How to transition to entertainment as a second career

It’s no secret that the entertainment industry has had its fair share of gatekeepers, and many folks with a passion for storytelling may not have considered entertainment as a viable career path earlier in their professional lives. We work with many clients who, for one reason or another, start pursuing their entertainment careers later in life. It’s not an easy path, but it is doable, if you approach your transition thoughtfully and strategically.

First, be very honest and clear with yourself about what you want to do within the industry. If you want to be a writer or director, you may not need to spend time “paying your dues” on the assistant track. You can certainly try applying for entry-level assistant jobs, but the reality is that many hiring managers are looking for younger candidates fresh out of school, and there are no guarantees that being a great assistant (whether on a desk or in a writers’ room) will lead to a creative role. Be realistic about your financial needs and how much time you can devote to dues-paying. If being an assistant doesn’t work for your life, consider the many other ways to obtain these creative positions – applying for fellowships, submitting your work to contests and film festivals, writing other forms of media (short fiction, novels, newsletters, personal essays, humor blogs), directing independent projects in other formats (web series, spec commercials, short films, plays), etc. Prioritize attending workshops and networking events and collaborating with other creatives. You might also consider getting a full-time role within the industry that aligns with skills from your previous work that will allow you to integrate into Hollywood while honing your craft – for example, if you worked in sales, you might apply for jobs in the ad sales department of a network. Your day job will still be somewhat siloed from the creatives, but you will likely meet more people who can introduce you to folks who can check out your work.

If you’re hoping to get on the producer, executive, or agent/manager track, starting as an assistant is more important. It’s unlikely that you can move laterally from your previous field into a mid-level or senior-level role in these coveted areas, unless you’re coming from a similarly creative role that involved storytelling (think: video games, publishing). Hiring managers want to make sure you understand the nuances of the industry and have a strong network of contacts before they’ll hand you a multi-million dollar production to oversee. Applying for Hollywood assistant jobs is a pretty unique process – you’ll want to highlight your administrative acumen and have a resume that focuses on your ability to answer phones, handle heavy scheduling, maintain organization, provide customer service, and process various types of paperwork. It’s okay to show some achievements, and you definitely want to highlight how your unique perspective will make you an asset to the organization, but make sure your resume clearly indicates that you understand the role of an assistant, and that your cover letter expresses your humility. You may still find some ageist hiring managers -- this is an unfortunate reality of the business that is hopefully changing but not yet changed -- but all you need is one to take a chance on you.

Breaking into Hollywood later in life is difficult, but not impossible. And as the industry opens up to include more historically marginalized perspectives, we hope it will also make room for people who didn’t have the opportunity to pursue their entertainment dreams at 23. If you’re a storyteller, you’ll find a way to tell your story – and we’re here, excited to help however we can!

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-- Angela Silak & Cindy Kaplan