How to prepare for business tax season…..I live in Queens. Born and raised-ish. And every year, like clockwork, business tax season sneaks up on me the same way winter does in New York—one day it’s kinda chilly, next thing you know your face hurts and you’re questioning all your life choices.
The first time I really thought about how to prepare for business tax season like a pro, I was sitting on the E train, scrolling through emails, and realized I had exactly zero idea where my receipts were. None. Gone. Probably living their best life in a drawer with old takeout menus and mystery USB cables.
You ever get that sinking feeling? Like, “Oh. Oh no. This is my fault.”
Yeah. That.
So this isn’t some buttoned-up tax guide written by someone who’s never panicked at 11:47 PM in March. This is me, telling you what I wish someone told me years ago—before I paid a late fee I still refuse to emotionally process.
Let the writing breathe, right? Cool. Let’s go.
First Things First: Accept That Tax Season Is a Thing (I Know, I Hate It Too)
This might sound obvious, but hear me out.
For years, I treated tax season like an annoying pop-up ad.
“I’ll deal with it later.”
Later never came.
Later ghosted me.
Preparing for business tax season like a pro starts with admitting that taxes aren’t optional. They’re not vibes-based. The IRS does not care that you were busy, tired, or emotionally fragile that quarter.
Once I accepted that—really accepted it—things got weirdly easier. Still annoying. But easier.
Get Your Numbers Together (Before They Become Sentient)
I used to keep track of expenses like this:
- “Yeah, I think I spent money on that.”
- “This sounds deductible… probably?”
- “I’ll remember.”
Spoiler: I did not remember.
If you want to prepare for business tax season like a pro, you need some system. Not a perfect one. Just… a system.
I don’t care if it’s:
- Accounting software
- A spreadsheet
- A folder labeled “TAX STUFF DO NOT DELETE”
- A notebook that smells faintly like bagels
Just pick one.
Now I dump everything into one place all year. Not daily. Not perfectly. But consistently enough that I’m not reconstructing my life from bank statements in April like some kind of financial archaeologist.
Separate Your Business and Personal Stuff (Seriously, Please)
This one hurt my feelings when my accountant said it.
“You used your personal card for this?”
“Yes?”
“…for everything?”
Cue silence.
If you’re still mixing business and personal expenses like it’s one big chaotic smoothie—stop. Please. For future-you.
Open a separate business account. Use it. Even if you forget sometimes (I still do), reducing the overlap makes tax season… survivable.
Preparing for business tax season like a pro doesn’t mean being perfect. It means making fewer messes to clean up later.
Receipts: The Villains of My Story Arc
I once tried to deduct something and my accountant asked for the receipt.
I said, “I can probably find it.”
Reader, I could not.
Now? I snap photos. Immediately. While I’m still annoyed about spending the money. It takes five seconds and saves me hours of stress later.
Is it glamorous? No.
Is it professional? Kinda.
Does it work? Yes.
Know Your Deadlines (Because Panic Is Not a Strategy)
I used to rely on vibes.
Bad move.
Now I keep a running list of tax deadlines. Federal. State. City. Because NYC loves a form. Loves it.
When you actually know what’s coming, you can prepare for business tax season like a pro instead of reacting like, “WAIT THAT WAS DUE WHEN?”
Highly recommend setting calendar reminders. Multiple. Aggressive ones.
Deductions: Where the Magic (and Confusion) Lives
This is the fun part. Kind of.
I didn’t realize how much stuff counted as deductible early on. Internet. Software. Home office. A portion of rent. That coffee you bought while working? Sometimes yes. Sometimes no. (Taxes love nuance.)
I once said out loud, “So… my laptop is a business expense?”
My accountant nodded like this was very obvious information.
If you’re not asking questions about deductions, you’re probably leaving money on the table. And I don’t know about you, but I like my money on my side.
Stop Waiting Until March. Please. I’m Begging You.
I know.
January feels early.
February feels doable.
March feels… spicy.
Preparing for business tax season like a pro means starting before panic sets in. I aim for January now. Even if it’s messy. Even if I half-do it.
Progress beats perfection. Every time.
Emotional Prep Counts Too (No One Talks About This)
Tax season messes with your head. It’s not just numbers—it’s guilt, stress, and that voice that goes, “You should’ve done better.”
Ignore that voice.
You’re running a business. That’s already hard.
Preparing for business tax season like a pro also means being kind to yourself when things aren’t perfect. Because they won’t be. Ever.
My Extremely Unofficial “Pro” Checklist
Not laminated. Not fancy. Just real:
- Separate accounts
- Track income monthly-ish
- Save receipts (or photos)
- Know deadlines
- Ask questions
- Start early
- Breathe
That’s it. That’s the list.
If You Want to Go Deeper (Optional, No Pressure)
I’ve bookmarked a couple resources over the years that actually helped:
- A personal finance blog that explains stuff without sounding smug
- This surprisingly funny take on small business money stress from The Cut (if you like relatable chaos)
No pressure. Just… options.
Final Thought (Not a Conclusion, Don’t Worry)
You don’t need to be perfect to prepare for business tax season like a pro.
You just need to be a little more prepared than last year.
And if you’re reading this thinking, “Wow, I should probably start…”
Yeah. That’s the sign.
You’ve got this.
Even if you’re wearing mismatched socks.
(Been there.)
