How can I determine if leaving a lower paying, tax advantaged, job for a higher paying one makes sense financially?
You'd be moving from 33.5K of taxable income + 16.5K of untaxable income, to 65K of taxable income (worst case). So the question is whether the net from the extra 31.5K of taxable income is more than the 16.5K, and since marginal tax rates in the relevant brackets are no more than 32% according to the table you posted (22% federal and 10% provincial), it's definitely a win to move jobs. More precisely, the marginal tax rate is 25% on the first 8044 (41544-33500) and 32% on the rest, making for total extra tax of about 9.5K and thus net income (beyond the 33.5K baseline) of 22K. Compared to the 16.5K this leaves you 5.5K up. If you end up at the 70K end, you're another 3.4K up beyond that. It looks like a coin toss. What you have isn't bad at all.  If you have enough free time with your $50k job to do extra stuff on the side, you can use that time to build a business.  You're obviously a go-getter type, so this might suit you. Which job is closer to your calling?  All other things being equal, the more fulfilling job should win, no?
&gt; Most businesses operate at a loss for the first year or two, and reinvest all the profits for expansion for a few years after that. So higher income taxes won't affect them one bit.  Yes, but tariffs, licenses, excise taxes, payroll taxes, and the like do. I say this as a business owner. I agree that the personal margin income tax brackets should go higher, I was just making a comment about how you form a healthy ecosystem for businesses. It takes tax friendly policies on the corporate level.  &gt; Half of all incomes goes to the top 10%. They have more than enough money...   Well, if we open it up to the top 10% now instead of only 1% (which is what I was referencing with the whole Occupy movement), we are starting to get somewhere. They already pay the largest proportion of taxes, obviously raising taxes would impact them the most no matter how you look at it. I have no disagreement with doing that, in fact I encourage it.  &gt; (Note: I intentionally ommitted health care because money alone won't fix that mess.)  I would say education fits within that category too. Per capita we spend more than any other country on our children already.  But yes, raising taxes will be necessary to fund what we need to fund, but I'd like to start with cutting government spending, reforming the fucked up programs, and creating a real economic / jobs plan for the next 50 years and then, at that point, we can determine who pays what taxes rather than asking the wealthy to pay more so we can fund useless wars. "In England, currently and for most of the last fifty years, the standard length of the mortgage term is 25 years. A mortgage can be either a capital-and-interest mortgage, or interest-only. In the former, you pay off part of the original loan each month, plus the interest on the amount borrowed. In the latter, you only pay interest each month, and the original amount borrowed never reduces: you pay premiums on a life insurance policy, additionally, which is designed to pay off the original sum borrowed at the end of the 25 years. No one in England thinks that a 25 year loan has any drawbacks. The main point to appreciate is that the longer the period of the loan, the less you need to pay each month, because you are repaying the original loan - the capital - over a longer period of time. Thus, in principle, a mortgage is easier to repay the longer the term is, because the monthly payment is less. If you have a 12 year mortgage, you must pay back the original amount borrowed in half the time: the capital element in your payment each month is double what it would be if repaid over 25 years - i.e. if repaid over a period twice as long. Only if the borrower is less than 25 years away from retirement is a 25 years mortgage seen as a bad idea, by the lender - because, obviously, the lender relies on the borrower having an income sufficient to keep up the repayments. There are many complicating factors: an interest-only mortgage, where you pay back the original amount borrowed from the maturity proceeds from a life policy, puts you in a situation where the original capital sum never reduces, so you always pay the same each month. But on a straight repayment mortgage, the traditional type, you pay less and less each month as time goes by, for you are reducing the capital outstanding each month, and because that is reducing so is the amount of interest you pay each month (as this is calculated on the outstanding capital amount). There are snags to avoid, if you can. For example, some mortgage contracts impose penalties if the borrower repays more than the due monthly amount, hence in effect the borrower faces a - possibly heavy - financial penalty for early repayment of the loan. But not all mortgages include such a condition. If house prices are on a rising trend, the market value of the property will soon be worth considerably more than the amount owed on the mortgage, especially where the mortgage debt is reducing every month, as each repayment is made; so the bank or other lender will not be worried about lending over a 25 year term, because if it forecloses there should normally be no difficulty in recovering the outstanding amount from the sale proceeds. If the borrower falls behind on the repayments, or house prices fall, he may soon get into difficulties; but this could happen to anyone - it is not a particular problem of a 25 year term. Where a default in repayment occurs, the bank will often suggest lengthening the mortgage term, from 25 years to 30 years, in order to reduce the amount of the monthly repayment, as a means of helping the borrower. So longer terms than 25 years are in fact a positive solution in a case of financial difficulty.  Of course, the longer the term the greater the amount that the borrower will pay in total. But the longer the term, the less he will pay each month - at least on a traditional capital-and-interest mortgage. So it is a question of balancing those two competing factors.  