You hear it all the time: “Everything happens for a reason.” Let it sit there for a minute. Marinate. Steep. What exactly prompted that thought? You flunked a class. You got fired. You presented a really wacky idea in a pitch meeting when something more conservative would have won the gig. Regrets. We all have ‘em.
Does everything really happen for some indefinable reason? Probably not. Call it a defense mechanism, something you say when you’ve screwed up and you need a way to move on. But sometimes we need to live with our mistakes. Own them. How else will we remember not to make them in the future? A little wallowing, as long as it’s not paralyzing, never hurt anyone.
So we decided to throw this query out to designers of all stripes, from leaders at Airbnb and Shake Shack to those guiding bold studios like La Tortilleria: If you could look back at your career and rethink one of your big decisions, what would it be? And why?
Sure, we wanted to hear about the do-overs, but our main premise wasn’t to make anyone dredge up unpleasant moments. Rather, our goal was to have them weigh the choices they made then, based on what they know now. We were looking to commiserate. We were looking for a little wisdom. We got both.
I would have trusted my instincts and drawn every damn day.
Creative director, Argodesign / Austin, Texas
I would recognize that the future is by our design, but some things never change and that is the ability to communicate our ideas across mediums. Because we rely on the visual medium more than any other, I believe it has the greatest weight and importance to the design profession. My instinct was to take art in high school. At the time, my mom suggested typing or writing…something more “practical,” in her mind. That was before the internet and touch screens and a world we had not imagined. I remember my first interview with the VP of creative at frog design. I was applying for an interaction design position. When I decided to show my versatility by sharing a few visuals, like a T-shirt design, he asked me, “Are you applying to be a visual designer?” I said no. He replied, “Then don’t show me that stuff.”
Design consultancies sell expertise, and they often have specific design roles. At the time, visual and interaction design were very much separate, and I was clearly in the interaction design camp. We “didn’t do” visual design. So, while I was at one of the most esteemed design firms, I did not improve any of my visual design skills. Instead, I became an expert in the field of interaction design as well as design research and strategy. However, my greatest regret is not taking the art path. I think some of the strongest designers are a combination of art and science. And while I have an eye for design, while I can creatively direct designers of all types, I can never bring my ideas to visual life in a gratifying way. For a designer, that is the most painful and frustrating limitation. People can hear me, but they cannot see me. If I had to do it all over again, I would trust my instincts and draw every damn day.
I wouldn’t have worked for companies that didn’t completely trust us.
Creative director and cofounder of La Tortilleria / Monterrey, Mexico
Last year I went to a master class with Bob Gower, who teaches responsive organizational design. He mentioned something really simple but important: If people are not kind, you don’t want to work with them. That is something our firm forgot twice in the past, once five and then again three years ago. Both times, we were caught thinking that a large client and large account would be a good thing for the agency. That was a big mistake. We realized that sometimes large companies don’t know how to work with agencies. They don’t know how to collaborate. All they want to do is impose. And it begins at the top, with owners or heads of companies not really knowing how their people manage their teams or the people they work with.
They don’t realize this affects the entire organization. Both times we completed our work obligations. But one of those times someone from our agency quit because she couldn’t handle the client anymore. She didn’t want to be in touch every day with this person because the client was too much work and too exhausting. If the client had been nice, kind, conscientious, the work would have been just work, instead of a nightmare. We now have a couple things that we think about before deciding to work with a new client. First, do we have contact with the person who makes decisions for the organization? If we do not, we need to be sure the person we are working with has the power to make decisions. Otherwise you will not be able to do good work. Then you have to decide if this person, the contact person within the client’s organization, knows how to work and collaborate. If they don’t trust you, don’t let them hire you.
I would have picked my projects more carefully.
VP of design, Airbnb / San Francisco, California
Look, we all have to do this as a designer – just take a job sometimes. I know that. But in the past, I think there were months and years that maybe I lost some of the drive because I was working on projects and for companies that I didn’t believe in. It’s good training when you’re starting out to say yes to everything. However, there’s a time when you start to negotiate with yourself about saying yes all the time. The internal conversation changes because something you fell in love with becomes the worst part of a job. Sometimes you’re using all that creative energy on companies and projects you don’t believe in. Working with people you might not really like all that much can be draining.
It’s hard for me to want to change those decisions, because I’m very happy today. I do feel that I could have saved myself a couple of years here and there if I’d just told myself, This is not what I want to be doing. So just make sure that you don’t fall out of love with designing something because you are not designing it in ways that enrich you. Working enough to be able to say “I don’t love this project” is a nice problem to have. Lots of people out there are thrilled to get the gigs they do get. But falling out of love with design can happen to anyone.
