Self-Employment Tax Experience & Pain Points Survey

Thanks for taking a few minutes on this! We're trying to understand how self-employed people actually deal with taxes — the good, the confusing, and the stressful parts. Your responses are completely confidential and anonymized. About 8 minutes, and there are no wrong answers.

How do you currently handle your self-employment taxes?

• I do it myself using tax software
• I do it myself manually (spreadsheets, paper)
• An accountant or CPA handles it for me
• A friend or family member helps me
• I honestly don't have a consistent process

How confident are you that you understand what you owe in self-employment tax and why?

In the last 12 months, how often did you make your estimated quarterly tax payments on time?

• All four payments, on time
• Most payments, occasionally late
• I made some payments but missed others
• I didn't make estimated payments at all
• I wasn't aware quarterly payments were required

How difficult do you find each of the following parts of managing self-employment tax?

Which of these self-employment tax challenges affects you the most, and which affects you the least?

• Calculating accurate quarterly estimates
• Tracking and categorizing deductible expenses
• Understanding the self-employment tax rate itself
• Saving enough money to actually pay the bill
• Overall filing complexity and paperwork
• Finding an accountant or advisor I trust
• Making sense of retirement account tax strategies
• Dealing with IRS notices or penalties

Thinking about a typical year, allocate 100 points across where your time and money actually go for tax prep.

• Software or apps
• Accountant or bookkeeper fees
• Your own time
• Penalties, interest, or late fees
• Other tools or resources

Have you ever been surprised by a much larger tax bill than you expected?

• Yes
• No
• Not sure

If the respondent said they've been surprised by a larger-than-expected tax bill, reconstruct exactly what happened: what they expected to owe, what they actually owed, and what caused the gap (missed quarterly payments, misunderstood deductions, income spike, etc.). If they haven't had that experience, instead probe their single most difficult challenge from the trade-off question and ask what would have made it easier — a tool, a person, or clearer information. Get concrete, specific detail, not general frustration.

Roughly how many years have you been self-employed or freelancing?

Which best describes your primary line of self-employed work?

• Creative or media (writing, design, photography, etc.)
• Consulting or professional services
• Trades or skilled labor (construction, repair, etc.)
• Tech or software (development, IT, etc.)
• Retail, e-commerce, or product sales
• Gig or platform work (rideshare, delivery, etc.)
• Other

What was your approximate self-employment income last year?

• Under $25,000
• $25,000–$49,999
• $50,000–$99,999
• $100,000–$199,999
• $200,000 or more
• Prefer not to say

What is your age range?

• Under 25
• 25–34
• 35–44
• 45–54
• 55–64
• 65 or older
• Prefer not to say

That's everything — thank you for the honest answers! We're using responses like yours to understand where self-employed people get stuck on taxes, so tools and services can actually be built to help.