What If You Didn’t Have to Fail?

What if you didn’t have to think about the possibility of failing? Here’s my close encounter with that question on something as deeply personal as… a UX portfolio.

A few weeks ago, I was thinking (yet again) of my UX portfolio especially the case studies I’ve written for it.

They’re not a total disaster (don’t believe me? Please look); but there’s this nagging sense that my cases aren’t working hard for me. They’re ‘killing’ my chances too early in the hiring process and that they have to be revamped, nuked, and built from the ground up.

It’s that perpetual frustration with whatever you make (that’s so common among designers), made worse by Design Managers who b*tch and moan over the portfolios they were unlucky to see.

Typically, this is a good sign. “Kill your darlings” is a good practice in design and writing, anyway, so it shouldn’t be so bad.

But sometimes, “kill your darlings” hurts rather than helps.

Instead of ushering you in the right path, it leads you towards yet another rabbit hole, and Lord knows if it’s going to get you out of that hole or not.

It often becomes an excuse to tear it up and do it all again.

UX portfolios, I have noticed, have increasingly resembled longer narratives. No longer must we show the before and after of a website redesign, but we now have to explain everything soup to nuts – from the moment we met the client (or the creative brief) all the way to its first month or year in deployment.

Typically, this is a good thing. It positions UX as a business tool than a factory of pixie dust and popping visuals. But what we don’t always talk about is how to build that case study. How do we create a case study that compels a hiring manager to give you a call?

Excitement and Resentment

Recently, I went face to face with these feelings of excitement and resentment towards a case study I’m planning to rewrite.

I thought of rewriting my Canadian Jewish News case study after years of being in my portfolio. I made sure that every word and paragraph worked hard for me and positioned me as that guy who knows research and product design.

It also kinda helped that one of Toronto’s Design Leaders weighed in on what a good product design portfolio ought to be especially if you’re looking to get hired at an early stage startup.

Ella Espinoza on Twitter

If you want to be a product designer, your portfolio shouldn’t be 70% research. What matters is how you take the INSIGHTS of that research and turn it into usable product, interaction, and visual design decisions. Research is important but only in so far as what it enables.

Ella Espinoza on Twitter

Particularly if you’re applying at an early stage startup. What matters is getting value into user’s hands and if all I can see from your portfolio is that you know how to do a card sort, that tells me you don’t fully understand why we do research in the first place.

I agree with Ella intellectually. I understand that early-stage startups do not have the bandwidth to separate research from design and that designers at startups have to provide immediate value straight out of the ballpark. The Head of Design must ensure that his/her designers are delivering those design files early and often because they’re in the business of shipping product and every delay is like courting disaster.

TL;DR, I agree.

But because I was having a bad day when I read the tweet, I went into “peak portfolio” mode a.k.a. me getting mad at the world and the people who make it confusing.

Related image
It me (Photo from redbubble.com).

So I carried that undercurrent until “D-day”, the day I decided to rewrite one of my case studies, where a strange question set me on a path I would have never dreamed of.

I asked myself, “What if you were to present this project to a friendly audience?”

As soon as I asked that, my mind went on Imagination Mode.

I imagined all the things that could possibly happen: Enchanting my audience with my narrative, the cool things that happened, the roadblocks I encountered, the buy-in I got, the completion of the project and its glowing review by a journalist my client adores.

I was piling on the storytelling factor; playing with my audience’s emotions until the grand finish and the denouement that solves it all.

*in husky voice*
“There’s a place… where people… become fish… it will change you!”

It felt very, very, very exciting.

But as soon as I used the term “case study” (instead of a “presentation” or a “story” to a ‘friendly audience’), my mood shifted quite darkly.

I suddenly saw recruiters and hiring managers rolling their eyes over my cases, passing judgment on them, complaining about the length, snickering at the visuals, tiring at its long-windedness, and then exiting the tab while dunking my application at the recycle bin.

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I wonder how many shoulder brushes happen when a hiring manager looks at a portfolio?

You didn’t even get the chance to plead your case in person!

It’s that bad.


For the record, I’ve had two external recruiters tell me that my portfolio website was “well-designed” and tells them “what [I’m] about”. 

That’s promising; but as we all know, a strong measure of portfolio success is if you’re getting interview calls to really cool places. A practical example is the legendary Toronto agency Teehan+Lax getting a direct message from Medium’s Evan Williams to collaborate on work “some time”.

Geoff, just wanted to say your company’s work looks stellar. Would be cool to work on something with you guys some time.

Evan Williams to Geoff Teehan on September 09, 4:28 PM

This leads me to my fundamental concern with “case study”: It’s an assessment tool, not a storytelling tool.

Now I know what you’re thinking: Of course, Jem, it IS an assessment tool. Always have and always will. We don’t design for design’s sake. We design for some sake, something other than us, something greater than us, something bigger than YOU.

I agree! We certainly do not create things in isolation and if we ever want to put food on the table, then we have to make the work of our hands translatable into money.

But wouldn’t it be great if we could suspend that assessment and/or profit-driven orientation during the first mile of the case study process? 

Wouldn’t it be great if we let our minds run free for a while and then craft the story that would capture hearts and minds for those who will hear it?

What if we didn’t have to worry about what others will think and instead create something that will be refined through fire, grind, and tremendous grit?

This doesn’t mean we’re doing away with the realities of portfolios, assessments, and hiring. Rather, we’re crafting a space where your imagination can run wild and free so that you can come up with version 1 of the case, which will be honed in versions 2, 3, and n+1 if you so desire.

What if you didn’t have to worry about failing?

Will you be able to craft the story more freely? 

Choose Happiness

You already know this, but it bears stating nonetheless: No matter what it is you do or create, there will always be someone out in the world for whom it is not a good fit. You simply can’t please everyone – and you shouldn’t strive to.

When you find the people with whom your work strongly resonates, you will have discovered the treasure trove of your “tribe”.

Denise Jacobs, Banish Your Inner Critic

There is no denying that looking for your next job/contract/whatever is about finding The One and becoming The One. It contains, in equal parts, convincing yourself and others that yes, you have it and you can hit the ground running by Monday morning.

But I hope this doesn’t come at the expense of ourselves.

Sure, I’ll still tell you my career story and how we could work to achieve our goals. But each individual has a unique story and context that tells you what matters to them and the decisions they might take in the future.

This unique perspective is something that shouldn’t drown despite the practical realities that life may bring. And that can only happen if we didn’t fear the possibility of failure.

So when you’re gripped with worry and frustration at yet another portfolio rant by another design manager, stop for a second and think about the possibilities if you didn’t have to worry about the manager’s rant. What if you knew, despite the b****ing and the moaning, that you can tell the story of your project in a way that captures the minds and hearts of those who listen?

What if you didn’t have to think about rejection for now and just focus on the story?

What would you be able to make?

And most importantly, how will it show the real you?

Published by Jem

Jem is a UX practitioner who builds insightful, creative and usable digital experiences. A journalist by trade, he transitioned to digital media upon discovering its power to create compelling (longform) stories that captivate and motivate. Today, he combines both UX research and strategy to design digital experiences that people love.