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
appy news! 
I was invited to be a panelist at the 
I can’t be self-promotional all alone here, people. I need your help! Vote for meeeee! My proposal is up for voting right now on the South By Southwest Interactive Panel Picker. It’s a geek frenzy over there. Vote early and often. VOTE HERE (login required) Panel Proposal: Video Game Research: Failing Our Way to Victory Users are weird. They tell [...]