Does an employee have the right to pay the federal and state taxes themselves instead of having employer doing it?
You can file a revised W-4 with your employer claiming more allowances than you do now. More allowances means less Federal tax and (if applicable and likely with a separate form) less state tax. This doesn't affect social security and Medicare with holding, though.  That being said, US taxes are on a pay-as-you-go system. If the IRS determines that you're claiming more allowances than you're eligible for and not paying the proper taxes throughout the year, they will hit you with an underpayment penalty fee, which would likely negate the benefits of keeping that money in the first place. This is why independent contractors and self-employed people pay quarterly or estimated taxes. Depending on the employer, they may require proof of the allowances for adjustment before they accept the revised W-4. No. An employer is legally obliged to deduct taxes from your pay cheque and send them to the IRS. The only way round that is to either provide evidence of deductions that would reduce your tax bill to nothing, or to become self-employed. No, even businesses pay taxes quarterly.  So if you formed Nathan, LLC, or otherwise became self employed, you'd still have to file quarterly estimates and make tax payments.  This would cause taxes to be a much more high touch part of your life. However, you should ensure that you're claiming the proper exemptions etc to avoid excessive withholding.
I actually think your boss is creating a problem for you. Of course it's taxable. The things IRS will look at (and they very well might, as it does stand out) what kind of payment is that. Why did it not go through payroll? The company may be at risk here for avoiding FICA/FUTA/workers' compensation insurance/State payroll taxes. Some are mandatory, and cannot be left to the employee to pay. On your side it raises your taxable income without the appropriate withholding, you may end up paying underpayment penalties for that (that is why you've been suggested to keep proofs of when you were paid). Also, it's employment income. If it is not wages - you're liable for self-employment taxes (basically the portion of FICA that the employer didn't pay, and your own FICA withholding). When you deposit the check is of no matter to the IRS, its when you got it that determines when you should declare the income. You don't have a choice there. I suggest asking the company payroll why it didn't go through them, as it may be a problem for you later on. I believe the answer to your question boils down to a discussion of tax strategies and personal situation, both now and in the future.  As a result, it's pretty hard to give a concrete example to the question as asked right now. For example, if your tax rate now is likely to be higher than your tax rate at retirement (it is for most people), than putting the higher growth ETF in a retirement fund makes some sense.  But even then, there are other considerations. However, if the opposite is true (which could happen if your income is growing so fast that your retirement income looks like it will be higher than your current income), than you might want the flexibility of holding all your ETFs in your non-tax advantaged brokerage account so that IF you do incur capital gains they are paid at prevailing, presumably lower tax rates.   (I assume you meant a brokerage account rather than a savings account since you usually can't hold ETFs in a savings account.) I also want to mention that a holding in a corp account isn't necessarily taxed twice.  It depends on the corporation type and the type of distribution.  For example, S corps pay no federal income tax themselves. Instead the owners pay taxes when money is distributed to them as personal income.  Which means you could trickle out the earnings from an holdings there such that it keeps you under any given federal tax bracket (assuming it's your only personal income.)   This might come in handy when retired for example.   Also, distribution of the holdings as dividends would incur cap gains tax rates rather than personal income tax rates. One thing I would definitely say: any holdings in a Roth account (IRA, 401k) will have no future taxes on earnings or distributions (unless the gov't changes its mind.)  Thus, putting your highest total return ETF there would always be the right move. Credit unions are mutually-owned (i.e. customer owned) financial institutions that provide banking services.  They take deposits from their members (customers) and loan them to other members.  Members vote on a board of directors who manage operations.   They are considered not-for-profit, but they pay interest on deposits.  They get some preferential tax treatment and regulation and their deposits are insured by a separate organization if federally accredited.  State-chartered credit unions don't have to maintain deposit insurance at all.   Their charters specify who can join.  They can be regionally based, employer based, or based on some other group with common interests.  Regulators restrict them so that they don't interfere too much with banks.  Otherwise their preferential tax and regulatory treatment would leave banks uncompetitive.   Other organizations with similar limits have gone on to be competitive when the limits were released.  For example, there used to be an insurance company just for government employees, the Government Employees Insurance Company.  You may know it better as GEICO (yes, the one with the gecko advertisements).  Now they offer life and auto insurance all over.   Credit unions would like looser limitations (or no limitations at all), but not enough to give up their preferential tax treatment.  Banks oppose looser limitations and have as much political clout as credit unions. Most people will never need to pay federal gift taxes. The federal gift taxes start after giving away 5.34 million over the course of your life. This number is adjusted annually for inflation. There are only two states that I know of which impose state gift taxes (Connecticut and Minnesota); in Connecticut, you need to start paying taxes if the lifetime value of your gifts exceed two million. In Minnesota, it starts at 1 million.  The federal tax is paid for by the person making the gift, unless other arrangements are made. There is an annual exclusion amount of approximately $14,000. You can give up to this amount to any number of recipients and it is not considered taxable. Therefore, when you give $100 to someone, it is not a taxable event.  