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Article: Pillow Talk with Caroline Diani

Pillow Talk with Caroline Diani

Pillow Talk with Caroline Diani

Just a few weeks ago Caroline Diani celebrated 16 years of business. A true trailblazer, Caroline continues to inspire customers all over the globe with her aesthetic, while maintaining a vision for the future of the DIANI brand. What better way to honor this incredible businesswoman than to feature her in the 8th addition of her very own Pillow Talk series. Co-worker Sarah chatted with Caroline about the creation of DIANI and the next phase for the website, stepping away to recharge and how Ayurvedic wellness oils make for the sweetest slumber.

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

My favorite subject was always art. I couldn’t wait to get into the art department and let my creativity flow. I found my voice there and loved that there was no right answer. Our teachers were also the coolest ladies and we would talk life with them and how there are so many different ways to live a productive life. It was very empowering and those ladies left a lasting impression. They created after school life drawing classes for us which helped us grow exponentially as artists. I can’t say enough good things about the whole experience and it’s where I created life long friendships. I also found a lot of freedom in sports and loved skiing, tennis, gymnastics and hockey. My dad was a rugby player and a golfer so I was naturally into a lot of different sports. After an amazing experience with my parent’s friend, who is a fashion designer, I decided that that was what I truly wanted to pursue as a career.

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

Growing up, I watched my dad do the business thing. He worked his way up and became retail operations director for a bakery chain in the UK called Greggs and helped take the business public. I have vivid memories of going into the office with him on Christmas Eve to wish the team Happy Christmas. We’d go from bakery to offices to the local Greggs shops and he’d take time to chat with everyone working. I enjoyed it so much that when I was old enough to work at 15, I took a Saturday job in one of the shops and that’s where I first learned customer service and how to manage my own money and be a professional. I loved it and worked all the way through until I left for college.

Which entrepreneurs do you admire?

There really are so many. I’m inspired by people who think about what they’re leaving behind, what their imprint on society is. Roxanne Quimby, co-founder of Burts Bees, is a pretty special lady. It’s not that she grew an amazing company, but what she did with her success after she sold it. She bought up thousands of acres of land all over the country with the sole purpose of preserving it instead of developing it. I love that. And then, I also have to mention Yvon Chouinard. He’s amazing in too many ways to count, and he gave me my start with an internship at Patagonia when I was studying fashion. Being there opened my eyes to what it feels like to work for a company where there are like-minded people all pulling on the same oar. It was very apparent that there was a culture there where everyone wanted the business to succeed while individually contributing to creating a healthy and inspiring work environment.

What was your inspiration behind starting DIANI?

I had moved back to the UK after my internship at Patagonia to finish my degree and start freelance work, but found my way back to the area in 1999. I worked in retail, interior design, personal assisting and started to meet these fascinating women who made me think there was a niche in the Santa Barbara market for me to explore my fashion and retail roots. I thought I could offer something that the women of Santa Barbara were looking for, and so I dove in.

 What propelled you to open DIANI Shoes and DIANI Living?

 As the boutique grew, shoes became an obvious element to complete customers looks, so I experimented with that category with a small space I acquired in the Plaza that I called DIANI Essentials. I would invite customers to see the “must-haves” of the season in an intimate walk-in-wardrobe like setting. It was where I also experimented with price points and was able to pick up Isabel Marant, as one of the first boutiques in the US. That was a really big turning point for my business as customers from all over the world were contacting us to buy the collection. It was then that I knew it was worth building out an e-commerce platform. I quickly outgrew the DIANI Essentials space and while I still had the original DIANI space, I needed more square footage to create a back-of-house office for my expanding web team. A space became available in the Plaza just at the right time and I moved out of Essentials and into what is now DIANI Shoes. I was so excited to start shopping for all my favorite shoe brands and accessories and bring them to my customers. And, it has continued to grow from there. After marrying my husband Jeffrey in 2012, we started to talk about collaborating on a project. He’s an actor and writer and by working on so many TV and live theater sets, has always had an interest in interior and furniture design. We had many conversations about where DIANI goes next. I realized I had always wanted DIANI to be more than curating clothing, but more a lifestyle brand, to encompass home and so we took our mutual interest and created DIANI Living.

What is one of your fondest memories of DIANI over the years?

I think it must be way back at the beginning in 2002. When I was looking for a space to open the store, I met my now landlord, Robert Gilson. I told him what I wanted to do, and what my goals were, and even though I had no track record to speak of and no formal business plan, I must have been very persuasive. He said to me, “Sometimes I like to bet on the jockey, not the horse.” And, so that’s how it all began. I felt very fortunate to be given the opportunity knowing what a risk he was taking on me and I’ve been focused ever since on making it something that we can both be proud of. In my business, I often operate the same way with girls coming in who want a chance, but don’t have experience or seem to fit the mold. It’s extremely rewarding to see them learn and grow and feel a sense of accomplishment at their hard work and leave better professionals. 

What is the story behind the name DIANI?

I was born in Kenya and on the weekends my parents loved to visit Diani Beach on the coast. They gave me Diani as a middle name and when I wanted to start a business that name was an obvious choice. Not only was it very personal for me, but the purity and simplicity of the sand and ocean there speaks to where I come from and what my aspirations are in all aspects of my life.

