Guide to a Stress-Free Tax Season: How to create a streamlined checklist for filing taxes

w2 form

Does the thought of tax season leave you feeling overwhelmed? Although tax season is often a stressful time for many, it doesn’t have to be. If you properly prepare yourself, you’ll find that it doesn’t have to be the nightmarish ordeal that we often associate it with.

Whether you choose to file your own taxes or work with an accountant, one of the most important elements is an organized approach. Make a list of the documents, tax forms, office supplies (calculators, pens, notepads, filing system) and other items you’ll need to get started. If you set up a system that works for you & maintain accurate records in a location that’s easily accessible, it will save you future headaches and make filing in the years ahead even easier! In this article, you’ll find a list of helpful hints and advice to streamline the process and hopefully reduce the level of anxiety that you might be going through, or perhaps you’ll want to pass it onto a friend, family member or colleague who needs some tax-season advice.


1.) Stay current

One of the most difficult problems people are faced with is when they don’t keep up with their annual taxes. This can occur when you reduce your withholding too much, but it can also happen when you don’t keep up with your estimated tax payment obligations. If you own an interest in a partnership or an S corporation, it can develop into an issue quickly, especially if you’ve spent the distributions you’ve received without saving any for taxable applications.

We recommend: If your tax preparer gave you a voucher, file it with your check as instructed – it won’t get any easier next April if you don’t.


2.) Be prepared; be aware

Believe it or not, you’ll be able to find the majority of your tax-saving opportunities at work – be aware of the different options your employer offers and if possible, discuss them in detail with Human Resources or whoever can assist you with your questions. Take advantage of the packages your company might offer and keep your paperwork in order for tax filing purposes. Here are a few pointers you might want to consider:

We recommend:

  • Maximize your 401(k) contribution: If you aren’t at least putting in enough to get the entire employer match, you’re doing yourself a serious disservice: more is better.
  • Review your health plan opportunities: If your employer offers a Health Savings Account (HSA) option, carefully reconsider before opting out. Many employers offer generous breaks to switch to high-deductible health insurance, and most of the time you’ll be financially better off with an HSA. If there is no HSA at your job, make sure you take full advantage of the cafeteria plan – speak with your HR department for more details if you’re uncertain.
  • Start funding your 2008 IRA: The main benefit of an IRA plan is tax-free buildup of earnings; if you fund it now instead of next April, your money is tax-sheltered an extra year.
  • For Students: If you are saving for college, a good way to save is to put aside money (as much as you can afford) to a Section 529 plan every month.

3.) Expect the unexpected

It’s always recommended to have savings put aside for any sort of unexpected financial circumstances. Some advocate that an individual should have enough to pay six months of living expenses, but you may be able to get by with less, especially if you have some other investments or if you have a house.

We recommend: If you are a homeowner, open a home-equity line of credit, and then don’t use it except for emergencies – like a $30,000 tax bill.


4.) Check, please!

Before dropping your taxes in the mail, take a few minutes to go through the IRS last-minute checklist:

  • Did you use the peel–off label and enter any corrections? If you used the label, did you enter your social security number in the space provided?
  • If you do not have a label, or there are too many corrections, did you clearly print your name, social security number, and address, including zip code directly on your return?
  • Did you enter the names and social security numbers for yourself, your spouse, your dependents, and qualifying children for earned income credit or child tax credit, exactly as they appear on the social security cards? If there have been any name changes be sure to go to or call at 1–800–772–1213.
  • Did you check only one filing status?
  • Did you check the appropriate exemption boxes and enter the names and social security numbers exactly as they appear on the Social Security Card, for all of the dependents claimed? Is the total number of exemptions entered?
  • Did you enter income, deductions, and credits on the correct lines and are the totals correct?
  • If you show a negative amount on your return, did you put brackets around it?
  • If you are taking the standard deduction and checked any box indicating either you or your spouse were age 65 or older or blind, did you find the correct standard deduction using the worksheet in the Form 1040 Instructions or the Form 1040A Instructions?
  • Did you figure the tax correctly? If you used the tax tables, did you use the correct column for your filing status?
  • Did you sign and date the return? If it is a joint return, did your spouse also sign and date the return?
  • Do you have a Form W-2 (PDF) from all of your employers and did you attach Copy B of each to your return? File only one return, even if you have more than one job. Combine the wages and withholding from all Form W-2’s, on one return.
  • Did you attach any Form 1099-R (PDF) that shows tax withheld?
  • Did you attach all other necessary schedules and forms in sequence number order given in the upper right–hand corner?
  • If you owe tax, did you enclose a check or money order with the return and write your social security number, tax form, and tax year on the payment? Refer to Topic 158 for more information, and
  • If you are due a refund and requested direct deposit did you check the routing and account numbers?
  • Did you make a copy of the signed return and all schedules for your records?

We recommend:

A few of the most common errors are:

  • Incorrect or missing social security numbers.
  • Incorrect tax entered from the tables.
  • Computation errors in figuring the child and dependent care credit or the earned income credit. Also, missing or incorrect identification numbers for child care providers.
  • Withholding and estimated tax payments entered on the wrong line, and
  • Math Errors. Both addition and subtraction.

It is important that you review your entire return because any errors may delay the processing of your return.


  • Signed, Sealed, Delivered: If you aren’t e-filing, opt for “certified mail, return receipt requested” to save you time and potential problems.
  • Extension = Less Tension: If you need more time to pay, get an automatic extension with Form 4868, which will allow you until October to file a timely return. Even if you can’t pay your tax, an extension can turn the 5% monthly failure-to-file penalty into a 1/2% monthly failure-to-pay penalty (that is, if you can ultimately file your completed 1040 and pay your taxes by the extended due date).
  • Check IRS Publication 1771 for more information.