From Passion To Paycheck: How To Build A Career In Entertainment

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Careers in the creative industries still carry something of a mystique, not least because finding a way into them rarely follows the four-year college degree > internship > entry-level job route. In this limited series of interviews, I spoke with creatives that have built their careers in some of the most desirable fields. I uncover what it took to get there, and what it’s really like once you’ve landed that dream job.

The Entertainer

Today, Jamsheed Master is a BAFTA-winning composer, music producer and entertainer. They travel the world giving piano-vocal concerts aboard the some of the world’s most luxurious ocean liners. When they’re not at sea, they spend time in the studio producing orchestral scores and production music for major stage and screen titles. But like many in the entertainment business, it wasn’t always so glamorous:

“At 15 I talked my way into a piano gig at a London restaurant for £50 a week and all the Chow Mein I could eat. That turned into weddings, then party bands, corporate events, then solo piano-bar gigs, then concerts on yachts for rich people and now I’m a headline act on massive cruise ships playing to audiences of thousands. The principle is the same though: make music, spread joy.”

Jamsheed believes that every creative goes through phases of boom and bust, successes and flops, and that you can find growth in each experience. Eventually this leads to a place where “you can politely turn down opportunities that come your way because you know your worth, or simply because you’re too busy with opportunities you’ve created for yourself.”

In an industry that is notoriously difficult to break into, Jamsheed believes that it’s critical to say yes to everything, and that it’s OK in the short term to over-commit yourself:

“Over-book yourself, do every audition, take every job you can. Don’t just learn your lines, learn the whole script. Nobody is just a singer or only a choreographer anymore. We’re everything from stage doorman to producer and opportunities are literally everywhere. Overload yourself with work and let it feel like your career is going to kill you, because guess what? You’ll live. And you’ll have a killer resumé to show for it, which will open every door when the time is right.”

Ultimately, though, Jamsheed recognizes that “fame is a shady cat. It will ignore you until you do something interesting!”

For all the roles in the spotlight, there are many more behind the scenes, and it is in this context that Andy Cassidy has built his dream career in the entertainment business:

The Head of Travel

Andy Cassidy works in the international division of a global entertainment company best known for acclaimed original TV content. He’s responsible for the travel logistics required to run in-house production and operations in 14 countries, that ultimately deliver more than 40 TV brands to viewers in 130+ territories. Andy previously worked in fashion, which meant negotiating and organizing photoshoot travel, supporting marketing events at luxury hotels, and juggling hard-to-find rooms at global fashion weeks.

Andy says that although he was always passionate about travel, it took him a long time to realize it was something he could make a living from:

“I attended business school part-time whilst working as a long-haul flight attendant. I knew I wanted to establish a career when I graduated but had no idea what that might look like. I took a job as a retail travel agent, which I saw as a steppingstone to something. Six months later I applied to a vacancy for a combined travel booker and executive assistant role at a fashion company. In my first interview I explained what I could bring to the travel role and how I thought that was a position of its own. To my surprise the company loved my idea and hired me as a travel manager!”

In retrospect, Andy believes that first opportunity presented itself because he went into the interview being highly prepared, having done a lot of research about the company. Furthermore, Andy says he made an effort to be well connected, both while flying internationally, and at business school. It was the combination of both those sets of experiences that set him up for success in his new career:

“I applied the principals I had learned at business school and the practical experience gained looking after first-class passengers on premium routes. Building a corporate travel program that combined cost governance and safety with an elevated experience for a demanding client group seemed like a logical follow on.”

Ultimately Andy has been able to build a career that both gives him a sense of purpose, and helps him feel part of a broader community operating at the intersection of travel and entertainment:

“I get to build strong relationships with wonderful people at amazing hotels in great locations: it’s always fun to check out new properties and make new connections. I feel very fortunate that my jobs have taken me to places I most likely wouldn’t have otherwise seen, and to some very cool events. I’ve even met some of my personal travel heroes including Sir Richard Branson and Ian Schrager.”

Andy says that although corporate travel is rarely an obvious career pathway, it’s a great way to build a career in an industry you’re passionate about. He highlights peers who manage travel and events across multiple desirable industries including TV, film, music, gaming, and advertising.

Whether you hope to pursue a career onstage or off, there are a surprising variety of ways into and around the industry, though both Andy and Jamsheed agree that forging relationships with the communities you want to be part of is a critical first step.

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