In ELLE.com’s series Office Hours, we ask people in powerful positions to take us through their first jobs, worst jobs, and everything in between. This month, we spoke to supermodel and business woman Cindy Crawford. Crawford has appeared on over 1,000 magazine covers and is largely credited as being one the first models to build herself into a far-reaching brand. She has created two businesses of her own, Cindy Crawford Home and Meaningful Beauty, the latter being her skin care company, which is celebrating its 20th anniversary. Ahead, Crawford discusses how she evaluates different opportunities, her summer job growing up, and the piece of career advice she’s shared with her kids.
My first job
I was 9 and would babysit with my sister, who was two years older. When we were 15, we would make 50 cents an hour, so we each got 25 cents. But the rules were that my mom had to be home, and it had to be in the neighborhood, so that if we needed help, we could just call her. Yes, people would leave their babies with us. That probably wouldn’t be OK today, but that’s how it used to be back in the Midwest. I had a lot of jobs. They made me really appreciate earning my own money and the value of a dollar.
My summer job
In the Midwest, there were a lot of cornfields. In the summer, you could detassel the corn. It was hot, sticky, and sweaty, but I was with my friends and would work about three weeks out of the summer—but with 12- or 14-hour days. I had my money for the school year, and I could use some to buy a dress for homecoming. If we ever wanted any non-generic shampoo or conditioner, my mom would say that we could buy it ourselves.
My favorite job
Modeling. Being in the fashion industry has opened up my whole world. I like the people I work with, being creative, and the storytelling aspect of fashion photography. But also I’ve gotten to travel and meet people from [everywhere] and live in New York City.
[Over the years,] I’ve been able to assert myself more. As a young model, you show up and don’t contribute much, but as you get more confidence, you can be like, I have an idea, or, can we do it like this? or, I don’t want my hair like that. That feels more collaborative. The more I felt like I was being heard, the more fun it was.
My worst job
You would think working in the cornfield, because it was so hot. We would come home so dirty that my mom would hose us off before we were allowed to go in the house. But it was probably cleaning houses for other people. I don’t mind cleaning, but cleaning other people’s bathrooms is pretty gnarly. I made $15 for three hours. I had another job at a clothing store, and my job was to refold. If there was a pile of sweaters and someone looked at it and put it back down, my job was to go around and refold. To this day, when I do that at stores, I really try to fold it back up properly.
My dream job
My dream job is being a mom. I just got to work with my daughter [Kaia Gerber], how fun is that? And I’ve done things with my son as well. But also, anything where I feel like I’m learning or stretching my brain and skills is exciting.
Career advice I got from my dad
One of the things my dad says is that they don’t call it work for nothing. What he means by that is, even if you love your job, there are those days where you’d rather not go or stay in bed. Even with your dream job, there are days that aren’t fun. Also, be on time. My dad was very punctual and so am I, and it’s definitely something that I have taught my kids.
The secret to always being on time
I am realistic about how much time things take. The common mistake people make is that they aren’t realistic. They think they can get up and out the door in a half hour, and it’s actually 45 minutes. I’d rather always be a few minutes early than late.
I like being on time, because then I know I’m going to leave on time. They can’t say, “Oh, she showed up late, so we have to work a little longer.” I’m like, “No, I showed up on time. That’s not my problem.” When I run on time, my game runs better.
How I built my brand
Previously, school was my job, and I took education very seriously. I was valedictorian, blah, blah, etc. When I started modeling, I approached that in the same way. I’m a lifelong learner. It was a lot of, “Why not try this, why not try that?” Not everything was successful, but I enjoy tackling new projects. I wasn’t necessarily looking at myself as a brand, because no one really talked about that then, but I had a pretty good sense of who my fans were and how to align myself with brands and projects that made sense.
I paid attention to different companies that were interested in working with me. I also knew that I had an all-American sexy feel, so I could work with companies like Pepsi and Revlon that were aspirational, but not out of reach for everyday people. When I started doing the exercise videos, health and wellness became part of my brand. For instance, I wouldn’t have done a cigarette campaign, because that would have been not aligned. Eventually, the confidence to do my own projects led me to do things like create Meaningful Beauty.
I have a team of people that I work with. I have my publicist who I’ve been with for 30 years, and my agent, and I love hearing everyone’s opinion. But in the end, I did realize that I’m the world’s No. 1 authority on Cindy Crawford. I go with my gut.
The questions I always ask when evaluating a business opportunity
“Is it on-brand for me?” I’m at the point in my life where I really have created a good work-life balance, and I don’t want to disturb that too much. I want to understand how time consuming [a project] will be, what it will actually require, and then the financial component.
I have my “business husband,” and he’s my partner on some of my licensing. When we evaluate a deal, he uses baseball analogies, and I really get that. I want to understand what a single is like. Sometimes you get a home run. Sometimes you strike out. But I feel pretty confident that if I give my all to a project, I can at least get a single. I want to make sure that a single is worth it for me, and I feel hope for a home run.
My strategy for Meaningful Beauty
I had been working with Revlon for many years, and I was 35 and felt like I should do my own thing. I felt most passionate about skin care, because that was something that was really important to me. I knew I wanted to do it with Dr. Sebagh. I didn’t know which partners to work with, and so we interviewed everybody. Eventually, I chose infomercials because they allowed me to be a full partner from a financial and opinion standpoint.
At the time, doing infomercials was risky. But I had a half hour to tell a story and felt like we had a very compelling and real one. I knew that trying to do a one-page ad in a magazine and compete against big beauty players was going to be an uphill battle. My main thing was: How do I make an infomercial that I’m proud of? My friends are going to see it. In a weird way, it was time to reinvent the infomercial. There are certain things that work for direct-to-consumer, so I had to learn and challenge a lot as well. When I started Meaningful Beauty, I thought it was maybe a five-year project, and now here we are, celebrating 20 years. I would definitely say it’s been a home run.
This interview has been edited and condensed for clarity.