What investments work for these goals?
If you will leave the money invested for a good long while (years) then dividend paying stocks would be appropriate. There are many that pay yields of 3 to 4 percent, which you can take as income or reinvest to compound the growth. There is a lot of good analysis of stocks (and mutual funds that specialize in dividend paying stocks) at Morningstar.com Assuming this will be a taxable account (since you want to pull income off of it, although this will lower wealth growth), you could open a brokerage account at some place like Vanguard (free on their ETFs) and look at tax efficient index fund ETFs (such as total stock market or their 500 fund), including  some international (foreign tax credit is nice in taxable) and muni funds for the (tax advantaged) income, although CDs are likely better for the income at this point.
Like most major decisions in life it entirely depends on your goals.  Do you know exactly what you intend to use the degree for? Are you aiming to go work for Ernst &amp; Young? Do you want to be a finance director at some Fortune 500 company? Do you want to start up your own financial advisory or accounting shop?  Going to school for school's sake is pointless after youve gotten your associate's/bachelor's degree. It's an investment. For the investment to be worth it you need to know exactly what youre investing in and why.  So Step 1: come up with a very concrete career plan. What kind of job exactly do you want next and what industry/company do you want it to be in? Then figure out whether you need the extra degree to make that plan possible. The goal of the kelly criterion strategy is to find a balance between preservation of starting capital and returns. One of extreme you could bet the entirety of your account on one trade, which would maximize your returns if you win, but leave you unable to further invest if you lose. On the other extreme, you could bet the smallest amount of capital possible over the course of several trades to increase the probability that you'll even out to 70% accuracy over time. But this method would be extremely slow.  So for your case, investing 40% each time is one way to find an optimal balance between these two extremes. Use this as a rule of thumb though, because your own situation and investing goals may differ from the goal of  optimal growth. Goal - What is it that you are saving or investing to have: Educational costs, retirement, vacation, home, or something else. Dollar figure and time period would be the keys here. Risk tolerance - What kind of risks are you prepared to accept with the investment choices you are making? What kind of time commitment do these investments have and are you prepared to spend the time necessary for this to work? This is about how wild are the swings as well as what beliefs do you have that may play a role here. Strategy - Do you know what kind of buy and sell conditions you have? Do you know what kind of models you are following? This is really important to have before you buy something as afterward you may have buyer's remorse that may cause more problems in a sense. Record keeping - Do you know what kinds of records you'll need for tax purposes? Do you know how long to hold onto records? Those would be the main ones to my mind. "Answers: 1. Is this a good idea? Is it really risky? What are the pros and cons? Yes, it is a bad idea. I think, with all the talk about employer matches and tax rates at retirement vs. now, that you miss the forest for the trees. It's the taxes on those retirement investments over the course of 40 years that really matter. Example: Imagine $833 per month ($10k per year) invested in XYZ fund, for 40 years (when you retire). The fund happens to make 10% per year over that time, and you're taxed at 28%. How much would you have at retirement? 2. Is it a bad idea to hold both long term savings and retirement in     the same investment vehicle, especially one pegged to the US stock     market? Yes. Keep your retirement separate, and untouchable. It's supposed to be there for when you're old and unable to work. Co-mingling it with other funds will induce you to spend it (""I really need it for that house! I can always pay more into it later!""). It also can create a false sense of security (""look at how much I've got! I got that new car covered...""). So, send 10% into whatever retirement account you've got, and forget about it. Save for other goals separately.  3. Is buying SPY a ""set it and forget it"" sort of deal, or would I need     to rebalance, selling some of SPY and reinvesting in a safer vehicle     like bonds over time? For a retirement account, yes, you would. That's the advantage of target date retirement funds like the one in your 401k. They handle that, and you don't have to worry about it. Think about it: do you know how to ""age"" your account, and what to age it into, and by how much every year? No offense, but your next question is what an ETF is! 4. I don't know ANYTHING about ETFs. Things to consider/know/read? Start here: http://www.investopedia.com/terms/e/etf.asp 5. My company plan is ""retirement goal"" focused, which, according to     Fidelity, means that the asset allocation becomes more conservative     over time and switches to an ""income fund"" after the retirement     target date (2050). Would I need to rebalance over time if holding     SPY? Answered in #3. 