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?
So we can lower your taxes, although at a cost of say 4 million federal employees. Now the fun begins... your market is flooded with new employees, so many people applying there isn't a reason to keep you at your pay. It's 2008 again, you lost your job, your $30 an hour job now pays $17, and you're unemployed, but at least your tax bracket went down. If you make 100K in the U.S., you are most definitely NOT paying 25.7% tax federally. Only money that you made over 37.5K is even charged at 25% AND you didn't even factor in that you get deductions which decrease your effective tax rate. Where are you pulling your numbers? "Given that the 6 answers all advocate similar information, let me offer you the alternate scenario - You earn $60K and have an employer offering a 50% match on all deposits. All deposits. (Note, I recently read a Q&A here describing such an offer. If I see it again, I'll link).  Let the thought of the above settle in. You think about the fact that $42K isn't a bad salary, and decide to deposit 30%, to gain the full match on your $18K deposit. Now, you budget to live your life, pay your bills, etc, but it's tight. When you accumulate $2000, and a strong want comes up (a toy, a trip, anything, no judgement) you have a tough decision. You think to yourself, ""after the match, I am literally saving 45% of my income. I'm on a pace to have the ability to retire in 20 years. Why do I need to save even more?""  Your budget has enough discretionary spending that if you have a $2000 'emergency', you charge it and pay it off over the next 6-8 months. Much larger, and you know that your super-funded 401(k) has the ability to tap a loan. Your choice to turn away from the common wisdom has the recommended $20K (about 6 months of your spending) sitting in your 401(k), pretax deposited as $26K, and matched to nearly $40K, growing long term.  Note: This is a devil's advocate answer. Had I been the first to answer, it would reflect the above.  In my own experience, when I got married, we built up the proper emergency fund. As interest rates fell, we looked at our mortgage balance, and agreed that paying down the loan would enable us to refinance and save enough in mortgage interest that the net effect was as if we were getting 8% on the money. At the same time as we got that new mortgage, the bank offered a HELOC, which I never needed to use. Did we somehow create high risk? Perhaps. Given that my wife and I were both still working, and had similar incomes, it seemed reasonable." TL;DR: The difference is $230. Just for fun, and to illustrate how brackets work, let's look at the differences you could see from changing when you're paid based on the tax bracket information that Ben Miller provided. If you're paid $87,780 each year, then each year you'll pay $17,716 for a total of $35,432: $5,183 + $12,532 (25% of $50,130 (the amount over $37,650)) If you were paid nothing one year and then double salary ($175,560) the next, you'd pay $0 the first year and $42,193 the next: $18,558 + $23,634 (28% of $84,410 (the amount over $91,150)) So the maximum difference you'd see from shifting when you're paid is $6,761 total, $3,380 per year, or about 4% of your average annual salary. In your particular case, you'd either be paying $35,432 total, or $14,948 followed by $20,714 for $35,662 total, a difference of $230 total, $115 per year, less than 1% of average annual salary: $5,183 + $9,765 (25% of $39,060 (the amount $87,780 - $11,070  is over $37,650)) $18,558 + $2,156 (28% of $7,700 (the amount $87,780 + $11,070 is over $91,150)) To be fair early in my career I did request significant raises as the job duties expanded.  I provided justification and showed that I was worth it, the company agreed.  My company is also in a growth phase so it made sense to them. So you may want to consider a jump or two to maximize your base salary.  However if you are happy somewhere, and they company is happy with you, you may want to just speak to your manager and find out what your options are.  Do some homework on the market for someone in your position and show just cause. "Assuming the numbers work out roughly the same (and you can frankly whip up a spreadsheet to prove that out), a defined benefit scheme that pays out an amount equal to an annuitized return from a 401(k) is better.  The reason is not monetary - it is that the same return is being had at less risk. Put another way, if your defined benefit was guaranteed to be $100/month, and your 401(k) had a contribution that eventually gets to a lump sum that, if annuitized for the same life expectancy gave you $100/month, the DB is better because there is less chance that you won't see the money. Or, put even simpler, which is more likely? That New York goes Bankrupt and is relieved of all pension obligations, or, the stock market underperforms expectations.  Neither can be ruled out, but assuming even the same benefit, lower risk is better. Now, the complication in your scenario is that your new job pays better.  As such, it is possible that you might be able to accumulate more savings in your 401(k) than you might in the DB scheme.  Then again, even with the opportunity to do so, there is no guarantee that you will.  As such, even modelling it out really isn't going to dismiss the key variables. As such, can I suggest a different approach?  