We’re officially in tax season, yaaay!  It’s a party, it’s a party, who’s excited?! ???

Ok…I know, tax season isn’t particularly sexy – especially for self made boss women entrepreneurs who always GET SHIT DONE no matter how daunting. I bet you could easily think of 10 things you’d rather do besides spend your Saturday shuffling through receipts, sorting out expenses and figuring out your deductions…


But… you’re a self-made, responsible, badass girlboss, so you know you have to eventually get down and dirty with the numbers. Besides, after everything you have accomplished in life, getting through tax season should (ideally) be a breeze. ??


Here are some key deadlines to remember (Deadline to send out 1099 forms was Jan. 31 – if you haven’t done it yet, do it now to minimize late filing penalties!)


March 15 – Partnership & S-Corp Tax Deadline

April 15 – Individual & C-Corp Tax Deadline

Alright, let’s get into 5 habits you can adopt now to make your life (and your lovely accountant’s life) much easier.


1. Track your income & expenses

One spreadsheet is all it takes. This is the most boring, I know, but it also happens to be the most important.

If you buy a new office chair to make working at home so much more comfortable or get a new computer, RECORD IT! Or at least keep your receipts in one place. It’s important to have a monthly tab for each month so everything becomes easy to organize. If tracking this manually in a spreadsheet sounds too tedious or paying for a Bookkeeper or Quickbooks is out of the question, then I suggest using software to track. Below are a few FREE (yes, free) bookkeeping software to check out.




2. Auto-file your emails

This is a little trick that saves so much time you wouldn’t believe it.

You should auto-file all of your receipts, e-statements, account information, any financial/tax related email you receive into one folder in your inbox. That way, you don’t have to search through millions of emails looking for that random big-ticket purchase receipt that arrived in your inbox last July when it’s time to file now.


Check this out for info on how to auto-file emails for Outlook and Gmail.


  1. Keep tax documents in a safe place


This seems obvious but keep your previous tax returns in one place. Get a folder, and make sure to label it by year and keep it in a desk with the drawer shut! You never know when you will need to refer back to your tax documents, so just keep them safe. And it’s crazy for me to suggest hiding them in a drawer because I’m a stickler for keeping everything in the cloud.  However you choose to keep old tax returns, the key word is to keep them — IRS states keeping tax returns for 7 years after the filing date is a great practice to implement.


  1. Shred documents you no longer need


I have two words: paper shredder


As a CPA, I’d rather not shuffle through a slew of unnecessary documents. In fact, my office is (mostly) paperless.  If you don’t need a document, get rid of it! And if you’ve securely uploaded the document in the Cloud, then shred the paper version!  There is nothing else you need to know here – we don’t have to carry around loose documents, it just confuses everything.


5. Ask your accountant questions

This isn’t your specialty, you didn’t study this, we know this ish is hard!  Don’t be afraid to ask questions. Accountants have worked very hard to get to where they are – that CPA exam ain’t no joke, trust me – so don’t worry about looking dumb, we’re here to help and we’re aware that this stuff is complicated af, true talk.

Anyway – you’re the one paying for the service, the last thing you need is to leave feeling even more confused.


My #ChikasTaxTip – adopt these habits ASAP. Maintaining these 5 things throughout the year will make your tax season ride smooth and pothole-free.


P.S. You’re a Boss you probably want to meet other Bosses, amiright? Join the Chika’s Tax Tips Facebook group to connect with the community. It’s LIT. Get freebies, your pressing questions answered and connect with other entrepreneurs. Oh, and follow me on Instagram @chikaobihcpa


8 Easy & Effective Tax Write-Offs for Creatives & Service Providers

8 Easy & Effective Tax Write-Offs for Creatives & Service Providers

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