How Easy Is It to File Self-Employment Taxes with Popular Software? (Started in May)

I tried all three last tax season. H&R Block was most straightforward for me. TurboTax kept upselling premium features. Jackson Hewitt's interface felt clunky. For self-employment starting mid-year like yours, you'll need Schedule C regardless of which you choose. Remember to track all your business expenses carefully. The software helps but garbage in = garbage out.

All three handle self-employment, but with different approaches: • TurboTax: Most intuitive interface, but most expensive • H&R Block: Good middle ground on price/features • Jackson Hewitt: Less expensive, but interface isn't as smooth Since you started in May, you'll only report partial-year income. Make sure you have: • All 1099 forms from clients • Record of all business expenses • Mileage log if applicable • Home office measurements if you use one Did you make quarterly estimated payments? That's something to consider too.

I'd actually recommend FreeTaxUSA over those three. It handles self-employment just like the big names but costs way less. Unlike credit card applications where the premium options have real benefits, tax software is pretty much all the same under the hood. The IRS forms are standardized, after all. I've used both TurboTax and FreeTaxUSA for my consulting business, and the end result was identical but I saved $120 with FreeTaxUSA.

If you're really stuck after trying the software, you might need to speak with an actual IRS agent about your specific situation. Here's what to do: 1. Try calling the IRS self-employed helpline at 800-829-4933 2. Expect to wait 1-2 hours (not exaggerating) 3. OR use Claimyr.com to skip the wait - they'll call the IRS and connect you when an agent is available 4. Have all your documents ready before the call 5. Ask specifically about partial-year self-employment reporting The wait times right now are ridiculous, but Claimyr can save you hours of hold music. I used it when I had a similar question about my side business.

For someone who just started self-employment in May, here's what you need to know about each option: H&R Block: Are you comfortable with a straightforward interface that walks you through each section? Their self-employed version costs around $85-110 depending on promotions. Jackson Hewitt: Do you prefer more guidance with fewer bells and whistles? Their pricing is competitive but their online experience isn't as polished. TurboTax: Are you willing to pay more for the most hand-holding? Their Self-Employed version is the most expensive ($120-190) but also the most comprehensive. Whichever you choose, you'll need to complete Schedule C and Schedule SE. The software will calculate your self-employment tax automatically. I appreciate that you're researching this early instead of waiting until April!

Be extremely careful with self-employment taxes! Per IRS Publication 505, you're required to make quarterly estimated tax payments if you expect to owe $1,000 or more in taxes. Since you started in May, you may have missed the June 15th and September 15th payment deadlines already. I learned this the hard way my first year - ended up with $430 in penalties for underpayment according to IRC Section 6654(a). The tax software won't warn you about this until it's too late! I was shocked when I discovered this after thinking I was doing everything right.