What are some pre-tax programs similar to FSA that I can take advantage of?
2014 Limit: $2,500 Notes 2014 Limit: $3,300 individual, $6,550 family Notes 2014 Limit: $5,000 Notes 2014 Limit: $2,500 Notes 2014 Limit: $250/month Notes 2014 Limit: $130/month Notes There is a dependent care spending account for child care related expenses. Also Medical and Dental expenses over a certain % of your income maybe deductible on your tax return.
I'm not a huge fan of tax-advantaged retirement accounts anyway, so I wouldn't fault you for not contributing even if you weren't likely to develop a disability. Do you have disability insurance?  I hope so.  If you already have the disease then you may not be able to get it now if you don't have it already because they may not cover existing conditions.  If not, try to get it however you can. You may be able to withdraw the money without much problem if you can prove it's a permanent disability.  (Information here.) Do you have 401(k) matching from your employer?  If that match is vested in a reasonable period of time, then even with the penalties you'll end up ahead. Beyond that (this wasn't part of your question but I'm just trying to help) I'd think about what kind of work you can do after you can't work at your current job.  You have the luxury of an early warning, so plan for it. Also, check out National Industries for the Blind.  Our Lions Club sells some of the Skilcraft products (brooms) as fundraisers and they're quality products. "The Roth/Traditional decision is complex, but can be broken down into a set of simple rules.  Ideally, you want to choose to tax your money at the lowest possible rate. This specifically refers to your marginal rate, the rate you last $100 was taxed or next $100 of income with be taxed. That, in itself, is another issue, answered with questions here discussing marginal rates.  My suggestion has been that if you are in the 15% bracket, use Roth. And continue to do so until you hit 25%. At that point, begin to shift to the traditional, pre-tax 401(k) or IRA. (My article The 15% solution, goes into detail on this, although it references the 2013 tax rates. I need to re-edit). If you are already in the 25% bracket, I'd suggest just going pre-tax. Given the ability to convert, it's not as if there are 2 points in time (deposit and withdrawal) but you can decide every year if your situation changes. It's not uncommon to get married, have a baby, buy a house, and find you just dropped back down to 15% marginal rate when you were solidly 25% prior.  Let me explain why you should go 100% pretax if already at 25%.  A single person hits the top of the 15% bracket (in 2017) at $37,950 taxable. Add the standard deduction and exemption, and you are at $48,350. The tax on this is $5226, less than 10% average, despite the next $100 being taxed at 25%. It would take over $1M to have an account large enough to withdraw $40K/yr.  If you blow through that number, you hit 25%, I agree, but why pay 25% now, for sure, to avoid 'maybe' hitting 25% later? You have decades of opportunities for conversion, and even more when the funds are transferred to IRAs if you have a job change. (And the conversion discussion has multiple layers when the IRA is involved) Say you are 'too' successful. You are hitting $2M before age 55. If you retire post-55, you can withdraw from the 401(k) penalty free. But, you have 15 years before you'd start to take SS benefits. 15 years to use conversions, even if pushing into 25%, to reduce the impact of SS taxation.  My advice is not a set-and-forget solution. It's an annual evaluation of the plan for the coming year.  Further notes on my choice of ""15% Solution"" - This is the 2017 tax table for singles -  I note that median individual income is ~$30K which puts that median single at ~20K taxable. This is where the analysis begins. This earner might have upward mobility, to reach the 25% bracket and begin to save pre-tax. The goal would be to have a mix of pre/post tax money, so that over the course of their life, the 25% bracket was avoided, perhaps completely.  In general, my writing tend towards the second highest quintile, the 60-80% slice of the population. The numbers might appear arbitrary, but, in the end, the discussion has to start someplace. The concept I described here is best implemented by the single or couple who is still at 15%, but soon pushing higher than the 15/25 line. This enables them to start by saving in the Roth, and slowly shifting towards pre-tax. The final mix at retirement depends on that timing as well as their opportunities for conversions along the way.  Part of my focus on that line is that the differential is greatest in bracket shifts between 15 and 25%. Much of the benefit in the whole IRA/401 discussion is in that shift, depositing at 25%, yet withdrawing at 15%. The 28% couple might wish to avoid the 33% bracket at retirement, but that level of income impacts far fewer people, and fewer still that are either reading these boards or my other writing." Another option if it is available is a Roth 401k.  