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

Resilience. Things often don’t go your way, you have to deal with some rough days, months and even years and learn that it passes but you have to stay strong and focus on what it is that you love and trust that it will work out. I work extremely hard at what I do and expect everyone around me to work hard too. Also, if there’s a rough time, I never blame outside forces. I always look for what I can do better to improve the situation. 

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

That there is never a switch-off button. When you own your own business, it lives in your mind 24/7. You have to have a lot of mental endurance for that. It’s not easy to stay sane when you wake up thinking about work and go to bed thinking about it. And I’m now responsible for dozens of people’s livelihoods, which is intense. Even though I think I never have the time, I try to do some things throughout the week to send my mind somewhere else…a hike, yoga, a movie, dinner with a friend, or date night with Jeffrey. It helps me reboot.

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

I’m really not great at it. When I’m in Santa Barbara, I’m pretty full-on with work and don’t do much else. I find myself having a bit more balance when I’m in a different element like traveling for work. Just sitting on a train gives me a chance to look out the window and take in the views or looking up when walking through the streets of Manhattan and smiling at passersby gives me a sense of being part of something bigger than what I’m pursuing. I love seeing how other people do things, observing their techniques, passions…it’s very inspiring and motivating. But in order to do that, I have to take a break from what I’m working on to be part of someone else’s journey. That gives me balance. I also recognize that I can’t do this alone and rely on a strong team of talented individuals. Jeffrey and I talk about it often, and are constantly striving to create that balance.

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

I’ve decided now is the right time to merge my two websites, dianiboutique and dianiliving together. It’s really the fulfillment of how I wanted DIANI boutique/shoes to interact with DIANI Living… one cohesive shopping experience and lifestyle brand. Now shoppers will be able to wander from clothing to shoes, to home goods, to blog posts and interior design inspirations all in one place.  I’m really excited to see this next phase unfold. I’m also looking to expand my interior design business. I’m adding a few new projects to my schedule, and that’s super exciting. 

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

I don’t know that I am that great at managing it. I have always had this sense though that everything will be ok. And like I referenced earlier, I know that there’s only one person who can help me through that fear and doubt, and that’s me. We all know that a vast percentage of fear and doubt is based in projection as opposed to what’s actually happening and when I remind myself of that, then I feel empowered by it instead of cowered by it. I can then take back control, make some choices, and inch forward. And when I’m really waging a serious battle with fear and doubt, I give myself permission to try to improve my situation the tiniest bit. I release myself from needing to be perfect or have a grand success. And that tiny step forward almost always evaporates the stagnation that I feel setting in. I do better when I work with people who aren’t fear driven either. 

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

I think every time I’ve contemplated a new business whether it was the online site, the shoe or home store, I’ve had a thought process where doubt creeps in and I become afraid that I’m not going to have what it takes to make it work and then I remember that the not trying will eat away at me. I try not to live day to day with fear as it can become paralyzing. I think recently the interior designer part of me had been a little timid to show her face, but I’ve gained some real confidence there, and it’s been really rewarding.

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

I’m known for being a yes person so I can’t think of any professional opportunity that I passed up when it made sense. I have said no to opportunities that didn’t make sense. In my personal life, I feel like I’ve passed up a lot of opportunities like vacations and family gatherings to stay in the groove of moving the business forward. In the second half of my life, I would like to think that I’ve earned the right to say yes to more of that.

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

I have to do something after I’ve finished working, whatever time that is to change my thought patterns and guide them away from work. If I don’t do that, I’ll be up all night working or laying there thinking about work. So, I’ll take a yoga class, chat with a friend on the phone, read, listen to some news, watch a movie, prepare food for the next day…anything that has nothing to do with work. The drifting off comes much easier to me then and my mind feels rested by those thoughts.

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

Alone time. I need it to stay level headed and keep creativity front and center. Whenever I feel like things aren’t right, it’s usually because I haven’t taken time to take a step back and let thoughts organize themselves. I find walking very soothing. Nature is my happy place and watching my dogs be free in it, is the ultimate. There’s nothing better to me than being with the whole pack… Jeffrey, Plum, Raisin and me going for a stroll. Everything is all right with the world.

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

I prop pillows up in bed and sit up against them and meditate for 20 minutes. If I don’t make that the absolute first thing I do, it won’t happen. I then throw on sweats and take my dogs for a walk. Then we all eat breakfast together and as soon as that’s over, I dive into work. 

What’s the last thing you do before bed?

I wash my face and smother my skin with oil and put UMA Wellness “rest” oil on my wrists and breathe it in. It helps me doze off quickly.

How do you make your bedroom a sacred space?

I’ve paired back a lot in our bedroom lately…we have our favorite DIANI Living linen bedding which is the most comfortable bedding I’ve ever slept on and we have some of my favorite DIANI Living pillows and have to always have dimmer switches on our nightlights so it’s always soft lighting. I like having the whole pack together to sleep, so our dogs are in the room with us. I love falling asleep to their heavy breathing or snoring. 

If you’re on the East coast this weekend, catch Caroline and all her favorite DIANI Living goodies at the annual Field + Supply modern makers crafts fair at the Hutton Brickyards in Kingston, New York. Come say hi to Caroline and shop her custom designed pillows and succulent arrangements. October 5th-7th. Visit for more info.


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