Unintuitive Lessons on Being a Designer

I sometimes joke that everything I have ever learned about design, I learned from my first job. Nowadays, this first job has extended to nearly ten years, its soul consistent even as its shape unfurls in depths and colors I could never have imagined in the beginning.

Though I’ve always been an obsessive journaler, this year, I am particularly reflective. What a decade. What a place to have learned the things I have learned. I have had the privilege of working with the best of the best. I have had them show me, teach me, change me.

And change — there is nothing that feels so human as realizing that who we are today is not who we were yesterday, and will not be who we are tomorrow. It is this process of looking back that I savor like a sweet-toother with a prize-winning pastry. I can still crisply recall the ways I used to think, the views I used to hold, and see how they have morphed through the years, sometimes slowly, sometimes as swift and suddenly as a storm.

This list is certain to be outdated — and perhaps contradicted — in another ten years. If you are on the same journey, I hope these lessons will help you.

Of everything I believe, this goes deepest to my core: we can all be better. And so we should be.

1. What looks like genius is actually the result of brute force.

When we see a perfect end result, we usually never see what it takes to get there. So I used to assume that great work came in flashes of brilliance. I’d see a stunning end design and think to myself, wow, this designer is a genius. I’d imagine her sitting down at her desk, opening up Photoshop, and quietly translating the marvelous vision in her head onto the screen while sipping chamomile tea. I’d assume she was in possession of some mystical talent that I simply did not have.

In the years since, I’ve gotten a peek inside the “genius” of many top designers, and I know this now: the path to great work is one of brute force.

If you have literally tried every possible variation, you will have come across the best solution.

That’s it. Simple. This was never made more apparent to me than when a designer with an immaculate handle of the craft showed me what it took to get to a stunning final design of a complex layout that I’d considered leagues above my own current skill level: about a hundred variations of every possible combination of composition, type, line height, color, and more.

Brute force isn’t magic. It might even feel uncreative or boring. It’s like learning that what it takes to get a fit and toned body isn’t some miracle diet but just a lot of hours of sweating at a gym. Sure, as your skills develop, your brute forcing gets faster. You start to hone your instincts for which paths are less likely to succeed. You begin to make decisions more automatically. But to get to that level, every great designer has walked the path of brute force. Trying to take too many shortcuts too quickly is the reason why most designers end up slowing in their growth.

2. Developing your eye is the single most important skill to hone.

How good your work product is will always be limited by how good your eye is, and by that I mean your critical discernment of the strengths and weaknesses of a design. It is always better to learn how to become more critical in every dimension: product, interaction, craft, communication, etc. Even if for practical reasons you end up making tradeoffs on how much time and focus goes into each dimension, you cannot make those tradeoffs well without a clear understanding of what excellence looks like.

How can you develop your eye? Three tips:

  • Don’t assume your eye is “good enough.”
  • Constantly be asking yourself at every stage What would make this design better? even if you don’t end up implementing the suggestions.
  • Always seek out the most critical person you know in a particular dimension (craft, product, etc) to get their feedback on your work.

In practice, the third bullet is hard to do — it’s like watching a recording of yourself giving a speech— because it reveals in obvious and cringe-worthy ways all your gaps. It takes a certain amount of courage to take your work to a person you know will handily pick it apart.

I’ve sometimes rationalized this need away by saying to myself, Getting this design to be slightly better executed isn’t really a priority— people get the flow, and that’s what really matters. This either-or trap is a dangerous one to fall into. It makes you believe you need to make a tradeoff between good interactions or a good product strategy or good visuals, and so long as you’ve made sure the most important parts are solid, you’ve done a good job.

If I’m to be honest, my reluctance to seek more critical feedback came from a place of pride rather than an actual desire to improve myself. I was seeking validation rather than learning. In doing so, I was only hurting myself in the long run.

The either-or trap is completely false. A design can be easy to understand AND feel exceptionally well-crafted. It’s entirely possible to do good work across multiple dimensions. That should be the bar we aim for.

(Note: please don’t take this point to mean that you need to be that smart-ass who always has to point out every flaw in every design. There is a difference between trying to be helpful and trying to show off your knowledge, and we humans have a finely-tuned radar for these things.)

3. To do things of great impact, you cannot be a lone wolf.

Some of my greatest frustrations in design come from with my interactions with other people. Sometimes, I can’t get an engineer or PM to agree with me that a particular feature is important. Sometimes, I have a completely different vision of how something should work than another designer. These disagreements can feel like battling a room of mosquitos— annoying, draining, sometimes pointless. How nice it would be, I find myself thinking sometimes, to go it alone. To be my own creative master and do the things I think are right.

