The Unbearable Sexiness of Filing Taxes

Marc Ardizzone
9 min readJun 7, 2021
From the album cover of ‘Talking to the Tax Man About Poetry’ by Billy Bragg

The ‘invisible’ experience

One of the best experiences that one can have while using a digital product for solving a problem is when you are barely aware that you are using it. Whether the task requires a single step or fifty smaller ones that build upon one another towards some larger final goal, your awareness of the interface almost drops away entirely, the affordances on the screen becoming nearly invisible; the task at hand becomes the naked thing, running unhindered towards its completion. It is like when you are engrossed in a good novel and you reach that zen-like point when the story no longer seems defined by the words printed on the page, but fall away as you are swept completely into the current of the narrative.

I will posit that the ultimate goal of a UX designer is not so much to make stuff as to make stuff as invisible as possible. The task should be always in the foreground, the rest of the experience should, as much as possible, fade into the background, leave little or no imprint on the user’s mind as they move through their journey towards completion.

This is of course the ideal result of a concerted UX effort, and depending on the complexity of the project, the time allotted to it, and whether or not its owners are committed to improve upon it iteratively as a result of user feedback and/or success metrics outcomes, will often dictate how close you end up getting to this ideal. Like most ideals, the concept of the invisible interface may not always be attainable, but if used as a North Star to guide us in our designs, we can make better products and happier users.

It used to be a rare phenomenon to experience a digital product like this, but with UX now a pretty evolved discipline and UX teams becoming more and more integral in the corporate product-building stack, it is, thankfully, becoming less so. UX folks across dozens of industries are making huge strides in improving the usability of digital products, even in categories traditionally known as having a bad reputation for accommodating ease-of-use, such as banking and finance, insurance, and even Ye Olde Governmental Services.

Which brings us to…

The unbearable sexiness of filing taxes

What inspired my idea for this article was my recent use of a web-based app that I visit exactly once per year around the end of March, and one that I masochistically look forward to using: my online tax-filing app.

The specific product shall remain nameless, but I wanted to cite it here as a study in how a complex digital utility can be designed in a low-friction, “invisible-ish” manner. I think it provides a solid and transferable set of examples and approaches for building a multi-step journey that minimally taxes (pun intended) the brain or nervous system of its users.

The list of expectations implicit in such a dull and simultaneously stress-inducing tool as a tax-filing app is short but lofty. For starters, such an app cannot afford to be a nuisance, the very thought of filing one’s taxes being a nuisance in of itself. Thus to succeed, such an app is burdened with a short but formidable list of expectations — namely, it should:

1) Do no harm (alla Hippocrates);
2) Attempt to improve the process;
3) Dare to go out on a limb and give its users a little joy.

Okay, I’ll grant you that expecting to find joy in the course of doing one’s taxes may very well be a cry for help, but one can always hope!

Taxes’ dark materials

The universe of income taxes, like Masonry, The kabbalah, or the stuff your wife talks about with her friends when you’re not around, is cloaked in a fog of mystery and arcane impenetrability. Even if you sort of get it, there are numerous factors conspiring to prevent you from completing the task at hand — lack of time for one, a propensity for procrastination (ahem!), missing paperwork, shoddy calculating skills, misunderstanding the rules and permissibility of certain deductions. What’s more, to file a complex return, you need to supply countless pieces of data points culled from disparate records, scores of receipts stuffed into wallets or tossed haphazardly into shoeboxes, then calculate it all against a confusing assortment of IRS-supplied tables and schedules. If you’re filing as an independent contractor it gets even stickier — for example, knowing what you can and can’t write off — and once you figure this out you need to know how much of each of these write-offs would be allowable before you risk raising a red flag with Uncle Sam and possibly get audited.

If only there was some AI to do all this…hmm…

More than just a fancy calculator

When you think about it, a tax-filing application is fundamentally an interconnected set of formulas driven by user-supplied data inputs and modified by complicated rules prescribed by a governing body (the IRS) that change every year, thus keeping accountants and tax attorneys among the well-heeled.

But more than this, a well-designed tax-filing application, or any application for that matter, should add value to the process above and beyond acting as a mere fancy calculator. It should bring together UX best practices that work in tandem to usher you through a relatively frictionless process, making a normally fraught undertaking not only easy but maybe even pleasant and fun.

Since I have been using this particular tax-filing application annually for the past six years now, I have had the opportunity to witness its evolution and every year brings with it a more streamlined workflow, a more process-responsive UX, more subtle bells and whistles that make the overall experience more pleasant, the tasks more focused — the UI, in essence, less “visible”.