Which job is going to make you happier now?  Part of that may be money, part of that may be what you are actually doing.  But you should focus on that question. The marginal consideration of retirement is really moot - in theory, an IRA contribution can be made that would equalize your 401(k), negating it from the equation.  Grant you, there is very slightly different tax treatment, and the phaseout limits differ, but at the salary ranges you are looking at, you could, in theory, make decisions that would have the same retirement outcome in any event. The real question is then not, ""What is the effect in 20 years?"" but rather, which makes you happier now?" Yes. Not doing so would be like turning down a raise. The best advice in almost every situation is to at least contribute up to the amount that the company will match so you get the full benefit. One thing to clarify that you might not be understanding. The vesting period is only for the money the company matches, not your own investment. Even if you leave the company before the account is vested or fully vested, you can transfer to a 401k at your new employer, or roll over into an IRA, or take as taxable income (and pay a penalty if it is an early withdrawal), all your contributions together with any investment gains or losses that have occurred. Ditto whatever part of your employer match that has vested by the time you leave. Often, the employer matching contributions are invested in the  same funds in the same proportions that you have chosen for your own contributions and thus will have incurred the same gains or losses as your own contributions, but  what you are entitled to take with you is the part that has vested. Also, you mention that it is unlikely that you will stay the entire 5 years. However, if you plan to at least stay a couple of years it makes sense to get the 20%, 40%, etc. of the match that you vest during your stay. Again, it's free money. "In Australia there are cases for the argument. 1) We have laws against unfair dismissal that do not apply above certain thresholds. Your position is more secure with the lower salary. 2) Tax benefits for families are unfairly structured such that take home pay may actually be less, again due to a threshold. This tends to benefit charities as people need to shed the taxable income if a repayment of benefits would otherwise be triggered. 3) You do not want to ""just cross"" a tax bracket in a year where levies are being raised for natural disasters or budget shortfall. In this case a raise could be deferred ?" "I have a related issue, since I have some income which is large enough to matter and hard to predict. Start with a best guess. Check what tax bracket you were in last year and withhold that percentage of the expected non-withheld income. Adjust upward a bit, if desired, to reflect the fact that you're getting paid more at the new job. Adjust again, either up or down, to reflect whether you were over-withheld or under-withheld last year (whether the IRS owed you a refund or you had to send a check with your return). Repeat that process next year after next tax season, when you see how well your guess worked out. (You could try pre-calculating the entire tax return based on your expected income and then divide any underpayment into per-paycheck additional withholding... but I don't think it's worth the effort.) I don't worry about trying to get this exactly correct. I don't stress about lost interest if I've over-withheld a bit, and as long as your withholding was reasonably close and you have the cash float available to send them a check for the rest when it comes due, the IRS generally doesn't grumble if your withholding was a bit low.  (It would be really nice if the IRS paid us interest on over-withholding, to mirror the fact that they charge us interest if we're late in returning our forms. Oh well.) Despite all the stories, the IRS really is fairly reasonable; if you aren't deliberately trying to get away with something, the process is annoying but shouldn't be scary. The one time they mail-audited me, it was several thousand dollars in my favor; I'd forgotten to claim some investment losses, and their computers noticed the error. Though I still say the motto of the next revolution will be ""No taxation without proper instructions!""" Having lived in both places, I have to say you can find a higher income in the US for the same job and can live in a small town versus having to live in a big city in Canada to find decent salaries.  For similar sized cities, the cost of housing is significantly lower in the US than Canada.  That is your biggest factor in cost of living.  If you are thinking of NYC or San Francisco, there are no comparable size cities in Canada and you would probably be better off in Canada.   My tax preparer was amazed at how much I paid in Capital Gains taxes when I left Canada.  Maybe it is different now but I doubt it. The biggest free lunch in the US is a generous capital gains exemption when you sell your primary residence without any lifetime cap or cap on the number of times you can do it.  There are rules on how long you have to live in it before selling. For investment real estate, all expenses are deductible in addition to fictional depreciation so with a mortgage you can have positive cash flow and pay no income tax.  You can keep doing tax deferred exchanges into bigger and bigger rentals.  