Cindy Crawford on staying grounded, life lessons and her trademark mole

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One positive gift of aging is becoming truly comfortable in one's skin. It's something that hasn't been lost on Cindy Crawford, the supermodel who splashed on the scene in the mid 1980s and gave new meaning to beauty throughout fashion's heyday in the 90s. I first met her shortly after she launched her career, and was immediately impressed by her down-to-earth attitude and inherent business savvy. Now on the verge of turning 50, the native of DeKalb, Ill. is the mother of two teenagers and is happily married to former model and nightlife entrepreneur Rande Gerber. Residing in California, with a summer home in Muskoka, Ont., and juggling duties with her skincare and furniture lines, Crawford still enjoys some modelling assignments (see the sexy new spring campaign for French brand Balmain for her latest stint in front of the camera), and has just come out with an impressive and spirited coffee table book entitled Becoming. It features a collection of photographs of some of Crawford's most memorable work, as well as a candid narrative of growing up in fashion's fast lane. Saks Fifth Avenue brought the statuesque beauty to Toronto recently to share her stories with an exclusive crowd, and I had the chance to talk with Cindy about staying grounded, making choices and her trademark mole.

You really impacted the world in a profound way because you were just about the first model that we looked at as a beauty who was bolder than some of the waifish girls that were on the scene at the time. Did you see it that way or were you so caught up in the moment that you were oblivious to it?

I think we just got up and went to work everyday, and we were just lucky to catch that wave. It was a time in fashion where there was a lot of focus on the models, much like there is again today. I think that the things that made us different were celebrated. We all were allowed to have our own persona and the designers and the magazines wanted to help make us stars.

You say in your book that you weren't into the kissy kissy, phony thing. Was that something that was hard to be during those days – to be a real person in a very unreal world?

I don't think it was hard because for me; it would be harder to be different than who I am. Like I say in my book, modelling's what I do – it's not who I am. So my whole world and identity was not caught up in being seen at the right parties and wearing the right designers. I love fashion. And I made great friends and I travelled the world and I made money. I've had so many great experiences, but that's just one aspect of my life.

The candour with which you speak about your life in the book is almost disarming because I don't think most people would expect you to be that open and honest. It wasn't easy for you growing up. There was a lot of love in your family but you suffered hardships. How would you say that those kinds of things shaped who you would later become?

Coming from a place of feeling loved as a kid is like your backbone, because that helps you get through all the other stuff. We did have some tragedy, like my brother dying. And I think from that I learned two things: One is philanthropy, and two is that you can't take life for granted. Especially when you're a young teenager or young adult, you think you're invincible. But when you experience death so close up, you realize no one's invincible. I think that is good, because you're not taking anything for granted. And then with my parents divorced, those were harder lessons. I guess in some ways, it made me want to be able to take care of myself, which was a good thing in a way. You don't want to close yourself off so much that you can't have a healthy relationship either, but it made me want to be financially independent.

You say that one thing you wish you could have told your younger self was to have been a little more fearless. What did you mean by that?

I was from a very small town and very unsophisticated. And I think sometimes I felt like, "Oh what if I say the wrong thing, or I don't know what fork to use?" But one of the blessings of getting older is you get to the point that you realize everyone at that table probably has some version of that in their head. So it's just, like, get over yourself! You can use the wrong fork, you can not know what a word means, you can not know if they're referring to some famous painter or artist. It's okay to ask questions or admit that you've never heard of someone. I kind of felt like The Emperor's New Clothes. Do I really belong here? And maybe no one thought I was feeling that way, but sometimes I would not do things if I wasn't sure, thinking that I wouldn't know what to talk about, or what to wear, so I'll just stay home.

You were afraid to admit your vulnerability. But that's what endears you to people now. It's even sweet the way you talk about your trademark mole, and how an agent pressured you to have it removed.

As a kid, you're self-conscious about anything that makes you different. And my sisters didn't make it any easier by teasing me. I had talked to my mom about removing it, but we never really got serious about it. And then I went to my very first modelling agency and they said I might want to think about removing my mole. I was like, "See mom…I told you we should remove it!" My mom was really smart, and instead of saying no, which I think a lot of parents would do, she just said, "Well, okay. But just remember what your mole looks like. You don't know what a scar would look like." She really let it be my choice instead of telling me no. Then as I started working as a model sometimes people would try to cover it up with makeup or retouch it out of the picture. But eventually, that became the thing that people remembered about me. "Oh, it's the model with the beauty mark!" Even the other day, I met someone at the airport who had a mole and she's like, "I just want to thank you because you made this okay." The message I try to teach young girls is that something you could think was weird as a teenager could end up becoming your calling card when you're older.

What do you find to be the most daunting thing about getting older?

It's not really daunting, but getting older does keep your vanity in check, let's put it that way. You have to rise to your higher self. It's very easy in your twenties, when your skin and hair are beautiful, to say that beauty is on the inside. But when you start seeing the signs of aging, you really have to put your money where your mouth is and be kind to yourself, just like you would be to a girlfriend.

You have turned into this figure that women look up to – someone who seems to have it all, at a time when so many of us wonder if that's possible. What do you say to people who look at you and go, "Yeah Cindy…you've got it all!"

Well, something's got to give usually, and when my kids were little, I applied myself less to my work. I think that women can have it all, but it's very hard to have it all at the same time. I don't travel as much because I want to be home with my kids. It's not a hardship, it's a choice that I make and everything's a choice. Every choice that you make with something that you do, you're not doing something else. And that's how we create our own lives, by making those choices that are priorities for us. So I'm very blessed. And yes, I have a career, but I'm an almost 50-year-old model! That's not a super rock solid job, you know. There are a lot of question marks about what's next. But that's exciting, too.

You said in your book that writing it was a gift to yourself – it allowed you to reflect on your career.

It really was. We're always measuring ourselves against other people and sometimes all you see are other people's highlights reels. So many times we forget to just stop and pat ourselves on the back for what we've accomplished or what we've gotten through, or how we've grown. I think maybe some people think, "Oh, Cindy Crawford's book is going to be about modelling, or makeup tips, or whatever." But it's really about lessons that I learned in the world of modelling but that really are universal.

This interview has been condensed and edited.