As long as you do not have a mortgage condition that penalises the borrower for paying off the loan more quickly, it can make sense to have as long a term as possible, to begin with, which can be shortened by increasing the monthly repayment as fast as circumstances allow. In England, we used to have tax relief on mortgage payments, and so in times gone by it did make sense to let the mortgage run the full 25 years, in order to get maximum tax relief - the rules were very complex, but it tended to maximise your tax relief by paying over the longest possible period. But today, with no income tax relief given on mortgage payments, that is no longer a consideration in this country. The practical position is, of course, that you can never tell how long it might take you to pay off a mortgage. It is a gamble as to whether your income will rise in future years, and whether your job will last until your mortgage is paid off. You might fall ill, you might be made redundant, you might be demoted. Mortgage interest rates might rise. It is never possible to say that you ""can"" pay off the loan in a short time.  If you hope to do so, the only matters that actually fall within your control are the conditions of the mortgage contract itself. Get a good lawyer. Tell him to watch out for early-redemption penalties. Get a good financial adviser. Tell him to work out what you will need to pay in additional premiums on your life policy if you are considering taking an interest-only mortgage. Try to fix your mortgage rate in the first few years, for as long as possible, so that in your most vulnerable period, with the greatest amount owing, you are insulated against unexpected interest rate fluctuations. Only the initial conditions can be controlled, so it might be prudent to take as long a term as possible, even though a prudent borrower will leave himself room to reduce that term, and a prudent lender will leave room to extend it, in case of unpredictable changes in the financial circumstances. In England, most lenders are, in my experience, reluctant to grant mortgages for less than 25 years. That is simply a policy. Rightly or wrongly, the borrower usually has no choice about the length of the mortgbage term. Hence, in the UK it can be difficult to find a choice of interest rates based on differing mortgage terms. I am aware that the situation in the USA is rather different, but if I personally were faced with the choice I would be uncomfortable about taking on a short term mortgage, because of the factors I have outlined above." "In general taking money out of a 401k to repay a loan is a bad idea for a number of reasons.  Taxes and penalties if you are under 59 and 1/2 you will pay a 10% penalty on withdrawals from a traditional 401k plan. Then you are going add the amount you withdraw to your income in determining your current tax bill. If you make a large withdrawal you will likely push yourself into a higher tax bracket and will end up paying additional taxes than if you made several smaller withdrawals or waited until retirement when your income would presumably be lower. Taxes and penalties will mean you will need to withdraw ~225k in order to pay taxes and penalties while still having 150k to pay toward the mortgage (this assumes you are single and have no other income). You miss out on the growth your 401k could have had.  Lack of diversification the average person has the majority of their net worth tied up in their home and by paying off your mortgage you are putting even more of your money into residential real estate. By moving money from a 401k to your personal residence you could also lose some protection from creditors and lawsuits. Retirement accounts are generally off limits to creditors where as your house is limited by the homestead exemption (varies greatly from state to state). There are a few times when it might makes sense to use 401k money to pay off a mortgage. If you are older than 59.5 and have little tolerance for risk it might make sense to take the amount of money between your current income and the next higher tax bracket and ""invest"" the money in your mortgage each year. You would still want to avoid taking out a large chunk at one time though to avoid pushing yourself into a much higher tax bracket." I don't believe there exists a tax-advantage for paying employees a bonus instead of increased salary. It's all expense to the employer, it's all income to you, and it's taxed the same (bonus checks might have more withheld, but your end of year tax burden doesn't change). It does benefit your employer to delay a significant portion of your pay until the end of the year, delaying payment provides buffer in case of delays in getting paid by the client. Your employer could even put the extra money to work earning more money over the year.  It would depend on your contract, but are you due your bonus if you were to leave your job before year-end? If not, that's a great reason to delay payment, because it makes you less likely to leave mid-year, and should you not work out they can keep the difference. Take another job.  From a personal finance perspective this is the wrong reason to dip into a retirement account.  You will lose so much ground towards actually retiring.  Sure you won't be taxed, but you will be missing so much opportunity where that money won't be working for your retirement. The off-topic answer to take to the start-ups stackexchange site is:  don't quit your day job until your business plan is written out and you have an idea of where to get your startup capital. Without more information about what tax bracket you are in, I cannot make a recommendation about what your best option is, but here are a few things to consider: 4% of 30k ($1,200) is dwarfed by an $18,000 base pay increase. At 48k maxing out IRA will take ~11.5% of gross income, so at current position (30k salary) 401k contributions would likely be limited to the matching portion anyway. The long-term benefit of a deferred tax retirement plan can't fully be known since tax rates can change over time. If rates increase, the benefit can be mitigated. Personally, I only contribute to 401k enough to get full employer matching, and then I prioritize HSA, IRA, after those, some people like to go back to 401k to max, but I prefer other investments. At this low of an income range, the increase in base pay is far too significant to worry over potential differences in tax-deferred vs after tax investments. Don't forget to take into account the tax deductability of the interest and PMI into the equation. Of course, this would based on your current pay rate, and your rates after marriage.  Your mentioning the flexibility in future changes is also a key aspect to take into consideration.