If you had told me 10 years ago that I would photograph Taylor Swift in concert not once, not twice, but over three different tours, and that I would be hosting a Taylor Swift-themed photography exhibit showcasing all those photos, I would have thought these statements were the stuff of fantastical dreams.
Taylor Swift? Front row, taking photos? Three tours? Hosting an exhibition? Impossible.
Because 10 years ago I was an unemployed production assistant lost in the swamp of the Los Angeles entertainment industry, hoping for any bit of work to justify the life decisions I had made at that point: leaving Canada where I had grown up, putting aside my master’s degree in journalism from Columbia University, and venturing out to the Wild West for a shot to be a part of creating culture that got exported around the world.
What saved me from a slow slide to abandoned dreams into a much more practical life path, was the ace up my sleeve of cold-emailing, and the ability I seemed to have via earnest paragraphs to somehow convince much more important people to take a shot on me and offer opportunities to try out this thing called photography, in particular behind-the-scenes photography on music video sets, where I first got my start assisting a music video director.
When one of those emails worked and an executive producer (shoutout to Joseph Uliano!) invited me to be the behind-the-scenes photographer on an upcoming Cage the Elephant music video, it started a nearly decade-long path of photographing live concerts that culminated in photographing Taylor Swift’s Eras Tour, and displaying work from her three tours (including 1989 and Reputation) at Kimpton Epic Hotel Miami’s artist-in-residence program.
Since that fated Cage the Elephant music video set (for their song “Cigarette Daydreams”), I have photographed the aforementioned Taylor Swift tours as well as Ed Sheeran, Adele, Janelle Monae, Nicki Minaj, Olivia Rodrigo, The Killers, Maisie Peters, HAIM, Gracie Abrams, and SIA. I seem to have been destined to work at the heart of the celebrity-driven world even when I transitioned to working in the tech industry in San Francisco, where for six years I was producer then a creative director at the video-streaming platform MasterClass, joining as one of their earliest employees. At nights I would wander around San Francisco venues just experimenting and honing my photography and during the day, I was part of building a fast-growing once-in-a-lifetime startup that eventually led to me producing, directing, and interviewing more than 30 MasterClasses including with the likes of Hillary Clinton, Anna Wintour, Lewis Hamilton, and Shonda Rhimes.
If all this sounds like some sort of lucky dream version of a career come-up, it is, and I never take it for granted. But what’s important to mention is that it was the combination of creating strategic opportunities to build a portfolio, doing what I call “practicing serendipity,” and having the fortitude to continually be bold and put myself out there that led to where I am today.
Let me explain each point.
Creating strategic opportunities to build a portfolio
One of the best things that I did during my assistant days in Los Angeles was being conscious about how to find and create things that I could put my name on to showcase what I did. The most obvious example was taking photographs on set. Here was something tangible that I could point to and say, “I did that.” Even though I was an assistant for some exciting people on some exciting sets, people don’t hire you into progressively higher responsibility positions because of tangential associations with cool projects or organizations. Those may offer credibility and help you pass an initial vetting process, but people hire you because you’re able to offer a showcase of your skills and because of your ability to initiate and bring things from beginning to end, even if those projects are unsexy or small in scale.
One of the pieces of advice I offer to college students when I give talks is to find jobs that allow you to practice the skills you want to be known for right away. In other words, do the job that you want to do as soon as you can. It’s my personal opinion that a job at a small unknown startup or organization that allows you to take ownership and do the skill-defining work, even if you are a junior employee, is a much better choice than a job at a large outfit or at a globally-known buzzy company where you are relegated to prolonged support work.
Of course this is not black and white, as nothing in life is. I’ve seen plenty of examples of people who start out at big companies, build a valuable network, and then move on to great success, progressively climbing the career ladder. And I’ve also seen people hang in long enough at a big company to be tossed opportunities to flex and grow and earn a valuable skill set and get their name on projects. But those paths often require a lot of luck and the good will of a generous manager invested in your growth. Perhaps you can create the best of both worlds, like I did, as you work to build a reputation and gain access to a network at one job (in this case, my assistant work around Los Angeles), while staying focused on building skill-set-driven work on your off time (my photography).
Case and point: My former manager and the co-founder of MasterClass, Aaron Rasmussen, recently informed me that it was my concert portfolio that stood out to him in my initial application for MasterClass. It showed initiative, and the ability to have the “eye”, the latter of which was extremely crucial at MasterClass where we worked to create Netflix-quality online educational videos.
Focus on building a skills-showcasing portfolio, and if your current work is not allowing for those opportunities, create them on your own.
Practicing serendipity
Well I’m sure you’re now asking, “Jasmeet, how do I create these opportunities?” The answer to that is what I’ve already referenced in this article through the cold-emailing anecdote, and it is what I called “practicing serendipity.” What do I mean by that?
Practicing serendipity essentially means giving yourself as many shots as you can for wondrous opportunities to come your way. It’s sending out cold emails, attending talks and conferences, posting on LinkedIn. In essence, it’s making it easier for you to be on someone’s mind when an opportunity comes up, or to spark the interest of a generous someone who remembers what it’s like to be early in their career and offer a chat, an experience, or a referral.
I call this practicing serendipity because I’ve found that being in “the right place at the right time” involves a lot of intentional work to make something the right place or the right time. You have to continually put yourself out there and make this a habitual part of your career development.









