As Lumifer said, if you sell stocks (and they're up) you pay taxes on the capital gains - the difference between the price of the stock when you bought it and the price now. If the price now is lower, you get a tax credit for the losses, up to a certain point. Capital gains taxes tend to be lower than regular taxes (in America, at least). Selling shares of an index fund works the same way, where you pay taxes only on the gains, so selling stock to buy what is essentially more stock is pretty much a wash - you don't pay more taxes overall, you just pay them now instead of later. I'm not sure whether being a gift affects the taxes, or what your basis is for capital gains. Investopedia might know, or ask an accountant.

Pretty much the choice of whether to sell the stock and buy more shares of the index fund is like any other choice in investment: which will make you more money? To simplify the math, imagine you sold all the shares now and paid taxes, so you had $X and could invest that in stocks or an index fund. Keep in mind the status quo bias - it is unlikely you would invest in this specific stock if you had $X to invest, and you should only keep the stock if that were the case (tax issues exempted - you'll have to do the math yourself).

(I'd be remiss if I didn't link this Mr. Money Mustache post on index funds that explains why they are a good idea)

To buy an index fund, you buy shares of a mutual fund. That mutual fund invests in every stock in the chosen index, balanced based on whatever criteria they choose. Each share of the mutual fund is worth a portion of the underlying investment. At no point do you own separate stocks - you own shares of the fund, instead.

Toy example: You have an index fund that invests in every stock listed on the New York Stock Exchange. The fund invests in $1,000,000 of stock split evenly among every stock on the NYSE, then issues a thousand shares of the fund itself. You buy one share. Your share is worth $1,000. You can sell your shares back to the fund and they will give you $1,000. Over the next year, some stocks go up and some stocks go down. The fund doesn't buy any more stock or sell any more shares. On average, the nominal value of the NYSE will go up by about 7%. The fund now owns $1,070,000 of stocks. Your one share is now worth $1,070.

The dividends go wherever you want them to. The one share of a thousand you bought above entitles you to 1/1000 of the dividends for the underlying stocks in the fund's entire investment. If you're smart, they go to buy more shares of the fund because compound interest will make you rich. You can have them disbursed to you as money you can exchange for good and services, though.

Investing in an index fund is very easy. You will pay by direct withdrawal from a bank account, so you will have to do something to confirm you own the account, but other than that it's like buying anything else online.

Index funds cover costs - which are low, because buying more stock and re-balancing existing stock can be done by a not-that-sophisticated computer program - by charging you a small percentage of your investment. This is reflected by your shares (and dividends) not being worth quite 100% of the fund's value. Index funds are good because they have a very low expense ratio. Many normal mutual funds charge upwards of 1% annually. A good index fund can charge about 0.20%-0.05%. That means you pay your fund about $20 for the privilege of making you about $700, every year.

Opinion time: I own shares in index funds. They are amazing. For a few hours work setting up an automatic transfer and filling out paperwork, I am slowly getting rich. I don't need the money any time this decade, so even if the market crashes tomorrow in a 2008-level event, overall the occasional 1990s-style rises cancel that out, leaving real growth at about 5% assuming you use any dividends to purchase more shares.

I will let you skip the next part of this process and recommend a specific fund: The Vanguard Total Stock Market Index, VTSMX. It invests in every stock listed on the NYSE and NASDAQ. If you have $10k invested in it, the expense ratio is a super-low 0.05, and American stocks are very broad and exposed to world conditions as a whole (this is good - you want to spread out your portfolio as much as possible to reduce risk). Go to vanguard.com , you can figure it out online.

I think I could talk about the minutiae of investing all day. It's fascinating. I should write that post about investing and the Singularity one day.

The "you're interviewing them too" line is absolutely true if you are in a competitive market and are not desperate for a job. If you are unemployed, your best strategy is to get any job in your field, work there for a few months, then start hunting for another job. If you have a job and skills the market values (and thus expect to be able to get multiple job offers in the course of a few months), you can afford to be selective. This means you should not take a job offer unless it's an improvement from your last job, and it's enough of an improvement that you it's worth it to stop searching. There is a post somewhere on LessWrong about the decision theory on how long you should look on an open ended issue like this, I believe with marriage as the subject, but "don't take a job that sounds like it would grind your soul to dust" is a good starting point, as is "never take a pay cut, or a non-significant pay increase". Switching jobs is a pain, and you can't do it too often.

Getting back to the point, in an interview you should ask three main kinds of questions: questions that make you seem smart, questions that you show you were paying attentions, and questions that you actually want to know the answer to. If you can do two or all three at once, great. A good stock question is "Can you walk me through what a typical day in this position is like?", because it's rarely answered earlier and it's good to know. It's amazing how often people will talk about a job in generalities and not say, e.g., whether you are going to be sitting in a chair pressing buttons all day or whether you're going to be traveling, attending meetings, washing beakers, whatever. "How big a team will I be working with?" is another one, because again it sounds like you care about the particulars of the job, which you should if you're going to be working there for months or years. You should be able to get two or three relevant questions in your specialty too to trot out.

Finally, don't wait until the end of an interview to ask questions. It's best if you have a conversation, not a monologue. Don't interrupt, but if there's a break in the interview ask about something that you want to know about. You might find you have no questions left at the end - just tell the truth, that you already asked everything you wanted to know.

Source: I have a job. I also know quite a few people who are part of the process from the employer end.

By the second point, do you literally mean it's legal to conscript soldiers (it is in America at least, although starting a draft would be politically impossible absent an immediate existential threat to America as a state), or do you mean that figuratively, in that if we pay soldiers enough, we'll get more volunteers? I'm not sure what point you're making.

I will see if I can find the data on the poor performance and high cost of mercenaries.

Tell me your rough beliefs and I will pigeonhole you. If you want me to, of course. It might lead you towards a school of political thought you'll agree with, or at least enjoy reading about.

What about the practical effects? Correct me if I'm wrong, but explicit mercenaries (like Blackwater) give worse results for vastly more money than normal volunteer (paid) soldiers.

I am with you on the preference for incentivizing people to go in to the military, rather than using conscription. Not being able to conscript more soldiers limits our ambitions to smaller wars against inferior powers. Then again, America seems to have a really good track record fighting giant military machines and great empires (Germany, Great Britain) and a really bad track record accomplishing our stated objectives in these regional wars against inferior militaries (Vietnam, Korea, Iraq, Afghanistan). Maybe I should be pushing for us to expend our military might on European plains?

I downvoted you because I mostly agree - depending on how broadly you mean broadly. I suspect this is a not uncommon position here, and I would not even be surprised if it were a plurality position.

This sounds great, what's it called?