4 Simple Ways to Make Filing Taxes Easier Every Year

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Filing taxes can be a painful experience for many. With a little planning and preparation you can remove much of the pain associated with tax season.

If I were in a public setting I would ask for people to raise their hands to indicate whether or not they enjoy filing taxes. I’m certain I’d see more hands raised for the “not enjoying” taxes option than the other. It is often said that there are three certainties in life: birth, death and taxes.

Taxes are never a fun subject, especially when it means we have to pay out more money to Uncle Sam. I like to do all I can do minimize that cost.

There can be a lot of work that goes into filing taxes and while many hate doing so, it still requires our attention to ensure the tax filing process goes smoothly so we can make sure we have jumped through all of the hoops the IRS throws our way.

However, there are a number of things you can do to make it simpler for you each and every year. Just make sure to consult a tax professional if you have any tax specific questions.

Keeping Good Records are Key to Filing Taxes


One of the best ways to make filing taxes smoother is keeping good records. There are various things that might impact your taxes for the better or worse and a good record keeping system is vital for this. Do you have business mileage or mileage for trips to the hospital/doctor? If you do, then it’s possible that mileage would be deductible for you per a user friendly tax calculator.

An easy way to keep track of this is by having a small notebook in your car. Do keep in mind that the IRS wants specifics and often looks at bloated mileage as a red flag, so make sure to notate the Who, What, Where and Why of your trips along with the specific to/from mileage and date. We do this ourselves for our business and it takes only a minute to record the information.

A similar thing can be done for medical expenses, giving to charities, etc by keeping a folder of all pertinent information that relates to giving or expenses that might qualify as a tax deduction. Please keep in mind that many deductions are only available if you itemize your taxes.

Keep Your Professional Life Separate From Your Personal Life


If you run your own business like I do, then you know how hectic life can get when you’re dealing not only with your personal finances and your professional finances. Some of these things might be difficult to keep completely separate, but the easiest way to do so is by setting up a business checking account. We have our business account with US Bank, as they have no fees and are easy to use. This allows you to deposit all of your professional income into the account and not have to worry about co-mingling it with your personal income.

This might seem like just ANOTHER thing to manage, but it actually makes life much easier and did not take much for us to set up. We set it up with the same bank we have our personal accounts with and thus have the same login for both accounts and can take care of everything from one place. Having a business account will also make it much easier when your filing taxes as you should be paying for business exclusive expenses straight from your business account throughout the year and won’t have to separate it from your personal expenses.

It’s not just your bank accounts you want to keep separate. You also want to keep charges separate from personal charges – thus the need for a business credit card. If you don’t have a business credit card, here are some of the best available – some even offer nice sign-on bonuses.

Don’t Wait For the Last Minute


I hate to break it to you, but tax deadline is coming up very shortly, don’t put off taking care of all the steps associated with filing taxes to the last minute. I’ve seen way too many people in my line of work do this and it only ends up in having headaches at the end of the day. I know that staying on top of your records might not be the most fun, but a little bit of work throughout the year should make it much easier for you when it comes time to be filing taxes.

Mrs. Frugal Rules and I discuss our business mileage and expenses each month and I enter them into an Excel spreadsheet. This allows me to know where we are at at any given time, but it also means that at the end of the year the majority of my work is done and I can forward all of our information to our CPA. Another benefit of not waiting until the last minute is that you can also use it to analyze your withholdings so you’re not getting too big of a tax refund the following year.

Filing taxes can be a painful experience for many. With a little planning and preparation you can remove much of the pain associated with tax season.

Hire Professional Help to File Your Taxes


With the rising popularity of filing taxes online and tax preparation software it allows many to handle filing taxes simply as the program walks you right through it. For years I used H & R Block’s software and had no issues (and enjoyed it, to be honest). With the growth of our business we’ve hired this out to save time and have an expert do them for us.

As someone who likes to be frugal and do things myself, this was a difficult but necessary decision. It has saved me a lot of time and I now have the confidence that our taxes are done correctly and done by an expert who’ll maximize our return. If you find that you’re over your head in filing your own taxes, then a tax professional is a great option. If you’d rather handle filing taxes on your own there are several good options to choose from, as seen below:

I’ve personally used three out of the four above, and had a relatively good experience with each though defaulted to the H & R Block option for a number of years prior to hiring out our tax preparation needs. If you do use one of the above options keep in mind that most of them offer some sort of free Federal filing as well as discounts on State filings.


Additional resource: If you’re looking for a simple way to stay on top of all your finances, then check out my favorite new tool – Personal Capital. Completely free, it allows you to track your spending, monitor your bank and investment accounts and watch your net worth plus many other tools. 

Open your free Personal Capital account today!