It is similar to a Roth IRA in that you pay taxes up front, but the withdrawals are tax free. Employer match doesn't incur FICA tax (social security, medicare) for you at all - either current year or when you withdraw. All you have to pay is income tax when you withdraw after retirement age. (Disclaimer - I'm not tax professional but has done my research) "The FSA, in contrast to the HSA, is not an ""account"" that you put money in.  FSA stands for ""Flexible Spending Arrangement,"" not ""Account.""  Technically, it is a defined-benefit plan.  Here is the difference: With an account such as an HSA, you put money into the account, and you get that same money out.  You can't take money out unless you first put money in. The FSA doesn't work that way.  Instead, you pick an annual amount that your FSA will cover, and work out a monthly fee to pay for it.  For example, you might decide on a $1800 FSA, which will cost you $150 per month.  However, the $150 you pay each month does not go into an account for you; instead, it goes to your employer, who is managing the plan. Let's say that in January, at the beginning of the plan year, you have a large medical expense of $1000.  You've only had $150 taken out of your paycheck so far this year, but you are covered for $1800, so you get reimbursed the full $1000.  This is referred to as ""uniform coverage"", meaning that you get the full $1800 of coverage on day 1 of the year. Now let's say that you leave your job in March.  You've only paid $450, and you've received $1000 in benefit.  You do not owe your employer the rest of the money; your employer eats this cost.  This is the trade-off that the FSA offers over other types of accounts: depending on an employee's circumstances, an employer might make money (use-it-or-lose-it) or might lose money (uniform coverage) on an individual employee. The idea behind the use-it-or-lose-it provision of the FSA is to help the employer pay for the uniform coverage provision. The details behind the FSA (and other types of health plans) are outlined in IRS Publication 969. I'm sure that a secondary reason behind the use-it-or-lose-it provision is that it encourages an employee to keep his FSA plan small, so he can use it all up and not have to lose too much of it at the end of the year.  And a smaller FSA contribution means more tax money for the government. To address your point that it shouldn't be this way: I'm personally not a fan of the FSA because of the use-it-or-lose-it provision.  But participation is voluntary, for both employers and employees.  You proposed an alternative set of rules for the FSA, but you are basically describing an HSA, in which you cannot spend more than you have, and you get to keep whatever is left over.  The recent rules changes that allow plans to feature a grace period or a small carryover balance were an attempt to make the FSA a little more attractive/useful, but if you want the ability to keep your money and not have to spend it at all, use an HSA instead." First, you need to understand the difference in discussing types of investments and types of accounts. Certificate of Deposits (CDs), money market accounts, mutual funds, and stocks are all examples of types of investments. 401(k), IRA, Roth IRA, and taxable accounts are all examples of types of accounts. In general, those are separate decisions to make.  You can invest in any type of investment inside any type of account.  So your question really has two different parts:   Tax-advantaged retirement accounts vs. Standard taxable accounts FDIC-insured CDs vs. at-risk investments (such as stock mutual funds) Retirement accounts are special accounts allowed by the federal government that allow you to delay (or, in some cases, completely avoid) paying taxes on your investment.  The trade-off for these accounts is that, in general, you cannot access any of the money that you put into these accounts until you get to retirement age without paying a steep penalty.  These accounts exist to encourage citizens to save for their own retirement.  Examples of retirement accounts include 401(k) and IRAs. Standard taxable accounts have no tax advantages, but no restrictions, either.  You can put money in and take money out whenever you like.  However, anything that your investment earns is taxable each year. Inside any of these accounts, you can invest in FDIC-insured bank accounts, such as savings accounts or CDs, or you can invest in any number of non-insured investments, including money market accounts, bonds, mutual funds, stocks, precious metals, etc. Something you need to understand about investing in general is that your potential returns are directly related to the amount of risk that you take on.  Investing in an insured investment, which is guaranteed by the government to never lose its value, will result in the lowest potential investment returns that you can get. Interest-bearing savings accounts are currently paying less than 1% interest.  