How to build a career in entertainment

How to build a career in entertainment

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


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

“At 15 I talked myself into a piano gig in 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 piano-bar solo gigs, then yacht gigs for rich people, and now I’m a headliner on massive cruise ships playing to audiences of thousands. However, the principle is the same: make music, spread joy.”

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

In an industry that’s notoriously difficult to break into, Jamsheed believes it’s critical to say yes to everything, and that it’s okay to overcommit in the short term:

“Over book yourself, do every audition, get every job you can. Don’t just learn your lines, learn the whole script. No one is just a singer or just a choreographer anymore. We are everything from stage janitors to producers and the opportunities are literally everywhere. Overwork yourself and make it feel like your career is going to kill you, because guess what? You will live. And you’ll have a killer resume to show for it, which will open every door when the time is right.”

Ultimately though, Jamsheed admits that “fame is a dark 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:

Head of Travel

Andy Cassidy works in the international division of a global entertainment company, best known for its acclaimed original television content. He is responsible for the travel logistics required to run domestic production and operations in 14 countries, which ultimately deliver more than 40 television brands to viewers in 130+ territories. Andy previously worked in fashion, which meant negotiating and arranging travel for photoshoots, supporting marketing events at luxury hotels and tricking out 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 that it was something he could make a living from:

“I attended business school part-time while working as a long-haul flight attendant. I knew I wanted to create a career when I graduated, but I didn’t know what that might look like. I took a job as a retail travel agent, which I saw as a stepping stone SOMETHING. Six months later I applied for a job opening for a combined travel booking and executive assistant at a fashion company. In my first interview I explained what I could bring to the travel role and how I thought it was a position in its own right. To my surprise, the company liked my idea and hired me as a travel manager!”

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

“I applied the principals I had learned in business school and the practical experience gained by taking care of first class passengers on premium lines. Building a corporate travel program that combined cost governance and security with an elevated experience for a demanding customer group seemed like a logical next step.”

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

“I get to build strong relationships with amazing people in 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 probably wouldn’t have seen otherwise, and to some very interesting events. I’ve even met some of my travel heroes, including Sir Richard Branson and Ian Schrager.

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

Whether you’re hoping to pursue a career on stage or off, there’s a surprising variety of ways to get in and around the industry, though both Andy and Jamsheed agree that building relationships with the communities you want to be a part of is a first step critical.

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