ESPP advantages and disadvantages
The typical deal is you can put 10% of your gross pay into the ESPP. The purchase will occur on the last deposit date, usually a 6 month period, at a 15% discount to the market price.  So, the math is something like this: Your return if sold the day it's purchased is not 15%, it's 100/85 or 17.6%. Minor nitpick on my part, I suppose.  Also the return is not a 6 month return, as the weekly or bi-weekly deductions are the average between the oldest (6 mo) and the most recent (uh, zero time, maybe a week.) This is closer to 3 months. The annualized rate is actually pretty meaningless since you don't have 4 opportunities to achieve this return, it's important only if the cash flow hit causes you to borrow to support the ESPP purchases. The risk is whether the stock drops the 15% before you can execute the sell to take advantage of the gain.  Of course the return is gross, you need to net for taxes.  Edit to respond to comment below - When I said meaningless, I meant that you can't take the 17.6%, annualize it to 91.2% per year and think your $1000 will compound to $1912. It's as meaningless as when an investor gets a 10% gain on a stock in one day, and (with 250 trading days per year) decides his $1000 will be worth $2 quadrillion dollars after a year. The 17.6% is significant in that it's available twice per year, for a true 38% return over a year, but if borrowing to help the cash flow, that rate is really over 3 months. It would be difficult to answer without knowing specifics about a particular offer. In certain cases, it's definitely great and one could become a millionaire [Google for example]. In other cases one could lose money. In most cases one makes a decent return. As the specifics are not available, in general look out for: Most of these would determine if the plan is good for you to get into. Advantage: more money.  The financial tradeoff is usually to your benefit: Given these, for having your money locked up for the average length of the vesting periods (some is locked up for 3 months, some is locked up for nearly 0), you get a 10% return.  Overall, it's like a 1.5% bonus for the year, assuming you were to sell everything right away. Of course, whether or not you wish to keep the stock depends on how you value MSFT as an investment. The disadvantage lies in a couple parts: You should always always enroll in an espp if there is no lockup period and you can finance the contributions at a non-onerous rate. You should also always always sell it right away regardless of your feelings for the company.  If you feel you must hold company stock to be a good employee buy some in your 401k which has additional advantages for company stock.  (Gains treated as gains and not income on distribution.) If you can't contribute at first, do as much as you can and use your results from the previous offering period to finance a greater contribution the next period.  I slowly went from 4% to 10% over 6 offering periods at my plan. The actual apr on a 15% discount plan is ~90% if you are able to sell right when the shares are priced.  (Usually not the case, but the risk is small, there usually is a day or two administrative lockup (getting the shares into your account)) even for ESPP's that have no official lockup period. see here for details on the calculation. http://blog.adamnash.com/2006/11/22/your-employee-stock-purchase-plan-espp-is-worth-a-lot-more-than-15/ Just a note  For your reference I worked for Motorola for 10 years.  A stock that fell pretty dramatically over those 10 years and I always made money on the ESPP and more than once doubled my money. One additional note....Be aware of tax treatment on espp.  Specifically be aware that plans generally withhold income tax on gains over the purchase price automatically.  I didn't realize this for a couple of years and double taxed myself on those gains.  Fortunately I found out my error in time to refile and get the money back, but it was a headache. The answer is simple. If your employer is offering you a discount, that is free money. You always take free money, always.