A CD will get you a slightly higher interest rate in exchange for you agreeing not to withdraw your money for a period of time. However, it takes a long time for your investments to grow with these investments.  If you are earning 1%, it takes 72 years for your investment to double. If you are willing to take some risk, you can earn much more with your investments.  Bonds are often considered quite safe; with a bond, you loan money to a government or corporation, and they pay you back with interest.  The risk comes from the possibility that the government or corporation won't pay you back, so it is important to choose a bond from an entity that you trust. Stocks are shares in for-profit companies.  Your potential investment gain is unlimited, but it is risky, as stocks can go down in value, and companies can close.  However, it is important to note that if you take the largest 500 stocks together (S&P 500), the average value has consistently gone up over the long term.  In the last 35 years, this average value has gone up about 11%.  At this rate, your investment would double in less than 7 years. To avoid the risk of picking a losing stock, you can invest in a mutual fund, which is a collection of stocks, bonds, or other investments.  The idea is that you can, with one investment, invest in many stocks, essentially earning the average performance of all the stocks.  There is still risk, as the market can be down as a whole, but you are insulated from any one stock being bad because you are diversified. If you are investing for something in the long-term future, such as retirement, stock mutual funds provide a good rate of return at an acceptably-low level of risk, in my opinion. (Note: The OP does not state whether the employer-sponsored retirement savings are pre-tax or post-tax (such as a Roth 401(k)). The following answer assumes the more common case of a pre-tax plan.) This is a bad idea, IMHO. IRS Pub 970 lists exceptions to the 10% early withdrawal penalty for educational expenses. This doesn't include, as far as I can tell, student loan payments. So withdrawing from your retirement account would incur both income tax and penalties. Even if there were an exception, you'd still have to pay income taxes, which, depending on the amount and your income, could be at a higher marginal rate than you are currently paying.  If you really want the debt gone as soon as possible, why not reduce the amount you contribute to the retirement plan (but not below the amount that gets you the maximum employer match) and use that money to increase your monthly payments to the student loan? Note that, if you do this, you will pay taxes on income that would have been tax-deferred in order to save money on interest, so there's still a trade-off. (One more thing: rather than rolling over to your new company's plan, you could roll over to a self-directed Traditional IRA.) "Retirement accounts often can be invested with pretax money, with the exception of Roth accounts that use post-tax and have tax-free growth if you follow the rules, rather than after tax money as well as provide a shelter so that you aren't having to pay annual taxes on dividends and other possible distributions. Another point would be to consider how much money you'd be investing as some funds may have institutional versions that can be much cheaper than others, e.g. compare Vanguard's index funds that the 500 Index in Investor shares, Admiral shares and institutional forms where the tickers would be VFINX, VFIAX, VINIX, VIIIX to consider. Some companies may have access to the institutional funds that aren't what you'd have unless you are investing millions of dollars upfront. Lastly, if there isn't an employer plan and you make a ton of cash, you may not qualify for a deductible IRA or Roth IRA contribution for something else that may happen if you want to start playing with, ""What if.""" One thing that kept me from doing a budget for years is how complex some people make it.  For example you list your gross pay, then deduct the taxes, 401K, FSA, etc...  Why?  Those are pretty consistent. For me, the way this is budgeted is I list my net pay, and go from there.  If you were perfect in predicting your FSA, you would have no medical expenses on your budget!  Simple, easy budget! Now this year, you will probably have to pay out of pocket for some expenses.  Can you predict how much?  Can your disposable income absorb the overages?  If not you will need to start a sinking fund.  That is put a sufficient amount of money into a savings account each month to cover the shortage.    Keep in mind you can go over a bit on your FSA contributions.  If you find yourself near the end of the plan year with extra money, you can also claim mileage reimbursement for your medical appointments.  