How do you handle your taxes? Will you be filing taxes on the day of the tax deadline, or do you get them done early? What tips do you have to make filing your taxes easier?


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John is the founder of Frugal Rules, a dad, husband and veteran of the financial services industry whose writing has been featured in Forbes, CNBC, Yahoo Finance and more.

Passionate about helping people learn from his mistakes, John shares financial tools and tips to help you enjoy the freedom that comes from living frugally. One of his favorite tools is Personal Capital , which he used to plan for retirement and keep track of his finances in less than 15 minutes each month.

Another one of John's passions is helping people save $80 per month by axing their expensive cable subscriptions and replacing them with more affordable ones, like Hulu with Live TV.


  • Greg@ClubThrifty says:

    Good tips John! I’m one of those who would say that they hate doing taxes. Anything that makes it easier is alright in my book:)

    • John says:

      Thanks Greg! I am not a huge fan of them either, but for some reason I always enjoyed working with all the numbers…I know, I am a nerd. πŸ˜‰

  • DC @ Young Adult Money says:

    This was a much-needed post for me and my wife. Our taxes are getting more and more complicated each year and we seem to have one-offs or new side income to add each year (Not a bad thing!).

    • John says:

      I know the feeling DC. That is not a bad problem to have at all and really is why we hired a CPA last year.

  • AverageJoe says:

    Great lessons! I used to wait until the last minute, only to realize that something I THOUGHT I had was missing. Then I’d be stuck and have to file an extension…and just elongated the process. Now I gather everything in a file at the door (as the mail arrives all tax stuff goes in it) and then get the information compiled a little bit every day. Tomorrow I’ll have everything completely together and will file next week. Because I always owe, it’s gonna be about April 15th at 11:59 pm before that check hits the mailbox!

    • John says:

      Thanks Joe! I hate when that happens and it’s just a complete hassle to take care of. I am the same way when we owe, it goes in the box on the 15th. πŸ™‚

  • Jose says:

    I keep a tax file that I start at the beginning of the year, everything that happens during the year that is tax related such as charitable donations, property taxes and the like goes into that file. having everything handy in a single location makes it so much easier to prepare my taxes. I usually have everything done and ready to file by the end of January and it only takes a few hours worth of work.

    • John says:

      We do the same thing Jose. It makes life much easier in the long run and only takes a few hours to take care of once all the forms start rolling in.

  • pauline says:

    I am filing today thanks to your reminder! My limit is March 30th and I have been procrastinating on that for months. I always spend a ridiculous amount of time resetting passwords and looking for log in information so this year I will save it somewhere obvious. Like every year :s

    • John says:

      Glad I could remind you. πŸ˜‰ I hate all those passwords, I need to make a sheet of them all myself. I know you’re not “supposed” to do that, but it would make life much easier.

  • Catherine says:

    So I actually like doing my taxes…I like playing with numbers, total loser I know. The day I owe a bunch of money it won’t be so fun anymore I know.

    • John says:

      Well, I must be a loser too Catherine. πŸ™‚ I always enjoyed doing the taxes…I know, I am a nerd. πŸ˜‰ I hated handing them over to a CPA, but the cost is worth it in the long run.

  • Brian @ Luke1428 says:

    I’m learning that hiring professionals to handle things I’m only marginally good at or don’t really have time for is a must. I’d rather spend the money and get it done than be frustrated because it took too long. In regards to taxes, I’m amazed at how much more the professionals know. Now that my wife is in the industry, she has discovered many new ways to save on taxes (through deductions and simple tax planning) that many business owners don’t know anything about.

    • John says:

      I completely agree Brian. I love doing our taxes, but I simply don’t have the time and with our business now I would rather have an expert handle them. It is definitely worth the cost in the long run.

  • Jim says:

    So important to hire professional help! Having rental property, I actually interviewed 3 different CPA’s in order to find the one I have, who is a real estate investor. He helped me create a partnership and save considerably on taxes. You pay for what you get for sure!!

  • Grayson @ Debt RoundUp says:

    All great tips John. I need to start with a new business checking account. I haven’t been able to find any good free ones as of late and I don’t have a lot of transactions, so I don’t want to pay a fee for a business checking account.

    • John says:

      Thanks Grayson! I would definitely recommend one as you grow your side gig, it’ll make things much easier. We have ours through our main bank so we get by with having no fees which is nice. Our next step is to get a business credit card.

  • Mackenzie says:

    Ugh, I hate doing our taxes! We have to get on that; like you said, April 15th is right around the corner.

    • John says:

      You’re definitely not alone Mackenzie, though for some twisted reason I always enjoyed doing them. April 15th is coming up, hard to believe that it’s only five weeks away.

