Confidence is Overrated: Debbie Millman’s Road to Success

Debbie Millman: Confidence is Overrated
Lettering by Debbie Millman

As the voice and founder of the Design Matters podcast, Debbie Millman has interviewed designers, authors, musicians, photographers and entrepreneurs learning not only the secrets of their successful journeys, but also the failures and rejections they’ve experienced along the way. Her keynote for the HOW Design Live Conference, which was streamed live here on Creative Live, is called, On Rejection: A Cautionary Tale of Dreams, Hopes and Rejection. In her talk, she draws from her own experiences of rejection and despair through revealing and sometimes hysterical anecdotes.


Here, we asked Millman about how vulnerability and courage have played major roles in her successful creative journey, along with the disappointments and missteps along the way. She holds nothing back.  

You’ve built your career as this brand strategy leader at Sterling Brands, but in recent years, you started publicly sharing your personal art and it’s very revealing. How did you summon the courage to do that? 

That’s an interesting question, as I don’t really see this as a courageous act. I think that something is only courageous when it feels scary. By the time I started sharing my personal story and art, I was grateful to have the opportunity and platform in which to do it. It took a long time to get here.

I recently met a very engaging young person and asked her what she wanted to be when she grew up. Her answer astounded me, both in its optimism and its confidence. When I asked what she wanted to be when she grew up, she answered, Everything.

I was the opposite. I went through a whole series of career aspirations, but never felt that I was good enough, smart enough, pretty enough, or thin enough to do much of anything, let alone everything. In 1979, when I went off to college, I decided that majoring in English Literature would ultimately give me the most options to choose from, and I minored in Russian Literature because I loved Dostoyevsky and Tolstoy. I often joke now that I got my college degree in reading.

Despite my grand dreams of being an artist or a writer, the dominant influencer in my decision-making was the imperative to be utterly self-sufficient. I never once felt that I had what it took to make a living making art. My only marketable skills were the tasks I learned working at my college newspaper: basic design, layout, and what we called “paste-up” of a publication (since we used an actual mechanical, not a computer, to compose the pages). My first job was in the design department of a cable magazine earning $6 per hour.

I lived in a fourth-floor tenement walk-up in Manhattan and because my paychecks were so low and my rent was so high, I had to make a monthly decision about what I would use my money for: eating, rent, or paying off my student loan. When the first September came around after graduation and I sensed autumn in the air, I knew I had compromised. But I felt trapped. I could barely make enough money to pay my rent working as a commercial artist! How could I ever conceive of making a living as an actual artist? I assumed it would be harder and never considered I had any other choice.

Debbie Millman: Confidence is Overrated
Photo by John Madere

About a year later, I was offered a position in a real estate development company in Westchester as the business’s Director of Marketing. It was a big title with a big increase in salary—now I would be making $25,000 a year—and it came with a car. I took it. Everyone congratulated me on my good fortune and the potential of this prestigious new opportunity. But on my first day at the new job, I hated it so much that when I finally got home after the long commute, I climbed into bed, pulled the blankets over my head, and cried. I hated my new job for the entire time I was employed there. I loathed the work, real estate, and my mean boss.

And this was SETTLING! This job and the job before it were jobs I had taken because I thought pursuing my dreams of being an artist or a writer were too hard. WHO WAS I KIDDING?

Every job is hard. Design is hard, marketing is hard, and working at McDonald’s and Starbucks and Walmart is hard.

Call out: Why does it feel “easier” to do something we don’t love than to do something we actually feel passionate about? I think we lose our courage to pursue our creative dreams when we feel that the only way we can make a living is to conform.

I realize now that making a living doing what you love requires a personal belief that you have something meaningful to contribute. What makes this particularly difficult is that making a living doing what you love doesn’t come with a real “rule book.” There is no single process for anything. For example, you may have a process for being creative, but the actual act of living creatively is organic and (nearly) involuntary: You have to do it—you have no choice—or a part of you dies. So if you’re considering settling because going after what you want seems too hard to do, remember that hating what you do every day is even harder.

Were you ever worried that your art might affect your branding career/reputation at Sterling? Your art is so personal, and you’re basically letting all the wolves in. 

Not at all. Branding is all about being proudly authentic. I believe you need to know how to talk about your work and you need to know how to talk about yourself and what you do, even if you are afraid, even if you are nervous.

