The Self-Employed Guide to Stress-Free Tax Time
It’s time to file your taxes. Gulp. Cue the horror movie soundtrack.
Taxes are intimidating when you’re self-employed. Your income tax isn’t automatically withheld from your paycheck like when you’re a traditional employee, which means you need to be proactive and intentional about filing (and paying) your taxes correctly.
Filing your taxes correctly means filing them on time—and that’s way easier when you’re in the loop on the tax deadlines.
This guide has all of the important due dates you need to know so you can get prepared and make the end of tax season 2024 a little less daunting.
Running your solo business has already shown you that deadlines have a way of sneaking up on you. Fortunately, you can avoid those, “Oh, that was due yesterday?!??!” moments of panic by putting the following end-of-year tax deadlines on your calendar right away:
If you need more time to file your annual return, you can request an extension. Filing a tax extension gives you until October 15 to file without any penalties. But, be aware that you need to request this extension by April 15 to avoid paying any late fees.
While this guide focuses on year-end tax deadlines, these certainly aren’t the only due dates you need on your calendar for this year. Remember that you also need to pay your quarterly estimated tax payments throughout the year. The due dates for these payments are:
TIP: Worried about missing a deadline? Lettuce can put your taxes on autopilot and make payments for you all year long.
Knowing the year-end tax deadlines is important—but it’s only the starting point. Spending a little bit of time on preparation and organization can save you plenty of stress as those due dates close in.
This starts by gathering all of the paperwork you need to support your tax return. When you’re self-employed this includes your:
Profit and loss statement that summarizes your business income and expenses
You’ll use this information to fill out your tax return forms. The exact forms you need depend on your business setup—you’ll need different forms if you’re a sole proprietor or LLC than if you’re an S Corp. Here’s a quick look at which forms might apply to you:
Form: | Purpose: | Sole Proprietor: | LLC: | S Corp: |
Contribution Limits | Primary annual income tax return for individuals | |||
Ease of Setup |
Attach this to Form 1040 to report your business income and expenses |
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Roth Option | Income tax return specifically for an S Corporation | |
Not looking forward to sorting through your forms and documentation? Lettuce can do it for you with professional tax preparation for both your individual and business filings.
Whether you go the DIY route or opt to have Lettuce (or an accountant) handle your end-of-year tax prep for you, this fact holds true: staying organized throughout the year can make tax time way less stressful. Here are a few tips to stay ahead and avoid a big mess as the tax deadlines close in.
Take a quick look at Schedule C and you’ll see that the IRS has different categories for business expenses. You don’t just need a total expense amount—you need to know how much you spent on insurance versus office supplies, for example.
You’ll save yourself a lot of time and effort if you categorize your business expenses as they happen (instead of saving them all for tax time). That’s why Lettuce automatically recognizes and categorizes all of your business expenses for you.
Any client that paid you more than $600 in the calendar year should send you a 1099 form by January 31. This simple form reports how much that client paid you over the year.
If you have a lot of clients, you’ll receive a lot of these forms—and it’s tempting to throw them in a stack or save them in your inbox to deal with later. But, it’s smarter to open them up and confirm that the information is correct right away.
Accounting mistakes happen. So, if there’s a discrepancy between the total payment your client reported and what you logged in your income records, you’ll still have time to identify the issue and request a corrected form, if necessary.
Even with the best of intentions, the small admin tasks that are important for your business are easy to let slide. Block off some time in your calendar (even just an hour per month) where you can make sure you’ve correctly categorized your expenses, logged your invoice payments, and set aside money for your quarterly tax payments.
Of course, if you want to be completely hands-off, Lettuce can make that happen. Lettuce’s automated solution will track and categorize your expenses and payments, handle your tax payments, and prep your annual return.
Tax season is usually enough to trigger groans and eye rolls among the self-employed. And, while it’ll likely never be your favorite time of year as a business-of-one, it doesn’t have to be quite so harrowing.
When you know the key end-of-year tax deadlines, stay organized, and rely on automated tools like Lettuce, you can move into the end of tax season with less chaos and more confidence.
Ready to simplify your taxes (and your entire solo business)? Check out Lettuce today.
It’s time to file your taxes. Gulp. Cue the horror movie soundtrack.
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