Talking to Jasmeet Sidhu allowed me to have a glance at a career in a creative field. Creative fields have some unique features as well as common factors with many other fields. Interpersonal and communication skills, collaborative work, and project management are some of the aspects that Jasmeet mentions as part of her career as a creative producer and director at MasterClass. I believe that being a good team player, conveying your ideas clearly, managing your time efficiently, and being able to multitask are crucial skills in almost every job. Building upon Jasmeet’s insights, even though your career is not related to your major at college, your experience in college is highly valuable to gain these skills while doing academic research, writing, and trying to meet deadlines.

Another key takeaway from my conversation with Jasmeet is regarding mentors who can guide you through your academic, professional, and personal life. Jasmeet provides very valuable insight when she mentions the importance of one’s own initiative in seeking out opportunities to form their own path. I think having mentors is helpful as long as they don’t prevent us from being proactive and independent. Mentorship shouldn’t be something we fully depend on but should be a support mechanism that helps us build on our personal efforts. Ultimately, we should be able to stand on our own feet.

Jasmeet’s career path illustrates how taking on new challenges and opportunities, and being adaptable and brave can open up new worlds. As much as planning our future might provide us with a clear goal and action plan, I find it valuable to always keep my mind open to the unexpected, which allows for flexibility for exploring interesting fields. In that sense, there needs to be a distinction between limiting our mindset and planning our academic and career paths with an open mind.

Having an open mind is especially important in creative fields because very strict guidelines might hinder the creative thinking process. We should maintain a balance between having some kind of a framework to make production more streamlined and efficient and having the opportunity to think freely devoid of any restrictions, which contributes to creativity. For me, the production process in MasterClass is a good example of finding this balance. Finally, I would argue that having an open mind and enabling creativity both at the individual level and in collaborative work are becoming more and more relevant in various sectors. This is because organizations are tackling increasingly complex problems exacerbated by the realities of today’s world such as the pandemic, climate change, and rising economic inequality. That is why all professions have a lot to learn from creative fields and their thinking process if they want to generate effective and impactful solutions to today’s challenges.
 

Highlights from the interview:

Everyone’s family, community, friends, or where they come from, life circumstances in general, creates an initial role for them in society. I was wondering what was expected from you. Did you adhere to it or stray away from it?

I wouldn’t say there were very strong expectations on me career-wise. I think my family just wanted me to have a clear goal. I first considered becoming a doctor and studying life sciences. Then, I realized that I was interested in media and journalism, and that studying political science and peace & conflict studies would make me a strong journalist. When I graduated, I decided to pursue journalism more fully; so, I received an internship at the Toronto Star, which is Canada’s largest daily newspaper. That’s how I started my career in media. 

You’re the supervising creative producer and director at MasterClass. What led you to your current position and what does this position entail?

I joined the company when we were about 20 people, definitely in the early stages of the company. The company now has more than 250 people. I’ve seen it grow from a very small start-up to a well-run organization.

I started off as a senior creative producer and have just got promoted to a supervising creative producer. I help shape the creative direction of each class that we film. That involves working with the instructor on what they want to teach, what’s on their mind; researching about the topic and the instructor; shaping the visual design; occasionally directing and interviewing on the set and for the shoots; and working with an editor to put together the class. 

In terms of how I got into the job: when I graduated from college, I was interning at Toronto Star, and then I decided to take a few months off in preparation to apply for graduate school. I knew I wanted to continue in the media field; so, after researching a few programs, I was very interested in the journalism program at Columbia University in the U.S. I felt like that could open up a lot of opportunities for me. I applied and got accepted. I moved to New York to pursue the Master’s degree. I won the Stabile fellowship for investigative journalism. I learned a lot from that program. I was exposed to digital video and how to film and edit for the first time. I made the decision that I wanted to pursue that aspect of media full-time. When I graduated, I got another internship working at a production company for a few months in New York. Since a lot of media and entertainment opportunities are based in Los Angeles, I moved there after that internship and decided to pursue working in the entertainment field. I got involved with the music video industry. I reached out to music video directors and music video production companies and was able to work for a director and his production company for about a year. That’s where I really got to be on set for the first time and see how everything comes together for a music video. I began to take more responsibilities to learn the operations, and do photography and behind the scenes stuff. Then I took on an opportunity with Facebook in New York, working with their Public Content and Media Department. While I was there, I was made aware of a company called MasterClass that was just starting and looking for producers. I connected with the co-founders, they hired me, and I moved to San Francisco. Four years later, I’m still here.

