Deducting SEP-IRA contributions as a sole proprietor with no employees
SEP IRA deduction goes to line 28 of your 1040, which is above the line (i.e.: pre-AGI). It should not be included in your taxable income (AGI) for Federal purposes.
"Unfortunately, not directly.  For IRAs and HSAs, we have an annual maximum contribution limit. What you can do (which doesn't ""initially seed"" it) is to put the money aside in a savings account that you want to contribute to your HSA or IRA and then put it in the IRA or HSA when the timing is right for you.  The key here though is that the contribution cannot exceed the maximum limit for the year. Another ""way around"" this (which really isn't because it just means that you'll have a new higher limit) is to become self employed, see this from the IRS about SEPs: Contribute as much as 25% of your net earnings from self-employment   (not including contributions for yourself), up to $51,000 for 2013   ($52,000 for 2014). Still, none of these methods are pre-seeding an account, as the maximum contribution limit is never exceeded." Please note that if you are self employed, then the profit sharing limit for both the SEP and Solo 401(k) is 20% of compensation, not 25%. There is no need for a SEP-IRA in this case.  In addition to the 401(k) at work, you have a solo-401(k) for your consulting business.  You can contribute $18,000 on the employee side across the two 401(k) plans however you wish.  You can also contribute profit sharing up to 20% of compensation in your solo 401(k) plan.  However, the profit sharing limit aggregates across all plans for your consulting business.  If you max that out in your solo 401(k), then you cannot contribute to the SEP IRA. In other words, the solo 401(k) dominates the SEP IRA in terms of contributions and shares a limit on the profit-sharing contribution.  If you have a solo 401(k), there is never a reason to have a SEP for the same company. Example reference: Can I Contribute to a solo 401(k) and SEP for the same company? If you want to 'offset' current (2016) income, only deductible contribution to a traditional IRA does that. You can make nondeductible contributions to a trad IRA, and there are cases where that makes sense for the future and cases where it doesn't, but it doesn't give you a deduction now. Similarly a Roth IRA has possible advantages and disadvantages, but it does not have a deduction now. Currently he maximum is $5500 per person ($6500 if over age 50, but you aren't) which with two accounts (barely) covers your $10k.  To be eligible to make this deductible traditional contribution, you must  have earned income (employment or self-employment, but NOT the distribution from another IRA) at least the amount you want to contribute NOT have combined income (specifically MAGI, Modified Adjusted Gross Income) exceeding the phaseout limit (starts at $96,000 for married-joint) IF you were covered during the year (either you or your spouse) by an employer retirement plan (look at box 13 on your W-2's). With whom. Pretty much any bank, brokerage, or mutual fund family can handle IRAs. (To be technical, the bank's holding company will have an investment arm -- to you it will usually look like one operation with one name and logo, one office, one customer service department, one website etc, but the investment part must be legally separate from the insured banking part so you may notice a different name on your legal and tax forms.) If you are satisified with the custodian of the inherited IRA you already have, you might just stay with them -- they may not need as much paperwork, you don't need to meet and get comfortable with new people, you don't need to learn a new website. But if they sold you an annuity at your age -- as opposed to you inheriting an already annuitized IRA -- I'd want a lot of details before trusting they are acting in your best interests; most annuities sold to IRA holders are poor deals. In what. Since you want only moderate risk at least to start, and also since you are starting with a relatively small amount where minimum investments, expenses and fees can make more of an impact on your results, I would go with one or a few broad (= lower risk) index (= lower cost) fund(s). Every major fund familly also offers at least a few 'balanced' funds which give you a mixture of stocks and bonds, and sometimes some 'alternatives', in one fund.  Remember this is not committing you forever; any reasonable custodian will allow you to move or spread to more-adventurous (but not wild and crazy) investments, which may be better for you in future years when you have some more money in the account and some more time to ponder your goals and options and comfort level. Traditional IRA contributions can be made if you  have compensation and the amount of the contribution is limited to the smaller of your compensation and $5500 ($6000 if age 50 or more). Note that compensation (which generally means earnings form working) is not just what appears on a W-2 form as salary or wages; it can be  earnings from self-employment too, as well as commissions, alimony etc (but not earnings from property, pensions and annuities, certain types of partnership income) You must also not have attained age 70.5 in the year for which the contribution is made.  