If I pay taxes on my earnings, would someone also pay taxes on the same earnings if I subcontract them and pay a share?
If you want to subcontract some of your excess work to somebody else, you better be in business!  While some kinds of employees (e.g. commissioned salespeople) are permitted to deduct some expenses on their income tax, generally only a real business can deduct wages for additional employees, or the cost of services provided by subcontractors. Do you invoice your clients and charge HST (GST)?  Or do you tell your clients each pay period how many hours you worked and they compensate you through their payroll system like everybody else that walks through the door?  If you're not invoicing and charging HST (GST) (assuming you exceed the threshold, and if you have too much work, you probably do!), then perhaps your clients are treating you as an employee – by default – and withholding taxes, CPP, and EI so they don't get in trouble? After all, Canada Revenue Agency is likely to consider any person providing a service to a company to be an employee unless there is sufficient evidence to the contrary, and when there isn't enough evidence, it's the company paying for the services that would be on the hook for unpaid taxes, CPP, and EI. Carefully consider what form of business you are operating, or were intending to operate.  It's essential for your business to be structured appropriately if you want to hire or subcontract.  You ought to be either self-employed as a sole proprietor, or perhaps incorporated if it makes more sense to your situation.  Next, act accordingly. For instance, it's likely that your business should be taking care of the source deductions, CPP, and EI.  In fact, self-employed individuals shouldn't even be paying into EI – an independent contractor wouldn't qualify to make an EI claim if they lost a contract. As an independent, one doesn't have a job, one has a business, and EI doesn't cover the business itself, only the employees that the business deals with at arm's length.  As a business owner, you would be considered non-arms-length, and exempt from EI. Growing your business in the way that you are suggesting is an important enough a step that you should seek professional advice in advance.  Find a good accountant that deals with self-employed individuals & small businesses and run all this by him.  He should be able to guide you accordingly.  Find a lawyer, too.  A lawyer can guide you on how to properly subcontract others while protecting you and your business. Finally, be mindful of what it is you agreed to in your contract with your client:  Do they expect all services to be performed by you, personally?  Even if it wasn't written down who exactly would be performing the services, there may be an assumption it's you.  Some negotiation may be in order if you want to use subcontractors.
"Be careful here: If ACME were in California, I would pay taxes on USD 17,000 because I   had revenue of 20,000 and expenses of 3,000. To CALIFORNIA. And California taxes S-Corps. And, in addition, you'd pay $800 for the right of doing business in the State. All that in addition to the regular Federal and State taxes to the State where you're resident. Suppose that ACME is in Britain (or anywhere else for that matter). My   revenue and expenses are the same, but now my money has been earned   and my expenses incurred in a foreign country. Same thing exactly. Except that you'll have to pay taxes to the UK. There may be some provision in the tax treaty to help you though, so you may end up paying less taxes when working in the UK than in California. Check with a licensed tax adviser (EA/CPA licensed in your State) who won't run away from you after you say the words ""Tax Treaty"". Does it even make sense to use my S-Corporation to do business in a   foreign country? That should be a business decision, don't let the tax considerations drive your business." &gt; Operating in a country that allows you to make profit, in my opinion, establishes a duty to pay one's fair share of taxes. Paying legislators to make laws enabling tax avoidance is, in my mind, unethical. Clearly we have a different idea of what is ethical and not.  You have stumbled upon the heart of exactly why Burger King's actions (and those of other companies that do similar things) are perfectly justified, although perhaps not in the manner you intended.   In the entire developed world, corporations are taxed at a certain rate on the income that they make as a result of business operations in that country.  In the US, US headquartered corporations are taxed at a certain rate not only on the income that they make a result of business operations in that country, but also on the income that they make as the result of business operations in other countries.   Operating in a country that allows you to make a profit established a duty to pay one's fair share of taxes. Operating in a country that allows you to make a profit does not establish any duty to pay one's fair share of taxes *to an entirely different country*. Or at least, no moral or ethical obligation to do so. The US may try to make a legal obligation to do so, but I certainly can't fault any company which tries to avoid that obligation, since the obligation is inherently unjust in the first place.  If you don't want companies doing stuff like this, might I suggest that your country should stop imposing such ridiculous tax laws, and get in line with the rest of the developed world. Every other country in the world is content to tax their fair slice of the pie for stuff that happens in their borders; only the US expects a bite out of everyone else's pie too.   Same should go for personal income earned by US citizens living abroad. They should have no obligation to pay US income taxes. "This answer is about the USA. Each time you sell a security (a stock or a bond) or some other asset, you are expected to pay tax on the net gain. It doesn't matter whether you use a broker or mutual fund to make the sale. You still owe the tax. Net capital gain is defined this way: Gross sale prices less (broker fees for selling + cost of buying the asset) The cost of buying the asset is called the ""basis price.""  You, or your broker, needs to keep track of the basis price for each share. This is easy when you're just getting started investing. It stays easy if you're careful about your record keeping.  You owe the capital gains tax whenever you sell an asset, whether or not you reinvest the proceeds in something else. If your capital gains are modest, you can pay all the taxes at the end of the year. If they are larger -- for example if they exceed your wage earnings -- you should pay quarterly estimated tax. The tax authorities ding you for a penalty if you wait to pay five- or six-figure tax bills without paying quarterly estimates.  