Wisest option to pay for second career education
Tl;dr by anecdata I paid for my master's degree from investments/savings with a HELOC backstop  It appears you don't have the 62k cash needed for tuition and living expenses so your decision is between financing a degree by selling your investments or a loan.   Ultimately this comes down to the yes/no sell decision on the investments.  Some things to consider: To me it sounds like you need to come up with 67K (30+37), part of the time you can work in the current job, part of the time you could work a lower paying part time job (for a year).  Lets assume that you can earn 15K for that year, and you can save 5K from your current job.  (I'd try and save more, but what ever you can do.) 67 - 15 - 5 = 47    I'd sell the investment property.  First you will have some funds to throw at this need, second you expense should go down as you don't have a payment on this property. 47 - 26 = 21  You have 32K in cash which is a lot for someone in your expense range.  Six months would be 15K, so I would use some of that cash: 21 - 17 = 4 Now you are really close.  If needed I'd use the investments to cover the last 4k or even more of the on hand cash.  However, could you do something to reduce that amount further ...like working more. Your first step should be to visit with the financial aid office of the university that you are considering attending, perhaps even before filling out the FAFSA. You may be eligible for grants, scholarships, and subsidized loans, as well as unsubsidized loans. You should pursue the first two options first, and then when you know how much remains to be financed, we can evaluate which of your investments you might liquidate if further financing is needed. There are a range of views on debt on this board. I take a very cautious approach to going in to debt. I worked full-time and took night classes to finish my degree without debt, but depending on your program that might not be an option. It seems that you also have a healthy relationship with debt considering the shape of your savings and finances as outlined above. Apart from the above information about how much money could be obtained and at what interest rates, the other missing information is your current salary, and your expected salary range after completing the program. With all of that information I could make specific recommendations, but at this point, my only recommendation is to avoid liquidating any retirement accounts in your effort to invest in yourself if at all possible.
While the US hosts most of the world's innovative startups, its own financial and banking systems are very slow to change.  The infrastructure exists, however the ACH transfers are not wide-spread between individuals. Banks much prefer the option of bill-pay (i.e.: as you said, mailing a check, something in other countries people wouldn't even think of), than letting you do it yourself.  Why? Because they can. There's no real competition over consumers, and the consumers themselves are not educated or sophisticated. Thus, the banks are comfortable with the lack of innovation - since as long as they are all lacking innovation - consumers won't demand it because they won't even know things are possible. And it is definitely cheaper for the banks not to innovate and keep your money for a week while the bill-pay check is en route, than try and develop new things. In other countries, the regulator would step up and force banks to develop new infrastructure and widen the options, but in the US regulation is considered a bad thing, and people are easily swayed, being uneducated and uninformed, by the corporations to support politicians who act against their (people's) best interest in protecting the corporations and reducing and limiting the regulators even further. I have lived in communal houses. Most people don't want roommates. Especially if that means having several kids.  I feel like your arguments are practical, I suppose, but not realistic. If I had 3 kids right now, if anything I would probably be earning less money because my flexibility would be much less. I couldn't pursue an education to earn more money because I would still have bills to pay for my kids. My parents are poor, and they live in an area that my job options would be about 3, and none would pay much more than minimum wage. I am 26, but I have known plenty of 19 year old single moms who just aren't able to get a job that pays well enough to support them, and again, they have few options to develop new skills. I guess you can say it is their fault, but we can hardly say that subway shouldn't have to pay them overtime or what is really less than a living wage. Economists and reality have shown us time and time again that more wages overall means a healthier economy. Every state that has raised wages in the past few years is better off because of it. Every state that has done so has seen their economy grow, and joblessness go down. I don't understand why these things are always either/or. It's not just lucky circumstances and it's not just hard work that makes someone successful. Example abound of rich kids who don't pan out and poor kids who make it.   Personally, I had access to a good education growing up and I pushed myself hard to capitalize on it. Luck is the access, but hard work was necessary to convert. I've had success in my career. Part of it is that I had opportunities to tackle tough challenges, but I also pushed to convert on those opportunities. &gt;Companies have been hiring younger workers because of purely cost-based considerations.  Nope all the economic evidence shows that young people without higher education pre-recession and pretty much all under 30s since the recession have been pushed out of the labour market in favour of older workers, already established workers taking pay cuts and part time work and in many lesser skilled areas immigrant labour.  &gt;The problem is that most of the children we've dealt with feel completely entitled to a baby boomer salary   The entitled/not prepared for work etc arguments that people have started to make is bullshit and a ridiculous piece of nonsense spouted by business groups when asked why arent you hiring more. It was the same 10,20,30 years ago and i bet if you look back at any major recession businesses will spout the same nonsense.   You also complain of them jumping ship, then provide a career ladder, training and a competitive salary. Businesses destroyed job security and career progression in so many areas to save money they never think it costs them money and productivity in the long term. At the very least I'd look closely at what you could get from the RESP (Registered Education Savings Plan). Depending on your income the government are quite generous with grants and bonds you can get over $11,000 of 'free' money if you qualify for everything CESG - Canada Education Savings Grant  By applying for the CESG, up   to $7,200 can be directly deposited by the Federal Government into   your RESP. The Canada Education Savings Grant section offers   information about eligibility requirements for the grant as well as   how to use it when the beneficiary enrolls at a post-secondary   institution. CLB - Canada Learning Bond CLB is available to children   born after December 31st, 2003 if an RESP has been opened on their   behalf. Browse the Canada Learning Bond section to find out who is   eligible, how to apply, and how much the Government of Canada will   contribute to your RESP. I can recomend the TD e-series funds as a low cost way of getting stock market exposure in your RESP So if I were you... As an example if you earn $40k and you pay in the minimum amount to get all the grants ($500/year, $42/month) assuming zero growth you'll have almost $14k of which $5.4k would have been given to you buy the government, if you can afford to save $200/month you'll get over $11,000 from the government What is your goal? I would, under most circumstances, not recommend the Masters. I did it because I studied engineering in undergrad but wanted to transition to finance right away. The reality is that a good undergrad will give you most of the tools you need for success in a junior finance role. The critical piece is networking with professionals and working in the markets to elevate your stance before graduation. I am not an advocate for a lot of investment in education as the payback is less than most alternatives (IB analyst training, CFA, internships, etc.) Look into the Coverdell Education Savings Account (ESA). This is like a Roth IRA for higher education expenses.   Withdrawals are tax free when used for qualified expenses. Contributions are capped at $2000/year per beneficiary (not per account) so it works well for young kids, and not so well for kids about to go to College. This program (like all tax law) are prone to changes due to action (or inaction) in the US Congress.  Currently, some of the benefits are set to sunset in 2010 though they are expected to be renewed in some form by Congress this year. I'm not a 'rule of thumb' guy, but here, I'd suggest that if you can set aside 10% of your income each year for college, that would be great. That turns out to be $900/mo.  In 15 years, if you saw an 8% CAGR, you'd have $311K which happens to be in your range of expenses. And you'd still have time to go as the baby won't graduate for 22(?) years. (Yup, 10% is a good rule of thumb for your income and 3 kids) Now, on the other hand, I'd research what grants you'd be able to get if you came up short. If instead of saving a dime, you funded your own retirement and the spouse's IRA if she's not working, and time the mortgage to pay it off in 15 years from now, the lack of liquid funds actually runs in your favor. But, I'm not an expect on this, just second guessing my own fully funded college account for my daughter.