I was told that I should think about a different career, something that was not creative.
Illustrator, animator, and Adobe creative resident / Sarasota, Florida
I’m just starting out, having graduated last May from Ringling College of Art and Design in Sarasota, Florida, so I’m not entirely sure I can answer this question well. I’m not even 24, after all. But I did make a big mistake in school. For a few years I was in an animation curriculum, and I almost failed out. Well, failed sounds too severe, but my grades weren’t good enough to continue in the program. How did I get into that situation? I was trying to force myself to do work I thought, and others were telling me, was valuable. Sometimes I wish I had listened to my gut and switched majors to illustration earlier, because it would have saved me a lot of emotional turmoil.
But, I wonder if, had I done that, would I have learned the lessons I live by today?
I came out of high school in northern West Virginia, where I breezed through school and never failed at anything. I was accepted into this prestigious program and, two years later, I was struggling. Before that point, I never had the feeling of not being good at something I was trying really hard to do well in. The curriculum demanded a certain style, a form-and-volume-based drawing style. When I wasn’t able to make it work that way, I was simply told I was wrong, without any other explanation.
It’s the first time I felt like my style wasn’t a good fit for the program. After all, I was getting the feedback from professors via their critiques and my grades that it wasn’t working out. I was even told that I should think about a different career, something that was not creative. I was a wreck!
So here I am a few years later, and I’m an illustrator and an animator. The Adobe creative residency program plucked me out and has been sponsoring me for nearly a year and will continue to April. It wasn’t until I switched over to illustration that things began feeling more comfortable for me. All along, I knew it would be a better fit, but there was this stigma at school that illustration was for the weak, that it was the easy way out.
It wasn’t until a classmate made the switch that I realized I could switch, too. In the end it added up to another year of school, but it was worth it. I started rebuilding myself and my work from the ground up, because I had a clean slate and a fresh start. I now make work about what I like, by doing it how I like to make it. I’m building an online community (my streaming channel) around this idea, for others who might not have a good working or educational space, like I didn’t for a long time. I can do what I do now because of what I learned in both animation and illustration.
I rationalized the excuse due to cost and timing, but in reality I was just scared.
Art director, Shake Shack / New York City
If I had to do it all over again, I would have studied abroad for a semester as an undergrad at Cal State Long Beach. I was a fine arts and illustration major. We had opportunities to study abroad in places like Italy. I could imagine myself drawing and painting in front of an original Michelangelo. At the same time, the required art history course I was taking covered the Italian Renaissance. I picked up some pamphlets and did some research; it seemed like the perfect opportunity.
But once I learned how much more expensive it would be to travel abroad and that it would delay my graduation, I didn’t go through with it. In my head, I made excuses – too expensive and not the right time. In reality, I was just scared.
I moved to New York City for grad school and got some experience being on my own. After that, I didn’t want to miss another opportunity to travel abroad. When I started to freelance, I realized I could work remotely – from my apartment in New York or somewhere else. That’s when I knew I had to take advantage of the opportunity. I started to tell my friends that I planned to go to Paris for a month. By putting it out there, it made me accountable. In September 2011, I traveled to Paris for a month and even went to Morocco for a long weekend.
Looking back, I should have stayed longer! Traveling and challenging myself to be in an environment that was new to me was one of the best things I could have done personally and creatively. It is always inspiring to see what other creatives are doing out there in their own city, even if they can’t get on a plane for Europe. Of course, you should go to the local art museums. But there’s something to learn from walking the aisles of the grocery store, checking out the packaging. Now whenever I have the opportunity to travel, I make sure to take it.
I would have still sacrificed my personal life at times to jump-start my career.
Creative director, Bloomberg Businessweek / New York City
There was a certain point earlier in my career where I was basically sacrificing almost all of my time to work, and I didn’t have a lot of time for friendships and relationships and things like that. Some people might say they regret that, but I actually don’t. Early in your career, you’re proving yourself, and you just have to work five times as hard. There were days where I’d work a full day at one job, then come home, lock myself in my room and work on two other freelance client projects. Partly that’s because you have to work like crazy to make ends meet in an expensive city like New York. But also, I never considered myself naturally talented.