  • Midlife Finance says:

    Tax is hell this year. There are too many things to deal with.
    I started a couple of weeks ago and it will take me at least 3 more weeks to finish up. I only have a couple of hours per week to spend on it. not good…

    • John says:

      I can totally understand. It used to be that way for us until we started compiling stuff throughout the year which removed a lot of the hassle for us.

  • Money Bulldog says:

    Is it really that time of year again! I have the option to file mine at any point from April – January so I’m not stressing too much yet. Sean @ One Smart Dollar has put the idea of a business expense trip to FinCon13 in my head though, tempting!

    • John says:

      Unfortunately it is Adam, though we just got ours finished the other day so I am happy. Yes, FinCon should be able to count for a business expense generally. We’re looking forward to taking advantage of that ourselves.

  • Kyle James | says:

    Good tips John! I would also add that not only keeping good records is important, but also keeping a running tally of write-offs and expenses via an Excel spreadsheet. This makes it so much easier come tax time, especially if you have a home office deduction and business related expenses.

    • John says:

      Thanks Kyle! I totally agree, we do it ourselves like I had mentioned. It makes it much easier for us. That way at year end we just have to forward the Excel file to our CPA.

  • Tackling Our Debt says:

    We just found a new accountant for our business \ personal this year, which wasn’t an easy task, as Accountants in our city charge very high fees. Our stuff is all done as of yesterday. We have until April 30th to submit personal returns and 4 months after our business year end to submit business returns. I am not a big fan of this time of year but I’m sure glad ours are done now.

    • John says:

      That’s good to hear Sicorra. Do you get to write off the CPA fees? I know it’s not a dollar for dollar wash, but it helps. We just got ours finalized the other day, so we’re pretty happy too. πŸ™‚

  • Shannon Ryan @ The Heavy Purse says:

    Great tips, John. I do use a CPA since it just makes it easier with the business. I probably could figure it out on my own, but since I tell people to not be afraid to get help from a financial advisor … well, I figure I should follow my own advice. Tax law is always changing and I can’t keep up with it, but my CPA knows it inside and out. It gives me great peace of mind to know my taxes are done properly and maximized to my benefit. πŸ™‚

    • John says:

      Thanks Shannon! We use a CPA ourselves, we just started using one last year. I could figure ours out as well too, but having the business throws another ball of wax into the situation and would probably take me too much time.

  • Canadian Budget Binder says:

    If we had a business I’m sure we would be hiring an accountant to take care of our taxes. We have yet to file our taxes because I am going to try and do them on my own. It’s a scary thought but I read through it all on the CRA website and it doesn’t seem so bad. I’m sure I’ll report how I make out . Cheers!

    • John says:

      I can totally understand going it alone Mr. CBB. I don’t know how it is in Canada, but in the States, most should be able to handle doing their own taxes. I did ours for years and sort of miss doing them, but it’s worth it to me to pay an expert to do them.

  • Melinda Gonzalez says:

    Ugh, thanks for the reminder I have to do my taxes. Can you re-post this in a few weeks, LOL. I used to love taxes when I was in school and actually got something back. Now it just sucks.

    • John says:

      Not a problem Melinda! πŸ™‚ I actually have a post that I just wrote that will be going live the week of the 15th with what you should do if you’ve waited until the last minute.

  • Edward Antrobus says:

    I think asking if people LIKE filing taxes is the wrong question. It’s like asking if people like brushing their teeth. It’s a a chore, nothing more or nothing less. And based on conversations I’ve had, the idea that everybody hates taking care of the taxes is pretty over-blown. most people I know don’t have a problem. Since the average person seems to get some sort of a refund, why wouldn’t they be eager for tax time to come around?

    Granted I only had a couple dozen professional transactions total last year, but I didn’t have any trouble keeping track of professional expenses and income even though it was all done through my personal checking account.

    • John says:

      Thanks for your comment Edward. I would have to respectfully disagree though. In my experience in financial services industry I have seen a pretty broad range of individuals and their personal tax situations. I would say in general, most people that I have dealt with over the years were no fans of doing and filing their taxes. Why else would so many people put it off to the last minute, file for an extension and then wait until the last minute on their extension? I think it points back to either they just have not taken the time, are completely unorganized or greatly dislike doing it.

      I completely understand if you have only a small number of transactions per year to not get a separate account, but when they start adding up it’s in your (in general) best interest to get a business account.

      • Edward Antrobus says:

        You see all of the people who are running to a professional for help which would skew your perception. I would agree that the people with complex filings, or who owe money are generally going to dislike taking care of it. Vs I tend to talk to people with relatively simple returns and/or getting money back, which skews my perception in the other direction.

  • Kim@Eyesonthedollar says:

    Mine are not done yet, but everything is ready and waiting on the accountant to get them done. It’ too stressful for me to try and do it with all the variables that go on with my practice and now, with rental income. I hate tax season. It makes me anxious.

