We’ve all had at least one: a nightmare project that you wish you could walk away from.

Once you’ve abandoned the idea that it’ll end up in your portfolio, you just want to get that final approval, send off the invoice, and never think about it again. We asked a few seasoned design pros to think about it one more time. Why? Because those projects are the ones that teach us the greatest lessons – the ones that lead to revamped creative briefs, new paragraphs in your proposals, and updated clauses in your contracts. Sometimes they even lead to entirely new approaches to shaping your portfolio, sizing up new clients, and deciding when to say "No." 

Avoid “small” changes that create a ripple effect of additional work.

"Elefint was just a few months away from launching a new brand and a website for a nonprofit focused on end-of-life care when the client switched the project management role from a contractor to a newly hired staff member. Unfortunately, a lot of our efforts and insights were lost in the transition, and the client started asking for “small” changes that inevitably created a ripple effect – from logos to the website, animations to print collateral. Each request led to weeks in delays – waiting on feedback, explaining our rationale for the originally approved design, revisiting initial strategy. A project we thought would take 12 months ended up taking more than two years.

Knowing there had to be a more efficient way for us to work, I started experimenting with design sprints for our other nonprofit clients, to eliminate the inefficiencies that come with long feedback loops and broad scopes of work. Design sprints have allowed us to experiment with what’s possible within the context of building out complex digital projects and brands, and to work more iteratively and collaboratively with our clients, with timelines that are both practical and motivating. Working in shorter increments helps our team and clients stay focused, energized, inspired, and, most important, aligned throughout the lifeline of the project. We now integrate our “Design Sprint for Social Good” methods into the design process, and we’ve launched 10 complex digital projects in less than one year. As a small team, that’s a tremendous feat."

— Gopika Prabhu, Founder + Creative Director, Elefint, San Francisco

Show a healthy skepticism toward new and experimental technology.

"As an interactive designer at the Newseum, I designed touch-screen experiences for museum exhibits that teach visitors about their First Amendment freedoms and how news is made. This was years ago, when smartphones were just taking off, tablets were just entering the retail market, and pinch-to-zoom was a new behavior. On the eve of this digital boom, our in-house multimedia team had a unique opportunity to create a gallery that highlighted digital media and its effects on how we receive and consume news. Our team controlled the content and developed the software, and an external partner promised to provide the hardware: the latest in multiscreen surfaces and projection technology.

We were creating bespoke designs for screens that didn’t yet exist, weren’t available for testing, and wouldn’t be out for months. But our tech partner couldn’t nail down the specs. They often reported changes to the monitors’ and projectors’ aspect ratios and resolutions, rendering our interactives and graphics unusable until we adapted our files. This sounds ridiculous now – because everything is flexible, adaptive, and responsive – but back then, this wasn’t an option.

We had to expect the unexpected. We limped through development and recreated (and recreated and recreated) the files—never knowing if they were right until we finally installed them onto the hardware in the gallery. I learned that with any new and experimental technology – whether it’s hardware, software, a new tool, pattern, or process – it’s okay to feel wary. Use that healthy skepticism to look beyond the current deliverable, to evaluate where the product might show up once it outlives its current platform. Making design into a flexible system expands its utility and its reach, which is especially important across products. Devices, interaction patterns, communication, and tech change faster than our understanding of them. And that’s okay."

— Libby Bawcombe, Senior Visual Product Designer National Public Radio, Washington, D.C.

Clarify what exactly you are there to do.

"I was commissioned by an independent animation and advertising company to produce, or help produce, a very short film. It was supposed to be between two and three minutes long, and I had just three weeks to do it. I opted to be in-house rather than work at my own studio as, I thought it would make communication easier. On this front, I was wrong.

Initially, I had gone in for an interview where I was referred to as the freelance “talent.” (It was a little uncomfortable, and vague, to be referred to that way and not as the visual stylist or creative director or whatever my role was meant to be.) I started the next day, never having discussed the official job title: I was just given a loose concept (make the animation look like a Charley Harper painting) and no script. 

I was completely left to my own devices, with small deadlines at the end of each day. I should have taken the initiative and spent the first day figuring out storyboard, style guide, transitions, and color scheme, but I was too stressed and confused to do so. I had no idea that I was in charge of the entire direction of the project. It got a bit better in the weeks ahead as I navigated my way in the dark. 

Needless to say, I wasn’t proud of the final outcome, or of my performance as a freelancer. I should have been more vocal about needing clear signposts. In the end, I was credited as the illustrator, although I had ad-libbed the entire direction and narrative. The animation firm was fantastic but I think just as confused as I was about my role. I realize now that I shouldn’t have winged it, but clarified what I was there to do from the get-go. This is something that I now try to do with every new freelance commission." 

— Jon Jones, Illustrator, Port Elizabeth, South Africa

When a brief is conceptual, seek client feedback early on.

