Redefining creative failure

I want to talk about the role of failure in our process to write and share our work. I will frame this in the stories of two people who create with joy, and took the initiative to reframe what failure meant in order to live a life filled with creativity and a wide network of people who appreciate what they create.

It makes sense that we work hard to avoid failure. Often, we seek “best practices” to ensure our efforts don’t fall short of expectations. But our fear of failure is more than that, isn’t it? It’s that often we feel a sense of embarrassment or shame when something doesn’t work out as we hoped. Why address this? Because I worry that fear of failure stops people from writing and creating. It stops them from sharing. It prevents new writing and art from coming out in the world, and how that art can truly change someone else’s life for the better.

Creating and failing is a core part of the work we do as writers. It is how we discover our creative vision, learn to share, and find ways to connect our art to those who will love it.

I recently talked to two successful creators, Melissa Bernstein and Skeme Richards, whose stories are incredibly inspiring to me.

Let’s dig in…

All around my living room are toys that my 3 year old plays with that have two names on them: Melissa & Doug. That is the name brand of many of the wooden toys he loves. Well, recently I had a chance to chat with Melissa, who to my surprise, is a real person.


Melissa BernsteinIt’s easy to look at the life of Melissa Bernstein and just see the incredible accomplishments. As the co-founder of Melissa & Doug, she has designed nearly 10,000 products, and built a $500 million dollar company.

But that isn’t what Melissa wanted to talk to me about. She just released a new book where she shares her own lifelong journey through anxiety, depression, and despair. As we discussed her life and career, I asked about failure. Her reply:

“Failure is my favorite thing to talk about. Perfectionism nearly killed me, because I thought that anything short of 100% meant that I was worthless. I came close to believing that I wasn’t worth being here.”

Then she reframed how she thinks about her career:

“[I am] someone who has to fail for a living. A consultant we hired once calculated my ‘failure/success rate’ because they believed that if they lowered my failure rate, Melissa & Doug would be even more successful. They calculated that in three years, I was successful 40% of the time. Which means I failed 60% of the time. Which I absolutely loved. That became such a source of pride for me, because I realized that I failed more than I succeeded, and yet we are a $500 million dollar toy company now.”

To hear Melissa talk about failing 60% of the time, and that leading to success is astounding. She continues…

“Behind my desk at work, I have a wall of failure. I call it my ‘greener pasture wall.’ It’s about 500 to 1,000 of my favorite failures. The ones I truly thought were going to be the biggest thing ever. What you realize that the line between success and failure is so fine. It’s like a spider web. Failure is actually a fluid process from failure to success that every failure — if you can have the courage to look at it for what it is — you can see that is a tiny little thing that you could have tweaked. And I did. So many of my failures, I brought back, sometimes a decade later, and became a huge success. Or sometimes I tweaked a tiny little thing, like the packaging, and they became huge successes. Sometimes I tweaked the wording, how we communicate what it is and what it does, and became huge successes. Other times, I changed the price point. I began to see it not as buckets of success and failure, but as a rich process that went from spark all the way, following it, to failure, to plowing through the failure, to get it to be a success.”

Within what she shares here is so much of the creative process. As a writer, you may recognize aspects of the editing process that resonate with you, how you have reworked a chapter again and again, before finally hitting upon the missing ingredient.

But this also applies to one’s author platform and how we share what we create. All day I work with writers on this, and “success” is not just following a script or a “best practice.” It is the act of creativity, of honing, of trying again and again to find what works, and connects with your ideal audience.

The book Melissa just released, LifeLines, digs deep into this topic. She talks honestly about that space that I think so many writers and creators get lost: that line between what we create and our identity. She described her own journey this way:

“I do have every material bit of success you can imagine. In conventional definition, I’ve achieved it all. We have a $500 million dollar company, I have six children, I have every material need you could ever want, it is all perfect. But what I realized so clearly is that if you haven’t accepted yourself in totality and truly been able to revel in who you are authentically, you will never find a sense of fulfillment and peace.”

That word, “authenticity” comes up a lot when people talk about social media and marketing. What is amazing about seeing her book is that it is, well, kind of unusual. At 637 pages, it weighs more than 3 pounds, much more than longer books. Why? Because the page stock is ridiculously thick. It has an embossed cover, sewn binding, and throughout the book is not just the prose, but loads of verse and more than 100 high quality photos of nature. She laughed when I asked about this, understanding why I was asking:

“I could have created a commercially successful book. We sell 65 million toys a year. I know with my eyes closed how to create a product that will sell a lot of units. I could have easily made this that quintessential self-help book, tell the cute stories about my kids and forming Melissa & Doug, and make it that rags to riches story, that maybe would have been a best seller. But I know so deeply in my soul that was the antithesis of what I wanted to do. That is what I had done for 32 years at Melissa & Doug, to appeal to a lot of people through those toys. And this wasn’t about that at all.”

