How They Got There started out as the book I wanted to read when I was in my 20s, fresh out of school, looking for my first big break. It charts the career trajectories of 14 fantastic designers who got a few big breaks of their own and, through talent, hard work, guile and guts, turned those opportunities into big successes.
Along the way, I realised how universal their stories and lessons are, not just to those new to their careers, but also to those of us who are looking to reinvent ourselves – which should really be all of us, all of the time. Here are a few of my favourite excerpts.
01. Alex Cornell
Alex Cornell co-founded Firespotter Labs with veteran entrepreneurs in the midst of earning a graduate degree—and how he hesitated to reveal that to his co-founders.
"I was working as a contract designer with a startup in New York called Signpost, and it was a great, really fun, typical startup experience, working until four in the morning, eating ramen noodles, the whole deal.
"Around that time, when I came back to California, my friend Wesley Chan at Google Ventures introduced me to a guy named Craig Walker, who was leaving Google to start a new company. He'd started Google Voice and was leaving with exciting ideas and a few great people as well. They all three had just quit their jobs. We started hanging out and messing around with ideas.
"But I remember, I didn't tell them that I was in graduate school, because I was embarrassed. I wanted them to see me as available, as a resource. Eventually that professional relationship started to formalise, and there was talk of 'Hey, what if this was a company? We could actually turn this into a thing.' To work with those guys I had to drop out. I remember when I told them that. It was a funny moment."
02. Dan Cederholm
Dan Cederholm, co-founder of Dribbble, started out with ambitions to play rock music, and is a largely self-taught designer. That has hardly held him back, but in our interview he talked about how his lack of formal training still weighs on him in some ways.
You said something before about always feeling that you were going to be found out as a fraud. When you were freelancing, because you did it for a number of years, did you ever feel like, "Okay, now I'm legit and nobody can say otherwise"?
"Honestly, no. It could be because of not having a degree or being formally trained in design. Or going back to my childhood and not understanding what makes someone a designer. I always felt like a fraud. That's kind of cliché, but it is true. I think that's also healthy, in that it keeps you on your toes and it keeps you wanting to learn more. If you get too comfortable, things start to get stagnant and maybe the work would decline. Always being worried about your capabilities has a negative part and a positive part."
What are the positive parts? It pushes you harder?
"Yes, it pushes you to create and try to do the best you can and to care about what you're doing, regardless of who it's for or what it is. Because when you stop caring about the details, it shows and maybe it's time to do something new at that point."
03. Nicholas Felton
Nicholas Felton, author of the famous Feltron Annual Reports and co-founder of Daytum, talked to me about searching for the specific flavour of design work that he wanted to focus on, and how it took trial and error to finally arrive at infographics as a medium.
"I didn't think I would be a generalist forever. I knew that being a generalist wasn't a way to make myself unique. So I kept finding things that spoke to me. I thought maybe it would be making logos and brand identity work. For a while I was into designing typefaces and thought maybe that's where I could become an expert and settle into a niche. I didn't want my income to be reliant on doing a day's worth of work. I was interested in the typeface approach, where you could build something and then get a trickle of income off of it. I did release one typeface through T26, and that was not the case [laughs], so I had to re-evaluate that approach…
"When I started working for myself, the personal projects dipped again but over time they started increasing and increasing. I was making a lot stuff. The typeface through T26 was a personal project that didn't gain any traction. This was the era of pixel illustrations, so I was playing with that. I made travel logs whenever I would go traveling. None of those projects found a large audience."
Next page: four more pieces of expert career advice