How can I get the most value from my employer's ESPP?
A 15% discount is a 17.6% return. (100/85 = 1.176). For a holding period that's an average 15.5 days, a half month. It would be silly to compound this over a year as the numbers are limited.  The safest way to do this is to sell the day you are permitted. In effect, you are betting, 12 times a year, that the stock won't drop 15% in 3 days. You can pull data going back decades, or as long as your company has been public, and run a spreadsheet to see how many times, if at all, the stock has seen this kind of volatility over 3 day periods. Even for volatile stocks, a 15% move is pretty large, you're likely to find your stock doing this less than once per year. It's also safest to not accumulate too many shares of your company for multiple reasons, having to do with risk spreading, diversification, etc.  2 additional points -  the Brexit just caused the S&P to drop 4% over the last 3 days trading. This was a major world event, but, on average we are down 4%. One would have to be very unlucky to have their stock drop 15% over the specific 3 days we are discussing.  The dollars at risk are minimal. Say you make $120K/yr. $10K/month. 15% of this is $1500 and you are buying $1765 worth of stock. The gains, on average are expected to be $265/mo. Doesn't seem like too much, but it's $3180 over a years' time. $3180 in profit for a maximum $1500 at risk at any month's cycle. Short answer is to put the max 15% contribution into your ESPP. Long answer is that since you want to be saving as much as you can anyway, this is a great way to force you to do it, and pick up at least a 15% return every six months (or however often your plan makes a purchase). I say at least because sometimes an ESPP will give you the lower of the beginning or end period stock price, and then a 15% discount off of that (but check the details of your plan). If you feel like your company's stock is a good long term investment, then hold onto the shares when purchased. Otherwise sell as soon as you get them, and bank that 15% return. A 15% discount does not necessarily mean it is a good investment.  The stock price can go down at any point. 15% discount might mean you are getting a little better deal than the average cat.
In my opinion, separating your money into separate accounts is a matter of personal preference. I can only think of two main reasons why people might suggest separating your bank accounts in this way: security and accounting. The security reasoning might go something like this: My employer has access to my bank account, because he direct deposits my salary into my account.  I don't want my employer to have access to all my money, so I'll have a separate account that my employer has access to, and once the salary is deposited, I can move that money into my real account. The fault in this reasoning is that a direct deposit setup doesn't really give your employer withdrawal access to your account, and your employer doesn't have any reason to pull money out of your account after he has paid you.  If fraud is going to happen, it much more likely to happen in the account that you are doing your spending out of. The other reason might be accounting.  Perhaps you have several bank accounts, and you use the different accounts to separate your money for different purposes.  For example, you might have a checking account that you do most of your monthly spending out of, you might have a savings account that you use to store your emergency fund, and you have more savings accounts to keep track of how much you have saved toward your next car, or your vacation, or your Christmas fund, or whatever.  After you get your salary deposited, you can move some into your spending account and some into your various savings accounts for different purposes. Instead of having many bank accounts, I find it easier to do my budgeting/accounting on my own, not relying on the bank accounts to tell me how much money I have allocated to each purpose.  I only have one checking account where my income goes; my own records keep track of how much money in that account is set aside for each purpose.  When the checking account balance gets too large, I move a chunk of it over to my one savings account, which earns a little more interest than the checking account does.  I can always move money back into my checking account if I need to spend it for some reason, and the amount of money in each of the two accounts is not directly related to the purpose of the money. In summary, I don't see a good reason for this type of general recommendation. 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. I don't believe this.  Really, if you have the drive and motivation in this country, you really can do anything you want.  Sure, the mold says that you need a 4.0 gpa from Harvard and an MBA from Wharton... but that doesn't mean that its for everyone.  Employers value determination more than anything, so if you really want a job, you *will* find a way to get it; most of the time, the only thing holding us back is ourselves.  Sounds corny as shit i know, but its true.   If you bang on every door, network with every hiring manager, you will get a job.  and if for some reason they turn you down, you can still start your own business.  **tl;dr  no.** Yeah, me too, as I said. Actually what I'd really prefer is single payer, but failing that, getting health insurance separated from employment would be a big step forward. If people really knew how much they are paying for health insurance, things would change.  I've never worked for an employer that didn't renegotiate health insurance every year, often changing insurance providers every year. To the extent that HR departments are competent in finding the best value, the current environment is pretty dynamic and competitive. Are individuals going to be as competent and well informed as HR departments? I don't know, but I do know that simply making a market free doesn't guarantee lower prices if consumers are ill-informed and bad at making decisions.  As for wages, currently companies are not required to carry health insurance, and many have dropped it already without increasing wages, so I don't see an upward pressure on wages from greater employee mobility.  But it's true that if there were a single large pool for insurance to be based off of, large businesses would no longer get the pool advantage of health insurance over small businesses. Hence my preference for single-payer, or single-group/multi-payer. "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." At this stage of the game your best investment is yourself. Rather than putting it in stocks, use any spare money you have to get yourself the best education you can. See if you can drop that part-time job and give yourself more time to study. Or maybe you can go to a better, more expensive college. Or maybe college will give you some opportunity to travel and learn more that way. You don't want to exclude yourself from those opportunities by not having enough spare cash. So in short, spend what you need to get yourself the best education you can, and keep any spare money you have somewhere you can use it to take advantage of any opportunities that come your way. Usually points have different value depending on what you use it for and how much of them you convert. For many providers, if you have enough (10000+ usually) points, it is possible to convert them 1:1 (which means 1 point converted to 1 cent) to either cash or something that is almost as good as cash ($100 gift card for some popular store or $100 Amazon.com certificate, etc.). Some cards have more exotic ways of getting best value - such as transferring money to pay student loans, retirement accounts, etc. So to get the best value, I'd recommend to make a list of what you can get from your program (most types of reward are uniform - i.e., many gift cards with the same price, so the work may be less than it seems) and calculate point values of each of those. If you want to be really precise take into account that if you buy something with points, you do not earn points on that, which reduces the value a little. In general, these days it is very rare to get a card that produces more than 1% back, though some have up to 5% for certain categories of purchases. This is not an answer to all of your questions but merely an eleaboration on one of your comments: Are there any other areas in the UK that would return rental yields   much above 10% net?   Shares. I could withdraw the money and buy shares for the dividend income, but it is hard to choose shares that yield more than about 6% and they are volatile. I wrote a post about using shares to invest a pension pot. http://www.sspf.co.uk/blog/016/ You may find it of some interest. Of course, the investing would take place within the pension 'wrapper' so you'd only be paying tax on the income taken out each year. The other alternatives you mention suggest paying for the expertise and time of an IFA would be a very economical decision. £1,000 to best use £150,000 seems a bargain to me. Some of the avenues you mention seem very risky from my understanding so someone to determine your tolerances and propose a holistic solution is a good path forward. Best wishes!