1. Contribute to retirement accounts

If you haven’t already funded your retirement account for 2019, do so by April 15, 2020. That’s the deadline for contributions to a traditional IRA, deductible or not, and to a Roth IRA.

  • If you have a Keogh or SEP and you get a filing extension to October 15, 2020, you can wait until then to put 2019 contributions into those accounts.
  • To start tax-free compounding as quickly as possible, however, don’t dawdle in making contributions.

Making a deductible contribution will help you lower your tax bill this year. Plus, your contributions will compound tax-deferred. It’s hard to find a better deal.

For 2019, the maximum IRA contribution you can make is $6,000 ($7,000 if you are age 50 or older by the end of the year). For self-employed persons, the maximum annual addition to SEPs and Keoghs for 2019 is $56,000.

Although choosing to contribute to a Roth IRA instead of a traditional IRA will not cut your 2019 tax bill—Roth contributions are not deductible—it could be the better choice because all withdrawals from a Roth can be tax-free in retirement.

  1. Organize your records for tax time

Good organization may not cut your taxes. But there are other rewards, and some of them are financial. For many, the biggest hassle at tax time is getting all of the documentation together. This includes last year’s tax return, this year’s W-2s and 1099s, receipts and so on.

How do you get started?

  • Print out a tax checklist to help you gather all the tax documents you’ll need to complete your tax return.
  • Keep all the information that comes in the mail in January, such as W-2s, 1099s and mortgage interest statements. Be careful not to throw out any tax-related documents, even if they don’t look very important.
  • Collect receipts and information that you have piled up during the year.
  • Group similar documents together, putting them in different file folders if there are enough papers.
  • Make sure you know the price you paid for any stocks or funds you have sold. If you don’t, call your broker before you start to prepare your tax return.
  • Know the details on income from rental properties. Don’t assume that your tax-free municipal bonds are completely free of taxes. Having this type of information at your fingertips will save you another trip through your files.
  1. Find the right tax forms

You won’t find all of them at the post office and library. Instead, you can go right to the source online.

  • View and download a large catalog of forms and publications at the Internal Revenue Service website or have them sent to you by mail.
  • You can search for documents as far back as 1980 by number or by date.
  • The IRS also will direct you to sites where you can pick up state forms and publications.
  1. Itemize your tax deductions

It’s easier to take the standard deduction, but you may save a bundle if you itemize, especially if you are self-employed, own a home or live in a high-tax area.

Itemizing is worth it when your qualified expenses add up to more than the 2019 standard deduction of $12,200 for singles and $24,400 for married couples filing jointly.

  • Many deductions are well known, such as those for mortgage interest and charitable donations.
  • You can also deduct the portion of medical expenses that exceed 7.5% percent of your adjusted gross income for 2019 (10% of AGI beginning in 2020).
  1. Don’t shy away from a home office tax deduction

The eligibility rules for claiming a home office deduction have been loosened to allow more self-employed filers to claim this break. People who have no fixed location for their businesses can claim a home office deduction if they use the space for administrative or management activities, even if they don’t meet clients there.

  • As always, you must use the space exclusively for business.
  • Many taxpayers have avoided the home office tax deduction because it has been regarded as a red flag for an audit. If you legitimately qualify for the deduction, however, there should be no problem.
  • You are entitled to write off expenses that are associated with the portion of your home where you exclusively conduct business (such as rent, utilities, insurance and housekeeping). The percentage of these costs that is deductible is based on the square footage of the office to the total area of the house.
  • A middle-class taxpayer who uses a home office and pays $1,000 a month for a two-bedroom apartment and uses one bedroom exclusively as a home office can easily save $1,000 in taxes a year. People in higher tax brackets with greater expenses can save even more.
  1. Provide dependent taxpayer IDs on your tax return

Be sure to plug in Taxpayer Identification Numbers (usually Social Security Numbers) for your children and other dependents on your return. Otherwise, the IRS will deny any dependent credits that you might be due, such as the Child Tax Credit.

  1. File and pay on time

If you can’t finish your return on time, make sure you file Form 4868 by April 15, 2020. Form 4868 gives you a six-month extension of the filing deadline until October 15, 2020. On the form, you need to make a reasonable estimate of your tax liability for 2019 and pay any balance due with your request.  Requesting an extension in a timely manner is especially important if you end up owing tax to the IRS.

  • If you file and pay late, the IRS can slap you with a late-filing penalty of 4.5% per month of the tax owed and a late-payment penalty of 0.5% a month of the tax due.
  • The maximum late filing penalty is 22.5% and the late-payment penalty tops out at 25%.
  • By filing Form 4868, you stop the clock running on the costly late-filing penalty.
  1. File electronically

Electronic filing works best if you expect a tax refund. Because the IRS processes electronic returns faster than paper ones, you can expect to get your refund three to six weeks earlier.  If you have your refund deposited directly into your bank account or IRA, the waiting time is even less.

There are other advantages to e-filing besides a fast refund:

  • The IRS checks your return to make sure that it is complete, which increases your chances of filing an accurate return. Less than 1% of electronic returns have errors, compared with 20% of paper returns.
  • The IRS also acknowledges that it received your return, a courtesy you don’t get even if you send your paper return by certified mail. That helps you protect yourself from the interest and penalties that accrue if your paper return gets lost.

If you owe money, you can file electronically and then wait until the federal tax filing deadline to send in a check along with Form 1040-V. You may be able to pay with a credit card or through a direct debit.

  • With a credit card, expect to pay a service charge of as much as 2.5%.
  • With direct debit, you may delay the debiting of your bank account until the actual filing deadline.