Need guidance on 1099 taxes for side consulting work - what should I do?

Thanks for the advice! Quick question - for quarterly estimated taxes, is there a minimum amount I need to make before I'm required to do those? And how exactly do I calculate how much to pay each quarter?

Generally, if you expect to owe at least $1,000 in taxes from your self-employment income, you should make quarterly payments. With $15K in additional income, you'll almost certainly hit that threshold. For calculating quarterly payments, the simplest approach is to estimate your total tax liability for the year, divide by four, and pay that amount each quarter. You can use Form 1040-ES to help with the calculation, or many tax software programs have calculators for this. The payments are due April 15, June 15, September 15, and January 15 of the following year.

That sounds interesting! Does it connect directly to your bank or do you have to upload statements? I'm a bit hesitant to connect financial accounts to new services.

I've tried a few expense tracking apps before and they always seem to categorize things wrong. Does this one actually understand the difference between personal and business expenses? I bought office supplies for both my home and consulting work and my last app was useless at separating them.

You can either connect accounts or upload statements manually - I usually just download PDFs from my bank and upload them. They have pretty good security but I get the concern about connecting accounts. For categorization, it's much better than general budgeting apps because it's specifically designed for business expenses and taxes. It lets you easily recategorize anything it gets wrong, and learns from your corrections. So when I buy supplies from the same store repeatedly, it remembers which portion was business vs personal after I split it the first time.

Wait, how does this actually work? The IRS phone lines are always jammed... are they somehow jumping the queue? Is that even allowed?

I'm super skeptical about this. Sounds like something that would get shut down if it was actually bypassing IRS systems. How could a third party possibly get you through faster than calling directly?

They use a system that continuously redials and navigates the IRS phone tree until it gets through, then it calls you and connects you. It's completely legitimate - they're not doing anything that breaks rules, just automating the frustrating part. They basically save you from having to sit on hold for hours. Once you're connected, you're talking directly with an actual IRS agent just like if you'd called yourself. The difference is you don't waste half your day listening to the hold music!

Are there any good apps you'd recommend for tracking mileage? I always forget to log my trips and end up guessing at tax time which probably isn't the best approach.

I use MileIQ, but there are several good ones like Everlance and Stride. The key is finding one that tracks automatically in the background so you don't have to remember to start/stop for each trip. They usually let you swipe left/right to categorize as business or personal which makes it super easy. Most important is consistency - even a simple notes app works if you use it religiously. The IRS wants to see a contemporaneous log, meaning you record trips as they happen, not reconstructed months later.

I tried it for a year and honestly thought it was overkill for my situation. If you're just doing basic expense tracking with a handful of clients, I think there are cheaper alternatives that work just as well. I switched to Wave which is free for basic accounting.