How do you prepare for tax season?

Coach Natalie

Now that tax season is upon us, we want to hear how you prepare for filing taxes! Do you keep track of everything throughout the year so you're prepared to file right away, or do you tend to do maintenance at a certain point each year to get caught up?

Do you do your own filing, or do you have an accountant or family member file for you? If you have any advice to share with the rest of us when it comes to tax season, we'd love to hear it! 

And if you use Simplifi to keep track of deductions, business expenses, receipts, or anything else to prepare for tax season, tell us some tips and tricks you've discovered along the way!

MrGood

I find that it's easier to prepare for taxes by doing a little at a time throughout the year.  Though I don't necessarily enjoy taxes for 'other people', I do enjoy it when its my money.  Normally, our situation is fairly straightforward, so been able to do it myself and consult an expert where necessary.

• To keep track of tax-relevant transactions, I have separate tags depending on the credit (e.g., Dependent care credit, HSA reimbursable, etc.)
• For record-keeping, I employ an all-digital approach.  Helps with quickly finding information as well as having a safety net via cloud backups.
• For HSA transactions, I use the following naming convention so that it's easier to cross-reference against the Simplifi transaction register: <YYYY MM DD> - Vendor - <amount>.pdf

DannyB

I keep a folder in my desk file drawer for each years tax receipts/statements and stash anything having to do with filing tax returns in that folder. By the same token, I have a folder for each year on my hard drive and in a cloud service where I keep digital receipts, statements and documents.

When our various tax documents start showing up, if available digitally (and almost all are these days) I download them into my digital folder, if something arrives as hardcopy, I digitize it and save it to that same folder and keep the hardcopy in my desk folder.

Sometime in late February or early March my tax service will notify me that she is ready to start working on my return and I upload all my docs to her website.  We will chat back and forth about any questions or issues and then she will finalize my returns and that's it.

The only thing that is unique for me is my clergy status and certain rules that apply to clergy income.

2022 will be the penultimate year we will have W-2 or 1099 income and the majority of our income in 2023 will come from SSA, a pension, and distributions from our retirement accounts.  I'm working with our tax pro on how to prepare for our 2023 returns and beyond.