You pay NET capital gains tax. If one asset loses money and another makes money, you pay on your gains minus your losses. If you have more losses than gains in a particular year, you can carry forward up to $3,000 (I think). You can't carry forward tens of thousands in capital losses.  Long term and short term gains are treated separately. IRS Schedule B has places to plug in all those numbers, and the tax programs (Turbo etc) do too. Dividend payments are also taxable when they are paid. Those aren't capital gains. They go on Schedule D along with interest payments. The same is true for a mutual fund. If the fund has Ford shares in it, and Ford pays $0.70 per share in March, that's a dividend payment. If the fund managers decide to sell Ford and buy Tesla in June,  the selling of Ford shares will be a cap-gains taxable event for you.  The good news: the mutual fund managers send you a statement sometime in February or March of each year telling what you should put on your tax forms.  This is great. They add it all up for you. They give you a nice consolidated tax statement covering everything: dividends, their buying and selling activity on your behalf, and any selling they did when you withdrew money from the fund for any purpose.   Some investment accounts like 401(k) accounts are tax free. You don't pay any tax on those accounts -- capital gains, dividends, interest -- until you withdraw the money to live on after you retire. Then that money is taxed as if it were wage income. If you want an easy and fairly reliable way to invest, and don't want to do a lot of tax-form scrambling, choose a couple of different mutual funds, put money into them, and leave it there. They'll send you consolidated tax statements once a year. Download them into your tax program and you're done. You mentioned ""riding out bad times in cash.""  No, no, NOT a good idea. That investment strategy almost guarantees you will sell when the market is going down and buy when it's going up. That's ""sell low, buy high."" It's a loser. Not even Warren Buffett can call the top of the market and the bottom.  Ned Johnson (Fidelity's founder) DEFINITELY can't." "The cost of paying tax should be considered an additional financial expense, and the administrative burden of filing those taxes should be considered an additional labour 'expense'. Simplified, your question is asking how to determine whether these additional expenses are 'worth' it. There are many ways to calculate what your time is 'worth'. Consider two situations where you may consider picking up additional part time work at minimum wage: 1)  If you are working 80 hours a week at a stressful but high-paying job, working another 5 hours a week at minimum wage would likely not be worth your time [both because you already make 'a lot' of money, and also because your time is limited and therefore precious].  2) If you are working 20 hours a week at minimum wage, then another 5 hours a week at the same job would likely be worth your time [both because it would increase your income by 25%, and also because it would not put a heavy strain on your light schedule].  These two extreme examples highlight the inferred principle that I think generally applies to weigh such decisions: Competes with: In your specific example, the actual 'work' component will happen regardless of the money aspect. That is, your wife will be providing these services regardless. So your question is essentially ""would it be worth it for my wife to make $5k, given that she would pay tax on that money and would bear the burden of administrating the tax filings etc.?""  We can't answer this directly, because it relates to what your wife values. If doing this would make the activity (which is otherwise just a hobby) an unwanted chore, then it may not be worth the post-tax income. If doing this would not impact her enjoyment of the teaching, but would add on an unwanted ~1 hour / week of paperwork, is it worth spending 50 hours over the course of the year, to earn $5k? I assume the answer then would be ""yes""." "It seems I can make contributions as employee-elective, employer   match, or profit sharing; yet they all end up in the same 401k from my   money since I'm both the employer and employee in this situation. Correct. What does this mean for my allowed limits for each of the 3 types of   contributions? Are all 3 types deductible? ""Deductible""? Nothing is deductible. First you need to calculate your ""compensation"". According to the IRS, it is this: compensation is your “earned income,” which is defined as net earnings   from self-employment after deducting both: So assuming (numbers for example, not real numbers) your business netted $30, and $500 is the SE tax (half). You contributed $17.5 (max) for yourself. Your compensation is thus 30-17.5-0.5=12. Your business can contribute up to 25% of that on your behalf, i.e.: $4K. Total that you can contribute in such a scenario is $21.5K. Whatever is contributed to a regular 401k is deferred, i.e.: excluded from income for the current year and taxed when you withdraw it from 401k (not ""deducted"" - deferred)." Bartering is a tricky discussion. Yes, it definitely applies when you are self-employed and do a job that you would charge anyone else for, but what if you are helping a friend in your spare time? If you receive something in exchange, the value of the item you received would be your income, but what if you don't receive anything in exchange? If the company bought a computer that they loan to you to do occasional work for them, there's no reason you couldn't take the computer home and have that company retain ownership of the property. They could still expense the depreciation of the computer without giving it to you. If it were a car though, you would have to count mileage for personal use as income. What if you exchange occasional tech support for the use of an empty desk and Internet connection? As long as they aren't renting desks for money to others, there's probably no additional marginal cost to them if they allow you to use the space, so the fair market value question breaks down. "Income is income... it depends how it's structured.. personal or corporate.. but still you need to pay taxes... if you get audited, the tax man could look at your bank statements and ask, ""where is this money coming from""" The same as you would for an individual stock. A stock starts the year at $100, and has $4 in dividends over the year, why would the fact the the stock ends the year at say $90, confuse you?  You pay tax on the dividend at the favored rate, if held in a taxable account, obviously, and that's about it.