Since your FSA has a history of those, it is easy to calculate your mileage from your home to the DR's office and submit a claim. Not as you suggest. Since you are sole prop, you are taxed on a cash basis. Within reason, you can prepay vendors - so temp to hire through an agency might appear more attractive than direct hire. But there needs to be a justification other than avoidance of taxes. So pre-paying 100k on 12/25 would look fishy as fuck. Plus your quality of candidate will suffer if you need anything other than low skill labor.  Look at your other fully deductible expenses - anything you can prepay-prepay. For example, I set my liability insurance renewal January 15 to provide optionality. But it just shifts one year into another .. Means fuckall if you are in the same marginal bracket next year.  The IRS has also relaxed depreciation on office technology. Computers are now fully deductible rather than being capitalized.  @ 500k revenue you should have a CPA and legal counsel. Simply incorporating isn't tax magic. The purpose is to limit yourersonal liability, not a tax shelter - but shitty things happen once you have employees, don't create the potential for a disgruntled employee lawsuit put your shelter at risk of court judgment.  That said, assuming you aren't dumping a hypothetical on the Internet, congrats - for all the headaches, having employees is the ultimate leverage .. it's like a xerox machine for your labor (including loss of fidelity with each copy) .. These are plans similar to 401k plans. 457(b) plans available for certain government and non-profit organizations, 403(b) available for certain educational, hospital, religious and non-profit organizations. Your school apparently fits into both classes, so it has both. These plans don't have to allow ROTH contributions, but they may, so you have to check if there's an option. The main (but not only) difference from IRA is the limit: for 401(k), 403(b) and 457(b) plans the contribution limit is $17500, while for IRA its $5500 (for 2013). Additional benefit of 457(b) plan is that there's no 10% penalty on early withdrawal, just taxes (at ordinal rates). The software he is talking about readjusts your portfolio weights back to your original allocation on a semi-constant basis. Basically it's designed to replace the stereotypical, lazy financial advisor.  Your second point is quite valid though... One such example for anyone reading who has a young child is a coverdell ESA which allows you to put pretax income into an investment fund and withdraw tax free to spend on anything education related including the primary and secondary level (ie books, Supplies, field trips, tutoring, etc.). Basically money youd probably spend anyway, but this way you skip out on some taxes. As far as broad principles, I think that you are on track. The only suggestion I would have is to look into HSAs. They are another great tax-advantaged account, accessible to those with high incomes. "Some 401k plans allow you to make ""supplemental post-tax contributions"". basically, once you hit the pre-tax contribution limit (17.5k$ in 2014), you are then allowed to contribute funds on a post-tax basis. Because of this timing, they are sometimes called ""spillover"" contributions. Usually, this option is advertised as a way of continuing to get company match even if you accidentally hit the pre-tax limit.  But if you actually pay attention to your finances, it is instead a handy way to put away additional tax-advantaged money.  That said, you would only want to use this option if you already maxed out your pre-tax and Roth options since you don't get the traditional tax break on contributions or the Roth tax break on the earnings. However, when you leave the company, you can transfer the post-tax money directly into a Roth IRA when you transfer the pre-tax money, match, and earnings into a traditional IRA." One snag in your plan is that you alone can't undo your HSA contributions because you would also owe FICA taxes on that amount, and those need to be paid by both you and your employer. The only way for that to happen is for your employer to undo your HSA contributions from their point of view so those wages can be entirely taxed with both FICA and regular withholding. How that is accomplished will probably be up to them. It could mean you pulling the money out of the HSA account, and then either giving it back to your employer so they can re-allocate it with a new check, or, if you have enough pay due between now and the end of the year you could keep the money and they can reduce your next paycheck(s) by the total additional taxes due. Note that you should prefer the latter if possible, since this way you would get to keep the $1000 you shouldn't have gotten in the first place. Also, note that when you withdraw the money from your HSA account you need to inform your bank that you are undoing the contributions rather than taking distributions (and likely fill out a form). If you don't inform them they will improperly report to the IRS that you had contributions and an equal amount of distributions, which could muddy the waters with also having an FSA.