I don't think you are reading the stock chart right.  ORCL has a beta of 1.12 which means it has more volatility than the market as a whole.  See image below for a fairly wild stock chart for a year.   I would not truly consider ESPP participation investing, unless you intend to buy and hold the stock.  If you intend to sell the stock soon after you are able, it is more speculation.  ESPP's are okay based upon the terms.  If the stock was a constant price, and you could sell right away, then an ESPP plan would be easy money.  Often, employees are often given a 15% discount to purchase the stock.  If you can sell it before any price drop, then you are guaranteed to make 15% on the money invested minus any commissions.   Some employers make ESPP participants hold the stock for a year.  This makes such a plan less of a value.  The reasons are the stock can drop in price during that time, you could need the money, or (in the best case) your money is tied up longer making the ROI less. The reasons people invest in stock are varied and is far to much to discuss in a single post.  Some of your colleagues are using the ESPP solely to earn the discount in their money. "Which hedge fund outperforms consistently, year after year?  Hedge funds are over-rated, and few truly outperform... nor do many actually provide a hedge as they were originally intended to do.  Some funds have great years, but only because most hedge funds take much bigger risks via derivatives... and thus they have huge down years as well.  BTW being ""VERY well-funded"" is a DISadvantage, not an advantage.  It's tremendously more difficult to make large percentage gains on $1 billion than it is to make gains on $1 million." There's an odd anomaly that often occurs with shares acquired through company plans via ESPP or option purchase. The general situation is that the share value above strike price or grant price may become ordinary income, but a sale below the price at day the shares are valued is a capital loss.  e.g. in an ESPP offering, I have a $10 purchase price, but at the end of the offering, the shares are valued at $100. Unless I hold the shares for an additional year, the sale price contains ordinary W2 income. So, if I see the shares falling and sell for $50, I have a tax bill for $90 of W2 income, but a $50 capital loss. Tax is due on $90 (and for 1K shares, $90,000 which can be a $30K hit) but that $50K loss can only be applied to cap gains, or $3K/yr of income.  In the dotcom bubble, there were many people who had million dollar tax bills and the value of the money netted from the sale couldn't even cover the taxes. And $1M in losses would take 300 years at $3K/yr.  The above is one reason the lockup date expiration is why shares get sold. And one can probably profit on the bigger companies stock.  Edit - see Yelp down 3% following expiration of 180 day IPO lock-up period, for similar situation. The cycle has been continuously going for a couple generations now and seems to be getting worse. I don't have the answers but it seems obvious that doing what they've always done doesn't work.  I'm always entertained by people thinking that life should be fair. No where in nature is life fair. Some people are born with an advantage and still screw it up and others are born disadvantaged and succeed. I think it's obvious that people make choices that make one or the other outcomes more likely but nothing is guaranteed for them. "The company itself doesn't benefit. In most cases, it's an expense as the match that many offer is going to cost the company some percent of salary.  As Mike said, it's part of the benefit package. Vacation, medical, dental, cafeteria plans (i.e. both flexible spending and dependent care accounts, not food), stock options, employee stock purchase plans, defined contribution or defined benefit pension, and the 401(k) or 403(b) for teachers. Each and all of these are what one should look at when looking at ""total compensation"". You allude to the lack of choices in the 401(k) compared to other accounts. Noted. And that lack of choice should be part of your decision process as to how you choose to invest for retirement. If the fess/selection is bad enough, you need to be vocal about it and request a change. Bad choices + no match, and maybe the account should be avoided, else just deposit to the match.  Note - Keith thanks for catching and fixing one typo, I just caught another." The general idea of the PRPP is so that small business who cannot afford to offer a plan alone will be able to pool resources with others along with self-employed to create voluntary, defined-contribution pension plans that would be managed by private sector financial institutions. The PRPP concept would offer more options to individuals as well  as   small and medium-sized businesses - Tax Rules for Pooled Registered Pension Plans  You can also find an overview here THE NEW PRPP – A Pension for the Pension-Less Thank you for the summary! I live in a small city where it would never take more than 10 minutes to walk into the store and get your refund, so I don't see a huge advantage to this. Maybe for bigger and busier stores. I can't think of any more negatives apart from what you mentioned, but the positives might include higher cost base for when you sell the place (this only applies in Australia if it is an investment property) thus having to pay less tax on the capital gains, and being able to borrowing extra funds which may help with your cashflow (especially if you keep the extra funds in an 100% offset account so your interest payable is not increased until you really need the extra funds).