“I wish I had more ambition.” This is the last thing I was expecting to hear from Rachel Roy, renowned designer (who has dressed the likes of Michelle Obama, Oprah Winfrey, and Gwenyth Paltrow), philanthropist, and mother of two. Call it ambition or not, there’s no question that work ethic and determination has enabled Rachel to overcome a number of obstacles since launching her brand in 2004. Rachel has prevailed as a woman who leads by example—holding her head high, moving forward, and doing what she believes in. I spoke with Rachel about the privilege of working, the advice she’d give to her 28-year-old self, and what courage means to her.

“Growing up as the daughter of an immigrant father from a Third World country where people do not have the privilege of working, I have never been fearful of work. Rather, I was thankful for what it provided. That perspective has stayed with me. Work has provided me freedom, and I believe it does for others as well. I find work frustrating at times, but never difficult. Patience is difficult. Other things are difficult. Work is a privilege. When I was 14-years-old, my father dropped me off at a mall and wouldn’t let me come home until I got a job. In the years following, I worked for free as a stylist alongside retail jobs. Without being forced to work in my teens and continuing to work as a young person, I don’t believe I would have the work ethic I have now. The one thing all of the most successful people I know have in common is a lot of hard work. Hunger is key and so is ambition—two very different things. I have a hunger to help those in Third World countries, and for justice. I have a hunger for fashion, creativity, and joy. While I’ve been able to persevere through a lot, I still don’t consider myself driven. I wish I had more ambition. I was born to a father that always had a minimum of three jobs and told the best stories at the party—the person that others were drawn to—and to a mother that worked the same job for 35 years and went to church every weekend. I think my perseverance stems from childhood—that growing up with little has made me push myself.

My determination comes from believing in myself even when others may not.

I crave learning in most areas of my work, but I never doubt myself when it comes to design. In past collections, the items I needed to drop but didn’t (and subsequently regretted) were my fault. But everything I’ve been disappointed in within work has been a learning opportunity. What I’ve learned over the years is to listen to myself, and to not try and please or be overly polite (an important lesson to learn). If I had to describe my purpose, I’d say that it’s to be a voice for women and children who have no voice, to leave people a little bit better than how I found them, to help others design the life they wish to live, and to practice kindness—it is always fashionable! For anyone trying to figure out what their own purpose is, I tell my friends, team, customers, and loved ones to think about how they spend their time off. What do they love doing when they have the time for it? Make a career out of that. There is always a way. It may not always lead to a plethora of money, but it will lead to a plethora of happiness.

I’ve had a strong sense of myself and who I was from early on. I’m not sure if it’s something innate or learned, perhaps a bit of both, but mostly innate. Personally, I believe your intent matters most. Whatever you’re doing, if there’s not integrity, it just won’t feel good. I also value intelligence, humility, love, and compassion—all things that grow and develop with time. If those parts of yourself do not grow, there is a huge problem. We are meant to grow and evolve. I also believe in being courageous and fighting for yourself when you need to. For me, that’s meant fighting for my name, fighting for my company, relocating to California, and being a single mom. As much as you need to know how to fight, it is just as important to know when to bend. Not one or the other will lead to peace, only a balance and flow of both.


Children were always in my life path, but they are not in everyone’s, and that is OK. I didn’t have one drop of fear about how having children would affect my career. I give up many things professionally and personally for my children, and I would not have it any other way. I did not become the woman I was meant to be until I gave birth to my daughter, Ava. I learned to love myself for her. If you are willing, your children will provide the most self-love you will ever have for yourself. However, they are a piece or pieces of the pie, not the entire pie. No one person should be the entire pie. When it comes to having kids as well a career, there is no balance. You are either doing really well being a mom, doing really well at work, doing really well at working out, or doing really well in a personal relationship. But you do those things well one at a time. There is no such thing as doing it all. And you have to be OK with that.

I firmly believe that you get what you tolerate.

You should set the bar for yourself as high as you would for your child or your loved ones. If I was to give advice to my 28-year-old self, I would say: It was within you all along—all that you tolerate, all that you hope for, all of it. You have the capacity to give it all to yourself. You don’t need anyone to complete you. You complete you. You are whole.”

Rachel’s OKREALTALK Tips

  • Work is a privilege.
  • Knowing when to bend is just as important as knowing when to fight.
  • You are whole.

b. 1974

i. @rachel_roy

Interviewed by Amy Woodside, September 2016