Imposter Syndrome

Imposter syndrome is a common phenomenon. Especially among women. What is it? A false, often overwhelming belief that your wins and successes are fluke, not tied to your skill and hard work.

Olivia White is the CEO & Creative Director of sleep accessories brand, 41 Winks. She took over the company from her aunt in its early years, and has suffered from imposter syndrome ever since. We sat down with her to talk about what imposter syndrome feels like, how to deal with it, and what it’s taught her along the way.

Photos by  @maddytank

Photos by @maddytank

Hi Olivia! Tell us how you came to be the CEO & Creative Director of 41 Winks.

My aunt founded 41 Winks years ago, as a company that created fun, cute dorm-room bedding. When I was in college, I interned for her, helped launch the business, and loved it. Upon graduating college, I was deep in the mayhem of who am I? What do I want to do? My aunt asked if I wanted to move to New York to help get 41 Winks off the ground. I’d loved my summer there, so I said yes!

I really enjoyed the work, and my aunt slowly but surely gave me more and more responsibilities. After a year or so, she gave me the opportunity to take it over from her. And I did. It’s been amazing. I would have never imagined how much I’ve loved taking ownership of it and forming it into the business it is today.

What do you love most about what you do?

I love that I can create whatever I want to bring to life. If I have an idea, I can at least try to make it work. And if it doesn’t, that’s fine, I have to move on. There isn’t any politics or hierarchy hoops I have to jump through to make it happen. I love choosing who I work with and exactly what I create.

What do you dislike?

Having the freedom to create whatever I want is incredible, but also challenging. I often tell myself that I’m not qualified enough to make certain things happen or to work with certain people. I get in my head: I don’t have this experience, I didn’t go to business school... I’m learning as I go.

I didn’t found the business, and that’s definitely contributed to my imposter syndrome. It was a family business that was offered to me: I didn’t move to New York alone and start it, I didn’t do it as a side hustle until it was big enough to be my 9-5. I have to constantly remind myself that everyone’s story is different. Comparing isn’t helpful. Everyone has their own journey. I am where I am for a reason. 41 Winks is where it is for a reason. But still, the imposter syndrome can come in hot and heavy.

What are the biggest rewards and biggest challenges of owning a business?

The biggest rewards are getting to work with such great people: in the end, I have the power to get to interact with whoever I want to. It’s incredible! 41 Winks has helped me make friends I know I’ll cherish forever. I also love how flexible it is—what we work on and who we work with is ultimately up to me. This freedom comes from being in charge, and also from working with a family member who has total faith in me. I recognize how fortunate I am, and snap myself out of it when I take it for granted.

It’s been interesting, and challenging, to learn how my ego and pride manifest. They take shape in many ways. I really have to catch myself when it happens and look at what I’m avoiding, what I’m afraid of, and then put my concern about my appearance aside and take the leap.

Where do you get your confidence from to stay strong and true to your goals in the competitive business world?

I have attended so many conferences, panels, and events where incredible women and leaders have spoken. A big takeaway I’ve discovered is that they often feel the same imposter syndrome I suffer from. I was at the Create & Cultivate conference last year and Piera Gelardi, the Creative Director of Refinery29, was talking about imposter syndrome: I realized that if she’s up there, experiencing it, talking about it, then many other people must deal with it in some way! Recognizing that it’s a wider phenomenon, and talking about it with other people who feel it, helps me accept it, trust that it’s normal, and not let it hinder my confidence and growth.

My imposter syndrome always goes back to not founding the company. It’s as if I need that checkmark that says it was mine from the start. But what the company is now, is me, and it’s my job to own it and say that I’m so proud of it. I have a habit of selling myself short, so I make a point of surrounding myself with people who support me, hype me up, and call me out when I’m talking myself down. My support system is truly fantastic—I couldn’t do what I do without these people!


What three things should we know about running our own business?

  1. Recognize that everyone has their own journey. Stop comparing. Trust that everyone’s on their own path and the time it takes you to get where you’re meant to be is just right.

  2. Be persistent, but also patient. I know that my job gives me the power to bring ideas to life, but they always take longer than I think. I’ve had to learn how to plan more than I have in the past. In order to make things happen, you have to be patient, work on it, and trust the process. Everything worth doing takes time.

  3. Network, network, network. Go to as many events as you can (even if it doesn’t seem like the right fit), and have a plan in mind: Who are you looking to meet? How many business cards do you want to give out? It makes these events more purposeful. And having a goal helps me feel less overwhelmed because I have a clear target to reach!

What one piece of advice would you want give your younger self?

Don’t linger. There have been so many pivots within 41 Winks, but to start I didn’t pivot hard or fast enough. I wish I’d known that the more I keep moving forward, the more things fall into place. Things don’t need to play out (and won’t) perfectly. It’s true that the failures of 41 Winks have helped us get to where we are now. But learning to let go of them and start on the next thing has been challenging. Fail hard and fail fast: it’s the only way.

What are you not sorry for?

I’m not sorry for how long it’s taken to get to where I am, and where 41 Winks is now. Due to expectations set by society, the entrepreneurial world, and NYC, I can be so hard on myself as I compare what I’m doing to others. But I’ve discovered that I’m on my own path: I’m proud of where I am and where the business is now. I’m not sorry for the journey here.