If you do make a gift to an individual in excess of 14k, you'll need to file a gift tax return (IRS Form 709). When you file form 709, you won't need to pay taxes until the 5.34 million is exceeded. Instead, you can claim an exemption. Since most people don't exceed that amount, its rare to ever pay taxes even when exceeding the annual exclusion amount. The annual exclusion amount is adjusted each year for inflation. It's going to depend entirely on your tax situation, its complexity, and your willingness/interest in dealing with tax filings.  Personally I find that not only do I not enjoy dealing with figuring out my taxes, but I don't know even a fraction of the possible deductions available and all the clever ways to leverage them.  Plus the tax code is changing constantly and staying on top of that is not something I'm ever going to attempt. I am of the philosophy that it is my duty to pay only the absolute minimum tax legally required, and to utilize every possible exemption, deduction, credit, etc. that is available to me.  Plus my business activities are a bit on the non-traditional side so it requires some unorthodox thinking at times.  For me, a trained professional is the only way to go.  What it costs me, I way more than make up in savings on my tax bill.  I also go out of my way to never get a refund because if I get one, it just means I gave the government a free loan. The last time I computed my own taxes (used TurboTax if memory serves) was I think in the late 90s. "You're getting paid by the job, not by the hour, so I don't see why you think the employer is obligated to pay you for the drive time.  The only way that might be true, as far as I can see, is if he were avoiding paying you minimum wage by structuring your employment this way.  It looks like to me you're over the minimum wage based on what you wrote.  At maximum ""unpaid"" drive time (59 min each way) and maximum length of job (4 hours as you stated it), gives your minimum hourly rate of $8.83/hr. The federal minimum wage is currently $7.25/hr, so you're over that.  A quick search online suggests that NV does have a higher minimum at $8.25/hr under some conditions, but you're still over that too. The fact that you're required to pick-up the helpers and that you have a company car at home probably does mean that you're ""on the clock"" from the moment that you leave your house, but, again, you're not actually being paid by the clock.  As long as no other law is being broken (and it appears from your telling that there isn't), then the employer can set any policy for how to compute the compensation that he wants. Regarding taxes, the employer probably has no discretion there.  You're making what you're making, and the employer needs to tax it in total.  Since you're driving a company vehicle from home, I don't think that you're entitled to any reimbursement (vs. wages) that would not be taxed unless maybe you pay for gas yourself.  The gas money, if applicable, should be reimbursable as a business expense and that generally would not be taxed." "Short answer: Yes. For Federal income tax purposes, you are taxed on your total income, adding up positives and negatives. If business A made, say, $100,000 while business B lost $20,000, then your total income is $80,000, and that's what you'll be taxed on. As @littleadv says, of course any business losses you claim must qualify as business losses under IRS rules. And yes, there are special rules about losses that the IRS considers ""passive"". If you have wage income in addition to business income, business losses don't offset wage income for social security and medicare tax purposes. You can't get a refund of the social security tax deducted from your paycheck. I don't know if this is relevant to you, but: If you have businesses in different states, each is taxed by that state. For example I have two tiny side businesses, one in Michigan and one in Ohio. Last year the Michigan business made money while the Ohio business lost money. So my federal income was Michigan minus Ohio. My Ohio income was negative so I owed no Ohio income tax. But I couldn't subtract my Ohio losses from my Michigan income for Michigan income tax purposes. Thus, having, say, $10,000 income in Michigan and $10,000 in Ohio would result in lower taxes than $30,000 income in Michigan and a $10,000 loss in Ohio, even though the total income in both cases is the same. And this would be true even if the tax rates in both states were identical." As others have mentioned yes it is taxable. Whether it goes through payroll and has FICA taken out is your issue in terms that you need to report it and you will an extra 7.5% self employment taxes that would normally be covered by your employer. Your employer may have problems but that isn't your issue.  Contrary to what other users are saying chances are there won't be any penalties for you. Best case you have already paid 100% of last years tax liability and you can file your normal tax return with no issues.  Worst case you need to pay quarterly taxes on that amount in the current quarter. IRS quarters are a little weird but I think you need to pay by Jan 15th for a December payment. You don't have to calculate your entire liability you can just fill out the very short form and attach a check for about what you will owe. There is a form you can fill out to show what quarter you received the money and you paid in it is a bit more complex but will avoid the penalty. For penalties quarterly taxes count in the quarter received where as payroll deductions count as if they were paid in the first quarter of the year. From the IRS The United States income tax is a pay-as-you-go tax, which means that tax must be paid as you earn or receive your income during the year. You can either do this through withholding or by making estimated tax payments. If you do not pay your tax through withholding, or do not pay enough tax that way, you might also have to pay estimated taxes. If you did not pay enough tax throughout the year, either through withholding or by making estimated tax payments, you may have to pay a penalty for underpayment of estimated tax. Generally, most taxpayers will avoid this penalty if they owe less than $1,000 in tax after subtracting their withholdings and credits, or if they paid at least 90% of the tax for the current year, or 100% of the tax shown on the return for the prior year, whichever is smaller.