7 Ways to Crush Tax Prep

** Our Trainers are not tax advisors nor do we provide specific tax advice. The purpose and intent of this blog post is more is a general overview of how you can get your papers prepped for filing your taxes.

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1.Know what documents you need

The alphabet soup of tax forms boils down to documentation for your types of income you earned and tax-deductible expenses you spent.
For an average Financial Gym member who is employed by someone else, you will probably need:


  • W-2 from your employer

  • 1099-INT from your high yield savings account(s) if you earned more than $100

  • 1099-B or -S if you sold any stocks or other significant property


  • 1098-E for the interest paid on your student loans

  • 1095-A,B, C for proof and payment for health insurance

  • 5498, -SA, QA, ESA showing contributions to tax-advantaged accounts like an IRA or HSA

Other tax-deductible expenses will be more unique depending on if you own a home, have children, make charitable donations, or work a job that you can deduct expenses.

If the above scenario is you, then you are more than capable of filing your own taxes. Anything more complicated, you’re justified in wanting to hire a professional to help you.

H&R Block has a very helpful checklist you can use to figure out what you need based on what pertains to you.

2.Freelance or Self-Employed Income

If you are self-employed or a freelancer, you will be receiving 1099’s from your clients. It’s helpful to use your invoices to help you keep track of who paid you and how much so you can cross check the 1099’s that are coming in. If you use a cloud-based accounting software like Quickbooks, Freshbooks or And.Co to generate invoices, then the software can help you with this as opposed to having to manually do it yourself.

3.Set ground rules for tax-deductible expenses

Do your research and understand what type of expenses you are allowed to deduct. You can refer to the IRS website to see your options. The most important thing to keep in mind is that whatever expense you choose to deduct, in the event you are ever audited, you want to be sure you’re able to provide a good justification for WHY you felt it was appropriate to deduct it.

4.Corral all tax-deductible expenses to 1 account

Once you have decided the expenses you are able to deduct, then make sure you’re tracking these expenses throughout the year. The easiest way to do this is to dedicate a specific checking account or credit card for all of your tax-deductible expenses. That way when tax time comes around, you can just export the statements/transactions from that 1 account and know exactly how much you spent. The alternative is to use a software or app for you to manually categorize and tag these expenses throughout the year.

5.Keep your receipts

In the event of an audit, you will need to have the actual receipts to show for the expenses you deducted. Generally, the IRS can include returns filed within the last three years in an audit but can go back as far as six years, so you want to keep your receipts for at least that amount of time.

Whenever you use the account you dedicated for your deductible expenses, you ask and keep the receipt. Bonus points if you can make a quick note on the receipt on what it was for.

Ways to keep track of your receipts:

  • Hard Copies - get yourself an envelope or small folio to keep on your person, then keep a file in a filing cabinet or binder for each tax year.

  • Take Photos - snap a picture on your phone of your receipt, then you can choose to use your regular photo storage to keep track of these files or there are many apps that do this for you now. If you use accounting software, then they usually have a corresponding mobile app. If you don’t have a business, then you may not need a full-blown accounting software and could use apps like Expensify, Shoeboxed, or Receiptmate.

6.Organize your files

Keep an electronic file of all of your tax forms organized by Year. That way, next year, you can refer to the files from the year before to remind you of what you need to get organized this year.

7.Watch Our Tax Prep Webinar Here

Again, our Trainers are not tax advisors nor do we provide specific tax advice. The purpose and intent of this webinar is more of a 101 to give you a general overview of your tax prep for the 2018 calendar year and how you can get prepared. Wa talk about if you you should DIY or hire someone else and common questions we see at The Gym.

Caitlin Lyttle