"When the offer came in last June, I was all in. It was a commission for a governmental organization – a rather conceptual brief but with a generous budget. That’s a lethal combination, as one doesn’t want to disappoint and one definitely wants to please. What followed was a couple of rather stressful weeks and an ample dose of frustration. Both were completely avoidable in hindsight. 

The brief was to create a series of illustrations that clearly described the process of patenting in the science industry. I had to design images for a three-metertall, very narrow banner, which would be displayed at a conference. As I was dealing with American clients, most of my talks and feedback happened over Skype. This was the first part of the nightmare: Skype combined with a temperamental internet connection, conflicting time zones, and muffled accents is a tricky thing to navigate, and can add to unnecessary stress. I’ve learned to stick with emails.

The nightmare got worst. I should have pushed for image revisions at an earlier stage: The client decided to make small changes after I had everything in place and locked down in a very tight layout. That added massively to the workload. I formed a very close relationship and personal attachment to my color choices, too, but when the client at the very last minute decided we should go with murky, corporate colors instead of my usual palette, I said okay even though I didn’t agree. Lesson learned.

Through this experience, I realized that even if it’s a big client, it’s still just a bunch of humans trying to come up with a decent solution to the problem at hand. For the time that you’re working together, you are a member of the team and should act like one."

— Martina Paukova, Illustrator, Berlin

Creative projects need creative people in the room.

"A sister agency had asked my team to work on a massive experiential project for a meteoric-hot tech and transportation brand in San Francisco. And since my chief creative and I had the requisite sleeve tattoos and hipster facial hair, we were to lead the creative elements of this multimillion-dollar campaign. But on the day of the kickoff meeting, I chose to ignore the first red flag: The client hadn’t invited a single member of their own creative team: just the head of procurement, a couple of mid-level producers, and an account lead with two months on the job.

For the next four hours, not one minute was spent talking about the idea, let alone the intent of the idea. It was all about rate cards, travel plans, and the office politics required to get things done. Of course, this made sense coming from a tech company hell-bent on maximizing valuation. But this laser focus on margin and production timelines meant that the creative had to fit into increasingly oppressive and consequential parameters. Which proved to be a disaster.

Everything we presented was judged on feasibility and budget, not creativity or effectiveness. When we proposed a visual identity system for the campaign, the people in the room didn’t feel qualified or empowered to give direction. As the kickoff date approached, we got farther and farther behind. Ultimately, the campaign was pulled. The work went “in-house,” which is where it always belonged.

Yes, this is a clichéd story of how procurement and creatives don’t mix. But there’s truth in the cliché. If budget decisions require a leader, then creative decisions do, too, If you don’t see another creative when you walk in the room, run in the other direction."

— Max Lenderman, Founder + CEO, School, Boulder, Colorado

Money matters, but how much? 

"Since abandoning computer science to pursue commercial art as a living, I’ve struggled to balance the creativity of my dream job with work that’s comfortable, safe, and lucrative. The biggest frustrations and creative blocks that I crash into are the ones I could have avoided, if I’d just followed my internal compass. 

A few years back, a particular style of mine gained attention, and the commissions rolled in, at three or four times the fees I’d accepted a year earlier. I was happy to be getting the work, but something was off. I wanted to be doing work that was more colorful, fun, and whimsical than the things I was being hired for. I thought the money would keep me entertained, but I was wrong. Projects started becoming headaches for me: I’d put things off, I’d get stressed out, and I’d start to think I couldn’t complete the job. My clients were happy, but I was bored, and worried that I had “broken” my creativity and, in turn, my career.

The solution was simple: Put in the time to do what you really want, even if it requires a financial sacrifice. I started consciously turning down work that didn’t excite me, and spent any leftover time focusing on side projects that aligned with my creative goals. Soon, the paying work poured in again, and I noticed that my favorite clients usually discover me through my personal work, which we adapt for their commercial pieces. Now I know I have to constantly fine-tune my work to be sure it’s taking me where I want to go, rather than taking the easy path. Heck, I’ve already decided to throw job security to the wind by being a freelance illustrator – why start wearing a safety belt now?"

— Kirk Wallace, Illustrator, Boston

When outsourcing jobs, be crystal clear about what you’re requesting.

"Some years ago we were hired to design an exhibition. It was located in an old building (not your average white cube,) and we had commissioned a special orange carpet for the floor. It was going to be installed the morning of the show, right before the shelves and sculptures were brought in. We were working on a very tight schedule! 

When we arrived on the day of the opening, the carpet had been installed but the carpet installer had already left. What we found was the most sloppy, bubbly orange carpet that we had ever seen. When we called to ask for an explanation, the carpet installer told us that he thought the floor was going to be used for a one-night Queen’s day party instead of an exhibition. (Queen’s day is our national holiday, and orange is the national color.)

