Bloomberg Media Studios’ New Creativity Series: Finding Your Creative Voice With a MasterClass Director

What is the future of storytelling in video, podcasts, immersive articles, data visualization, social media and live events? How can data clarify and create new perspectives? Where are the new ideas and voices shaping tomorrow?

Bloomberg Media Studios started the New Creativity Speaker Series to connect with creators doing remarkable work across all mediums and to share best practices from leaders in their fields. In our first article, we learn about “the Creative Journey” from former MasterClass Creative Director Jasmeet Sidhu.

Stay tuned to this space for future speakers from the worlds of comedy, sports, Hollywood and artificial intelligence, all powered by Bloomberg Media Studios. 

Jasmeet Sidhu shared stories and advice from her remarkable creative journey at Bloomberg Media Studios’ New Creativity Speaker Series. (Photos by Nikki Duong) 

By Michael Walker, Bloomberg Media Studios

Filmmaker Jasmeet Sidhu’s creative journey has never been a straight line.

From working as a journalist at the Toronto Star to working on music videos in Los Angeles for Jay-Z and Taylor Swift, to working as a concert photographer on Swift’s 1989 and Reputation tours, to Facebook, and most recently to MasterClass, where she directed the popular education video series with Hillary Clinton, Anna Wintour, Lewis Hamilton, Nas, Yo-Yo Ma and many others, Jasmeet has built her remarkable career by always following her passion and internal creative compass.

“People get caught up in this idea that if you start over, you’re going to be losing time,” she says. “But momentum is only good if you’re on the path you want to be on.”

Jasmeet recently spoke at Bloomberg HQ in New York City as part of Bloomberg Media Studios’ New Creativity speaker series, where she shared the lessons that she’s learned from being a creative leader in technology, entertainment and journalism, as she prepares her own next act. Here are some highlights:

Maximize serendipity and casual interactions

“I once read that the vast majority of your introductions to your future spouse, introductions to future jobs don’t come from close friends or your best friends, but the people that you casually meet at a happy hour, or the guy who sits at the desk way over there,” Jasmeet says.

Her introduction to MasterClass, which she joined in 2016 as one of the first 25 employees, came through an acquaintance, not a close friend. Jasmeet is always looking to build these connections and maintain them, so when people see new opportunities, she’s on their radar.

“Look for ways to constantly maximize your casual interactions in serendipity,” she says. “Talk to people you haven’t talked to in the office. Attending conferences is a great way to increase your casual interactions in serendipity; so are happy hours. Just give yourself a 45-minute time limit. You don’t need to have five drinks. Those are the best ways to meet people who can help accelerate your career.”

Do the job you want now

Whenever Jasmeet has made a career pivot, she’s looked for a role where she would immediately be doing the work she wanted, instead of trying to climb through the company ranks.

“I think a lot of people coming out of university are attracted to the idea of working at a brand-name organization, even if they’re in an assistant role,” Jasmeet says. “And I would much rather direct them to join a smaller organization where they can immediately start doing the work that they want to be doing and building up that skill set, versus trying to climb the ladder in a big organization.”

For an aspiring film director, a startup like MasterClass offered far more opportunities than a more established production house.

“When I started at MasterClass, there were only five videos on the website,” says Jasmeet. “When I left, there were over 500 employees in three offices and more than 100 videos. I produced or directed 30 of them and consulted on probably 75% of them.”

Solving the “Sunday scaries”

“I used to get the Sunday scaries. You guys all know what that is,” she says. “And my way of tackling the Sunday scaries was just to start work on Sundays. And people would say, ‘Oh man, you’re working six days a week.’ But I always have a really nice Friday night and I  enjoy my Saturdays. When I started at MasterClass, putting in that Sunday work not only eased my anxiety, but I felt like I was starting the week way ahead of other people.”

She credits those extra days with moving her ahead quickly at MasterClass, from senior creative producer to supervising creative producer and, ultimately, to creative director.

“I was putting in one more day of work than other people, and that adds up over time,” Jasmeet says. “I’m a cross-country runner, and the way that we were trained is when you hit a big hill, a lot of people slow down, and that’s the moment when you want to sprint—when you face the big hill. When you sprint on a cross-country hill track, you’re passing 30 people. But you don’t want to be spending that energy on a flat track because you’re not going to pass as many people.”

Vocalize your accomplishments and always be ready with an informed opinion

“You should never, never, ever depend on anyone remembering what you did. When I became a boss, I realized that bosses are really busy,” she says. “Send weekly emails to your boss that say, ‘Here’s what I worked on this week.’”

When it comes to earning trust and boosting your visibility, sharing what you think is just as important as sharing what you’re doing. Providing an informed opinion is a powerful way to prove your value and become an asset to your team’s leadership. Being in charge led Jasmeet to turn to her team for a fresh perspective.

“You really do want to hear what people think,” Jasmeet says. “If I ask what you thought of this talk, and you tell me two things you think I could do to improve it, then I’m going to ask for your opinion again and again. Being agreeable doesn’t always work in your favor.”

Creative inspiration is everywhere

“If you want to do creative work, you should always be observing and feeding your creative eye, and building your mental reference library,” Jasmeet says.

She’s found inspiration for MasterClass set designs in book stories, musical performances, fashion magazines, architecture and Renaissance paintings. And she’s excited about the potential of new artificial intelligence applications like Midjourney as a creative spark.

“I used to keep a folder of shots that I liked of movies and TV shows, paintings, performances that I’ve seen,” she says. “Because you never know when you’re going to need to reference those things later on. A cinematographer once told me that every shot in a movie should be set up like its own painting, and that really stuck with me.”

The secret to being a good director

That reference library becomes especially important when you’re directing, because the most important job of the director is communicating the creative vision.

“Directing is about being communicator-in-chief,” Jasmeet says. “To be a director, it’s like you have to be the one person who holds the vision. Everybody else just wants to execute and know that they’re doing their job correctly. The DP wants to know what kind of lighting; the art director wants to know what the set should look like. And being able to communicate that vision clearly is the most important thing you can do as a director.”

Don’t waste your first three seconds

Even if you’ve never watched a full MasterClass course, you’ve almost certainly seen a MasterClass trailer. Dynamic, sometimes unexpected and always engaging, the trailers have become the calling card of the MasterClass learning platform.

“Our MasterClass trailers immediately start with the person’s face saying something provocative and dramatic,” Jasmeet says. “When you scroll, you’re given such little time to stop and actually stare at something, so the first three seconds are so important. So many people waste their first three seconds—and you have to immediately come in and hit them with the good stuff.”

Earn your confidence

“People sometimes ask me, ‘How do you get so confident?’ says Jasmeet. “I hate the idea of faking it till you make it. I became confident because I got really good at what I did. And when you get really good at what you do, confidence can come very easily.”

If you’re interested in attending a future Bloomberg Media Studios’ New Creativity Speaker Series event, please reach out to Michael Walker, Global Executive Editor, Bloomberg Media Studios,