Pillow Talk with Diana Wilson

After over 20 years in high-level business management and consulting – including stints as CEO of Bargain Network, Inc. and president of Deckers Outdoor Corporation, Diana Wilson isn’t stopping there.  Five years ago Diana transplanted from Santa Barbara to Bainbridge Island to spend time writing her first novel, inspired by her 106-year-old mother-in-law who grew up in Nazi-occupied France. With a whole new outlook and plenty of time spent in nature (thanks to Mt. Rainier), Diana is on to her next adventure and I can’t wait to see what she has up her sleeve.

I first met Diana as a customer at DIANI and fell in love with her brain. She’s so smart and so funny and can run circles around men in business. But what I love most is that she is always looking for a new challenge. For the 16th addition of my Pillow Talk series, I’m excited to feature a mentor of mine who has been a true inspiration as I navigate my own business path. On a recent visit to Santa Barbara, Diana and I caught up over lunch and chatted about everything, from her view on luck and favorite lady bosses to the gift of travel and her inspirational morning mantras.

When you were in school, what was your favorite subject and what did you want to “grow up” to be?

English, and all the arts and humanities. I particularly loved coursework that exposed me to fascinating new cultures and far-flung places—like Mrs. Barnes’ 5th grade social studies class. Once that slide of Machu Picchu went up on the screen, I just knew I had to see it for myself. And when I eventually did—forty years later—I raised a glass in gratitude to the woman who planted the seed.

Ironically, I ended up majoring in accounting—something I had zero interest in—but knew would provide me a reliable income and career. And while it all worked out just fine in the end, we could probably have an entire side conversation on what it means to deny yourself an authentically lived life.

As far as “what I wanted to be when I grew up,” well that’s a rather long and laughable list. One that runs the gamut from the understandable to the obscure: A lawyer—which we can attribute to my favorite character (Atticus Finch) in my favorite movie (To A Kill A Mockingbird)—and a nun. (Yes, a nun.) The nun bit we can probably blame on Catholic school and the Darth Vader allure of those 1960s-era habits. But through all those whiplashing desires, there has been a strong and steady undercurrent—a pull to words and story—it just took me a long time to give myself the permission to try.

What contributed to you becoming the businesswoman that you are today?

You know, it’s interesting. For years I downplayed the role I had in creating “my success”—shrugged it off as having “gotten lucky.” (I think as women that’s something we very often do.) But I recently heard a Master Class interview in which the individual said they didn’t believe in luck. Instead, they believed in the willingness to work hard, to show up prepared, to stay open to the opportunities that come your way. And I believe that’s the essence of “success.” As for luck, I think it’s just another name we have for being given a chance. At the end of the day, what we do with the chances we are given is entirely up to us.

Also—and maybe somewhat surprisingly—there was probably an element of cluelessness thrown in as well. The blissful ignorance that came from my being too naive to “know what I didn’t know.” If I had had any inkling of how difficult some of the goals I set for myself would be to achieve, I would have run for the hills.

Which entrepreneurs do you admire?

It’s a long list, and one in which I include all pioneering people and thought leaders. Like Michelle Obama, whose extraordinary book, “Becoming” is on my top ten list of “have to” reads. I am so moved and inspired by her grace and courage, her deep intellect. And I absolutely love the notion behind the title of her book—that we’re all in a state of “becoming” the people we have been put on this earth to be.

Oprah Winfrey tops the list—for all the myriad Oprah reasons. One of my favorite podcasts was the interview she did with Gwyneth Paltrow for Goop entitled: “Power, Perception & Soul Purpose.” It’s my go-to whenever I need a centering lift.

Speaking of Goop…I’m in awe of what Gwyneth Paltrow has managed to do with her company and brand—making the transition from actress to CEO, transcending the haters—and boy, did she have haters. But she stayed the course. I connect deeply with Goop’s raison d’être—the push to bring new ideas around integrated wellness to the forefront. The content Goop publishes, the topics covered in the podcasts make me feel like I have finally found my tribe.

And Caroline—I’ve been a raving fan of Caroline’s since DIANI’s inception. I’ve seen her vision evolve and refine into something that gets more lovely with each passing year. I’ve witnessed her weather economic downturns that would have brought lessor entrepreneurs to their knees—to do that successfully takes grit and tenacity—qualities I have always respected and admired. I particularly love Caroline’s willingness to venture into unexplored terrain—everything from expanded retail concepts, to new products lines and design, the wonderful case study that is Hudson Valley Farms, even a producer credit on an award winning movie! She lives and breathes an attribute that is essential for entrepreneurs—a willingness to jump off the mountaintop and trust that you can fly. I have this growing sense that the DIANI lifestyle brand is poised to make another big leap, and I can’t wait to see where Caroline takes it next.

What has been your favorite part about creating a business?

There are so many parts of business I love—each organization is such a complex and interesting human puzzle, and I love unraveling all the intricacies. But at the end of the day, my favorite role is the honor inherent in leadership—the chance to mentor and champion others on their path to success.