6. I'm pretty sure that contributing pretax to 401k is a good idea     because I won't be in the 28% tax bracket when I retire. How are the     benefits of investing in SPY outweigh paying taxes up front, or do     they not? Partially answered in #1. Note that it's that 4 decades of tax-free growth that's the big dog for winning your retirement. Company matches (if you get one) are just a bonus, and the fact that contributions are tax free is a cherry on top. 7. Please comment on anything else you think I am missing I think what you're missing is that winning at personal finance is easy, and winning at personal finance is hard" The Trinity study looked at 'safe' withdrawal rates from retirement portfolios. They found it was safe to withdraw 4% of a portfolio consisting of stocks and bonds. I cannot immediately find exactly what specific investment allocations they used, but note that they found a portfolio consisting largely of stocks would allow for the withdrawal of 3% - 4% and still keep up with inflation. In this case, if you are able to fund $30,000, the study claims it would be safe to withdraw $900 - $1200 a year (that is, pay out as scholarships) while allowing the scholarship to grow sufficiently to cover inflation, and that this should work in perpetuity. My guess is that they invest such scholarship funds in a fairly aggressive portfolio. Most likely, they choose something along these lines: 70 - 80% stocks and 20 - 30% bonds. This is probably more risky than you'd want to take, but should give higher returns than a more conservative portfolio of perhaps 50 - 60% stocks, 40 - 50% bonds, over the long term. Just a regular, interest-bearing savings account isn't going to be enough. They almost never even keep up with inflation. Yes, if the stock market or the bond market takes a hit, the investment will suffer. But over the long term, it should more than recover the lost capital. Such scholarships care far more about the very long term and can weather a few years of bad returns. This is roughly similar to retirement planning. If you expect to be retired for, say, 10 years, you won't worry too much about pulling out your retirement funds. But it's quite possible to retire early (say, at 40) and plan for an infinite retirement. You just need a lot more money to do so. $3 million, invested appropriately, should allow you to pull out approximately $90,000 a year (adjusted upward for inflation) forever. I leave the specifics of how to come up with $3 million as an exercise for the reader. :) As an aside, there's a Memorial and Traffic Safety Fund which (kindly and gently) solicited a $10,000 donation after my wife was killed in a motor vehicle accident. That would have provided annual donations in her name, in perpetuity. This shows you don't need $30,000 to set up a scholarship or a fund. I chose to go another way, but it was an option I seriously considered. Edit: The Trinity study actually only looked at a 30 year withdrawal period. So long as the investment wasn't exhausted within 30 years, it was considered a success. The Trinity study has also been criticised when it comes to retirement. Nevertheless, there's some withdrawal rate at which point your investment is expected to last forever. It just may be slightly smaller than 3-4% per year. There many asset allocation strategies to chose from that beat lifestyle funds. For example: Relative Strength Asset Allocation keeps your money in Stocks when stocks perform well, bonds when they outperform stocks, and cash when both bonds and stocks are under-performing.   The re-allocation happens on a monthly basis. Something not in answers so far:  define your goals.  What is important to you? My goals, if I were in your shoes, would include a debt-free home, passive (investment) income so I would not have to work, and have health insurance covered.  I could think of many more details, and already have, but you get the idea. To help determine which investment information to learn first, consider how much risk you can tolerate.  I know that's vague at this point, but if you're looking for safe investments first, you could learn about mutual funds, and then index funds specifically.  At the risky extreme, you could learn about stock options, but I would not recommend such risk. You are likely thinking of a individual variable insurance contract (IVIC) , better known as a segregated fund, or a principal-protected note (PPN). For a segregated fund, to get a full guarantee on invested capital, you need a 100/100 where the maturity value and death benefit are each 100% guaranteed. The PPN works similar to a long-term GIC (or CD) with a variable investment component.  The thing is, neither of these things are cheap and the cost structure that is built in behind them makes it difficult to make any real above market rates of return. In both cases, if you try to break the contracts early then the guarantees are null and void and you get out what you get out.