When you are close to retirement, you can exchange into your ultimate beach home, rent it out a few years, then convert to a primary residence. Obviously you don't know the full extent of our company, but I'd be forgoing my salary for a year. Is that worth it to get 10%? I mean assuming it becomes a 1 Million Dollar Idea, I'd get 100k while he gets 700k, working the same amount of time. Then i'd get put on salary. 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. "H.R. basically consults Publication 15 (this is the link to 2015) to determine how much to hold, based on filing status, exemptions, and pay amount. What's described here is a form of estimation, or, in other words, H.R. withholds what would be your actual taxes, dividing across the number of paychecks you receive. Assuming your gross pay and exemptions do not change, this usually results in a zero-sum for taxes owed (you will receive nothing, and owe nothing). As you can see from the charts, the year is basically broken down into equal tax units that reflect how much you would owe if you worked at that bracket all year. This estimation works best when you have steady hours from check to check. In other words, your taxes are based on the estimate of what you'd make if you earned that much all year, scaled down to the time frame (e.g. 1/52 if you are paid weekly, or 1/26 if you paid biweekly). They do not go ""up"" near the end of the year, because they're estimated in advance. You don't move up a tax bracket, but are instead taxed at a particular bracket every paycheck. There's also other forms of estimation mentioned there, but basically follow the same scheme. Note that all estimation forms are just that-- estimates. It's best to use a calculator and compare your current taxes whenever a significant change occurs-- a raise, a new child, getting married or divorced, etc. You'll want to be able to alter your exemptions so that enough taxes are coming out. That's also the reason for the ""withhold extra"" box, so that you can avoid owing. For example, if you're making $44 a week for the first 26 weeks, and then you make $764 a week for the second 26 weeks of the year, you'll end up with an actual tax liability of $2,576.6, but end up paying only $2,345.20. You would owe $231.40. Of course, the actual math is a lot more complicated if you're an employee paid by the minute, for example, or you have a child, go to college, etc. Paychecks that vary wildly, like $10,000 one week and $2,000 the next tend to have the hardest-to-predict estimates (e.g. jobs with big commission payouts). You should avoid living check-to-check with jobs that pay this way, because you'll probably end up owing taxes. Conversely, if you've done your estimates right and you're paid salary or exactly the same number of hours every week, you'll find that the taxes are much easier to predict and you can usually easily create a refund situation simply by having the correct exemptions on your check. So, in summation, if your check falls in the 25% category (which is, of course, 25% above the tax bracket break point), you're already paying the correct amount, and no further drop in your check would be expected." "If you're making $80k, and you're consulting for an extra $400/wk or $20,800/yr, you're earning a total of $100,800.  That's assuming you do it for a full calendar year of course.  Either way, assuming you can deduct/exclude at least $11k of income (as almost everyone can), you're paying 25% on your marginal dollars.  (This also assumes you're single; if you're married/filing jointly, this may not be true.)  Note, you're right at the edge of the 25% bracket if you earn this in a full calendar year - but if you have a 401k, health insurance, or other reductions you'll be fine.  Additionally, for this year you'll be under (again assuming single and no other income) because you aren't earning a full year's worth. Assuming your $80k is precisely taken care of by your regular withholding, then, you will literally pay 25%*$400/week in additional taxes - $100 per week.  So if you are paid biweekly, you need to add $200/week in withholding on your W-4.  If you expect to overpay taxes (if you own a house with a mortgage for example, you often do), you can reduce it some, but adding $200/biweekly paycheck should bring you right to where you were before the extra income. The general rule is to calculate your marginal (not effective) tax rate before the new income, assuming default withholding takes care of that, and then withhold the marginal rate for the new income [checking that the new income doesn't push the marginal rate up - if so, calculate in two parts, the part in the lower marginal rate and the part in the higher marginal rate]. You can google ""2014 tax brackets"", or look at the IRS tax tables for detailed information about marginal rates." Young vs old doesn't really make a difference.  What's in play in the Roth/After Tax vs Traditional/Pretax decision is your current marginal tax bracket versus your probable taxation in retirement.   Since your company matches something on the pretax account it makes sense to max out the pretax contribution match amount before considering roth contributions.  If the match is something like 50% of your contribution up to 3% of your salary, that's an instant 50% return on your contribution and you can't really beat that.