Designers on Career Path, Anti-Mentors and Creative Satisfaction

A conversation


In September of 2014, I had the pleasure of co-hosting a week-long online conversation with a group of designers linked together by dim sum and John Maeda. Aaron Perry-Zucker and I kicked off the discussion with a few questions about work/life trajectory:

How do you think about your career path? What was the plan when you set out and how has it changed? What roles do education and creative satisfaction play?

Many of the designers mentioned bumpy rides, wrong turns and chance when describing their paths so far. Most also talked about a creative drive that has served to propel them along their path, even if serendipity helped along the way.

Uday Gajendar described these factors so eloquently:

I’ve learned that design career path evolution involves an iterative combination of self-reflection around personal interests & talents (what am I missing, what am I gaining) with serendipitous intersections with opportunities that foster growth and learning (upon those areas self-reflected upon), with guided trajectory anchored by core areas like vision/strategy/culture/process/leadership/tools, etc.

Aaron talked about his strong desire to be in the driver’s seat of his own career. This conviction has served him well since graduating from RISD in 2009, taking him from working on Design for Obama, to starting his own design agency, then launching Creative Action Network with help from Matter.vc last year. As Aaron put it:

I never expected to call myself an entrepreneur but love how it can pretty much mean whatever I want it to. I’ve come to think of it as a mix between community organizer and compulsive maker. But it currently satisfies what I set out to find when I left school: the ability to simultaneously be my own designer and client (and make my parents think that I have a real job).

Karin Hibma of Cronan offered some advice for creative people who share this spirit of entrepreneurship:

As a life long entrepreneur, I enjoy getting to know some of those most creative minds in life, business, the arts and sciences; I study them deeply, serve them as clients — and it’s my pleasure to be their friend, colleague, employer and, for my sons, their parent. Being calm and centered in yourself allows you to appreciate the self in others. To mutually work to enhance that, achieve mutual goals, surprise yourself and others with the “aha!’s”

Alessandro Sabatelli talked about the “bumpy ride” of his career path, from film and computation to computer animation production, to freelance work, with VJ-ing on the side. He joined a startup, was acquired by ETrade, moved back to freelance, ran his own company doing installation work for high profile clients, then finally joined a product team at Apple. In spite of a career trajectory that looks like a success on paper (or, LinkedIn), he said it hasn’t been easy:

While I’ve been fortunate to have worked on some amazing things with some amazing people, I’ve had to fight very hard for my work. This not only includes the work I do on my own, but often having to inspire others to work equally hard in order to produce quality work.

My own path has also been a roller coaster ride, but I feel I have been lucky to meet the right people at the right times. At several times in my path, I’ve been fortunate to be in the right place at that optimal time when talented and creative people come together to create something special, what Uday called “serendipitous intersections.” I’ve learned to recognize and appreciate those times — they are precious.

John Maeda brought up the importance of “anti-mentors,” the people in your life who spur you on with their words of criticism and doubt. John mentioned a professor he had in Japan who called him into his office for 30 minutes to tell him he “wouldn’t amount to anything.” [Author’s note: Prof may have been wrong.]

Sarah M. Oppelt talked about an influential anti-mentor of hers:

I had a teacher back in art school that when I put my drawings on the wall would say, there is just something makes me inherently uncomfortable about your work (and not in a good way). Isn’t that what art and design is meant to do? It turned into some of the best feedback I ever got. Being a designer is often about trying things that make you uncomfortable.

These anti-mentors can motivate you in ways that your biggest supporters can’t.

Clare Corthell described her career path as a series of steps: “Learn, learn, be brash, learn, be humble, learn.” I found one of her remarks a great reminder for anyone confronting doubt about the next step in their career path. Clare wrote:

A friend who advises many startups explained recently that when people ask for advice, they’re really asking for permission. Our social compulsion to acquire approval runs incredibly deep. Waiting for permission is just another thing you’re allowing to prevent you from taking the next step.

Here’s to seeking out creative satisfaction and not asking for permission, to listening to the mentors and anti-mentors who push us, and to remaining open to being surprised along the way.


Thanks to all who participated in this and other seminars. I’ve found it personally helpful to be sharing our experiences with peers. As John puts it: Designers crave community. It’s a group effort, but I look forward to building and strengthening our community, one story at a time.

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