What follows are some aspects of the app’s design that I think work really well to this end and might be used as takeaway approaches for your own designs

  1. Bring the big questions forward first then get them out of the way

The experience
When first logging in after a year away, I was greeted by the message “Welcome back, Marc! So glad you’re going to file with us again! Let’s take a minute or two to verify a few things”. This is followed by a short list of data points carried over from the previous year which I was asked to confirm or correct based on any change my your status. Are you still married? Are you filing jointly again? Do you still have the same dependents that you will be claiming? Do you still own your house and mortgage? etc. I was ushered through these “yes/no” questions at a nice clip, then moved to a new set of questions, the answers to which may be impacted by the latest changes to the tax laws.

The takeaway
Don’t make the user enter redundant data. Front-load the rote stuff to get it out of the way and have them jump right in to the “meat” of the experience.

2. Design for velocity — illustrate (and celebrate!) progression

The experience
As you move through the various steps of filing, the system gives an excellent real-time feedback on how far you’ve come and how much you have to go via a dynamic progress bar at the top of the screen that by default remains collapsed to its barest “iconic” form (to reduce taking up too much real estate) but can also be hovered upon or clicked to expand for more details. As you complete each step, there are some subtle and playful interactions that make you feel like a genius for very little effort but it makes the whole experience more bearable and fun.

The takeaway
In a linear or semi-linear task sequence containing many steps, always keep the user apprised of where in the process they stand. Like being stuck in a traffic jam, there is nothing more frustrating than not knowing how far you have to go before you can drive unhindered. Even the longest and most tedious process can be made 110% more bearable when you have a sense of the road ahead. Throwing in some fun micro-interactions at certain milestones also helps to take the edge off the whole affair and adds personality to a system that might feel clinical or purely utilitarian.

3. Guide with “funnels”, but provide escape hatches

The experience
The “wizard” approach to design, used to great effect in this app, is for all intents and purposes a kind of funnel designed to usher the user through a more or less linear process. As with many wizards, information is necessarily collected in a certain order due to dependencies triggered by the user’s inputs — for example, answering “Yes” to the question “Do you have children?” will trigger more questions like “How many?” “What are their ages?” “Do they live with you?” etc.

One thing I found great about this app’s design is that the user will always have a way to skip a question and save it for later. In the case of tax filing, this is especially important since the user will invariably need to abandon the app at some point to go digging around for a data point in a drawer somewhere or asking her partner or log in to some other website. Perhaps more importantly is that the system will automatically save your place and bring you right back to where you left off should you get timed out.

The takeaway
Avoid rigidity in your IA — give the user escape hatches and easy means for returning to where they left off. Wherever possible, be flexible as to the order in which data must be collected. Lastly, allow the user to “swoop up” to a birds-eye view of the overall process at any time, and then “swoop back down” to jump back into a given task.

4. Speak to the user as a champion and friend. Be informative but not didactic!

The experience
The textual content of this application is really well written — it is obvious the copywriters were really doing their job. The consistency of the language, its tone and compactness adds to the pleasantness of the experience, motivates one to plow ahead despite the onerousness of the tasks at hand. There is also a whole layer of concise explanatory information running beneath the UI that can be summoned up by the user via tooltip icons and/or a very well written help-tips database. For the real wonks you can even dig into some tax law stuff, but who the heck has the time?

The takeaway
Interaction design and beautiful UI is only part of a good user experience. Don’t underestimate the power of the written word to add some pleasantness and clarity to the experience, and perhaps on a softer (but no less important) note, to impart a lasting impression on the user even after they have logged out as having just done their business in an environment created by people who really care.

The Net Net: may your greatest work not be noticed!

There is virtually no process that can’t be improved with great UX, where friction can’t in some way be reduced for the user, helping them shed their cognitive load, giving them a few minutes of their lives back or one less thing to worry about in the course of a hectic day. Think about buying insurance, taking out a mortgage, applying for a passport, a job, financial aid: all daunting, annoying and quite frankly boring tasks that with some effort we as UXers have the chance to make more bearable — or need one suggest — perhaps even throw in a smidgen of The Pleasant? Yes, The Pleasant he says!

The highest aspiration of the UX professional is to not to have the user stand in awe of our artful UI, or to be wowed by our clever screen transitions, intuitive IA, or vibrant color palette: it is to bend the fibers of our designs into the utmost posture of humility, to make them the quiet guest who listens intently and says very little, the Good Butler who has the dry towel waiting for you as you step out of the tub, the motor running outside, the cab warm and cozy on that wet, frigid day.

Let’s all agree then that the greatest things we will ever make as UX professionals will hardly be noticed — that the invisible is our friend. With this in mind we will make better products and happy users who will come back for more.

With that, I snap my fingers and vanish till next time…

Poof!

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