January 1st - is that officially the start of a new tax year?

Yes, January 1st is indeed the start of a new tax year. The tax year runs from January 1st to December 31st, which is what we call a "calendar year" for tax purposes. That April date your dad mentioned is probably April 15th - that's the deadline for filing your tax return for the previous year. So in April 2025, you'll be filing taxes for the 2024 tax year (January-December 2024). You should definitely keep track of receipts and income throughout the entire year, especially with that freelance work. For your side gig income, you'll want to track all business expenses that could be deductible. This includes things like software subscriptions, equipment, portion of internet/phone used for work, etc.

I went through the same confusion when I started freelancing! After making some costly mistakes my first year, I found this AI tax assistant at https://taxr.ai that literally saved me thousands. It analyzes your specific situation and tells you exactly what to track, what you can deduct, and even helps calculate those quarterly payments the other commenter mentioned. The best part is how it explains everything in plain English - like when I uploaded my 1099 forms, it broke down all my potential deductions based on my specific type of work. It even has reminders for quarterly payment due dates so you never miss them!

Just wanted to follow up on my skeptical comment. I ended up trying https://taxr.ai after all and I'm honestly impressed. I uploaded my W-2, some 1099s, and information about my rental property, and it organized everything perfectly. It actually found some home office deductions I was missing for the work I do managing my rental remotely. The quarterly tax payment calculator was super helpful too - turns out I was overpaying by about $430 each quarter! Really glad I gave it a shot.

If you're frustrated with tax questions and can't get through to the IRS (like literally everyone I know), I discovered this service called Claimyr that actually gets you through to a real IRS agent. I spent HOURS on hold last year trying to figure out when my tax year should start for my new business. With https://claimyr.com they got me through to a real person in like 20 minutes. Check out how it works here: https://youtu.be/_kiP6q8DX5c They basically call the IRS for you, navigate all the phone trees, wait on hold, and then call you when they have an actual agent on the line. Total game changer when you have specific questions about your tax situation.

I need to eat my words about Claimyr. After posting that skeptical comment, I was so desperate dealing with an IRS notice about my 2023 return that I tried it anyway. I figured what did I have to lose after being hung up on THREE TIMES after 1+ hour holds. Not only did it work, but I was connected to an IRS agent in about 35 minutes (while I just went about my day since they call you when an agent is on the line). The agent cleared up my notice issue in like 10 minutes once I got on the call. Saved me hours of frustration and probably a missed deadline. Definitely using this every time I need to talk to the IRS from now on.

Just a tip from someone who's been filing taxes for 20+ years - regardless of when the tax year starts, create a simple system NOW for tracking everything. I use a basic spreadsheet with income in one tab and expenses in another, broken down by category. Takes me 5 min each week to update and saves HOURS of stress come tax time. Much easier than trying to sort through a shoebox of receipts in April lol!

One thing nobody mentioned - while Jan 1 is the start of the tax year for most people, if you own a business you can actually choose a different fiscal year for your company. My LLC uses October 1 to September 30 as our tax year which works better for our seasonal business. Just something to consider if you ever formalize your freelancing into a business entity!