plans like 401K or Keogh, and personal plans like the IRA.  This is fairly straightforward.  Avoid any ""products"" the financial advisors want to sell you, like annuities.  Also if you have the Roth type IRA, learn the difference between that and a normal one.  There are some tricks you can do if you expect to have an ""off"" year in the future.  Charitable giving is worth considering at high income levels.  Do not donate directly to charities.  Instead, use a Donor Advised Fund.  It is a charity of its own, which accepts your tax deductible donation, and holds it.  You take the tax deduction that year.  Then later, when the spirit moves, tell your DAF to donate to the charity of your choice.   This eliminates most of the headaches associated with giving.  You don't get on the soft-hearted sucker lists, because you tell the DAF not to disclose your address, phone or email.  You don't need the charity's acknowledgement letter for your taxes, since your donation was actually to the DAF. It shuts down scams and non-charities, since the DAF confirms their nonprofit status and sends the check to their official address only. (This also bypasses those evil for-profit ""fundraising companies"".) It's a lot simpler than they want you to know.  So-called ""financial advisors"" are actually salesmen working on commission.  They urge you to invest, because that's what they sell.  They sell financial products you can't understand because they are intentionally unduly complex, specifically to confuse you.  They are trying to psych you into believing all investments are too complex to understand, so you'll give up and ""just trust them"".  Simple investments exist.  They actually perform better since they aren't burdened down with overhead and internal complexity.  Follow this rule: If you don't understand a financial product, don't buy it.   But seriously, do commit and take the time to learn investment.  You are the best friend your money will have - or its worst enemy.  The only way to protect your money from inflation or financial salesmen is to understand investment yourself. You can have a successful understanding of how to invest from 1 or 2 books. (Certainly not everything; those ingenious salesmen keep making the financial world more complicated, but you don't need any of that junk.)   For instance how do you allocate domestic stocks, foreign stocks, bonds, etc. in an IRA if you're under 40?  Well... how do smaller universities invest their endowments? They all want the same thing you do.  If you look into it, you'll find they all invest about the same.  And that's quite similar to the asset mix Suze Orman recommends for young people's IRAs.  See? Not that complicated.  Then take the time to learn why. It isn't stupid easy, but it is learnable.   For someone in your tier of income, I recommend Suze Orman's books.  I know that some people don't like her, but that segues into a big problem you'll run into:  People have very strong feelings about money.  Intense, irrational emotions.  People get it from their parents or they get sucked into the ""trust trap"" I mentioned with so-called financial advisors.  They bet their whole savings on whatever they're doing, and their ego is very involved.  When they push you toward their salesman or his variable annuity, they want you to agree they invested well.  So you kinda have to keep your head low, not listen too much to friends/family, and do your research for yourself.  John Bogle's book on mutual funds is a must-read for picking mutual funds and allocating assets.  Certain financial advisors are OK.  They are ""fee only"" advisors.  They deal with all their customers on a fee-only basis, and are not connected to a company which sells financial products.  They will be happy for you to keep your money in your account at your discount brokerage, and do your own trading on asset types (not brands) they recommend.  They don't need your password.  Here's what not to do: A good friend strongly recommended his financial advisor.  In the interview, I said I wanted a fee-only advisor, and he agreed to charge me $2000 flat rate.  Later, I figured out he normally works on commissions, because he was selling me the exact same products he'd sell to a commission (free advice) customer, and they were terrible products of course.  I fired him fast." There was a time that a rule of thumb stated your stock allocation should be 100-your age. That rule suggests that you are at 65%stock/35% bond/cash. If you are comfortable having this money 100% invested, the best advice would be dollar cost averaging, anything more specific would suggest market timing. "Here is the ""investing for retirement"" theoretical background you should have. You should base your investment decisions not simply on the historical return of the fund, but on its potential for future returns and its risk. Past performance does not indicate future results: the past performance is frequently at its best the moment before the bubble pops. While no one knows the specifics of future returns, there are a few types of assets that it's (relatively) safe to make blanket statements about: The future returns of your portfolio will primarily be determined by your asset allocation . The general rules look like: There are a variety of guides out there to help decide your asset allocation and tell you specifically what to do. The other thing that you should consider is the cost of your funds. While it's easy to get lucky enough to make a mutual fund outperform the market in the short term, it's very hard to keep that up for decades on end. Moreover, chasing performance is risky, and expensive. So look at your fund information and locate the expense ratio. If the fund's expense ratio is 1%, that's super-expensive (the stock market's annualized real rate of return is about 4%, so that could be a quarter of your returns). All else being equal, choose the cheap index fund (with an expense ratio closer to 0.1%). Many 401(k) providers only have expensive mutual funds. This is because you're trapped and can't switch to a cheaper fund, so they're free to take lots of your money. If this is the case, deal with it in the short term for the tax benefits, then open a specific type of account called a ""rollover IRA"" when you change jobs, and move your assets there. Or, if your savings are small enough, just open an IRA (a ""traditional IRA"" or ""Roth IRA"") and use those instead. (Or, yell at your HR department, in the event that you think that'll actually accomplish anything.)" "I'm going to discuss this, in general, as specific investment advice isn't allowed here. What type of account is the $60K in now? I mean - Is it in a 401(k), IRA or regular account/CD/money market?  You are still working? Does your company offer any kind of matched 401(k)? If so, take advantage of that right up the level they'll match. If not, are you currently depositing to pretax IRAs? You can't just deposit that $60K into an IRA if it isn't already, but you can put $11k/yr ($5 for you, $6K for hubby if you make $11K or more this year.) Now, disclaimer, I am anti-annuity. Like many who are pro or con on issues, this is my nature. The one type of annuity I actually like is the Immediate Annuity. The link is not for an end company, it shows quotes from many and is meant as an example. Today, a 65 yr old man can get $600/mo with a $100K purchase. This is 7.2%, in an economy in which rates are sub 3%. You give up principal in exchange for this higher annual return.  This is a viable solution for the just-retired person whose money will run out when looking at a 4-5% withdrawal but 1% CD rate. In general, these products are no more complex that what I just described, unlike annuities sold to younger fold which combine high fees with returns that are so complex to describe that most agents can't keep their story straight.  Aside from the immediate flavor, all other annuities are partial sold (there's a quote among finance folk - ""annuities are sold, not bought"") based on their tax deferral features. I don't suspect you are in a tax bracket where that feature has any value to you.  At 48/54, with at least 10 years ahead of you, I'd research 'diversification' and 'asset allocation'. Even $60K is enough to proper invest these funds until you retire and then decide what's right for you.   Beginners' Guide to Asset Allocation, Diversification, and Rebalancing is an interesting introduction, and it's written by the SEC, so your tax dollars paid for it.  Some months ago, I wrote Diversifying to Reduce Risk, which falls short of a complete discussion of asset allocation, but it does illustrate the power of being in a stock/bond mix. The ups and downs were reduced significantly compared to the all stock portfolio.  (for follow up or to help others reply to you, a bit more detail on the current investments, and how you are devastated, eg was there a huge loss from what you had a few years ago?) Edit - The original poster hasn't returned. Posted the question and left. It's unfortunate as this was someone who would benefit from the dialog, and the answers here can help others in a similar position, but I feel more discussion is in order for the OP. Last, I caught a downvote on my reply today. I take no offense, but curious which part of my answer the DVer disagreed with." The top long-term capital gains tax rate will rise to 20% effective 1 Jan, 2011, unless Congress decides to do something about it before then. (Will they? Who knows!! There's been talk about it, but, well, it's Congress. They don't even know what they're going to do.)  Anyway. The rules about when you can sell stock are mostly concerned with when you can realize a capital loss: if you sell a stock at a loss and then re-buy it for tax purposes within 30 days, it's a wash sale and not eligible for a deduction. However, I don't believe this applies to any stocks once you realize a gain - once you've realized the gain and paid your tax for it, it's all yours, locked in at whatever rate. Your replacement stock will be subject to short-term capital gains for the next year afterwards, and you might need to be careful with identifying the holding period on different lots of your stock, but I don't believe there will be any particular trouble. Please do not rely entirely on my advice and consult also with your tax preparer or lawyer. :) And the IRS documentation: Special Addendum for Nov/Dec 2012! Spoiler alert! Congress did indeed act:   they extended the rates, but only temporarily, so now we're looking at   tax hikes starting in 2013 instead, only the new top rate++ will be something   like 23.8% on account of an extra 3.8% medicare tax on passive earnings (brought to you via Obamacare   legislation). But the year and the rates' specifics aside, same thing   still applies. And the Republican house and Democratic senate/President are still duking it out. Have fun. ++ 3.8% surtax applies to the lesser of (a) net investment income (b) income over $200,000 ($250k if married). 