End-of-Year Tax Checklist for Individual Tax Returns

Can you believe it’s nearly the end of the year? Get your tax checklist ready.

We’re about four short weeks away from the New Year, which means it’s about time you started thinking about your 2020 taxes.

We’re always thinking about taxes, whether it’s helping our tax preparation clients file their tax returns in April, ensuring our clients avoid penalties by getting their taxes in by the tax extension deadline, or solving serious tax debt issues year round. And we know a few things about being prepared for next tax season.

In a sense, January 1st serves as a cutoff; it’s the end of your financial year that you, your business, and the IRS will be summarizing to figure out your tax obligation. And there are a number of ways to lower your tax bill for next year if you make the right moves now (as well as some consequences for a lack of forethought).

We’re proud to present you with an end-of-year tax checklist to ensure you know what you need to handle before the ball drops on New Year’s Eve.

The End-of-Year Tax Checklist for Individual Returns

Many taxpayers have a pretty straightforward tax situation: one employer, maybe a couple of investment accounts, and that’s it. If that’s you, this list may just help confirm that you’ve got very little work cut out for you in 2019. On the other hand, you may find something new—and that something new can mean big tax advantages.

Investment Accounts

If you’re an investor, active or inactive, the end of the year is your chance to make an account of your investment gains and losses and to act accordingly. Any investments or divestments you make before Jan. 1st will factor into your overall investment profile and may end up being taxable—or deductible.

If you’ve invested, take a moment to see if it might be in your interest to employ tax loss harvesting, where you strategically deduct your losses from your gains (or regular income). Or, if you’re considering selling an investment, it may be worth it to hold until next year to lock down a lower tax rate.

Investment Tax Checklist:

  • Review all investment accounts
  • For investments that have dropped in value, consider a tax loss harvesting strategy
  • For investments that have risen in value, consider holding investment longer

Retirement Contributions

The end of the year is the time for making money moves, especially when considering your retirement accounts. There are a number of tax advantages you can gain from contributing to retirement accounts, including your IRA and 401(k).

If your employer offers a 401(k) matching plan, your contributions are made with “pretax” dollars, so if you contribute $100 per $2000 paycheck, you are only taxed on the remaining $1,900. With an IRA, you can unlock tax deductions and tax-free growth or tax deferment when you make contributions.

Retirement Contributions Tax Checklist:

  • Review your 401(k) plan and match
  • Review your IRA
  • Consider making a one-time contribution or setting up recurring ones

Self-Employment Payments

If you’re self-employed, you’re probably already hip to this checklist, but it’s worth a reminder. When you work primarily by invoice and have signed W-9s, you don’t pay taxes annually, but rather, quarterly.

You’ll still file your taxes in April, but be sure not to miss your quarterly deadline for organizing your deductions, quarterly income, and payments.

Self-Employment Tax Checklist:

  • Review your Q4 income and deductions
  • Estimate your tax obligation and pay

Donations & Giving

We all know that our donations to charities are tax deductible, but many of us overlook the opportunity to make special contributions toward the end of the year. However, did you know you don’t have to donate cash?

It’s true. Financial and physical assets can both qualify you for a tax deduction, and in some cases can serve as a way to reduce your tax obligation elsewhere. (We recommend reviewing the full details on the IRS’s website.)

Donations Tax Checklist:

  • Determine if you want—or need—to make a donation
  • Settle on a short list (1-3) of organizations that accept your desired donation type
  • Confirm organization is a qualifying nonprofit
  • Retain receipt of your donation


Especially for those without employer-sponsored healthcare, insurance can put a big strain on your budget. Fortunately, the IRS is on your side when it comes to deducting for your out-of-pocket costs.

As the end of the year draws near, it’s a good idea to determine whether or not to make changes to your plan. And if you’ve been putting off a doctor’s visit, consider making it before the year draws to a close (and your deductible resets).

Insurance Tax Checklist:

  • Review your healthcare plan, and make changes as needed
  • If paying your own healthcare costs, schedule appointments before Jan. 1

Make a Tax Checklist (& Check It Twice)

Even if you have a fairly simple tax situation, you may still benefit from making some tax moves before the New Year. Your tax year lasts through the end of December, so use our checklist to search for opportunities, make those moves, and avoid a tax bill. There’s seriously no downside.

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