As a freelancer you’re responsible for all aspects of filing and paying your taxes, contributing to your retirement savings, and enrolling in health insurance. There are a lot of dates and numbers to keep track of, and if you’re like me you get annoyed at having to look them up them over and over again. That’s why I put together this handy reference for freelancers with all the key information you’ll need for the year ahead.
Circle these dates in your calendar and/or bookmark this post for future reference if you want to save yourself some Googling this year. 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. You should receive this form from each client or employer by January 31. If a client paid you less than $600 they may not send you 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 your employers’ could trigger an audit. If you haven’t received a 1099-MISC from a client by January 31, contact them to ensure 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 (or extension) 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 can apply for a six-month extension that gives you until October 15, 2019 to file. The extension 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 quarters are not of equal lengths: the second quarter covers only April and May while the fourth covers the last four months of the year.
| Time period | Payment deadline |
| September 1-December 31, 2018 | January 15, 2019 |
| January 1-March 31, 2019 | April 15, 2019 |
| April 1-May 31, 2019 | June 17, 2019 |
| June 1-August 31, 2019 | September 16, 2019 |
| September 1-December 31, 2019 | January 15, 2020 |
Contributing to retirement savings
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 to April 15, 2019. This date is for all types of IRAs including traditional, Roth, and SEP plans. You can also make 2019 contributions to these plans from now until next year’s tax filing deadline of April 15, 2020.
December 31, 2019: Deadline to set up an individual 401(k) plan for 2019
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 to April 15 of the following year). That means it’s too late to set up an individual 401(k) for 2018, but you can set one up for 2019.
See this blog 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 freelancers in 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:
| 2018 | 2019 | |
| Traditional or Roth IRA | $5,500 ($6,500 if age 50 or older) | $6,000 ($7,000 if age 50 or older) |
| SEP | Lesser of $55,000 or 20% of net self-employment income | Lesser of $56,000 or 20% of net self-employment income |
| Solo 401(k) | Employer: 20% of net self-employment income Employee: 100% of earned income up to $18,500 ($24,500 if age 50 or older) Total combined contribution: $55,000 | Employer: 20% of net self-employment income Employee: 100% of earned income up to $19,000 ($25,000 if age 50 or older) Total combined contribution: $56,000 |
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 Healthcare.gov currently runs from November 1 to December 15. Though national enrollment for 2019 coverage has ended, some state exchanges have extended open enrollment dates:
| Rhode Island | November 1-December 31, 2018 |
| Minnesota | November 1, 2018-January 13, 2019 |
| California | October 15, 2018-January 15, 2019 |
| Colorado | November 1, 2018-January 15, 2019 |
| Connecticut | November 1, 2018-January 15, 2019 |
| Massachusetts | November 1, 2018-January 23, 2019 |
| New York | November 1, 2018-January 31, 2019 |
| District of Columbia | November 1, 2018-January 31, 2019 |
Extended open enrollment dates for 2020 coverage haven’t been announced yet, but I’ll update this post when they become available.
Special enrollment periods for health insurance
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. You can usually enroll in a plan up to 60 days after the event that triggered the special enrollment period.
For more information on the ins and outs of healthcare for freelancers, check out my series The Freelancer’s Guide to Health Insurance.
Ben Henry-Moreland 