Year-End Money Moves for Self-Employed Self-Care Providers

The fourth quarter is here, which makes this the stretch that decides how your tax season feels. The work you do now, or skip now, is the difference between a calm April and a frantic one. This is not about year-end tax gymnastics or buying things you don’t need to chase a write-off - it’s a short, sweet, sane list of things that make the spring easier and, in a few cases, lower what you owe. Here is what is actually worth doing before December 31.

Catch up your bookkeeping (you knew this would be the first thing!)

Everything else here depends on knowing your numbers, so if your books are behind, this is the first thing to fix. Catching up in the fall means you can actually see what you earned and what you spent, which is what every other year-end decision is based on. If you’re staring at months of uncategorized transactions, I wrote about how to dig out when your books are behind, and it applies just as well in December as it does in April!

Know where your stand, and plan for the January payment

Your last estimated tax payment for 2026 is due January 15, 2027, for both your IRS payment and your New York state payment. Before then, take an honest look at your year. If your income ran higher than you expected, this is the moment to consider bumping that final payment so you aren’t caught short in April.

If your books are current, there is a small bonus option worth knowing about: you can skip the January 15 payment entirely if you file your full return and pay everything you owe by the end of January (technically February 1, since the 31st falls on a Sunday in 2027). Check out my post on estimated taxes for self-employed folks if you need a refresher on how the math works.

Collect W-9s from anyone you paid as a contractor

If you paid anyone as a contractor this year - a cleaner, a VA, a photographer - now is the time to collect their W-9 if you didn’t do it when you hired them. Starting in 2026, you owe a 1099-NEC to any contractor you paid 2,000 dollars or more during the year, and those forms are typically due on January 31. For the 2027 deadline, it’s February 1, because the 31st falls on a Sunday. The W-9 gives you the name, address, and tax ID you need to file your 1099s - tracking someone down in January, after the work is done, is much harder than asking for it at the time of hiring (or ASAP afterward).

Pull your deductions together

Gather your deductible expenses so nothing gets left on the table. If you have been recording things monthly, this is a quick review. If you have not, set aside some time to go through the year’s bank and credit card statements and your receipts, and sort out what belongs to the business. The expenses you forget are the ones that cost you, because a missed deduction is money you hand over that you didn’t have to!

The truth about buying things “for the write-off”

Every year around now, someone asks whether they should buy something before December 31 to lower their taxes. First I go and watch this excellent scene from Schitt’s Creek, and then I answer: a deduction isn’t a discount! If you buy a 1,000 dollar piece of equipment, you do not save 1,000 dollars. You save the amount you would have paid in taxes on that 1,000 dollars, and you are still out the rest.

Think of write-offs like a retail rebate. You still have to spend the full amount of cash upfront, and then you eventually get some portion of it back, via a reduced tax bill.

On the flip side, if you were already planning to buy that piece of equipment, it may make strategic sense to buy it before December 31 to lower your taxable income for the year. Just keep in mind that you want to buy for your business’s needs, and not for the deduction itself.

If a retirement contribution is on your to-do list, decide before year-end

Putting money into a retirement account can lower your taxable income, and the timing trips people up because the contribution deadlines vary by account type. Some accounts, like a solo 401(k), generally have to be set up and funded by December 31 to count for the current year. Others, like a SEP-IRA or a regular IRA, can be funded up until your tax filing deadline.

I’m not a tax pro or financial advisor, so the specifics are a conversation for those folks. But if a contribution is something you want to do to reduce your 2026 income, put the decision on your December to-do list, because sometimes April is too late.

None of this has to be dramatic!

A short, sane list handled before December 31 beats a frantic scramble in April every time. The version of you sitting down to file in the spring will be grateful for the work you do between now and the end of the year.

For the full operational run through, check out this post on year-end bookkeeping.

If you want more ways to hold onto what you earn, grab this PDF of practical moves for keeping more of your income.

And as always, if this all feels like more than you want to do yourself, book a free call with me and let’s talk about how I can help you!