Even if you don't have any compensation of your own, you can nonetheless make a Traditional IRA contribution if your spouse has compensation as long as you are filing a joint tax return with your spouse. For spouses filing a joint return, the  limits are still the same $5500/$6000 for each spouse, and the sum total of Traditional IRA contributions for both spouses also must not exceed the sum total of earned income of both spouses. The age limits etc are all still applicable. Note that none of this says anything about whether the contributions are deductible.  Everyone meeting the above requirements is eligible to make contributions to a Traditional IRA; whether the contributions can be deducted from current income depends on the income:  those with high enough incomes cannot deduct the contribution. This is different from Roth IRAs to which people with high incomes are not permitted to make a contribution at all. Finally, the source of the cash you contribute to the IRA can be the proceeds of the stock sale if you like; you are not required to prove that the cash received from compensation is what you sent to the IRA custodian. Read Publication 590 (available on the IRS website www.irs.gov) if you need an authoritative reference. In addition to the normal limits, A Solo 401(k) allows you to contribute up to 20% of net profits (sole proprietor) or 50% of salary (if a corporation), up to $49,000. Note that the fees for 401(k) accounts are higher than with the IRA. See 401(k)s for small business. FICA/SE taxes are not 30%. They are at most ~15%, including the employer portion. Employer also pays FUTA tax, and has additional payroll expenses (like fees and worker compensation insurance). The employee's FICA portion is limited up to a certain level of earnings (110100 this year, IIRC). Above it you only pay medicare taxes, not social security. S-Corp earnings are not taxed at 15%, these are not dividends. They're taxed at your ordinary income rate. You don't pay SE taxes on it, that's the only difference. I hope you're talking about tax treatment decision, because there are entirely different factors to keep in mind when you're organizing a business and making a decision between being it a LLC or a corporation. I believe you should pay some money to get a real advice that would apply to you, from a EA/CPA who would be doing the number-crunching (hopefully correctly). I'm a tax practitioner, and this answer was not intended or written to be used, and it cannot be used by any taxpayer, for the purpose of avoiding penalties that may be imposed on the taxpayer. Maryland treats income from pensions and annuities in the same manner that the federal government treats such income. Consequently, pensions and annuities can be subject to Maryland's income tax. The resident booklet for Maryland income tax filers states on page 4: Line 1d. Enter on line 1d the total amount of pension, IRA,   and annuities reported as income on lines 15b and 16b of your   federal Form 1040, or lines 11b and 12b of your federal Form   1040A. Line 1 of Maryland's tax return represents total taxable income, before deductions, exemptions, and adjustments. Line 16b of federal Form 1040 represents the taxable portion of your FERS annuity. Consequently, the federally taxable portion of your FERS annuity is also subject to Maryland's state income tax. The taxable portion of FERS annuities should be recorded on the 1099-R you receive. If it's not, IRS pub 721 records how to calculate the taxable portion of FERS annuities. Maryland does, however, allow filers to exclude up to $29,200 of the taxable portion of their pension income in 2015 from taxable income if: a. You were 65 or over or totally disabled, or your spouse was   totally disabled, on the last day of the tax year, AND b. You included on your federal return taxable income received   as a pension, annuity or endowment from an “employee   retirement system” qualified under Sections 401(a), 403 or   457(b) of the Internal Revenue Code. [A traditional IRA, a   Roth IRA, a simplified employee plan (SEP), a Keogh plan, an   ineligible deferred compensation plan or foreign retirement   income does not qualify.] You mention receiving SS disability, so you may be eligible for that exclusion. Regarding what kinds of disabilities qualifies for those exclusions, Maryland states that: To be considered totally disabled, you must have a mental or physical impairment which prevents you from engaging in substantial gainful activity. You must expect the impairment to  be of long, continued or indefinite duration or to result in your death. You must attach to your return a certification from a qualified physician stating the nature of your impairment and that you are totally disabled. If you have previously submitted a physician’s certification, attach your own statement that you are still totally disabled and that a physician’s certification was submitted before. If you feel you would qualify for that exclusion (and have the required supporting evidence), fill out the relevant table and include the result on line 10 of your Maryland tax return. In the future, to avoid a large state tax bill due to inadequate withholding on pension funds, OPM provides a web service which allows you to specify state tax withholding amounts on pension distributions. 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.