But then, reality sets in. What can I expect do on my own? Make a webpage. Make a simple app (although that would probably take me a super long time since my coding skills are rusty.) Make some cool conceptual demos. Start my own company. All of those options (except potentially the last one) would be fun, but they aren’t going to be impactful, which is something I have always personally valued. And if I did decide to start a company and by some lucky stars it somehow began to take off, I’d certainly end up having to work with others. Of course, I’d be able to call more of the shots at my own company, but I also know enough about leadership to understand that it is not about getting your way. It is about getting a group of people to share in your vision so that the whole is greater than the sum of its parts.

There is no eating your cake and having it too when it comes to complete creative freedom while doing things of great magnitude and influence. Not even at the very top.

The graph of impact tends to correlate with how many people you need to work effectively with. Once I realized this, I started to see my interactions with other people differently. It was no longer about winning battles and proving that I was right, but about developing stronger collaborative relationships. It was about getting to the point where the hum of working together became something I looked forward to. It was about the work that we did together being better than anything any of us could have done on our own, and recognizing that the debates and disagreements we had were a necessary part of getting there.

4. You cannot evaluate a design without knowing its intention

I used to think passing judgement on design was clear and objective. That, like a gymnastics competition, you could raise a scorecard, rank the contestants, and hand out some medals. This was the impression I got from hearing groups of designers debate the merits of Mac versus PC or try and rank which to-do list app was the best. This is how people make it sound when they discuss universal principles like make it simple or interactions should be delightful.

What I’ve learned since is that design is the art of solving specific rather than abstract problems. If the problem is not clear or well-understood, you cannot begin to evaluate how effective the solutions are.

When I used to look at a complex interface I didn’t understand, like an app that allowed a Fortune 500 company to manage its inventory of thousands of ads, I’d automatically apply the “universal” principles I’d learned from designing consumer products. I’d wonder why the interface looked so complicated, and why there was so much density. I’d question whether we really needed all the bells-and-whistles features exposed directly versus being hidden behind an affordance to hide some of the complexity.

Do you see what the problem was? I didn’t know anything about what a Fortune 500 advertiser needs, so how can I try and critique this interface? Yes, there was a lot of powerful functionality exposed, but what I later learned was that that is what those companies need to be efficient. There are dozens of people at these companies who would spend all day running through highly optimized workflows using this interface, and for them speed and efficiency were paramount. Density was preferred so they don’t spend more time scrolling. If you went with “smart defaults” and tried to hide complexity behind extra clicks, you’d be making those people spend an extra 30 seconds on each task, which at the end of the day adds up to a lot of wasted time.

When we pass judgment on a design, we are usually inferring the problem we think it is trying to solve. A lot of times this is obvious. But many times it isn’t. Not every app values reach. Not every service is trying to be profitable. It’s fine for something to be bespoke and appeal to a tiny audience if that is what the creator intended. Just make sure you know the intention before levying your criticism.

5. If you don’t want design to be treated as a service, you need to have an opinion about what problems are worth solving and why.

The idea that design is “problem solving” likely resonates with many designers. Certainly it is a much broader definition than “designers make things look pretty” which we can all appreciate is no longer the conventional wisdom. Until very recently, I thought of the role of a design team as taking well-defined people-centric problems and coming back with creative solutions. In my head, the main challenge to overcome was making sure everyone understood what a broad, people-centric problem was (i.e., the ask shouldn’t be Design a dashboard that shows you top nearby restaurants but Help people easily find great places to eat.)

The problem with that line of thinking is that it still relegates design to a service. This is fine if you are an agency and that is precisely the business you are in, but what I often hear from in-house designers (and researchers, content strategists, engineers, PMs, etc.) is I don’t want my role to be treated as a service. I hear instead, I want to have a seat at the table or I want to be involved in the strategy.

The thing is, you will always be treated as a service if you assume your role is to wait around for others to come to you with some specific problem to solve. The path to getting out of being a service is to have an opinion about which problems are worth solving and convincing other people of that. I remember a specific conversation with my boss where I was voicing a similar complaint to him around not being included in some strategy meeting and he replied, “Okay, let’s say you were there and you could have us do anything you wanted. What would you do?” to which I looked at him and blinked, completely at a loss because I hadn’t spent any time thinking about it.

To be involved in strategy is to be involved in the why — the identification of real problems, the prioritization of which of those problems are most pressing to solve right now. It involves understanding what makes the business tick and what specific advantages the company or team has. It involves having a handle on what the technical and people constraints are.

This is hard to do, and frankly not a core competency of the design discipline as it stands today. Even the most seasoned designers I know struggle with this. But this is what it takes to not be a service organization.

6. Investing in your communication skills gives you a 2x multiplier on your effectiveness.

I used to think good design was only ever about the design, and that if I could deliver a great idea and execution, I’d be able to give myself a hearty pat on the back for a job well done.