The exhibition content was about to arrive, so we had to think and act fast. We freestyled a new design by cutting up the orange floor into small graphic shapes that we combined with the original tiling. We barely made it by the time the shelves and sculptures were brought in, but it looked better.

The carpet installer had had no idea what the floor was actually going to be used for, and we should have briefed them better. In the end, though, we learned to surround ourselves with a network of creatives and suppliers that we really trust."

— Jaron Korvinus, Cofounder of Studio Spass, Rotterdam

Red flags won’t simply go away.

"Soon after I founded my design studio, a California chocolate company asked me to create a logo for their growing business and storefront. Given my slim portfolio from a previous in-house design position, I was eager to collaborate with a food brand on the West Coast. But my overt optimism made me blind to a few red flags – the client’s small budget and their unwillingness to hand over the creative reins – which ultimately doomed the project.

I pride myself on being able to understand and translate obscure client feedback, but in one of the early reviews, the client asked for the logo to “express more devotion,” words that baffle me to this day. I designed countless concepts and made countless revisions because I was determined to make the client happy. I even asked the client to share examples of other “devoted” logos, which was no help at all. For the first time ever in my design career, I was at a complete loss, utterly defeated. What’s worse, my contract had failed to note a maximum number of revisions or the fact that the deposit was nonrefundable. I gave it my all, lost thousands in unbilled hours, and endured weeks of self-doubt. And my other work suffered for lack of attention. Eventually, we parted ways and the client had a family friend create the logo, so you can imagine the final result.

Fast-forward to today. I still pour my heart and soul into absolutely everything I create, but all of my proposals and lawyer-looked-over contracts help avoid failure or confusion. Now I show clients a few rough concepts early on (rather than perfecting dozens of options) and my contracts clearly note that each project includes two revisions, with additional rounds charged at an hourly rate. With these processes in place, I’m able to demand a fair wage for my talents and time."

— Kelsy Stromski, Founder + Creative Director, Refinery 43, Massachusetts 

Have a strong understanding of the brand’s product story.

"A year after I completed MAX100 (a personal project illustrating the Nike AirMax 1 in 100 different ways), Nike asked me to use a similar approach to create 30 shoes for their Nike Air Reinvented campaign. Nike was a brand I had long admired and a bucket-list client, so I was excited and nervous. But I assumed the work would follow the same loose, stream-of-consciousness approach inspired by whatever mood hit me at the moment.

When I presented my first round of sketches, it became pretty clear that this was a very different animal. As you can imagine, a brand of Nike’s size had a lengthy and complicated approval process, which meant dozens of my ideas were rejected because they didn’t fit into the product’s brand story. In my personal work, I had generated three to five pieces a week, but this time I had completed only two illustrations after nearly a month. At that rate, I’d never complete the project on time.

I recognized that I had to abandon my early expectations and shift my way of thinking to become much more strategic: Each illustration had to tell the story of the product. Nike’s internal team was incredibly helpful in arming me with detailed background information, and the approval process started to accelerate. It was a grueling project, but by the end I could look at each piece and know that the work was better because of the focus on story and the feedback that helped shape the work.

Here’s what I learned: My success as an independent designer is built on a foundation of personal projects, which have created dozens of opportunities for client work. But once you get that opportunity, you have to be prepared to adjust your thinking. Work to maintain what makes you unique in the process, but find out how the client operates and what they respond to, then fold those ingredients into your process. Be prepared to let their direction and feedback make the work better."

— Matt Stevens, Designer + Illustrator, Charlotte

Just because something worked for one brand doesn’t mean it will work for the next.

"I’m currently rebranding a local flower shop for a client with enviable taste. Our kickoff meeting went great, but I soon realized that I hadn’t asked the right questions. The owner said she loved a clean, abstract logo I’d created for a local coffee shop, but I eventually realized she liked the brand and feel of the coffee shop itself more than the minimal mark.

I shared mood boards, and then the first round of logos (with far too many options), and the response was kind but somewhat tepid. A month later, the client finally shared specific feedback, and I revised the logos she liked best, although she wasn’t thrilled with any of them. Another month went by before she told me, “We need to start over – here’s an example of what we really like.” The sample made perfect sense, but it felt derivative and cliché; I was dejected and took it personally.

After I thought about the process for a long time, my frustration slowly turned into empathy. It was my fault. I didn’t get to know their brand: The logos I’d shown were cold and impersonal – the exact opposite of a flower shop. I’d been lazy and arrogant, thinking, “I’ll just do what I did for the coffee shop, and they’ll hoist me on their shoulders in a victory parade.”

So here’s what I’ve learned: Do your research up front, understand who the client is, and communicate expectations clearly. And when you inevitably get frustrated, try to put yourself in your client’s shoes. That empathy can lead to something unexpected."

