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What I Learned From Creating 30 404s in 30 Days (For My Own Website)

What I Learned From Creating 30 404s in 30 Days (For My Own Website)

A self-imposed challenge to beef up my portfolio of UX writing.

A year ago, I started taking steps to officially switch my career from copywriter to UX writer, as so many (bored, proactive, jaded, <insert your reason here>) copywriters have done before me.

After two years of a quiet, yet nagging suspicion that I should pursue UX, I was afforded the perfect opportunity to give it the serious consideration it deserved: a sabbatical. Technically, it was my wife’s sabbatical, but by association (and several months of saving), I got to go along for the ride. Why the corporate world doesn’t offer sabbaticals is another topic I’d like to discuss.

As I began my journey into the mostly unknown and slightly overwhelming world of UX, I was fortunate to have the expansive skies and grounding lands of New Mexico to support me. I signed up for a few free online courses, read all the Medium posts, and pulled the expensive trigger for a 4-month online course at the end of January.

Fast-forward 3.5 long, and let’s just say, eventful, months later to this past May: I finished the course, and had nothing but time, albeit very distracted time (as it goes during a pandemic), to work on updating my portfolio.

Though I’ve written copy of all shapes and sizes for the web for over a decade, my portfolio of “UX writing” was on the lighter side. Borrowing tips from articles I’ve read, like this one by Andy Welfe, I thought about ways I could fill that gap.

As the simplest ideas often do, The 404 Project came to me relatively quickly. Though I originally planned to create one 404 a month for a year, I quickly realized that that wasn’t quite impactful, challenging, or interesting enough.

So, I decided: one 404 a day for the entire month of June, or 30 404s in 30 days.

I started off with my own goals for the challenge:

1) Don’t miss a day.
2) Show variation in format, imagery, function, and tone, while still being “on brand.”
3) Don’t embarrass yourself.
4) Inject as much of your personality and writing style as possible, without being overindulgent.
5) Find ways to make it personal and let people get to know you.
6) Use it as a way to feature other projects.

I also set some very important expectations for viewers. To preface the project, I state that this is a very D-I-Y type of project, using only images from Squarespace (which is sourced from Unsplash), pictures I’ve taken, and any other easily-obtainable gifs, charts, etc. Big asterisks: this is for FCO (For Concept Only) and FWO (For Writing Only) purposes.

And then, June 1st, I went for it.

UX writer humor 404 page.

While I won’t bore you with a day-to-day account of how it went for me, here are some general observations, challenges, and takeaways now that it’s over.

More whimsical 404 page.

More quantity = less expected ideas. It also forced me outside of my comfort zone of the “clever, witty” space and explore places I wouldn’t normally let myself go (see whimsy and silly above). Those are the places where my most most “different” and “out there” takes on a 404 came from.

A few weeks ago, I heard Simon Sinek on How I Built This. He tapped his employees to come up with ways to pivot the business model in response to Covid-19. But instead of leaving it open, he tasked them with coming up with 15 ideas each, instead of 3 or 4. The reason being, if you ask for only 3, everyone would come up with the same 3. But when you have to come up with an “uncomfortable” amount, you can access ideas that scratch below the surface.

You have to ride the waves. When you are running a marathon, it’s important to take advantage of times when you have a lot in the tank. Every week, I spent some time brainstorming several ideas. Sometimes I would come up with 9 or so leads at once. Of those leads, usually about 1/2 or 1/3 would actually translate into an actual working execution.

These flows, where ideas came easily, is what made the challenge successful, even during the inevitable ebbs. You can’t expect yourself to be “on” every single day. Always try to stay a few ideas ahead to make up for the days when your brain isn’t firing on all cylinders.

My spoof of the famed Amazon 404 page.

Some days will be a S.T.R.U.G.G.L.E. Even though I tried to stay a few ideas ahead, there were 2–3 occasions where I had nothing. I either woke up with zero idea of what I was going to do, or I thought I knew what I was going to do, only to realize that I was surely going to embarrass myself, it felt to similar to another 404, it was too complicated, or it simply didn’t work. All I can offer here are the famous words of Tim Gunn: “Make it work.” There’s a deadline and no extensions. You will make it happen because you simply have to.

In times of creative struggle, I often remind myself of this “creative process” I found on the internet one day. It is 100% accurate, and always helps me persevere when I’m in the dreaded in-between of Stages 3-4.

Author of the “Creative Process” unknown. Design by JuneLetters.com.

Not being a brand made it harder. Having a tangible brand to play off of, adhere to, get inspiration from, and visually draw from is helpful in narrowing your parameters and grounding your ideas in some sort of truth. Conversely, not having those guidelines to work with/under made my 404 possibilities a little too limitless, and a lot more prone to feeling so completely and utterly random and not in the “good” way.

In lieu of a “brand,” I tried to ground my 404s in the following ways:

1) Not all, but most of the photographs I used were from my camera roll (many of which feature my very expressive dog, Neko).
2) The photographs that I didn’t take were from Squarespace (who sources them from Unsplash).
3) I didn’t bring in any outside fonts, icons, or illustrations. Other than gifs, any visual elements I used was provided by Squarespace.
4) I used the same format (or close to) for each 404 page (i.e., headline, descriptor, image, body copy).
5) Whenever I questioned my own critical judgement, I passed it by my second toughest critic (after me) and quarantine partner, my wife.
6) And though there was no need for “trying” for this last one, they were all in the same voice: mine.

Thanks for reading. In case you waited until the end of this post to check out my 404 project, here’s another link.

Feel free to message me with any questions or to share your experience with any self-imposed challenges you’ve taken on.

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