Top 5 Roadblocks to Tax Success

Everyone’s income taxes are different, but there are some common roadblocks to tax success that many people encounter. The MoneyThumb community has determined that these are the top roadblocks to tax success for you to avoid. We’ve also used real life problems and solutions to illustrate each point and give you the resources you need to overcome each roadblock.

1. Disorganized Tax Files

Tax season shows up once a year, but tax preparation is really an everyday task. Keeping your financial files organized throughout the year makes a HUGE difference when it’s time to fill out all those forms. You might go old school: paper files, envelopes full of receipts, and handwritten signatures. Or, you might be new school: finance apps, text alerts, and saving to cloud storage.

Most people fall somewhere in the middle, using online banking and home finance software to keep everything in order. Whether you use graph paper, Quicken or QuickBooks, or your iPhone, it’s important to keep all of your income and expenses clearly organized.

Real Life Roadblock:

Help! I’ve got to get at least nine months of historical financial transactions from my bank into Quicken and the bank only provides PDF statements! Quicken doesn’t natively import PDF files – what can I do?
-Darren, New York

Real Life Solution:

PDF2QFX CONVERT  removes this roadblock! This software makes it easy to get those PDF statements into Quicken’s QFX format, so you can have all of those transactions properly recorded in one place.

2. No Digital Financial Records

If you prefer to use paper statements and receipts, it is crucial to make sure they are entered correctly, in a timely manner. Where and how you enter them is up to you; some manually input transactions into a program like QuickBooks, and others note them by hand in their check register. Many create their own spreadsheet – either on paper or on the computer. Ideally you should be keeping track of these files on a regular basis, but you can input them all during tax season if you give yourself enough time.

It’s also worth noting that keeping electronic records of your documents can be more secure and easier to manage than paper hard copies. If you’ve struggled with miscalculations, lost documents, or overflowing file cabinets, you might want to add some new tools into your accounting toolbox. Having everything sorted and stored makes the process of filing taxes much easier on you and your tax preparer.

Real Life Roadblock:

I tried Quicken on my Mac for a few months – it wasn’t for me. I went back to using a simple spreadsheet for my transactions, but now I have three months worth of QFX files. I just want it all on Excel – do I have to enter them all in by hand?
-Thomas, Wisconsin

Real Life Solution:

QXF2CSV CONVERT will do the job, no problem! Use this software to convert the QXF documents into CSV format, which can be uploaded into Microsoft Excel or another spreadsheet program.

3. Hiring – Or Not Hiring – A Tax Preparer

We all know how it works – we can try to file our taxes ourselves (and hopefully save some money) or we can hire someone to help (and hopefully end up with some money). The tricky part about this tax time dilemma is that there’s no right answer for every person, every time. You should take a good, honest look at your finances and your personal accounting and computer skills to determine if it makes more sense to go on your own, or get some help.

When your taxes are fairly straightforward, it can be very easy to file at home. Depending on your state, you may be able to file some or all of your taxes online for free. Using the state and federal government websites generally means a much lower cost than using a third party type of tax software. If you have one job, for example, rent your home, and have no spouse or children, it might make sense to file on your own.

Generally speaking, most people consider switching to a tax preparer when their taxes get more complicated than they know how to handle. So, if you’ve started making substantial donations to charity, recently gotten married, or own your own business, it may benefit you more to have someone assist you.

Real Life Roadblock:

It’s my first year as a small business owner, and I’m not ready for tax time. It seems like I have a million different types of files, and my tax guy says I should have everything organized in QuickBooks. Help?
-Jeanette, Michigan

Real Life Solution:

Sometimes just one type of file converter isn’t enough to get the job done. We’ve put together a special 2QBO Pro CONVERT software package to help with this very problem. Historical bank transactions, credit card statements, personal Excel files, Quicken files, and more can all be converted into QBO QuickBooks format. This is a great option for business owners and professional QuickBooks users.

4. Missing Deductions

Tax preparers are often very helpful in this particular area of tax filing – finding deductions. These expenses play a big role in how much money you have to pay, or how much of a refund you get, so it’s imperative to claim all of your proper deductions. It’s equally important, of course, that you don’t claim anything that you shouldn’t. This can get very confusing, very quickly, if you’re not familiar with the tax laws and procedures for deductions.

Programs like Quicken have missing deduction finders and built in categorization that makes it quick and easy to spot every applicable deduction. The software can recognize charitable donations, for example, and note them accordingly so you don’t miss out. This is especially important for freelance or self-employed workers that don’t have regular paychecks for taxes to be deducted from throughout the year.

Real Life Roadblock:

I want to use Quicken’s missing deduction finder tool, but I’m confused because I have two kinds of files. What do I do when I have QIF and QFX files? I just want to deal with one file type, not two.
-Darlene, California

Real Life Solution:

For this particular situation, we would suggest using QFX as the main format. This is mainly because the Quicken Deduction Finder requires Quicken Premier, which was first available in 2011. Quicken switched from QIF to QFX files in 2005, so you should use QFX as your main file type for import into any version of Quicken from 2005 to present.

If you wanted to import files into older, expired versions of Quicken, or into other personal finance software, you might need to use QIF files instead. We have converters that do both – QXF2QIF CONVERT and QIF2QFX CONVERT are solutions for dealing with QIF and QFX exchange issues.

5. Filing – or Paying – Late

We’ve all heard horror stories about the IRS, but the government agency actually does give you some flexibility with filing taxes. If you can’t get your taxes filed by the standard deadline, be sure to file Form 4868, Application for Automatic Extension of Time To File U.S. Individual Income Tax Return. Just remember that this form does NOT automatically grant you an extension of time on paying what you owe.

Last minute concerns are when home tax software like TurboTax and H&R Block can save the day. If you tend to procrastinate, you might find yourself with just days – or hours – until the filing deadline hits. Luckily, if you have internet access, you have near immediate access to everything you need to file your taxes, or request more time.

Be sure to take the same care when it comes to paying your taxes. If you owe more than you can pay, you are often able to break up the balance into monthly installment payments. Use online banking or personal budgeting apps to ensure that your payment is made in full, on time, every month – or risk late fees and penalties.

Real Life Roadblock:

I’m doing my taxes at home – I waited until the last minute. I can’t afford any late fees and I don’t want to deal with an extension – I just want them done ASAP. I’m using TurboTax because I already have most of my records in QuickBooks. But I have some random files – like my PayPal records – that I can’t seem to get into the QBO format. I’m down to the wire, please advise.
-Jesse, Texas

Real Life Solution:

This problem is likely occurring because QuickBooks requires import accounts to have a FID (Financial Institution ID), and PayPal does not have one. This is because QuickBooks charges a fee for financial institutions to use their proprietary QBO format, and PayPal didn’t want to pay. This has happened with many other banks and companies, so this advice is applicable if you’re having trouble with other missing FIDs.

You will need to convert the PayPal CSV files into QBO format, and then import them to QuickBooks using an alternate FID. We suggest trying the FID of a big, well known bank – that’s the workaround that has worked best for other MoneyThumbers. Use CSV2QBO Convert for the first step, and get those taxes done quick!


What roadblocks to tax success have you encountered, and how have you gotten past them? The aforementioned suggestions are just the start when it comes to conquering taxes easily, quickly, and correctly each year.