Setting the Stage: How a Hollywood Internship Jump-Started My Career

With summer jobs on the horizon, professionals recall the first jobs that launched their careers. Read more, then write your own #CareerLaunch post.

I had a lot of jobs when I was young, from working in construction to 15-hour days unloading a beer truck in the back roads of central Virginia.

But the one that really jump-started my career was an internship in Hollywood between my third and fourth years of college.

I’ve written before on how it turned out that the film industry wasn’t for me. But the experiences I had there (and getting there) set the stage for the rest of my career, and taught me skills that I use to this day.

The art of the cold call (or letter)

Back when I was seeking an internship, people still sent physical letters to apply for jobs. I mailed one to anyone who might have an in: UVA alumni, family friends, friends-of-friends-of-friends. I offered to work for free, to do any task they needed. I just wanted experience.

It was amazing how many people were open to talking to me, simply because I asked. I had a lot of great conversations, but no one offered me a role. “Call me when you get to LA” was a common response. So I took the advice at face value, saved up some money, and drove across the country, determined to sort things out when I got there.

After arriving in Hollywood, I continued networking. And I got lucky: a friend who’d gone to film school introduced me to an Associate Producer on Stargate, which was going into reshoots and needed someone to help out around set. I was in. The job was unpaid, and I did everything from shoveling sand to directing extras around explosions to driving James Spader, who was just as cool as you’d expect him to be.

Networking and cold calling my way to this job was completely out of my comfort zone. I had absolutely no experience in filmmaking, so selling myself into one of these roles was hard. This is one of those things you can only learn by doing, so I’m thankful that this experience forced my hand. From recruiting to closing a round of funding, I regularly put this skill to use.

Commit (absolutely) to your dreams

When I’d driven 3,000 miles to LA, I had a place to stay, but no internship. It was nerve-racking – what if I’d spent all of my savings and a summer and had nothing to show for it? But if I’d waited in Virginia until I found something, I might never have moved. The bet paid off, which taught me the value in fully committing yourself to your dreams and goals, even if you have no idea how they might work out.

I’ve found myself in similar situations throughout my career. When we were building HotelTonight, my cofounders and I were all-in, even though we had no funding and way fewer hotels than we needed to launch the service. It could have failed, but it didn’t — because we were totally committed to making it happen.

Keep trying (and trying) until you succeed

All those letters I sent and calls I made over months and months – it would have been easy to get discouraged and give up when nothing materialized. But I was determined to stick with it and see things through. I learned that if you really believe in something, you’ve gotta keep at it and not get discouraged if at first you don’t succeed. A prime example of this was in the early days of TravelPost, when we were seeking funding so long we literally had a negative balance in our bank account. I didn’t let all the naysayers get me down, but kept at it until we got a yes. And you only need one yes.

I’ll always be thankful for my Hollywood experience, even though my career took me in a different direction. If you have a summer between school years, or between jobs, do something totally different, challenging and of personal interest. Worst case, you’ll learn something you can apply elsewhere in your career. The only wrong move is not making a move at all.

More posts on this topic:

• “Here’s the Scoop: Why My First Job Mattered” — President Barack Obama
• “How Winning This Contest Changed My Life” — Oprah Winfrey
• “My First Job Lasted One Summer — But It Changed the Way I See the World” — Katie Couric, Yahoo Global News Anchor  
• “Dream Big But Be Humble: Lessons That Led Me from the Factory Floor to the Executive Floor” — Ralph de la Vega, Vice Chairman of AT&T, Inc.
• “Before I Became a Stylist, I Sold Shoes at the Mall. Here's What I Learned.” — Rachel Zoe, CEO, Rachel Zoe, Inc.; Editor-in-Chief, The Zoe Report
• “What Designing a Shampoo Bottle Taught Me About Business” — Meg Whitman, CEO at Hewlett Packard Enterprise
• “Just Starting Out: The Life-Shaping Potential of Our First Jobs” — Arianna Huffington, President and Editor-in-Chief at The Huffington Post Media Group
• “What I Lacked in Qualifications I Learned to Make Up with Courage” — Suze Orman, television host and motivational speaker
• “Practice Makes a Career” — Bernard Tyson, Chairman and CEO of Kaiser Permanente
• “What I Gained from Choosing the Rocky Road” — Ban Ki-moon, Secretary-General of the United Nations
• “Summer Jobs Are Your First Shot at the ‘Grown-Up World.’ Soak Up as Much as You Can.” — Adena Friedman, President and COO at Nasdaq
• “I Used to Hate Doing Stand-up. Then I Discovered the Power of Showing Up.” — Chelsea Handler, Executive Producer and Star, Chelsea Does at Netflix
• “Delivering Papers and Working as a Security Guard Taught Me How to Hustle” — Maynard Webb, Chairman, Yahoo!; Former COO, eBay
• “My First Career Lesson: Know When to Ask a Stupid Question” — Jon Fortt, Co-host of CNBC’s Squawk Alley
• “Be Curious. No One Limits Your Career But You.” — Marcus Samuelsson, Chef and Author at Marcus Samuelsson Group
• “Everyone Should Have Access to That First Job” — Valerie Jarrett, Senior Advisor to President Obama
• “Remember Your First Job?” — Tom Perez, Secretary of Labor at U.S. Department of Labor
• “Employers: Young Workers Are Your Diamonds in the Rough” — Maria Contreras-Sweet, Administrator at US Small Business Administration