Okay, Lets Talk About That Dreaded April 15th Date
Look, Im gonna be honest with you – I used to be absolutely terrible with taxes. Like, I once filed three weeks late and got hit with a penalty that still makes me cringe. Learn from my mistakes, people.
The main date you need burned into your brain is April 15, 2024. Thats when your 2023 tax return needs to be in. Unless it falls on a weekend (which it doesnt this year), theres no getting around it. If youre the type who needs more time – and no judgment here because Ive been there – you can file for an extension and push it to October 15th.
But heres the thing nobody tells you: an extension to FILE doesnt mean an extension to PAY. The IRS still wants their money by April 15th. I found that out the hard way.
How I Actually File My Taxes (And What Ive Tried)
Ive done pretty much everything at this point. Started with TurboTax back in my 20s when my taxes were simple – W2, maybe some student loan interest, done. Cost me like $60 and took maybe an hour.
Then I started a side business and things got… complicated. Hired a CPA for about $400. Worth every penny that year because she found deductions I never would have thought of. The downside? I had to wait until late March to get everything back because she was slammed with other clients.
Last year I tried doing it myself again with tax software. Big mistake. Spent an entire Sunday afternoon second-guessing every entry. My spouse finally told me to just pay someone because I was driving everyone crazy.
Paper filing? I mean, technically you can still mail it in. My dad does this. I dont understand why but he likes it. Just know it takes forever to process and if youre expecting a refund, youll be waiting a while.
The Document Scramble – Get Ahead of It
Every January I tell myself this is the year I stay organized. And every March Im digging through email looking for 1099s I forgot about.
Heres what you actually need to find:
- W-2s from anywhere you worked (they usually show up late January)
- 1099s for freelance gigs, investment income, that kind of thing
- Receipts if youre itemizing – medical stuff, charity donations, etc.
- Your tax return from last year (handy for reference)
- Social security numbers for you, spouse, kids
Pro tip that took me years to figure out: create a folder on your computer called 2024 taxes right now and just dump stuff in there as it arrives. Future you will be grateful.
Deductions Ive Actually Used (And Some I Missed)
The standard deduction is pretty huge now – $13,850 for single folks. Honestly, unless youve got a mortgage or gave a ton to charity, youre probably just taking the standard deduction. And thats fine! Its not cheating, its just math.
Things Ive deducted over the years:
- Mortgage interest (this was actually worth itemizing one year)
- Student loan interest – theres a limit but every bit helps
- That child tax credit when my niece lived with us temporarily
Things I missed and kicked myself over:
- Home office deduction when I was freelancing – I had no idea
- Some medical expenses one year when I had surgery
If You Owe Money – Dont Panic
I owed $2,300 one year and almost had a heart attack. But there are options.
You can set up a payment plan with the IRS. Theyre actually pretty reasonable about it, believe it or not. I did a short-term plan and just paid it off over four months. The interest wasnt great but it beat putting it on a credit card.
You can also pay by credit card but theres usually a fee, so check the math first. Direct debit from your bank account is probably the easiest.
What Happens If You Miss the Deadline (Because Sometimes Life Happens)
So heres the deal. Missing the deadline isnt the end of the world, but its not cheap either.
The failure-to-file penalty is brutal – like 5% of what you owe for every month youre late. The failure-to-pay penalty is gentler at 0.5% per month. Plus interest on top of all that.
If you cant file on time, at least file for that extension. And if you owe money, pay whatever you can. Partial payment is better than nothing – it reduces the penalties.
When You Actually Need Professional Help
If youre self-employed, have rental properties, sold stocks, dealt with an inheritance, or anything remotely complicated – just get a CPA. Im serious. The money you might save DIY-ing it isnt worth the stress or the risk of messing something up.
VITA is also a thing – free tax help if you make under about $60K. My cousin used them last year and said they were great.
The IRS website has more resources than youd expect. Their withholding calculator is actually pretty useful if youre trying to figure out if you should adjust your W-4.
My Actual Advice After Years of Doing This
Start gathering your documents in February. Dont wait until April. If youre getting a refund, file as early as possible – why let the government hold onto your money longer than necessary? If youre going to owe, you can still prepare everything early but wait until closer to April 15th to actually submit and pay.
And seriously, make a folder. Right now. Youll thank me later.
