Key dates and numbers for freelancers to know in 2019

Jan 11, 2019

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As a freelancer, you have a lot of dates and numbers to keep track of. That's why I've put together this handy all-in-one reference for freelancers, with all the key information you'll need to know in the year ahead about filing and paying taxes, saving for retirement, and enrolling in health insurance.

Circle these dates in your calendar and/or bookmark this post for future reference. As with anything tax-related, this is all general information and you should talk to a professional for advice on what to do in your own situation.

Filing and paying taxes

January 31, 2019: 1099-MISC due to contractors
1099-MISC forms are sent by employers to independent contractors whom they paid at least $600 in the previous year. The contractor (that's you) should receive this form by January 31. If a client paid you less than $600 they may not send you a 1099-MISC, though the IRS still requires you to report the income.

It's important to keep track of who owes you a 1099-MISC so you can accurately report your income on your tax return. Employers also send 1099-MISC data to the IRS, and any differences between your numbers and the employers' could trigger an audit. If you haven't received a 1099-MISC from a client by January 31, contact them to ensure that it hasn't been lost.

If you used any subcontractors whom you paid more than $600 last year, you'll need to send them a 1099-MISC by January 31 as well.

April 15, 2019: Individual income tax filing deadline
You have until April 15, 2019 to file your individual income tax return for 2018 (e.g. Form 1040, Schedule C, and any other supplemental forms required). Note that this isn't the deadline to pay your taxes — tax payments for freelancers are due on a quarterly schedule (see "2019 quarterly estimated tax deadlines" below). If you wait until the tax filing deadline to pay your taxes, the IRS may charge you penalties and interest on top of the tax you owe.

If you're still waiting for information or if you're too busy to file a return by April 15, you may apply for a six-month extension that gives you until October 15, 2019 to file. The extension application needs to be filed by April 15, 2019. Remember again that the extension is for filing, not paying your taxes - payments are still due on the quarterly schedule no matter when you file, and penalties and interest can accumulate if you wait to pay.

2019 quarterly estimated tax payment deadlines

The IRS requires business owners to pay their income taxes on a quarterly schedule. This may seem like a hassle, but it's a lot easier to pay in four installments than to try and come up with a whole year's worth of income taxes all at once.

Here are the 2019 deadlines for quarterly estimated tax payments (including the final payment for 2018). Note that the four quarters are not of equal lengths: Quarter 2 covers only April and May while Quarter 4 covers the last four months of the year.


April 15, 2019: Deadline to set up and contribute to an IRA for 2018
Even if you didn't contribute to your retirement savings at all in 2018, you can still make a 2018 contribution to an IRA up until April 15, 2019. This includes traditional, Roth, and SEP IRAs. You can also make 2019 contributions to these plans from now up until next year's tax filing deadline of April 15, 2020.

December 31, 2019: Deadline to set up an individual 401(k) plan
An individual 401(k) is another type of plan that freelancers can use to save for retirement. One important detail is that an individual 401(k) must be established by December 31 of the first plan year (as opposed to an IRA which can be opened up until April 15 of the following year). That means it's too late to set up an individual 401(k) for 2018, but you may set one up for 2019.

See this post for more information on the difference between types of retirement accounts for freelancers and how to choose the one that's right for you.

Retirement plan contribution limits for 2019

The amount you can contribute to retirement accounts is increasing in 2019. Here are the 2018 and 2019 contribution limits for each type of plan:


Getting health insurance

November 1-December 15, 2019: Open enrollment for health insurance coverage on the national ACA exchange
Open enrollment for the national health insurance exchange through currently runs from November 1 to December 15. Though national enrollment for 2019 coverage has ended, some state exchanges have extended open enrollment dates:


Extended open enrollment dates for 2020 coverage haven't been announced yet, but I'll update this post when they become available.

Under certain circumstances, like getting married or divorced, losing a job, or having a baby, you could qualify for a special enrollment period outside of open enrollment to buy coverage for the rest of the year.

Ben Henry-Moreland is a financial planner who specializes in helping freelancers and business owners reach their financial goals. In his early career he was a professional opera singer. You can find out more about Freelance Financial Planning at or read more of Ben's blog posts at