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Let’s talk for a moment about why I misfiled my tax extension. Melty Jello brain aside, bad software design almost cost my little family $2,500.

Background:

When I’m not wrestling a one-year-old into tiny shoes, I’m a User Experience Designer. This means I work with software companies to create easy-to-understand interfaces.

It also means that when I screw up my tax extension, I look very carefully at the software path that got me there.

Dramatic Reenactment:

It was April. I needed to file an extension. Like most Bay Area tech nerds, I hate mail. I consider it a personal affront if I have to print out a form, write an address, locate stamps, and put a letter in the whatsit…mailbox…thing. Naturally, my first step was to search irs.gov for “file extension online“.

Problem one: Too many results

The IRS site is too damned helpful. There were 948 results for my search. Many results were press release or blog type articles hinting at the existence of online extension filing, but containing no direct links. I wanted to find one or two good matches. Instead, I found a sea of irrelevance.

Problem two: Too many names

I hopped down a bunny trail for about ten minutes, searching for a feature alternately referred to as “E-file an extension”, “Free file”, “Freefile”, “Free Fillable Forms”, “Free File Fillable Forms”, “Free Federal Extension”, “Form 4868″, “Traditional Free File”, and “IRS e-file”.

Problem three: Inconsistent design

I eventually landed on a modern-looking site that seemed likely. I clicked “Get Started” and wandered through four increasingly less-well-designed pages which jumped from site to site, forcing me to read and parse options despite having already told the system what I wanted.

Problem three: Asshole account requirement

The eventual winner was a page called “Free File Fillable Forms” which required me to create an account and update my Flash plugin. I was already logged in to irs.gov, but that didn’t count. I created “a password that is different than my User ID, between 8 and 32 characters, and contains at least 1 number and 1 symbol”. All the eye-rolling gave me a headache.

Problem four: Misleading email

I received a spammy looking ALL CAPS email telling me my account had been created. I filled out the IRS extension form, which was the easiest part of the process. I submitted, and received another spammy ALL CAPS email saying “Your federal return was successfully transmitted”.

At this point, I fell on the bed and whined to my husband for several minutes about information architecture. Then I fell asleep, secure in the certainty that I had filed an automatic extension. Taxes wouldn’t be bothering us for a few more months, by which time we would certainly be getting more sleep.

Mon

Yes, that was my letter from the IRS.

I misfiled our tax extension. My husband, who is hilarious, wrote a letter to the IRS asking for clemency due to new-baby-induced Jello Brain. The IRS, who are apparently also hilarious, quoted him in their response.

I scanned the letter and he put it on Facebook. It went viral.

That afternoon during a lull in the daily baby-management, I hopped on Reddit to post the letter and discovered that someone had put it up hours earlier. Our funny IRS letter was now at the top of Reddit’s front page.

Over 1,800 people left comments and opinions. Everyone was pretty nice and we enjoyed the discussion. Some IRS employees even chimed in, talking about their jobs and lives.

This is the nature of the Internet. Something strikes a chord in our collective subconscious, and we share it with ourselves at the speed of thought.

I think we are all a little afraid of the IRS.

They seem to speak a slightly different language. They use phrases like: “A nonbusiness bad debt must be treated as a short-term capital loss” and look at us expectantly.

Every year they make us do math. They know our financial secrets, and they remind us that our money will be spent by people we probably didn’t elect, on things we might not like.

They could put us in jail. They took down Al Capone.

As a result, people yearn for a bit of humor from the IRS. I think any reminder that the government is made of people who are themselves parents and taxpayers is welcome news.

Anything to break the tension.

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