Fearless: Rebecca Minkoff on Going After What You Want

Rebecca Minkoff book cover

“I’m not going to let fear take control of this decision.”

When Rebecca Minkoff arrived in New York City at age 18 with two suitcases, an internship that paid minimum wage, and nowhere to live, all she knew was that she wanted to be a designer. After years of struggling to get by, Minkoff’s business took off in 2005 with her Morning After Bag: A chic, edgy handbag that could hold a pair of dancing shoes and seamlessly transition from day to night to day again. Since then, Minkoff and her sophisticated, timeless designs have become industry icons.

In her debut book, Fearless, Minkoff lays out her 21 rules for overcoming fear and achieving success, whether personal or professional. Illustrated through stories from her life, Fearless reads like a conversation with Minkoff herself — funny, straightforward, and frank.

Minkoff talked to KCM about pulling her business out of the pandemic, knowing when to give up and when to keep pushing, and the constant challenges of entrepreneurship.

Katie Couric Media: How did the idea for this book come about?

Rebecca Minkoff: I’m sure Katie’s familiar with the “You should write a book” thing people say sometimes. And I was like, “About what? What would I write about? I’m not going to do a coffee table book. I hate coffee table books: They collect dust.” But a friend of mine who was actually an author said, “You have a vast amount of experience and 20 years of knowledge. How great would it be to impart that to other people?” The idea that you could have a book that’s entertaining and fun to read, but also give you some guideposts to help you on your career or your personal journey — that I could wrap my head around.

How did COVID-19 influence the book?

The book deal was signed at the end of 2019, and I started writing the bulk of it in January, February, and March. Then COVID hit, and as I’m sitting there seeing my company’s sales plummet by 70% due to canceled orders, I was thinking, Okay, what did I have to do to be successful? As I was writing and remembering what it took, I was also having to rebuild my company, so it was a really interesting time to reflect.

How did you decide which moments of your life to weave into the book?

I think that that was probably the hardest part, because you want to tell the whole story. You want to give your audience so much more, but I was thinking, “At the end of the day this has to be about helping her. So let’s do it chronologically, but make sure that every story has something she can take away.” That was how I wanted to shape it because it’s not a memoir: It’s technically a business book. 

It seems like a lot of your rules involve a tug of war between giving it your all, but knowing when it’s time to move on. How do you balance the contradictory aspects of those rules?

I definitely felt important that I wasn’t telling someone to go for it no matter what, because sometimes that’s just not how things go. I wanted to be like, “If you’re going to give it your all, and you’re going to try your hardest, here’s some guideposts when you do have fear and you want to quit. But shit, if it’s not working and it’s still a failure, let it go.” We had to let go of a lot of things because it didn’t matter what we threw at it — it was not gonna work. I think it’s important to recognize that we should fail fast, because you might be able to move on and make something new far more quickly. 

Let’s talk about self-reflection versus self-care in dealing with burnout.

I like the massage and the manicure-pedicure is as much as anyone else, but you know the reasons why you’re stressed or wanting to get away won’t be solved by them. We need to distill down what’s causing the problem: Is it that you’ve lost your passion for what you do? Is it a toxic work environment? What are the triggers? 

Burnout wasn’t a term when I was starting out. I was so passionate about my career and I worked all the time. That’s all I wanted to do. Burnout is not just something that “happens.” There’s actual real reasons why you’re experiencing this and you have to reflect and figure out those reasons. 

You make it very clear that “work-life balance” isn’t an effective way to talk about managing your life as an entrepreneur, wife, and mother, but you do talk about “life design.” Can you tell us more about that?

I get asked all the time, “How do you have balance?” First of all, why are we still only asking women that? But also, men have never had balance. The fact that anyone thinks it’s a word that should be directed towards a parent is a fallacy. As hard as COVID has been on people and parents, what also has been stripped away is the hiding and segmenting of your life: People know that your kids are on Zoom in the background, or they’re going to interrupt you for their smoothie. It’s about figuring out how you optimize your life for you, without looking at what other people are doing. What do you need uniquely that makes you happy? And I want to underline that this isn’t something that happens overnight.

You talk a lot in the book about your brand’s “girl.” When you think about the Rebecca Minkoff girl, who is she?

She’s me and someone else. It’s definitely the girl who couldn’t afford the designer bag, who felt like she wasn’t part of this exclusive club or had the money. We find that our bags are there for women who are celebrating milestone moments. Anytime I meet my customer, she’s like, “I first got your bag when I graduated, I got my first job, I got a raise.” When I started, the “it bags” thing got old real quick. There was something to be said about my bag, which was timeless and classic, but also cool. It wasn’t about the logo, it was about the woman wearing it. I still think it’s very much like that today.

How did the process of writing a book surprise you?

Maybe I was naive, but I just assumed that when you write a book and turn it in, that the publishers then sell it. That’s definitely not the case. I have to sell it. I have to sell all of it. So I was like, “Oh, damn, I now have to make sure this thing gets into bookstores and reader’s hands and I have to do the marketing.” To take that on was a lot, but I think as an entrepreneur, it’s always a nice test of: “Can I do something that I’ve never done and figure it out?” Then when you do, it’s kind of like, “Yep, I still got it.”

Did you imagine when you were writing the book that it might come out when the world was reopening?

I had to turn in the final manuscript in August and things were still pretty intense then. I called the book Fearless for many reasons, one of them being the idea that it’s not that you magically finish the book and say, “Now I’m fearless.” It’s more, “I’m going to be scared. I’m going to have challenges. I’m going to have things that push my boundaries, but I’m going to do it anyway. I’m not going to let fear take control of this decision.” That’s the end goal. 

This interview has been edited and condensed.

Written and reported by Ciara Hopkinson.