Have you ever envisioned yourself being in this role while in high school, or in college, or even in the early years?  Were you interested in media, film, or photography or music industry earlier?

I think those interests were always there. I took photography classes in high school. I did short films with my friends in high school or even earlier. I was always very interested in the media, media culture, media criticism, media studies, and just creating media like photography and video. It just didn’t click for me as to make it a real career until after I finished my graduate program. 

When you were deciding on all these things, was there a mentor who guided you or helped you cultivate your interests?

I have met many wonderful people along the way who have helped me, but I had to shape my own path because I grew up in Canada and I didn’t know anyone in the U.S. or in the entertainment industry. So, I couldn’t rely on finding the perfect mentor to open all the doors for me. I think that can be a little bit of a mistake for some young people to think that they just need to find a mentor who will bring them all these opportunities. You can have several mentors who can give you advice, guidance, and direction, but most of the work of shaping your own path and finding opportunities does fall on yourself. 

What are some of the most useful skills to have when working at MasterClass?

Project management is a big one, and it’s the one that I value a lot. Many different things could be happening at once and you have to not let the ball drop on either of them; multiple approaching deadlines, different documents that you need to create, different things and tasks you need to get done, different people you need to manage along the way to make sure they feel informed. I would say project management is the most useful skill set that I use. Writing is an important skill as well as communicating ideas clearly. Having an expanded vision and pushing the boundaries have also helped me along the way.

Do you feel like your college years prepared you for this type of work and for these skills?

Yes and no. To be honest, there’s very little that I directly use from my undergraduate degree in my current job because I studied peace and conflict studies. But, the rigor of research, writing, and working under deadlines are things that I face all the time.

What does storytelling mean to you and what makes it great based on your experience?

For great storytelling, you need great characters and narrative that needs to be resolved at the end. The events along the way should be compelling enough to make us interested in seeing that resolution or not. So, storytelling for me is how you are invested in watching, listening, or writing.

Could you give an example of a specific project you have worked on and talk about the process or the experience, challenges, and rewards?

I produced and co-directed Anna Wintour ‘s MasterClass. That was a big collaborative effort among our team and Anna’s team. I was responsible for capturing the work and legacy of this person who’s been at the helm of a very iconic magazine for 30 years. So, it required a lot of research and collaboration. I had to put together a lot of visuals for that class. I think it turned out great. It’s one of the classes that I have enjoyed the most working on and I think members really enjoy watching it.

Could you share one of your most memorable experiences that helped you develop as a person?

Shonda Rhimes’ MasterClass was one of the first classes that I did. She’s someone that I’ve admired for so long, and it was one of my first experiences at MasterClass where I had to speak with her face to face about what her class was going to be. It was intimidating at first, but it was a great growth process of presenting myself as an equal to her and not feel intimidated and really own my role as the project manager and the creative producer of that project.

Do you think there are any misconceptions about your work for people outside the industry?

I don’t think there are any misconceptions. Something that’s not talked about much is that there is a lot of collaboration happening behind the scenes among people internally at MasterClass and between MasterClass and the instructors. This is their class so, they’re very much involved. They’re executing and reflecting a lot of their vision. 

Do you have any advice for students who are interested in your field?

It connects back to what I was saying about the mentors. You should rely on yourself to create your path. Media and entertainment have a less clear path than other industries, less clear milestones and posts for you to keep hitting to make sure you’re on the right path. It’s about understanding what you want to do in the industry because there are a lot of different roles: in front of the camera, behind the camera, writing, producing, working on crews, production. A big part of it is trying to understand what it is exactly you want to do and then advocating constantly for yourself to continue on that path. 

The theme for my career path is being able to pivot and adapt very easily and to be bold to go forward and grab a few opportunities such as moving to the U.S., moving to Los Angeles, moving to San Francisco. Whenever I saw opportunities, I was able to make the most of them and that’s an important piece of advice for anyone pursuing their careers. 

Interview excerpts have been lightly edited for clarity and readability and approved by the interviewee. This article only aims to share personal opinions and learnings and does not constitute the interviewee’s current or former employer(s)’ position on any of the topics discussed.