Unfortunately, that is like rewarding a lemonade stand for successfully producing a lot of juice regardless of how much lemonade it actually sells. The true outcome of a designer’s work is whether it had the intended effect in the real world.

The best designers I know excel at communication. This is because they apply the same theories of designing products — imagining how the person on the other side will think and feel as they encounter the design work — to telling the story of the design. They think deeply about what hooks would best get and keep someone’s undivided interest. They consider what is critical to convey up front, and what details can be saved for later. They use easy-to-understand language, visuals, storyboards or animations to convey what the outcome of the idea will be.

Being a designer is like having a superpower that allows you to show other people the future. You can help make a bunch of abstract concepts tangible through your work. You can help other people visualize what a better version of the world might look and feel like. This is an incredible thing to be able to do. But wielding the power effectively means the work must be paired with a strong narrative. And the first step is recognizing that clear, succinct and compelling communication is a key skill to master as a designer.

Too often I see designers discounting the importance of this, leading to explanations that are hard to follow, long-winded, or incorporating too much design-speak. If you think you have a brilliant idea but other people just don’t seem to get it, you have two options. You can either chalk it up to the environment — it’s not design-friendly, your colleagues aren’t thinking as big or as creatively, they’re not giving you the time of day, etc — or you can look inward. If you still think your idea is brilliant, then maybe you aren’t effectively conveying what’s in your head to others. What problem does your idea solve? Why is that an important problem to solve? Why is your idea the best way to solve that problem?

We don’t blame the user when they don’t end up taking to the product we’ve designed. So why should it be any different when it comes to getting our teammates excited about our designs?

7. Everyone feels like an imposter sometimes.

If you feel like an imposter, you are not alone. I guarantee this. In fact, I am certain that everyone who works in a creative profession — no matter how outwardly successful they appear to be — feels this way.

How do I know this? Well for one thing, there probably didn’t exist a week when I didn’t feel like an imposter in the first four to five years of my career. It was the dark shroud through which I saw everything. A criticism of my work was painful little jab at my capabilities. A misinterpretation of an e-mail I wrote would wound me for days. I constantly questioned whether I fit in, whether I’d be happier or better set up for success elsewhere. Even when I started this blog, I wondered if I knew enough to write anything worthwhile.

But it turns out that it isn’t just me. Everyone I’ve spoken to has felt this way, including industry titans, world-famous luminaries, and people who you’d think are ridiculous to feel this way because they have proven themselves time and time again. Everyone wonders if they can actually succeed, especially when they were just starting out. Everyone struggles. They don’t always admit it publicly, but in confidence, I’ve found myself floored by confessions from people I have long admired. This, in turn, makes it easier for me to accept my own self-doubts.

To question oneself is part of the human condition. And yet, we’ve managed to hide this fact behind curated posts and photos, behind reassuring smiles and articles purporting success. Ours is a culture that values effortless perfection. In fact, we even unconsciously prefer people who seem innately talented over those who work hard.

In design especially, it is hard to separate what people say about your work with what they think of you as a designer. Over the years I’ve found it helps to talk about and acknowledge this. The revelation itself helps to cast off the burden of the pretense. The second thing that helps is recognizing that every designer is different, and that the only competition worth engaging in between yourself of yore and yourself today. We should be inspired by and learn from those whose skills are stronger than ours in a particular dimension, but this isn’t a rat race (see #3 above). If I am better today than I was last week at X, even if I’m not as good as Y at X, then that is progress, and that is worth celebrating.

8. Good design is obvious.

A good design should be obviously good to the people it is intended for. I’ve already written about this one at length here, so I’ll keep this brief.

I used to think that evaluating design work should be left to designers. After all, we are the experts, and so when non-designers would interject with their opinion, I’d listen half-heartedly. They don’t have all the context, I’d think. They don’t know the history of this discussion.

Unfortunately, what I failed to take into account was that the people whose evaluation matters the most are the people you are designing for.

And those folks are likely not designers. They’re probably not even all technically-savvy.

Certainly, context and history help make for more productive product discussions. But at the end of the day, evaluating the success of a design isn’t complicated. If you could wave a magic wand and make the perfect solution in your head a reality, I’d bet that there would be very little discussion needed. We’d read the user’s mind, of course! We’d show them the exact results that they’re looking for!

We, the makers, are the ones who complicate the discussion because the constraints we face prevent us from getting to perfect. There is no mind-reading API currently available, alas. So in light of these realities, we are often in the weeds discussing and debating the tradeoffs and which path is the most good/least bad.

Picking the best path is the messy part. But it is quite straightforward to pass judgement on whether a particular path feels objectively good or bad.

At the end of the day, the people whom we are designing for don’t have any of that context, history, or understanding of the constraints we face. And yet, they will still pass judgement.

The only thing that matters is whether your design works for them in solving the problem you intended to solve.

It is really quite simple.