But then she said something so inspiring, and so emblematic of why I work with writers and love books:

“This book was about, for the first time, sharing who I was. And with the courage to do that with vulnerability, that it would encourage others to do the same thing. I wasn’t speaking to the masses, I believe myself to be speaking to the creative misfits in the world. Those who feel so stigmatized for being that way, and that the world will not want what we create. “To finally be able to give brith to verses and journal writing that came directly from the pain I felt my whole life, was accepting that part of myself for the very first time.”

I mean, there it is. That is why we create. That is the power of writing of art, and the value of a book. She said of the book: “I’ve created close to 10,000 products for Melissa and Doug, but creating this book was the most incredible experience of my life.”

You may think that with her success, with being the head of a company, that meant she had a lifetime of feeling free to be herself. But she described it quite the opposite, and it underscores why this book is so powerful to her:

“I was never trying to be authentic and honest. I knew that doing so would be so stigmatizing, because my true self is really overly sensitive. I had never accepted that in myself. It made me odd, it made me weird, it made people give me this look that is a combination of terror and disgust. A look that made me say, ‘Oh my, I’m showing them too much.’ It made me, from a very early age, hide all that stuff from the world, and adopt a facade of ‘I’m fine today, I’m perfect today.’ I felt I could never share [my authentic] qualities. Something in me wanted to fit in.”

Along with the book, she has created a LifeLines community. Her goal is to show people that you are not alone, that you can create a sense of purpose and hope in your life, and that accepting who we are is a critical part of our journeys.

You can listen to my entire interview with Melissa Bernstein here. At the end of the interview, she shares her email address, promising to give a direct reply to anyone who emails her.


Skeme RichardsI want to share the story of one more person who I met recently, DJ Skeme Richards.

When Skeme was 10 years old, he got his first set of turntables. He says, “I would buy records with my lunch money,” skipping lunch to instead save up buy the music he loved. His first DJ gig was when he was in 6th grade, providing the music for the big party at the end of the year, carrying his equipment three blocks to the school. I asked how he got this opportunity, and he said simply, “I just asked.” That is so powerful to me, he didn’t wait to be chosen by others, He saw a chance to play music in front of a large audience, and he created the opportunity that would define his life.

As he went through school, he told me how he found mentors and honed his skills as a DJ turned into a finely honed skill as be became a teenager. But then he said something that really surprised me. I asked about what career he thought he wanted to pursue when he was in high school, and his answer was immediate: “Not DJing.”

Instead he got a job at a teleconference company, saying, “Suit and tie every day, making amazing money, 18 years old.” For more than two decades, these were his days, moving from that company to Bell Atlantic as a directory assistance supervisor, to the SmithKline Beecham clinical laboratory, and finally to BMW.

Why am I telling you — the writer and artist — about these jobs? Because I was inspired by Skeme’s wisdom in this choice. Too often, I think our creative dreams die because we equate “success” with it as being a full-time career filled with monetary reward that derives directly from our art. But sometimes that can kill one’s creative muse.

So much of managing our own narratives of failure can come into play when we get clarity on our creative goals and expectations. Skeme knew this instinctively. Instead of trying to build a full-time professional career as DJ, he said, “I never wanted this to be my 9-5. Music is the hobby I do every day of the week. Music kept me going.”

Yes, on nights and weekends, he was shopping demos and finding ways into the industry. But each day, he went to work at his job and developed a solid base from which to pursue his creative passion.

Something I noticed in what Skeme shares on social media is this: Skeme lives with total joy and celebration of his creative work and what inspires him. He also seems to regularly connect with others who appreciate the work he creates.

Something happened midway through his career. For the 80s and 90s, his DJing was mostly focused on his local market: Philadelphia and New York. But then the world seemed to open up. Around 2003, he began traveling around the world for DJing events. It started in London, where he paid his own way to fly out.

Since then, he has traveled all over the world playing shows and connecting with like-minded fans of the music and culture he loves. He says, “me going to work every day, funded my tours to Japan, funded my tours to Europe.”

In 2012 he took a corporate buyout and left his job. What did he do next? He went on a monthlong tour of Japan, and then booked gigs from April through October of that year. He says of the life he created for himself: “I’ve built up a network of people where I can go anywhere I want to go, with a phone call. I can just say, ‘Hey I want to tour there,; and make it happen.”

I asked about how he has adjusted in the past year, when travel and gatherings around music wasn’t really possible. He explained how he used the time to catch up on creative projects, and talked about this was an opportunity for reinvention in his work. He also said that, “Social media opened up a whole world,” of connecting his music and passions to like-minded people.

You can listen to my entire interview with Skeme here.