Stressed about filing your taxes? Get it done smoothly with these best practices and checklist.

by Rob Bertman, CFA, CFP® in Tax
March 12, 2016


Come March or April, many of us in our 20s and 30s start feeling the tax filing pressure.

Am I doing this right?  Am I getting the most deductions and credits?

Whether you’re filing your taxes on your own, using TurboTax, H&R Block or another tax professional, it can seem like there’s something we’re missing.

So, I’ve put together a list of the most common tax forms and documents to organize in preparation to file your taxes.

There’s something different about this list though.

They are organized by what you have going on in your life.  Did you just get married, have a kid, buy a house?  Do you or your employer contribute to a retirement plan?  Do you have a student loan?

Some things will generate tax forms that you will receive, but there are others that won’t, and I’ll list them below.

But, before getting to the checklist, here are 5 keys to get in control.


5 Keys to Tax Filing Success

1. Get it over with!

Once you receive all of your documents, just get it done.  Come April, the banks and post offices are jammed and there are indefinite hold times to answer your questions. Waiting until the last minute will just create stress that you didn’t need.

2. Start a file

Keep a file for the tax year, and add the tax documents as you receive them.  That way, there’s no searching around come tax time. Everything is in one place.  You can have a physical file, electronic file, or both.

3. Make a process

Like it or not, we all have to do this each year, so make it easy on yourself. The best way to get in control of your taxes is to put a process in place. Start simply with what you know and make improvements over time.

4. Use a checklist

Put a checklist in your file of the tax documents you know you should be receiving and compiling. Update the list each year as your situation changes.

5. Double check the work

It’s a busy time of year with documents flying everywhere. Take some time to review your IRS Form 1040 and state tax form before sending it.


Here’s The Checklist


  • Did you get paid wages or salary?  W-2 for all jobs held
  • Did you collect any unemployment benefits?  1099-G
  • Did you get a tax refund last year?  1099-G
  • Do you have any accounts at a bank, brokerage firm, or mutual fund company (not including retirement plans)?
    • Were there any transactions?  1099-B for each account
    • Did you receive any dividends or interest payments?  1099-DIV & 1099-INT for each account
  • Did you do a rollover funds from a retirement plan into an IRA?  1099-R for each account.
  • Did you do a Roth IRA conversion?  1099-R
  • Less common: Do you have ownership in a partnership or S corp?  K-1 for each entity


Retirement plan contributions – 401(k), 403(b) and others

  • Did you contribute to a retirement plan through your employer and before your take home pay?  It should show up on your W-2
  • Did you make a new IRA & Roth IRA contribution?  5498
  • Did you rollover a retirement plan to an IRA  5498
  • Did you do a Roth IRA conversion?  5498 (This is especially important to have with a rollover from a retirement plan or Roth IRA conversion that generated a 1099-R so they can match up.


Student Loans & School

  • Did you pay back any student loans?  1098-E (Up to $2,500 deduction but it phases out as income goes up)
  • Were you in school?  1098-T (Tuition statement)


Newly Married?

  • You may have to change your filing status.



  • Do you have kids?  No tax forms, but you may be eligible for the following:
    • $1,000 child tax credit.
    • Take a dependency exemption for each kid ($4,000 deduction each)
  • Are your kids in child care?  No tax forms but get receipts from your child care provider. You may be able to deduct up to $3,000 credit for 1, up to $6,000 for 2 or more.
  • 529 plan contributions? No tax forms. The deduction is only against your state taxes.


Health Insurance Coverage:  New form for 2015 that is proof of your health insurance coverage. You should have one of the following:

  • 1095-A – If you purchased your insurance through
  • 1095-B or 1095-C – If you purchased health insurance through your employer


Home/Condo Ownership

  • Do you have a mortgage that you’ve been paying?  1098 – Mortgage Interest Statement
  • Property taxes? No form but it can be deducted in the year you paid it. Keep the payment receipt.
  • Did you buy a house or condo last year?  HUD-1 statement. You can deduct the following:
    • Real estate taxes
    • Prepaid mortgage interest
    • Loan points


Charity & Donations

  • Did you donate money?  No tax form (Keep your receipts and letters from the charities)
  • Did you give away any clothes or household items?   No tax form (Keep your receipts and letters from the charities)
  • Did you donate stock?  No tax form (Keep your receipts and letters from the charities)
  • Did you volunteer your time?  No tax form but track the most common things:
    • Supplies purchased
    • Parking for your personal vehicle
    • Mileage for your personal vehicle – You can deduct $0.14/mile for 2015



  • Did you pay someone to do your taxes?  Keep you invoice or receipt. You can deduct that.
  • Did you pay any personal property taxes on vehicles?  Keep your receipt of payment. You can deduct it in the year you paid it.


Ok, you’re ready to go! Follow these best practices and use the checklist as your framework to get organized, and gain more confidence as you file your taxes this year.

All the best,

Rob Bertman, CFA, CFP®
Founder & CEO
Money With Impact



If you started a new business, own rental properties, had a major medical event, received an inheritance, or another significant event, I highly suggest you consult with a qualified, reliable tax professional.

Since I don’t know the specific circumstances of your life and finances, the above information may not be applicable or suitable for you nor comprehensive, so I urge you to consult a tax professional or service for a more comprehensive list and actual deductions and credits that apply to your specific situation.

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