Our Last Late Messy Tax Year

By Linda Walker

Before Duane, my husband with ADHD, and I, got our act together, we were five years behind filing our income tax returns.

Part of the issue was that, at the time, we didn’t know about Duane’s ADHD. Since he wasn’t receiving treatment and had no strategies in place to help him cope, the responsibility for all household details (managing the kids’ schoolwork and communications with school, grocery shopping and meal preparation, bill payment, home and car repairs and maintenance, etc.) fell to me. I don’t have to tell you that a lot of details fell through the cracks. To make matters worse, we had moved four times in fewer than four years and some documents got lost in transit.

Some years, it was a mad scramble the week before the tax deadline to find all the various documents to get the taxes done. Some years, we didn’t get to it at all!

Eventually, Duane was diagnosed with ADHD, received treatment and coaching (and put in a lot of hard work himself) and I finally had a partner I could count on for help, instead of another child (he’s still very much a kid at heart, but that’s one of the things I love about him). Together, we worked on a plan to avoid the mess in the future.

Our Turning Point

Fifteen years ago, after realizing we were not going to make the deadline once again, despite a huge amount of work and stress trying to get all the documents in on time, we decided that preparing for the next tax season was going to start that very day. Here’s how we did it:

Document Drop-Off Center

First, we created a space where all documents were dropped off all year long to be processed. This “Documents Drop-Off” space is a clear plastic box that is easily accessible (you don’t have to look for it, you don’t have to move things, you don’t have to think about it) to put any potentially relevant papers in whenever you come across them.


Once a week, or once a month, depending on how many papers we had, I performed triage on the documents in the box.  This took place in two steps.

  1. First, I sorted through the papers and asked “Do we need this for tax purposes?” If not, garbage!
  2. I then separated the documents into separate, clear plastic folders according to category, since these needed to be added up and recorded before being included in our personal income-tax returns. Our group of file folders included:
  • One for medical expenses
  • One for expenses related to our property, and
  • One “catch-all” for personal income tax purposes, like donations, income-tax documents from employers, tuition and student loan receipts, interest revenue, childcare expenses, contributions to our personal retirement savings plans, etc.

H&R Block has a great checklist (click the link for the American checklist, for the Canadian checklist or do a search for “Income tax documents <your country>) for the types of documents most people need to collect. If you own businesses or have a complicated income tax situation, check with your accountant for a list of documents you need to collect.


We tallied medical and revenue property expenses monthly. I did this by adding up the expenses in each category, putting the corresponding documents in envelopes, and then writing the total on the envelop and/or recording the totals in a spreadsheet.

If this is something you find yourself procrastinating, do yourself a favor and hire someone to do it for you.  If you’d like to hire someone, but are concerned about money, I suggest Duane’s approach to delegation: “Instead of wasting time trying to coax myself into doing something and then finding time to get it done, I hire someone to do it and work a few extra hours to make the money to pay for it.” Believe me, it is totally worth it.

By delegating tasks such as tallying expenses and filing taxes, we save:

  • Late fees
  • Time and energy
  • Frustration and sleepless nights worrying about what’s not done

THE Game Changer

Taking these steps to prepare our documents in advance has relieved a lot of strain on our lives, especially in the spring when we could be enjoying nature’s awakening. However, the biggest change that has occurred for us is delegating the actual preparation of our income tax returns.

While you may think you’re saving money doing it yourself, you don’t know what deductions you might be missing out on or what costly mistakes you might be making. It’s difficult to stay up-to-date on all tax laws and even with new tax software, you’re bound to miss some things.

Many ADHDers think “normal people” do their own taxes, but contrary to ADHDers’ beliefs, most sane neurotypicals don’t prepare their own income tax returns. Instead, they use the time they would have spent preparing their taxes (usually a stress-filled weekend) to develop their strengths or do something they truly enjoy doing and leave the taxes to the experts.

Your mission, should you choose to change your tax filing experience next year, is to:

Get your supplies:

  • Determine the categories of documents you need to account for. Check H&R Block’s  American checklist or Canadian checklist
  • Purchase one clear box for your Document Drop-Off space that’s convenient for and visible to everyone who needs to use it.
  • Purchase clear folders/envelopes (9 X 12” or bigger), one for each category of document and one as a catch-all space for all other tax documents.

Let everyone in your household know where every document goes:

  • Make sure your Documents Drop-Off space is easy to access and is visible so it will trigger everyone to drop off their documents there.

Create a fool-proof system for processing each month:

  • Set recurring dates (and reminders!) for processing these documents. We used to do this on the first and third Sunday morning of the month because it was usually a quiet time and we used to pay bills during that time, but now once a month is enough since most of our household bills are paid automatically.


  • Delegate what you know you hate or are not great at doing.
  • Enjoy a stress-free tax season in 2017.

Following these steps, we have never ever been late filing our taxes since and tax time is stress-free. (Yes, really!)


Linda Walker is an ADHD coach and trainer who offers online and mentored programs to help adults with ADHD manage their lives. Want more tips on unleashing your creative genius by freeing up more time for yourself, enroll in her free Productivity Myths Busted program.



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      • Chuck Bramlet
      • April 17, 2016

      I have been doing our taxes since a friend helped me one year, and another friend turned me on to Turbo-Tax. I began this _after_ receiving a note one year from the IRS that our paid tax accountant was not very good, and listing our with a copy of our tax return, all the deductions that had been missed, as well as some income mistakes. Added to that was another note that we should consider doing them ourselves, or getting another tax preparer. All in all, we got an extra +/-$300 back that year.

      There was a period of 6-8 years when everyone at work was amused/appalled, that I was filing for extensions every year. I think that might be under control, now.

      One problem that I have, _continually_, is that my non-ADD wife refuses to help by following my requests to put things in the places I request, or to put things in the folder (or cardboard soda flat) in the computer room. It’s not much help that I have these same problems myself.

      I keep a record of all our expenditures on MS Excel, and label medical, donation, etc. With that, all I need to do is to sort the spreadsheet to get all the expense categories, and then track down the missing documents. The biggest problem with this method is when my wife stuffs a receipt in her purse, and doesn’t remember to give it to me until I ask for it. Hopefully it hasn’t gotten lost. She also gets really annoyed when I ask for the receipt right away when we’re out.

      This system isn’t foolproof either, because it falls down when we’re on vacation, where I don’t have the access to my computer with Excel on it. Hopefully, all the receipts get into the envelope that we have for them, but that has the same problems as I mentioned above.

      That’s my taxing story. 😉

      BTW, thanks for the interesting links.

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