I started a podcast last year to talk to people who have designed inspiring lives, who are successful doing work they love. What I wanted to understand is how do they do it. What are their tools, tactics, and tricks that can help inspire me and my listeners? How do these successful people deal with fear and  failure, find excitement in their work and have so much confidence? At the end of season one, I went back and re-listened to the interviews.

Here are the top five lessons I've learned.

1. When stakes are high, levity and playfulness are critical to the process.

Jocelyn Wyatt is the CEO of ideo.org, a nonprofit organization focused on how design can change the social sector by putting an end to global poverty. She says that she sees levity fly out the window when you're designing to solve a social problem and the stakes are high. People tend to approach serious problems seriously which is the exact opposite of what actually is needed. You need joy and optimism to believe the situation can be different. She says because the stakes are high, levity and playfulness are critical to the process. "We can be our best selves and we can unlock the best in the partners that we're working with, and in the communities where we're working, when we do bring that playfulness and joy, rather than bringing sadness," Wyatt says.

2. To fight fear, put yourself in a place where you can't back off. 

Paolo Antonelli, the fearless senior curator of MoMA's department of Architecture and Design and the director of R&D, is not immune to feeling fearful. She says, "My life is ruled by fear." Her way of confronting her fears is by putting herself in situations where she can't back off or change her mind. Like the time as a young journalist and terrified, she interviewed architect Frank Gehry. Once she buzzed the door bell, it was too late to back out. She had to walk through door and conduct the interview. "If you have to jump off a cliff, you're already halfway through, so you better jump well," Antonelli says. 

3. If you are not making enough mistakes you are not trying hard enough. 

When I asked Amit Gupta, entrepreneur, designer and founder of the wildly successful Photojojo, what advice he'd have for my teenage daughters he said, "make lots of mistakes." Gupta believes that much of the good in his life comes from doing the wrong thing, failing and trying again. "The perfectionist is the worst possible thing," he says. "If you are not making enough mistakes you are not trying hard enough."

4. If you don't want boredom, keep trying new things.

Every time Stefan Sagmeister, one of the world's leading graphic designers, repeats himself, there is less excitement. He admits that it makes him lazier and the work worse. And that he gets bored. That is why he's developed this idea of the seven-year sabbatical. Taking a year off every seven years to reinvigorate himself, try new things, and to take on new activities, like filmmaking with The Happy Film. With each sabbatical creating the start of a new chapter in his life and work. 

"Try out as much stuff as possible. See what you like and see what you don't like," Sagmeister says. "Stick with the stuff that resonates and leave the other stuff alone. And here and there go over your comfort zone."

5. Confidence is overrated. It's courage that is needed.

Debbie Millman--author, educator, curator, and the host of her own podcast, Design Matters--makes a very useful distinction between confidence and courage. She advocates that you don't need the confidence to try to do something; you just need the courage to take the first step. "Courage is the birthplace of confidence," Millman says. "[It's when] you feel that you can take that first step no matter what the outcome."

I look forward to sharing more of my learnings from my podcast with you. Now, go out and talk to someone you admire and see what you learn.

Published on: Feb 26, 2018