Self-Employed? Here’s How to Ditch the Tax-Time Headache

Being your own boss is awesome… until tax season hits. Scrambling for receipts? Guessing mileage? Wondering what you can even deduct? Yeah, no thanks.

Here’s what to track now so you can cruise through tax time later (and maybe even keep more of your money).Being your own boss is awesome… until tax season hits. Scrambling for receipts? Guessing mileage? Wondering what you can even deduct? Yeah, no thanks.

Here’s what to track now so you can cruise through tax time later (and maybe even keep more of your money).

1. Track Every Dollar You Earn

The IRS wants to know about all your income, no exceptions:

• Client payments (PayPal, Venmo, checks, cash—you name it)

• 1099-NECs from clients who paid you $600+

• Other income (refunds, rebates, bonus payments)

Quick fix: Use a bookkeeping app or even a simple spreadsheet. Update it weekly—it’s way easier than digging through bank statements in April.

2. Know Your Write-Offs (Hello, Schedule C Deductions!)

Every business expense you track is money that stays in your pocket. Some big ones:

• Home office (if you work from a dedicated space at home)

• Supplies & equipment (laptop, printer, paper, even office coffee)

• Mileage & car expenses (use an app—it’s painless)

• Meals & travel (business lunches, conferences, client visits)

• Professional fees (tax prep, bookkeeping, courses)

• Insurance premiums (health, liability, business)

• Marketing & ads (websites, business cards, social ads)

Pro tip: Snap pictures of receipts with your phone and save them digitally. No shoebox required.

3. Pay Quarterly Taxes

Expect to owe more than $1,000? You need to make estimated tax payments four times a year (April, June, September, January).

Easy fix: Stash 25–30% of your income in a separate “tax fund” account. You’ll thank yourself later.

4. Keep Business & Personal Money Separate

One bank account for business, one for personal. That’s it. It makes your life easier, your books cleaner, and an IRS audit way less stressful.

5. Stay Organized Year-Round

Spend 15 minutes each week updating your income and expenses. Hate doing that? Outsource it. (Yep, that’s what we do!)

Ready to Stay on Track All Year?

We’ve made it easy for you—Download our Free Self-Employed Tax Checklist to know exactly what to track and when.