The Ultimate Self-Employed Tax Calendar

When freelancers and solopreneurs take the leap into self-employment, tax planning isn’t high on the list of things they’re passionate about. But, regardless, it’s an important part of business ownership.

Wondering how you’ll stay on top of your business tax? It all starts with knowing and understanding the important dates on the typical tax calendar.

With these deadlines marked down, you’re prepared to do all of your important tasks—like tax filing, tax payments, and more—on time (or even ahead of schedule).

Key Tax Deadlines Solopreneurs Need to Know

Wondering what dates you need on your calendar? We’ve pulled together the big ones you need to know in this helpful guide. But, before we get into the individual dates, keep the following things in mind:

• We’re breaking down the must-know federal business tax deadlines for you, but many states have state-specific due dates and requirements. Try searching “[Your State] business tax calendar.” Your Department of Revenue likely has helpful resources to keep you on track.
• If one of the below deadlines falls on a weekend or a holiday during the calendar year, generally, the deadline is pushed to the following business day.

With those disclaimers out of the way, let’s get to what you really want: the tax dates you need on your calendar.

January 15

Your fourth-quarter estimated tax payment for the previous year is due. Your payment needs to be submitted (or, at the very least, postmarked) by this date to avoid penalties.

As the name implies, you pay your quarterly estimated tax payments four times per year. If you’re worried about losing track or missing one, an automated tax and accounting system like Lettuce can set aside money and make your payments for you—without you even thinking about it.

January 31

You should have received all of your 1099-NEC forms from your clients. This simple form reports how much they paid you over the previous calendar year so you can report it as part of your taxable income. Anybody who paid you more than $600 over the year should send you one.

As a business-of-one, you might also be on the other side of this process. If you paid any contractors (like your web designer or a virtual assistant, for example) more than $600, you need to send them a 1099-NEC form before this deadline too.

March 15

If you operate your business as an S Corp, this is your deadline to file your S Corp tax return (Form 1120-S). Alternatively, if you’re planning to operate as an S Corp but haven’t made the switch yet, this is the deadline to elect S Corp Status (Form 2553).

Think making the switch will be a major pain? It doesn’t need to be. Lettuce will take care of your S Corp election for you. Doing so unlocks tax benefits and can save you some major money.

If you run your business as a partnership, then your tax return (Form 1065) is due on this date.

April 15

This is the big one: Tax Day! This is the deadline for submitting your federal individual income tax return (Form 1040). If you need an extension, you’ll need to request one by this date.

This is also the due date for your first-quarter estimated tax payment. This one can easily get lost in the shuffle of all of the other Tax Day hullabaloo. That’s why it’s important to have it marked down—or, better yet, automate your payments.

June 15

Your second-quarter estimated tax payments are due.

September 15

Your third-quarter estimated tax payments are due.

October 15

If you filed for an extension back in April (or before), this is the final deadline for submitting your income tax return for the previous year. There aren’t any more extensions, so you’ll need to submit and pay by this date—or risk penalties and interest charges.

December 31

f you are 73 or older, you’ll need to take your Required Minimum Distribution (RMD) from your IRA, 401(k), or similar tax-deferred retirement plan by the end of the year. It’s important for staying compliant and managing your taxable income.

5 Essential Tax Tips for Your Business-of-One

Keeping track of deadlines is an important part of the tax planning process—but it’s not the only part. Here are a few more best practices to keep in mind to make your tax planning less stressful and more successful:

1. Reconsider your business structure: Your business entity—whether you’re a sole proprietorship, LLC, or S Corp—affects your tax obligations. Just because you’ve stuck with something until now doesn’t necessarily mean it’s the best fit for your business. Switching to an S Corp, for example, could lead to major savings at tax time.
2. Track and maximize your deductions: As a solopreneur, your legitimate business expenses are tax deductions. This means you can write off these expenses to lower your taxable income (and reduce what you owe). Keeping track of these deductions throughout the year means you’re ready to maximize your savings without stressing over deadlines.
3. Explore tax-advantaged retirement accounts: You might not have an employer-sponsored retirement plan when you’re self-employed, but that doesn’t mean you can’t save. There are retirement accounts built specifically for solopreneurs (like a SEP IRA or a Solo 401(k)) that can reduce your taxable income while also helping you plan for your future.
4. Stay informed and up-to-date: The tax code is constantly evolving. Consult a professional (or LettuceHead AI) to guide you through the tax planning process and provide helpful answers to your burning tax questions.
5. Embrace automation: Feel overwhelmed by the process? You don’t need to go it alone. Lettuce can automatically track and categorize your income and expenses, save for and pay your quarterly taxes, and make your annual tax prep a breeze.

Tackle Your Taxes (On Time)

While taxes might not be what your self-employment dreams are made of, they’re important—and you need to be prepared to pay them correctly and on time.

Staying up-to-date on the tax calendar can help. Download our 2025 tax calendar to ensure you’re prepped and ready to take control of your taxes this year.

And, while you’re at it, take a closer look at Lettuce to see how an automated platform can help you take the pain out of tax planning so you can invest your time and energy where it belongs: the billable work you’re passionate about.