When I was an associate art director at New York, I worked my first 24 hours straight. The magazine is known for these immersive infographics, and I had to design a four-page infographic on my own. I remember very distinctly being in the office one day and then it was 7:00 a.m. [the next day] and no one was in the office yet. And I was like, I need to get out of here before someone sees me. Working extremely hard is always a risk. If I was out in the streets or something, I would have been like, Oh man, I wish I had spent more time with my friends. How I wound up at Bloomberg Businessweek is an amazing stroke of luck. But obviously I owe some of that to all the work that I did. So yeah, I do feel in a lot of ways happy that I put in the time.
I used to think that a concept would be more valuable the longer I worked on or thought about it.
Cofounder, onformative / Berlin, Germany
The biggest piece of advice I have for someone who is faced with an important decision is don’t hesitate if it feels right. Take the example of how we started onformative. My cofounder, Julia Laub, and I decided to start the studio seven years ago without having met in person. We had been talking online for about a year, but never worked together or spent more than a day in the same room. Still, we had the feeling that there was an opportunity for us if we moved quickly.
That was a big decision for me, since I moved to Berlin from the south of Germany and founded onformative a few months later. Maybe it was a bit naive of me to decide to move so quickly back then, but I think if we had thought about it too long, we might have missed our chance.
The idea of not overthinking something can apply to everything from a big decision, like moving across Germany to start a business, to making new hires and even working on individual projects.
If you think about ideas or concepts, they’re not necessarily going to improve the longer you think about them. That was a hard thing for me to learn, because earlier in my career, I used to think that a concept would be more valuable the longer I worked on it. After a while, you learn that the simplest idea is usually the best one. Remember, just because a project feels easy for you doesn’t mean it feels easy for someone else. A lot of the time that’s just proof of why you’re doing the work you’re doing.
Although I was continually diving into the unknown, I grew, and I had a ton of fun.
Design partner at Khosla Ventures / Menlo Park, California
After I graduated with my master’s degree in industrial engineering and human-computer interaction, the advice some people gave me was to join an established company, like Hewlett-Packard, to learn the ropes and then go on to a company that had a higher risk and higher reward factor. But I decided to become an interaction designer at Netscape, which had only started two years earlier. My friend’s parents told me they couldn’t believe what I was doing by choosing Netscape over a Hewlett-Packard, and that I was making the wrong choice. However, I knew that my life didn’t have time to wait. If I had gone to work at HP at the time, I would have missed my window of opportunity at Netscape. When I reflect on my career, this is a theme that I have seen play over and over again – diving in to build something that has never been built before. That is my tribe, and those are my people – right in the middle of where it feels like the action is happening, even if people looking in from the outside can’t fully understand my decision. When I was looking for my next job after Netscape, I chose between Yahoo!, Excite, Webvan, and a couple of design firms. I chose Yahoo! because they had the best mind-set for making the internet useful and accessible to everyone. The company was filled with fun, smart people who had a lot of heart and genuinely cared about serving the people who used the site. Most of my design peers, though, thought of Yahoo! as a Web directory that lacked any design. They didn’t see that Yahoo! was a useful place to start your internet experience, that it could grow into something more interesting and bigger, and they couldn’t understand why I would want to join the company, because it didn’t obviously value design.
Yahoo! proved to be a great career move for me. No other internet company was using human-centered design practices to conceive and create their services, and my boss gave me tremendous leeway to lead our efforts and figure out how to do this on internet time, at internet scale. Yahoo! became the premier destination for people all over the world on the internet. We redefined what it meant for a product to be well-designed – it wasn’t just about aesthetics but, more importantly, the extent to which it solved people’s needs and was easy to use.
My decisions to join Google after Yahoo!, then Udacity, then Khosla Ventures were all motivated in the same way: go where I can work with great people, follow my curiosity, and choose the path with the most heart. When I get asked for career advice now, these are the same factors that I ask people to consider.
Each experience we have in life, each challenge we accept, sets us up for the next endeavor we take on. My experience at Yahoo! taught me how to build and scale design teams and understand at a deep level the impact organizational design has on a company’s product design. At Google, I learned how to operate in a bottom-up, engineering-driven environment, so that we could engage engineers and product managers to think like designers. At Udacity I gained tremendous empathy for early-stage startups and their occasional need to pivot while they find product-market fit. These experiences have equipped me with perspective and insight that allow me to add value to the Khosla Ventures portfolio as a design partner.
If I had to do it all over again, I would take the same journey. Although I was diving into the unknown with no guarantees of what the future would hold, I learned something from each experience. I grew, and I had a ton of fun.