Constraints are Hard

But please don’t confuse that with “uninspiring”

Julie Zhuo
The Year of the Looking Glass
6 min readAug 27, 2014


I’m always intrigued when I come across a design portfolio that includes a personal rethink of an already-existing popular product. Regardless of the result, one has to admire the moxie of the designer who attempts to tackle such a problem. To do so without being asked, without any prompting or any promise of money or wishes or praise or whatever, requires a non-trivial investment of time and energy mixed with a dash of audacity.

Depending on the result, however, that admiration either ratchets up to 9000 (holy geez, Company X was just graced with a gift from the heavens and if they knew what was good for them, they’d implement these ideas immediately!), or turns into a face palm.

It’s usually the face palm.

Now, this isn’t because the work doesn’t look good. Usually, it’s a solid execution highlighting some clear areas of improvement, like a more on-the-trend visual style, reduced clutter, and richer multimedia. Often, at first glance, the redesign looks simpler and more modern, appealing in the same way as one of those reality show “extreme makeovers” finales, where some bold new change breathes a waft of freshness into a routine or look gone stale.

The problem is, most redesigns of popular products would simply just not work. I am so sure of this fact that I would be willing to bet good money that if you had a magic wand that could actually change a popular product’s design to one of those “cleaner” redesign posited by a third party, nine times out of ten, the third party design would perform worse by pretty much any metric you’d care about—usage, revenue, engagement, consumer happiness, etc.

I know this because I have gone through this script myself and seen this play out too many times to count. It’s an old story, a classic tale. You probably know it well. Behold…

The Designer’s Journey

  1. The Wisdom of Observation: Okay, so this feature/service/product is pretty good and it’s wildly popular, but it’s not amazing. I mean, there are so many areas where it’s kind of jank. What’s up with that? If I were working on this, I’d definitely redesign it to be awesome. I mean, don’t the people who use this app deserve a better product?
  2. The Audacity of Inspiration: Hey, why don’t I work on it? It’d be a seriously awesome project. I’ve got a bajazillion good ideas. In fact, I stayed up all last night working. Here’s a demo video of what the whole experience could be, annotated with 87 reasons why it’s better than the original.
  3. The Snowball of Support: Hellz yeah, everyone who sees this redesign loves it! They’re all down to help me make it happen! It’s the best thing since tabbed browsing! Let’s build it and ship it quick!
  4. The Intoxication of Launch: It’s out! We did it! We are the winningest winners in all of winnertown!
  5. The Trough of Reckoning: Hmm, most people who use this feature/service/product don’t seem to love our changes. And it doesn’t seem like it’s helping people use the product in a better manner…
  6. The Hell of Sisyphos: All right, we gotta tweak this thing. Let’s try this change… No? Didn’t work? Hmm, how about this change? Still no good? How about we update this section?… Any improvements?
  7. The Despair of the Hard Truth: %^*#^%! The old design had its issues, but apparently the new design does as well. It’s not obviously better. Why is it so hard to change things? Let’s go shopping.
  8. The Path of Perseverance or Disillusionment: see below

Perseverance or Disillusionment

The last step of the journey is a critical branching point. This is where many teams fall into a state of disillusionment. There are mumblings of it’s impossible to change anything in this environment and we’ll never achieve anything good if we have so many constraints. I have seen many designers weary of all the iterations, of trying this change and that to see if there are any measurable improvements. Even when changes do ship, they feel like a series of small tweaks, nothing impressive or inspiring, nothing that feels like the fresh, shiny new redesign that once sparked the imagination.

Eventually, the desire of wanting to work on the next great incarnation of a well-known product gets snuffed out to nothing, and instead the designer yearns to work on a new concept, something in the v0 or v1 stages, ideally pre-launch, because those are the types of projects that are said to be more innovative, more creative and where good design can truly shine.

There’s a small amount of truth to those sentiments. You can only pivot an existing product so much. Sometimes, to deliver an entirely new kind of value, you have to do it in a different context. You won’t be able to iterate your way into it.

But treading on the path of Disillusionment can also be a form of laziness. To design for a new concept or product, you’re essentially starting from nothing, and pretty much every something you make will feel significantly better than nothing. Especially on aesthetics or usability, you can get away with a lot of objectively subpar designs, because there’s no directly measurable benchmarks. Does it matter if icons with text are slightly easier to understand than just icons? Certainly, if your app is widely used. Not really, if your app hasn’t launched yet, because there are bigger things to worry about.

Designing for a pre-launch project may be more liberating. You can invent new design patterns. You can go with whatever color palette you want. You can imbue it with your own personal touch, and fewer people will argue with you. The process might seem like it’s a lot more fun. (Well, up until launch, that is. After launch is another story, because the vast majority of new concepts fail, and failing isn’t fun because it takes you back to steps 5–8 in the Designer’s Journey.) But I contest designing something new is not inherently more innovative or creative than designing for an existing product. It’s not the only place where good design can truly shine.

Designers who work on an existing product only succeed if they make something that’s truly and clearly better than what came before it. Most people don’t realize how hard that is at first blush. If a product has been around for five years, then that’s five years worth of the blood, sweat, and tears of past designers whose ideas you’re trying to best. Certainly this is possible as nothing is perfect, and our constant culture of learning and improvement means we should expect ourselves to do better year over year, but to think that anyone’s single-night-redesign will work without a hitch is a bit of a stretch.

Constraints are hard because they represent the bar, and the bar is high on existing, successful products. Designers who persevere to ship something beyond this bar have achieved something remarkable, but they’re often unsung heroes because what they accomplish doesn’t come across as big or splashy. It’s often the quiet hum of a product getting better and better through the years—a common action made a little easier, a confusing interaction made simpler, a habitual gesture made more delightful. Maybe the average person never notices, but the product continues its upward trajectory. It grows more popular. It has more impact in the world.

Making a better version of an already-successful product is hard. Not everyone can do it successfully. But please don’t confuse hard with thinking that there’s something deficient about the environment or the nature of the work.

It takes enormous reservoirs of creativity, practicality, dedication, and inspiration to tread the path of perseverance.

Even in the shadow of failure, I hope that’s the path you and I both take.

Photo by Brian Walter



Julie Zhuo
The Year of the Looking Glass

Building Sundial ( Former Product Design VP @ FB. Author of The Making of a Manager. Find me @joulee. I love people, nuance, and systems.