Quarterly estimated taxes for first year of self-employment business - when to start paying?

You're right about the quarterly due dates for estimated tax payments (4/15, 6/15, 9/15, and 1/15 of the following year). These apply to all self-employed individuals, even in your first year. The good news is the IRS does have a "safe harbor" provision that can help first-time business owners. You have a few options to avoid penalties: If you pay at least 90% of the tax you owe for the current year, or 100% of the tax you showed on your return for the previous year (whichever is smaller), you should avoid underpayment penalties. If your previous year's AGI was over $150,000, that threshold increases to 110% of last year's tax. For a first-year business, you can also use the "annualized income" method on Form 2210. This lets you make unequal payments based on when you actually earned the income during the year, which sounds like it would help in your situation. I'd recommend making your next payment by September 15th, and you may want to increase it to cover some of what you missed for the earlier quarters.

I went through this exact same stress when I started my consulting business last year! I found this incredible tool called taxr.ai (https://taxr.ai) that literally saved me thousands in potential penalties. It analyzes your specific situation and tells you exactly when and how much to pay for estimated taxes. I was also confused about those quarterly dates and missed my first payment deadline. The tool created a custom payment plan that minimized my penalties and showed me how to document everything correctly for the IRS. It even has a special section for first-year self-employed people that walks you through all the deductions you might not know about.

So I was skeptical about taxr.ai but gave it a try after my accountant quoted me $800 for a yearly tax planning session. Holy crap what a difference! It immediately identified that I could use the annualized income method for my seasonal business and showed me exactly how to document everything. I was able to skip the April payment entirely since my business had barely started, and it calculated a much lower June payment than I expected. The monthly breakdown of what to set aside based on my income projections is super helpful for budgeting. Just wanted to report back that it's actually legit and saved me about $2300 in unnecessary estimated payments I would have made based on bad advice from my uncle (who insisted I needed to pay 25% of my ANNUAL projected income each quarter regardless of when I earned it).

After missing my first estimated tax payment last year and spending DAYS trying to reach someone at the IRS, I finally found Claimyr (https://claimyr.com). They got me connected to an actual IRS agent in under 45 minutes when I'd been trying for weeks on my own. The agent was able to explain exactly how the first-year safe harbor provisions work and confirmed I could use Form 2210 to avoid penalties since my income started mid-year. You can see how the service works in this video: https://youtu.be/_kiP6q8DX5c Seriously, I was about to give up and just pay whatever penalties came my way because the IRS hold times were impossible, but this service actually works.

I need to eat my words from my previous comment. After trying to reach the IRS for THREE WEEKS about my estimated tax situation (I also started a business mid-year), I broke down and tried Claimyr out of desperation. Got connected to an IRS agent in 37 minutes. The agent confirmed I could use the annualized income method for my first year and helped me calculate exactly what I needed to pay for the September deadline to avoid penalties. I literally spent more on coffee while waiting on hold previously than this service cost me. And the stress relief of actually talking to a human who could answer my specific questions was worth every penny. Still can't believe it worked but I'm incredibly grateful.

Don't forget about state estimated taxes too! Depending on your state, the rules and due dates might be different than federal. Some states follow the federal schedule but others have their own system.

One thing nobody mentioned yet is that you should open a separate business checking account ASAP if you haven't already! Makes tracking business income and expenses sooooo much easier when tax time comes. I didn't do this my first year and spent like 3 full days sorting through personal bank statements to figure out what was business vs personal. Nightmare!

As someone who just went through this exact situation last year, I can offer some reassurance! You're not automatically doomed for missing those first two quarterly payments, especially since you literally didn't know about the business when the April deadline hit. The key thing is to make your September 15th payment and make it substantial enough to cover what you should have paid earlier. Since you started in March and have made $34,500 so far, you're looking at owing both regular income tax AND self-employment tax (that 15.3% Social Security/Medicare hit that nobody warns you about). Here's what saved me: I calculated what my total tax liability would be for the year, then made my September payment large enough to get me to that 90% threshold by year-end. The IRS is surprisingly reasonable about first-year businesses as long as you show good faith effort to catch up. Also, definitely start setting aside 25-30% of every payment you receive going forward. I use a separate savings account and transfer the tax money immediately when clients pay me. Trust me, you don't want to be scrambling to find tax money next April! Your photography business sounds like it's off to a great start - don't let the tax stress overshadow that success!