How a cold-email led me to professionally photograph Taylor Swift

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. 

One of the best books I recently read that summarizes this theory well is Christian Busch’s “The Serendipity Mindset: The Art and Science of Creating Good Luck.” Busch discusses how some people are better at creating the conditions for coincidences to arise and taking advantage of them. These involve, as he explains, seeding triggers, giving out hooks, increasing exposure and connecting with influencers (used in the broadest sense).

What does this look like in practice? It means crafting the perfect cold email or DM, paying money to attend an industry conference, finally creating or cleaning up your website, and diligently talking about your accomplishments or work experiences on social media. Taking these actions increases your serendipity to life-changing opportunities and builds up your “weak ties”, a theory from Stanford sociologist Mark Granovetter that shows that much of our important life-changing information (referrals to jobs, introductions to our future spouses) tend to come from casual acquaintances rather than our strongest relationships. 

What did this mean in my lack-luster assistant days in Los Angeles? It meant that I shelled out $200 (an absolutely huge amount of money for me) to attend an industry conference on music videos, where I got to introduce myself to music video directors and producers, and where I met Joseph Uliano (who, as I mentioned, facilitated my first behind-the-scenes photo gig with Cage the Elephant). It meant I kept up with casual work acquaintances doing interesting things over many years, including the person who would eventually connect me to someone at MasterClass when they were hiring.

Some people absolutely get lucky in life and get plucked out of obscurity to the career of their dreams. For the rest of us, practicing serendipity allows us to tweak the strings of luck in our favor and to be ready to pounce on them when they do. 

Fortitude 

A note on creating and managing careers: It can and will be some of the most emotionally exhausting work of your life. I can’t tell you the amount of tears that I have shed over real and harsh rejection, including some rejection that was pointedly personal. As a woman of color from a lower-income background in Canada with immigrant parents, it can be particularly exhausting to navigate privileged white and male spaces, as I’ve often had to do in my work at the very upper echelons in tech and entertainment from New York to Los Angeles to San Francisco. 

Creating any career of meaning and impact is going to require high fortitude, especially if you’re not in one of those aforementioned groups of privilege. 

How I’ve learned to mentally deal with the harshness and the roller coaster of my chosen career and build that fortitude is to view everything like a video game. Some people are going to start the video game three levels ahead of you and with special boost-ups. You may be starting at Level 1 with no special powers (yet). While you may be envious that others have started a few levels ahead of you with special advantages, staying fixated on those people and their advantages is not doing anything to get you out of Level 1.

Sometimes you need to hit pause on the video game and take a break. That’s OK. You may even realize this particular video game is not for you, and you want to try another game. That’s OK! The point that I’m really trying to make with this overwrought video game analogy is that nothing should weigh so heavily on you as you’re learning which video game to play and how. It’s just a game, and it’s up to you to figure out how to do the best you can at it. 

And if you hit a dead end, simply reverse course and find a different way. Don’t hate yourself if your princess is in another castle. Just take a pause and start again. 

What I hope you take away from my story is that although so many things about your career are out of your control, there are so many things that are. I had no idea that cold emails sent ten years ago would lead to experiences and relationships that created the doors to my present career-defining opportunities, including photographing Taylor Swift. As Apple co-founder Steve Jobs once infamously said, you can’t connect the dots looking forward; you can only connect them looking backwards. Start to throw out those fish hooks today, and see where they will lead you in years to come.