20% tax rate applies to people in the 15% income tax bracket for ordinary income or higher. Additional tax discounts for property held over 5 years may be available. Consult tax law and your favorite tax professional and prepare to be confused. "Once again I offer some sage advice - ""Don't let the tax tail wag the investing dog."" Michael offers an excellent method to decide what to do. Note, he doesn't base the decision on the tax implication.  If you are truly indifferent to holding the stock, taxwise, you might consider selling just the profitable shares if that's enough cash. Then sell shares at a loss each year if you have no other gains. That will let you pay the long term gain rate on the shares sold this year, but offset regular income in years to come. But. I'm hard pressed to believe you are indifferent, and I'd use Michel's approach to decide.  Updated - The New Law is simply a rule requiring brokers to track basis. Your situation doesn't change at all. When you sell the shares, you need to identify which shares you want to sell. For older shares, the tracking is your responsibility, that's all." "Aganju has mentioned put options, which are one good possibility. I would suggest considering an even easier strategy: short selling.  Technically you are borrowing the stock from someone and selling it.  At some point you repurchase the stock to return to the lender (""covering your short"").  If the stock price has fallen, then when you repurchase it, it will be cheaper and you keep the profit. Short selling sounds complicated but it's actually very easy--your broker takes care of all the details.  Just go to your brokerage and click ""sell"" or ""sell short.""  You can use a market or limit order just like you were selling something you own.  When it sells, you are done.  The money gets credited to your account.  At some point (after the price falls) you should repurchase it so you don't have a negative position any more, but your brokerage isn't going to hassle you for this unless you bought a lot and the stock price starts rising.  There will be limits on how much you can short, depending on how much money is in your account.  Some stocks (distressed and small stocks) may sometimes be hard to short, meaning your broker will charge you a kind of interest and/or may not be able to complete your transaction. You will need a margin account (a type of brokerage account) to either use options or short sell.  They are easy to come by, though. Note that for a given amount of starting money in your account, puts can give you a much more dramatic gain if the stock price falls.  But they can (and often do) expire worthless, causing you to lose all money you have spent on them.  If you want to maximize how much you make, use puts.  Otherwise I'd short sell. About IPOs, it depends on what you mean.  If the IPO has just completed and you want to bet that the share price will fall, either puts or short selling will work.  Before an IPO you can't short sell and I doubt you would be able to buy an option either. Foreign stocks?  Depends on whether there is an ADR for them that trades on the domestic market and on the details of your brokerage account.  Let me put it this way, if you can buy it, you can short sell it." When you sell a stock that you own, you realize gains, or losses. Short-term gains, realized within a year of buying and selling an asset, are taxed at your maximum (or marginal) tax rate. Long term-gains, realized after a year, are taxed at a lower, preferential rate. The first thing to consider is losses. Losses can be cancelled against gains, reducing your tax liability. Losses can also be carried over to the next tax year and be redeemed against those gains. When you own a bunch of the same type of stock, bought at different times and prices, you can choose which shares to sell. This allows you to decide whether you realize short- or long-term gains (or losses). This is known as lot matching (or order matching). You want to sell the shares that lost value before selling the ones that gained value. Booking losses reduces your taxes; booking gains increases them. If faced with a choice between booking short term and long term losses, I'd go with the former. Since net short-term gains are taxed at a higher rate, I'd want to minimize the short-term tax liability before moving on to long-term tax liability. If my remaining shares had gains, I'd sell the ones purchased earliest since long-term gains are taxed at a lower rate, and delaying the booking of gains converts short-term gains into long-term ones. If there's a formula for this, I'd say it's  (profit - loss) x (tax bracket) = tax paid