What has been your favorite role to date?

I used the word “champion” in the last question—and that’s an important word for me. Early in my career, I had a boss who believed in me before I was ready to believe in myself. His generosity of spirt changed my life. If I can do that for someone else—if I can change someone’s life for the good—that’s the best way I know of to create legacy.

What’s the most challenging part of your professional life?

My answer to this question is from a historical perspective because I think it’s more relevant for where we are today. If I think about what ‘was’ the most challenging part of my professional life it’s that when I started my career in the 1980s, I was very often the only woman in the room. For years I overcompensated for not being a man in ways that I can look back on now with eyes fully rolled. That overcompensation cost me—not only in my personal life—but ultimately it downgraded my potential as a leader.

While I believe each of us owes a huge debt of gratitude to the first wave of feminism, I am even more encouraged by what we are seeing today. If there is any silver lining to the 2016 election, it’s that the blatant exclusionary nature of the current administration has been a call to action for many marginalized groups. I attended the first Women’s March in Seattle—walked alongside multiple generations of women. Grandmother’s linking arms with their daughters and great-granddaughters. It did my heart good.

What inspired you to write a novel and how has that journey been for you?

My novel was inspired by stories told to me by one of the most amazing women I’ve ever had the honor to know—my soon to be 106-year-old mother-in-law. I met her when I was in my early 30s, and was absolutely captivated by the stories she told me of her family’s life in Nazi-occupied France. Chilling tales of her own mother’s bravery as an active participant of the Resistance. The counterpoint of her aunt’s devastating betrayal when she began a love affair with a high-ranking German officer. For years I used to say, “Mama, someone needs to write this.” Eventually I knew it had to be me—or at least a version of it. While my novel was inspired by these stories, it is a totally fictionalized version in which the WWII story is bookended with a modern-day parallel. I use the modern day story as a means to further explore the differences between love and obsession, to work through the intergenerational impact of shame, and to reflect on the complex nature of healing and redemption.

It’s been the most fascinating—and challenging—journey of my life. I never intended—or even wanted to write a novel. The story came to me in full cinematic relief while out on a run in Western Ireland. I mean I could see it all so clearly from beginning to end—could hear the soundtrack, even. But I was not so delusional as to think the movie would ever have a chance in hell of getting made without my writing the novel first.

What do you think is the single most important ingredient to success?

If I have to pick a single ingredient, it’s definitely faith—in yourself, in your ability to manifest your dreams—even when—especially when—everything around you calls that faith into question.

But there’s also a caveat here, too—sometimes you need to know when to let go. One of my favorite quotes is something Oprah said in the Goop interview:

“Don’t hold anything too tightly. Just wish for it, want it, let it come from the intention of real truth for you, and then let it go. And if it’s supposed to be yours it will show up, and it won’t show up until you stop holding it so tightly.”

I love that—and when I find myself getting frustrated that things aren’t working out the way I believe they should, I say those words aloud and loosen my grip.

How do you try to manage your work/life balance?

To say that this is not my best skill is an understatement of epic proportion. I can get so lost in my work that I forget to shower and eat—and I mean, for days. The one thing I know for sure is that in the long run, this kind of “all or nothing” behavior doesn’t do you, or your work any good.

For me, managing work/life balance always begins with a commitment self-care. Healthy eating, juicing, exercise. When I remember to make self-care the priority it deserves to be, everything else in my life—including my work—get’s easier.

What do you see yourself doing next to express yourself professionally?

I moved up to Bainbridge Island to finish my novel, and for the past five years I’ve lived a writer’s life, which is a very solitary one. I’m not precisely sure what’s next, but I know it involves reengaging with the world in what I hope will be a very meaningful and connected way.

How do you manage the fear and doubt that inevitably creeps in when you’re paving a less trodden path?

Exercise is the best tool I know of. That, and grounding rituals such as morning meditation and visioning exercises. My favorite way to start the day is with a pre-sunrise walk—a cup of coffee in my hand. There’s a wobbly old plastic chair at the end of a waterfront trail that no one ever goes to. As I watch the sunrise over the marina, I’ll sit and ruminate on whatever is currently troubling or challenging me, and visualize the outcome I hope to achieve. For me, this ritual is succor for soul.

What have you been most afraid of trying in your career, but you did it anyway?

Taking Deckers public in 1993. I was in my early thirties when we staged the public offering, and I still have such a vivid image of sitting in my hotel room the night before we began the road show, crying my eyes out and wondering if it was too late to escape to South America. But…the next morning—terrified as I was—I got up and somehow managed to pull it off. And as it turned out, the multi-week road show that took us from NYC to Europe, and back to the States for a zigzagging journey across the country, eventually landing us in NYC again for a final presentation at the 21 Club-—was hands down the best, most fun experience I’ve ever had in my career. Which of course is the beautiful irony of fear—the things we are most afraid of often turn out to be the accomplishments that give us the greatest satisfaction and joy.

