How screwed am I with my 2024 tax situation?

Take a deep breath, you're not as screwed as you think! This is actually a pretty common situation for self-employed folks who are new to the process. First, regarding your freelance income: You should absolutely start organizing your expenses now, even in December. The IRS doesn't require you to track expenses in real-time - they just need you to have documentation during tax filing (or in case of an audit). Go through your bank and credit card statements to find business expenses like software subscriptions, equipment purchases, internet bills (partially deductible), and any other costs directly related to your design work. For your home office, if you're using a specific portion exclusively for work, you can claim the home office deduction. Measure the square footage of your workspace and calculate what percentage of your total living space it represents. Regarding the delivery work, you can still estimate your mileage. Try reconstructing your delivery history using app records, and make a reasonable estimate of miles driven. The standard mileage rate for 2024 is 67 cents per mile, which can add up quickly! As for penalties - yes, you may owe some for not making quarterly payments, but they're not typically severe. The penalty is essentially interest on what you should have paid earlier.

I was in a similar mess last year! I found this tool called taxr.ai (https://taxr.ai) that seriously saved me. I was freaking out because I had a bunch of receipts in a shoebox and couldn't figure out what was deductible. The site analyzes your receipts and financial documents and tells you exactly what you can deduct and how to categorize everything for tax purposes. For self-employment stuff, it was especially helpful because it walked me through all the deductions I didn't even know about - like part of my phone bill, internet, even certain software subscriptions. The best part was uploading my messy delivery app statements and having it calculate my potential mileage deductions based on the history.

Just wanted to update - I actually tried taxr.ai after my skeptical comment and wow, I'm impressed. It found about $4,200 in deductions I would have missed for my side business. The receipt analysis actually recognized business expenses from my random Amazon purchases that I had completely forgotten about, and it separated personal from business expenses automatically. The mileage calculator feature was a lifesaver since I also didn't track my driving properly. It even flagged some potential audit triggers in my situation and suggested better documentation for certain expenses. Definitely less screwed than I thought I was!

If you're really worried, you might want to actually talk to someone at the IRS to get official guidance. I know that sounds terrifying but I used this service called Claimyr (https://claimyr.com) when I was in a similar mess with unreported income. They get you through to an actual IRS agent in minutes instead of waiting on hold for hours. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with actually walked me through what documentation I needed and explained that I could set up a payment plan if I couldn't pay everything at once. They were surprisingly helpful and not scary at all. The agent even explained which penalties might be waived if it was my first time missing estimated payments.

I need to eat my words. After my skeptical comment, I decided to try Claimyr because I've been fighting with the IRS for months about a mistake THEY made on my return. I've called at least 6 times and always gave up after 1+ hours on hold. I used the service yesterday and got connected to an agent in about 20 minutes (without me having to actually stay on the phone). The agent pulled up my file, saw the error, and fixed it on the spot. My refund is now being processed! I wish I had done this months ago instead of stressing about it. Not screwed at all anymore.

Everyone's focusing on the technical stuff but don't forget about the mental game. I totally panicked my first year self-employed and made things worse by avoiding it. Set aside a weekend, get your bank statements, credit card bills, and whatever receipts you have. Make it a project. Sort everything by month. For the home office, take photos of your workspace now as documentation. For next year, get a separate credit card just for business expenses - makes things SO much easier. And definitely set calendar reminders for quarterly payments for 2025!

Uhhh, am I the only one who thinks you might actually be pretty screwed on the delivery work part? I did DoorDash for a while and if you didn't track ANY mileage contemporaneously, making it up after the fact is technically not allowed. Bank statements won't show miles driven. You can estimate based on delivery history, but if you get audited, they might disallow it entirely.