— Matt Lehman, Designer + Illustrator, Nashville

Creative briefs demand details, details, details.

"Years ago, my previous agency landed a web project for an East Coast client that runs a popular cycling event. We’d pitched them on designing their logo as well, but they chose to go with a local agency. So I started the project a little bummed about the lost opportunity.

A few weeks in, the client asked for daily email updates on top of our weekly phone calls. Requests for features that were outside our scope quickly turned into demands and requirements. Unfortunately, our proposal lacked concrete details regarding features, functionality, and timelines, so it’s not surprising that the client’s expectations went way beyond our own. Eventually, the client got angry, asked for their deposit back, and said they wouldn’t be using the site, even though it was close to completion. I had to talk to my boss about it (not fun) as well as their lawyer (even worse). 

The first thing I learned? Don’t take on projects you’re not interested in. Once we’d missed the chance to do the work we specialize in (branding and identities), we should have passed; taking on creative work that doesn’t excite you rarely leads to a great client relationship or stellar results. Second, I promised myself I would make every proposal as clear as possible. Sometimes I feel like a hack, writing ultra-specific agreements that suggest I don’t trust our clients. But that’s not the case. A crystal-clear scope of work allows for open and honest conversations with clients – a project where no one yells, cries, or gets sued in the end."

— Michael Benjamin, Creative Director, Anthem Branding, Boulder, Colorado

Don’t shortchange your design approach in the interest of time.

"A few months after I moved West to take a new position at a small studio in Boulder, Colorado, we lost a crucial account. We quickly realized that we needed a new identity and website to separate ourselves from previous leadership challenges and to reveal our new business model. To get it done quickly, we abandoned our typical design approach and skipped some key steps. I was tasked with the design deliverables, but I never had an opportunity to think holistically about the experience or collaborate with the internal team, since the leadership wanted to keep the brand reveal a secret. Instead, I went straight to the computer and wasted a lot of time, suffering in silence. Who was our audience? What was our message? What experience were we hoping to design? And where was everyone else?!

I took a step back, restarted the process, and insisted that two of the agency leads – a married couple – invest some time in the discovery and user experience. There were arguments every step of the way, secret talks about the direction, and clear disagreements about the new business model. In the end, the design came out okay, but the process highlighted misalignments on the leadership team, including the married couple themselves. Shortly after the design went live, the couple divorced and the studio went out of business. I wasn’t sure if I’d torn my new family apart or if the project was just another symptom of a difficult relationship.

The experience reminded me that the discovery and strategy process is essential prior to diving into any design deliverable, no matter how personal or painful it may. It ensures that we’re identifying pain points, solving the right problems, and capturing the full story that will lead to a more compelling design and, in the end, more customers."

— Sumiko Carter,  Creative Director,  Gorilla Logic,  Boulder, Colorado

Chuck the calendar and embrace the stress.

"I’m a very chaotic guy. I procrastinate. I don’t ever check my calendar. Every deadline that seems a long way off quickly and suddenly becomes a very short deadline. I‘ve tried over and over again to organize myself but it’s never been very productive. One particular commission was especially frantic. It was a lettering piece, for which I had to draw 19 letters out of landscapes, people, machines, cities, cars, and other doodles. I completely forgot that I had to do it and then suddenly realized my oversight the night before the delivery date, when I got a reminder email from my agent. I had it in my calendar, but I never looked at my calendar.

I was busy with two shows in Düsseldorf, Germany, at the time and I had a few other commercial commissions on the go, so I stayed up all night sketching and drawing to make the deadline. Luckily, in the end, the client was incredibly happy with the results. And so was I. 

What I came to realize – through this experience and many others like it – is that I need stress to be motivated and succeed. The things that I’m most proud are the things I drew on the day of a deadline. So you could say, in a way, that all my illustrations are nightmare projects. I need the nightmare: It’s my vital source of energy."

— Jonathan Calugi, Illustrator, Pistoia, Italy

The client is the client, not the designer.

"Every project has its own level of complexity and comes with different challenges, though the nightmare project will always be the one where the client tells us exactly what to do. It’s always detrimental if the client doesn’t give us creative license and doesn’t trust us to do our job. 

Our error with these scenarios has been to give up and follow along with the client’s opinion and direction. Over time, we’ve learned to be more convincing and not to allow the client to be the designer. In the end, we want to create graphic design that makes an impact, but if the client is the creative director, then it’s hard to make something incredible. It’s also, of course, very important to keep clients happy and satisfied, so in these situations it’s often a tough balancing act.

To deal with these nightmare projects, we try to be honest. Sometimes it’s about showing multiple options and saying, “We could have done this, but here’s what you asked for,” making it clear which idea we prefer. In the end, it’s the nightmares that encourage us to grow."

— Marissa Gutierrez, Graphic Designer, Anagrama, Mexico City