Was there any opportunity that you had in your life that you didn’t take?

There’s nothing necessarily specific, but a general observation is that I didn’t always leverage my successes in the way I could have. I think as women we spend a lot of time discounting ourselves, thinking our achievements are somehow flukes. While that’s changing, we’ve still got a long distance to travel—which is why I enjoy working with young female entrepreneurs. I want to be the ‘yes you can” voice I wish I’d had when I was coming up through the ranks.

Any sleep rituals that you use to help quiet the mind after a long day?

I’m inconsistent here, but what works best is when I’ve had some level of exercise during the day—and it doesn’t have to be a production. A few burpees, a couple minutes of planks, some air squats. A ‘clean’ dinner of healthy, whole foods, a lavender hot pack on my neck, candles, and an hour or so of reading some beautifully written book. Heaven.

What’s the biggest gift you give yourself to recharge?

Adventure travel. For my 50th, I went to Machu Picchu, and in 2016 I hiked the 500 mile Camino de Santiago de Compostela—which was absolutely phenomenal. Next stop: Patagonia!

What’s your favorite indulgence?

Long, luxurious massages and facials in a beautifully crafted space.

What gifts has moving to a new state brought you?

It’s reinforced a belief I have that every now and again we need to shake things up. When I sold my house in Santa Barbara, I put all my belongings in storage, threw my cat and a few clothes in my car and moved to a place I’d never been before. It was a boundary pushing decision, but one l knew I had to take. I had a strong intuitive sense that in order to write the book I wanted to, I needed to leave the noise of my former identity behind—at least for awhile. Bainbridge Island, with its homespun, small town charm, has been the perfect place for me to accomplish what I set out to do.

The other gift—Mt. Rainier! The first time I saw Rainier in its full majestic glory, it nearly brought me to my knees.  And btw…the hiking here is GREAT.

What’s the first thing you do after you wake up?

After I make my bed—and yes, this involves a LOT of pillows—I pad off downstairs and put the kettle on.

While I’m waiting for the water to boil, I apply a of small dab of DoTerra’s InTune and Elevation essential oils to my wrists, and pull a Sub Rosa Questions and Empathy card. www.questionsandempathy.com I love these cards because they engage my brain in a more expansive way. For example, this morning’s question was: “How does courage manifest in your work?” What a great thing to contemplate as you go about your day!

Once my coffee is ready (pour over coffee is my weapon of choice) I sit down and do a couple quick entries in my “One Line a Day” 5 year memory book and my Gratitude Journal. Remembering all the things I have to be grateful for is a great way to put any of the day-to-day annoyances in perspective.

Then, depending on how much time I have, I read at least a few lines from something that inspires me to keep working toward my highest self—like Dr. Wayne Dyer’s Wishes Fulfilled—followed by something that connects me to integrated health topics such as Dr. Tom O’Bryan’s, “You Can Fix Your Brain.” Finally, I’ll read a poem to feed my creative self. I’m currently working through the Mary Oliver anthology, “Devotions.”

All followed by a few moments of meditation, a quick prayer up to the Universe to help guide me through the day.

What’s the last thing you do before bed?

There’s a bit of a disconnect between what I know I should be doing right before bed—like all the things I talked about above—and what I actually end up doing—especially on the days that I’ve been going at it full throttle. I’m a sucker for all BBC/PBS mysteries, and I’ll often drift while streaming an episode of Vera or Shetland. I really do know that murder and mayhem are probably not the best images to plant in your subconscious before you go to sleep, but those shows are my favorite guilty pleasure.

How do you make your bedroom a sacred space?

When I was staging my Santa Barbara home for sale, I wanted every inch of my house—including the closets and drawers—imbued with a sense of “artful curation.” I try to carry that philosophy into the way I live my daily life—especially in the bedroom—which should be the most restorative space in your house.

My preference is clean, fresh lines. Neutral colors. Absence of clutter. Beautiful objects. Bed linens are key since sleep is where you heal your body and soothe your soul. For as long as I can remember, I’ve been a fan of pompoms, and am particularly drawn to the Kesh Bed Cover with Large Pompoms, and all of DIANI Living’s vintage linen pillows with poms!

I seriously didn’t want this to end! You’re an inspiration. Thank you so much, Diana! I’m so proud to call you a friend and so honored that I have you as a mentor. Your fearlessness and vision, especially for women is so essential in a time when we all need those sometimes not so gentle reminders that “you’ve got this”. Whenever I’m in your orbit, I feel assured in my place on this journey as a business owner and you are a natural born leader with a legion of women behind you who look up to you. This is exactly why I started Pillow Talk….I wanted to shine a light on women like you. You have blessed so many with your wisdom and vote of confidence and now so many more will feel bolstered by your words and inspired to keep putting one step in front of the other towards their wildest dreams. You are one in a million, Diana and your talents know no bounds. What a gift to have you in my life and in my corner. Thank you from the bottom of my heart.

                                                    Caroline xo