Many years ago, in The New Yorker, I read an article about Barbra Streisand. The reporter asked her manager what her greatest talent was. He replied that her greatest talent wasn’t singing, directing, acting, or even her longevity in the business. Her greatest talent was doing all of those things while experiencing debilitating stage fright. Despite the fact that she was terrified of performing, she did it anyway. She did it “as if” she wasn’t afraid.

Being nervous or scared about expressing what you want or who you are is not an excuse to NOT do it. I believe you should try with all of your heart to do it anyway. Try to do it “as if” you are not scared or nervous. You can’t wait to be less scared or nervous. The only way to alleviate that feeling of being scared or nervous is actually doing the thing you are scared and nervous about over and over until you get better at it. Very few people ever do something the first time and do it perfectly right out of the gate. Being nervous and scared is normal. But the fears will lessen over time as you get more and more comfortable actually doing the thing you are scared of doing.

Were people critical? What was the feedback?

I have connected to people more deeply and more authentically. As Brene Brown, author of three #1 New York Times Bestsellers: Rising Strong, Daring Greatly and The Gifts of Imperfection, suggests, the best way to experience empathy is to look at someone in the eye and say ME TOO. I’ve experienced a lot of that and it is incredibly gratifying.

What is it about being vulnerable that is so difficult for most people? 

I think people are ashamed of not being perfect or totally in control or to show a lack of confidence. After an interview with the great writer Dani Shapiro on my podcast, Design Matters, she and I started to talk about the role of confidence in success. During the conversation, Dani said that she felt confidence was highly overrated. I was instantly intrigued. Most overly confident people, she said, were really annoying. And the most confident people were usually arrogant. Over-exuding confidence was a sure sign that a person was compensating for some type of internal psychological deficit.

Dani argued that courage was more important than confidence. When you are acting from a place of courage, you are saying that no matter how you feel about yourself or your opportunities or the outcome, you are going to take a risk and take a step toward what you want. You are willing to allow yourself to be vulnerable—in showing your art, starting a business that might succeed or fail, having an opinion on something, being in a relationship. You are not waiting for the confidence to mysteriously arrive.

I believe that confidence is achieved through repeated success. Repeated success provides a foundation that exudes confidence. Really smart people don’t have to prove that they are smart; they exude intelligence. It isn’t heavy-handed or showy. You can’t tell someone you are smart or intelligent and expect they will automatically believe you. Authentic confidence is more internal; it isn’t cocky or arrogant. If you have to “tell” people you are confident, chances are you are insecure about its authenticity.


Confidence is achieved through that willingness to continually put yourself in vulnerable situations. Success or failure has nothing to do with it. I know people who launched a startup that tanked, had their art project excoriated by critics, or went through a difficult breakup, yet they’re still confident; they see the experience as something that helped them along their path, and they remain willing to continue on it. Perhaps confidence comes from a certain equanimity that arises from not putting too much stock in whether you’re celebrated or rejected. “Failure” is an arbitrary label, and the most psychologically healthy people I know tend to reframe it as an experiment that gave them valuable insight. So celebrate your flubs, your rejections, your vulnerability—they mean that you’re taking the risks necessary to grow.

I believe that the act of being courageous—taking that first step—is much more critical to a successful outcome than the notion of feeling confident while engaged in the process. Courage requires faith in your ability before you experience any repeated success. But that doesn’t mean taking that first step will be easy. It won’t. Taking ANY step for the first time is difficult and there is a tremendous amount of vulnerability and nervousness you are likely going to experience. But experiencing that vulnerability and nervousness doesn’t give you an excuse not to take the step.

Why is it important to be vulnerable in the arts and design? 

Vulnerability is the birthplace of creativity. If you aren’t able to be in touch with and express universal human feelings—and this includes all the good and “bad” stuff—you won’t ever be able to connect authentically.

There are some who see vulnerability as a weakness. Why do you think that is? 

My guess is that they are afraid of being rejected or they are ashamed of what it means to be authentically who they are. I believe the real weakness is in criticizing others for whatever genuine human emotions they feel.

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Emily J. Potts has been a writer and editor in the design industry for more than 20 years. Currently she is an independent writer working for a variety of clients in the design industry.