    • John says:

      I can relate Kim. We have income and expenses from so many different sources that it’s just too much for me to adequately handle. I was anxious this year too, thinking we’d have to owe quite a bit but thankfully I was wrong. πŸ™‚

  • K.K. @ Living Debt Free Rocks! says:

    Thanks to employing a great accountant, I really don’t mind filing taxes. I have already given her all my paperwork to file for 2012. I provide her with everything on a silver platter (organized receipts, an annual expense and income report along with a summary of my quarterly tax filings). I also opened a business account as soon as I became self-employed to help keep things in order. In the event of an audit, I am definitely prepared.

    • John says:

      Sounds like we’re in the same boat K.K.! We do virtually the same thing ourselves. It make things much easier and I can do other things as opposed to spending hours and hours on preparing them.

  • Justin@TheFrugalPath says:

    I wish that some people I knew would follow the “keep your work life and personal life separate” tip. It drives my wife nuts because they have to dig through at the end of the year and take out everything that isn’t legitimate.

    • John says:

      I hear ya Justin. Now that we have our business it would drive us beyond batty if we did not keep things separate.

  • Nick @ says:

    If you use a tax professional, keeping the same person year over year really helps. We have used the same person for the last 3 years and he has all of our information saved. It makes things much easier when he can see what we did last year and copy most of that information forward into the new year.

    • John says:

      I agree Nick. I always did our taxes, but having our business it just became too much for us to handle. We love our guy and the time savings is much worth it.

  • Kay Lynn says:

    I prepare the family tax return and must admit I procrastinate. This year, I’ve made it a goal to file before March is out.

    Unfortunately, last year we had a family emergency and I was away from home from April 4-April 18th. Needless to say our returns were late!

    • John says:

      I can understand that Kay Lynn. I would say getting them done by the end of the month is a good goal to have. That still gives you two full weeks of leeway.

  • Kurt @ Money Counselor says:

    I think ‘keep good records’ is the most important of your list. It’s so hard to reconstruct the past year in March without good records! Breaking up the tax prep task into tiny chunks over the course of the year almost makes tax prep effortless. Well, not effortless (and certainly not painless!), but easier. πŸ™‚

    • John says:

      Great point Kurt. It can be incredibly difficult and it does make it much easier to keep track of over a weekly/monthly time frame than all at once.

  • Laurie @thefrugalfarmer says:

    Great post, John. I’m totally with you about hiring a professional. We’ve had the same guy for years, he knows our deal, and it’s a 20 minute appointment. Well worth paying him, to us anyway, considering the amount of time it would take me to figure out how to do it.

    • John says:

      Thanks Laurie. That sounds great. Thankfully we do not even need to meet with our guy and can do everything over email. I agree that it’s well worth the money spent to save that time.

  • Budget & the Beach says:

    I remember when I was employed full time and because of my situation at the time filing taxes was a breeze. But I’ve been self-employed for four years and I HATE doing prepping my taxes. I don’t even do them myself, but the prep that goes into it is a drag. In fact I’m on lockdown this weekend doing them before my tax appt on the 29th. I’t’s gotten more streamlined over the years, but I still have trouble with organization over the course of the year, especially with mileage. I just totally forget every time I get into my car.

    • John says:

      I totally agree Tonya. The prep can be a drag, especially as you start compiling more and more expenses and income. The car can be a tricky thing to track. We just keep our little notebook in the front seat to make it easier to remember.

  • Alan says:

    These are some good tips John. Whenever I get something throughout the year I have a folder I put things into like receipts or whatever else I think may be tax worthy. I use Turbo Tax to do my taxes. The last two years have been brutal trying to get everything done while being in school. Earlier this year I did a quick preliminary to get somewhat of an estimate. Didn’t like what I saw so I haven’t had a chance to go back to finalize the returns yet. I am hoping to get them done within the next night or two. Turbo Tax makes things pretty easy but it is always a stressful time of year.

  • CF says:

    I usually use Turbo Tax for my taxes. Our tax situation is still pretty straightforward. I would consider using a CPA in future years, if things got more confusing.

  • Tony@WeOnlyDoThisOnce says:

    Great tips, thanks for this. Definitely key to stay far ahead of the deadlines. Great point about the traps of “easy” online tax services.

  • KC says:

    Sometimes, I don’t understand it that people wait until the last minute before they file taxes. It’s a pain waiting in line and cramming and panicking… Great tips by the way.

  • Tahnya Kristina says:

    I don’t know if I’m weird but I actually love filing my taxes. I am not crazy about the preparation, but once all the totals are tallied up I just take my paperwork to my accountant and bing, bang, boom it’s done. 4 to 6 weeks later I get my refund and it’s all good.

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