Your paycheck
Three questions for anyone with a W-2.
Will your 401(k) or 403(b) be full by your last paycheck of the year?
The 2026 limit is $24,500, plus $8,000 if you are 50 or older. Contributions come out of pay, so the only way to catch up is to raise the percentage on the paychecks you have left. Call HR this week, not in December. If your employer matches, make sure you are at least getting all of the match.
Did anything change your income this year that your withholding doesn’t know about?
A raise, a bonus, a second job, a spouse who started or stopped working, a side business. The W-4 you filled out years ago is still running. One extra line on a new W-4 for the last few paychecks can save you an April bill and a penalty.
Do you have money in a flexible spending account you haven’t used?
Health FSAs are use-it-or-lose-it, with a small carryover or a short grace period depending on your plan. Check the balance. Glasses, dental work, and prescriptions all count.
Your future health care
The HSA is the best account in the tax code, and most people underuse it.
If you have a high-deductible health plan, is your Health Savings Account full?
For 2026 that is $4,400 for self-only coverage and $8,750 for a family, plus $1,000 if you are 55 or older. The money goes in before tax, grows untaxed, and comes out untaxed for medical costs at any age. You can still contribute for 2026 until April 15, 2027, but a payroll contribution before December 31 also skips Social Security and Medicare tax.
Your future retirement
The accounts you fund outside of work.
Have you funded an IRA, traditional or Roth, for 2026?
$7,500 for 2026, plus $1,100 if you are 50 or older. You have until April 15 to make the deposit, but deciding now, while you can still see the whole year, is the point. Whether traditional or Roth is better depends on your bracket this year against your bracket later, which is exactly the kind of question worth ten minutes with a planner.
Is this a low-income year for you? Would a Roth conversion make sense?
A year between jobs, the first year of retirement before Social Security starts, a year with a big loss. Moving money from a traditional IRA to a Roth in a year when you are in a low bracket means paying the tax now at a low rate instead of later at a higher one. The conversion has to be done by December 31.
If you are 73 or older, have you taken your required minimum distribution?
The penalty for missing it is steep. If you have several IRAs, the total can come from any of them, but it has to be out by December 31. If you are 70½ or older and you give to charity, see the giving section below first.
Your life this year
The return follows the life. Tell us about the life.
Did you sell a house?
Most people owe nothing on the sale of a home they lived in, up to $250,000 of gain, $500,000 for a couple. If the gain is bigger than that, or it was a rental or a second home, there is real planning to do, and some of it has to happen before the year ends.
Did you get married, divorced, or widowed?
Your filing status for all of 2026 is decided by your status on December 31. A wedding in December changes the whole year. A divorce that could close in December or January is a conversation, not just a date.
Did you have or adopt a child? Did a child start college?
New dependents, the child tax credit, dependent care, and the education credits all have rules that reward knowing them in advance. Paying a spring tuition bill in December, for instance, can move a credit into this year.
Did you start Social Security, or retire, or start taking money out of retirement accounts?
The first year of retirement is the year people are most surprised in April. Social Security can be taxable, pensions and IRA withdrawals often have too little withheld, and Medicare premiums two years from now are set by this year’s income. Worth a look before the year closes.
Did you inherit anything, receive a large gift, or move to or from Colorado?
Each of these changes something. Inherited IRAs have their own withdrawal clock. A move changes which state gets your income and when.
Your investments
For money outside of retirement accounts.
Did you sell something at a big gain this year? Is anything sitting at a loss?
Losses you take before December 31 offset gains you already took, and up to $3,000 of ordinary income after that. The reverse is also true: if you have losses already, this may be the year to take a gain you have been putting off. The trade has to settle in 2026.
Are you about to buy a mutual fund in a taxable account in December?
Many funds pay out their capital gains in mid-December. Buy the day before, and you get a tax bill for gains you never enjoyed. Check the distribution date first.
Your giving
The rules for charitable giving changed for 2026. Timing matters more than it used to.
Do you give regularly but take the standard deduction?
Starting with 2026, you can deduct a modest amount of cash gifts even without itemizing. Beyond that, giving two years’ worth in one year, so that you itemize in that year and take the standard deduction the next, often beats giving the same amount evenly. A donor-advised fund makes this painless: you deduct now and send the money to your charities over time.
Are you 70½ or older with an IRA?
A qualified charitable distribution, money sent straight from your IRA to the charity, is not taxed to you at all, counts toward your required minimum distribution, and keeps your income low for Medicare premiums. For most retirees who give, it beats writing a check. It has to leave the IRA by December 31.
Do you have a stock that has gone up a lot?
Give the shares, not the cash. You deduct the full value and nobody ever pays the tax on the gain.
If you own a business
A separate page is coming for business owners. For now, the three questions that can’t wait.
Do you know roughly what your profit will be this year?
Everything else depends on this. If you don’t know within a reasonable range, that is the first conversation.
Have you set up a retirement plan for the business?
Some plans, including a solo 401(k) for a one-person business, must exist on paper by December 31 even if the money goes in later. A SEP can wait until you file, but it also holds less.
Do you need equipment or a vehicle in the next few months anyway?
Buying it and putting it to use before December 31 can move the deduction into this year. Buying something you don’t need for the deduction is never a good trade, and we will tell you so.
If one of these applies to you, you probably already know what to do. If two or more do, or if you read one and thought “I’m not sure,” that is what a planning conversation is for. It is a short meeting, it is not expensive, and it is the only part of the tax year where the outcome is still up to you.
Want to talk it through?
Todd Mata, JD, LLM, CPA · Tax planning at the Tax Shop
Thirty years in tax, from Fortune 500 tax departments to small business owners in Highlands Ranch, and ten years teaching corporate income taxation at Metropolitan State University of Denver. The same kind of planning the big companies get, at the Tax Shop’s prices.
Ask for Todd. In person in Lone Tree or by phone. More about Todd →
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Dollar limits are the IRS figures for tax year 2026. This page is general information for Colorado taxpayers, not advice about your return; the right answer depends on your numbers. Published October 24, 2026.