In the latest installment of our anonymous interview series, we talk to fashion stylist who gets celebrity clients red-carpet ready.

I’m a fashion stylist, and got into the business twenty years ago in Toronto, Canada. I started out by styling models for their portfolios. At the time, there were a lot more fashion magazines in Europe, so it was easier to get a portfolio together over there than it was in North America, and that’s exactly what I did. It seemed to be what a lot of people were doing back then.

SOMETIMES, THE PEOPLE YOU’RE WORKING WITH have so much on their plate that they forget to communicate everything they want. There are a lot of surprises on the job. A lot of times, clients will want something the night before or the day of the shoot. There was a time when I might’ve said, “That’s not be possible.” But now it’s like, “Whatever you need. Absolutely!” It’s all about keeping a positive attitude, though, of course, deep inside you’re compelled to snap. “What are you talking about? This wasn’t part of the deal!” You just try to stay calm, organized and prepared for whatever might come your way, for instance, making sure that you’ve got a seamstress on hand for the fitting. There can be a lot of miscommunication, so you learn to ask questions and clarify things in advance.

IT’S A WELL-KNOWN FACT THAT EDITORIAL PHOTO SHOOTS don’t really pay well. There are frequently scenarios where you have to spend money to work. This is across the board in fashion, from makeup artists to hair stylists. But you do it anyway because it’s great for your portfolio.

For instance, I recently did a shoot with Matt Dillon. The client was like, “Oh, sorry we have no budget.” But, then again, you’re getting pictures of a celebrity for your portfolio, which only helps you book more work down the line. It’s an investment in your future, in your profession, because the more people see your name and work circulating, the more people will want to hire you.

On the flipside, you have to make sure you’re booking a nice balance of unpaid editorial work and well-compensated commercial work. The jobs you really want to do for financial gain are TV commercials, print ads, things like that.

I WAS SPEAKING TO ONE OF MY ASSISTANTS in Toronto yesterday and she said, “Nobody I know that’s a stylist, except for one person, really has children.” It takes up a lot of your time and that’s what we focus on. Keep in mind, this is someone in Toronto, where I feel people are a little more family-oriented than people in New York might be. This profession is self-selecting in the sense that it attracts people who are ambitious, individualistic and possibly a little self-centered.

I don’t have kids myself. I’m dating a person now, and when it comes to relationships, I need someone who is open-minded and easygoing. I had one boyfriend who couldn’t understand my constantly fluctuating schedule. There were definitely times when we’d have plans, but I’d have to say, “Sorry! Just got a job,” and cancel on him. It’s definitely not a place for codependency.

YOU REALLY HAVE TO BE CAREFUL. The physical aspects of styling can be pretty taxing. The average amount of stuff you’re schlepping around town is at least 200 or 300 lbs per job—just huge hockey bags overloaded with clothes, shoes, accessories, steamers, lint rollers, body tape, you name it. In New York, I don’t have my own car, so I use a lot of car services to lug it from one place to the next.

I also hire plenty of help because I know some older colleagues who now have knee or back problems because they didn’t want to shell out for assistance in the past. I like to have two people helping me at all times. I feel like it’s totally worth it, because a good chiropractor is going to cost you a lot more money in the long run.

I HATE TO SAY THIS, BUT IT’S TRUE. In terms of the ideal subject, it’s usually someone with a slim figure who can fit into sample sizes. That applies to males and females alike. You just get a lot more options for someone if they’re a size 2. It’s an unfortunate reality of the industry, but that’s the system that we’re presently dealing with.

Especially when you’re working with a big celebrity, you can call in so much amazing clothing, but only if it’ll fit them. If you’re working with someone who is plus-size, it can be a more challenging. That’s when you have to have things custom made for the person, since most womenswear designers, at least, produce clothing that terminates at, like, a size 10 or 12.

USUALLY, WITH CELEBRITIES, it’s more of a collaboration. There’s definitely a lot of back and forth. You’ll have your curated rack of clothes, and you say, “This is what I’m thinking: I love everything here because I’ve pulled it all, but these are my 3 favorite things. What do you think?” And sometimes they don’t like those things, and you’ll have to go and re-shop the whole wardrobe for the client. And, of course, there have been times when a celebrity just wants to do things their own way. You’ll roll up the shirt sleeves a certain way, and they’ll go, “No, I don’t like it rolled up” and take it upon themselves to roll them down. Or they’ll have something specific in mind that they want to wear. There are those times when I’ve had celebrities bring me their own clothes that are just atrocious. They’ll show something that’s all wrinkled and say, “Oh, I just love this jacket!” Deep down, I’m like, “Hello! I’ve got a rack full of amazing suits!” or “My god, it looks terrible on you. What were you thinking even buying it? Forget wearing it for the shoot, it’s not even good to wear on a day-to-day basis!”

It’s definitely frustrating at times. But you just kind of have to go with it. “Sure, whatever makes you happy,” you’ll say. The most important thing is making the celebrity comfortable, because that’s what will make the best picture in the end. If I have a problem with the celebrity, the photographer could have a problem with them, and it can unravel into this domino effect of negativity.