The Guide to Being a Pessimistic Designer

Whether it’s marketing, advertising, web design, or software, designers as a whole have gotten a reputation for being a bit too optimistic. We are supposed to be the ones who always have our heads in the clouds—the ones who think about the details later. We are supposed to generate thousands of ideas, and throw a fit if any of the ideas are expensive, impossible, or just terrible.

Sure! We Can Do That…

Luckily, very early on in my career, I had to adapt to be much more pessimistic in my approach, especially in meetings. I worked for a marketing agency that also tried to dabble in product design and software. Client meetings were often unstructured, with a lot of “blue sky thinking” about the possibilities. Stakeholders would get easily excited about early ideas, and other members on my team would often feed this terrible fire.

There was a lot of energy, along with a lot of promises and a lot of optimism. And then a lot of looking at me, asking, “Any questions before we begin?”

There were a lot of questions, but I was young, I was naive, and I hadn’t yet found my voice. I felt like I was forced to agree to bad ideas. But going along with bad ideas soon caught up to me. When it was time to deliver on “promises” that were made by other people, I couldn’t.

I knew in the meeting that what they wanted to do wasn’t possible. I knew it wasn’t a good idea. I also knew that I had to figure it out anyway, and when I couldn’t, it was my problem.

As the one responsible for delivering, I had to adapt. I had to play a much more active role in the ideation phase, making sure that whatever we were planning to make was actually possible.

Over the years, I’ve learned a number of lessons (the hard way). This is my guide to being a pessimistic designer.

How to Be a Pessimistic Designer

1. Don’t be a jerk.

Okay, this is just a good rule for being a decent human, but it’s especially important if you’re going to be a pessimist. You’ll be nay-saying a lot. You’ll have to tell people their ideas aren’t good, aren’t affordable, or aren’t feasible. These conversations need to be professional, non-confrontational, and come from a place of mutual understanding.

At Atomic Object, it is mandatory that everyone reads Crucial Conversations, which explains how to handle these conversations tactfully. I recommend it to all pessimistic designers.

2. Draw from your experience.

Telling someone their idea isn’t worth executing, or even exploring further, is hard when you are just speaking from gut instinct. Early on, I would get the comment, “Well, you haven’t even tried.”

Even though an idea “smells,” without concrete proof, it can be hard to convince someone, or a group of people, that it’s not a good approach. Instead, I suggest using phrases like this:

  • “On [project name] we ran into a similar issue. It didn’t work because…”
  • “I think the idea is cool, but executing will cost 2X because…”
  • “This idea sounds exactly like what [competitor company]…”

3. Be harder on your own ideas.

Being a pessimist is often construed as being an elitist know-it-all. I would often get a lot of criticism for thinking that I was the only one with the “correct” answer.

I took this criticism personally. It was never my intention. But after some introspection, I realized I was presenting my own suggestions as concrete ideas, not early concepts.

To combat this, I’ve done a few things differently:

  • Invite criticism. – Make a point of calling out specific people who would have better context on the feasibility or viability of the idea. Ask the developer to look hard at the development cost, or similar, cheaper ways we could produce a comparable result.
  • Start low-fi. – As a designer, it’s much easier to develop hi-fi design mockups for low-level concepts. But as Ryan Russell said, “Don’t push the fidelity of your design work further than the maturity of your thinking.” This is not a novel idea, but remember that in terms of presenting concepts, people react to higher-fidelity designs as actionable solutions, rather than an invitation for conversation.
  • Don’t “withhold” your own concerns. – Conversations are not about winning. Play all of your cards. If you have an idea, but there are aspects you are concerned about, call them out. This approach is especially helpful when you’re inviting criticism.

4. Listen and think more than you speak.

People are weird. During conversations, we absolutely hate silence. But as the saying goes, “Silence is golden.” During meetings, I’ll try to spend most of the time not speaking. This is great for a number of reasons:

  • As a pessimist, it prevents me from looking too negative all of the time.
  • It allows me to recall, and remember correctly, real experiences that I can draw from to frame my rebuttals.
  • People will just keep talking to avoid silence. It is during this time that people can even talk themselves out of bad ideas. The more they think through ideas and find that they can’t explain them clearly, the more likely they are to break them down.

5. No one wins when everyone loses.

Winning a conversation is like winning a battle. But if a project isn’t successful, that’s like losing the war. As a group, document what “success” looks like. Write it down, and refer to it often. If an idea does not promote success, that should be reason enough—no matter whose idea it was—to reject it.

Go be a pessimist!

With these simple rules, you can now effectively be a pessimist. But remember, every project needs a balance of optimism and pessimism. It’s within this tango that projects can achieve realism. So have humility, don’t be a jerk, and, especially, remain aware of how you are being perceived.