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My Advice for Navigating the Industry Ebbs and Flows to Ensure a Longer Career in Entertainment

Showing up is half the battle.

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Media Whalestock —

Opinions expressed are solely those of the author and do not reflect the views of Rolling Stone editors or publishers.

How come some people in the entertainment industry are one-hit wonders, while others have careers that last for decades? A lot of it comes down to talent, timing and mindset.

When I first started out in the business in my teens, I somehow believed that once you got that big break, that was it — you had made it. In reality, this is the furthest thing from the truth. Working as an artist is not only a balancing act of ups and downs, but also requires learning to cruise through the motions — a new skill many have to learn entirely. Over the past year, I’ve interviewed iconic celebrities and rising stars, and their stories all share some common ground.

Showing up is half the battle.

Often, you’ll have an audition come up, and before you even have the info, you’re already talking yourself out of why you’re not right for the part/gig. This is a common feeling. You wonder if you have the right outfit and if you’ll measure up to the other talent — the list goes on.

Don’t sabotage your efforts before you’ve even started, and remember, you’re not the casting agent. Show up.

Always go with your gut.

With any business venture or decision in life, go with your gut feeling. If something doesn’t feel right or feels off, don’t do it.

Don’t expect anything from anyone else — get involved.

It’s easy to sit back and wait for new opportunities to roll in. The artists I know who do well are the ones who put themselves out there, whether it’s on TikTok and other social media platforms or attending events in person or online. Mentors and PR agents can be great, but you have to do your part. Share your knowledge with your social media outlets and meet people. The more people you know in your industry, the more of a support group you’ll have.

Don’t let rejection deter you.

Once you realize it’s a numbers game, the word “no” no longer carries such a burden. There may be times when a job doesn’t work out and you end up getting a different role or going in another direction entirely. The world works in mysterious ways. I recently conducted an interview with an iconic singer-songwriter, Don McLean, who shared a wonderful story about how he got started. He found the phone number of a successful folk musician he looked up to and actually called up that person, who, in fact, answered. They became friends, and the rest is history.

Make your own opportunities.

I interviewed a TEDx speaker, Michelle Enjoli, who solely speaks about connecting people. We had a long conversation about connecting over coffee, and we both agreed that some of the best conversations occurred in our family homes around the kitchen table, watching our families gather to talk over tea and coffee. It’s where problems are solved and stories are told. I firmly believe this kind of connection can help those looking to weather the entertainment industry. Apply this in your own life, and if you’re inspired by someone, offer to take them out for coffee.

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Be yourself: Make sure you know who you are and where you’re going.

People like authenticity and want to see your true self. It’s such a simple thing, yet easily missed — especially in entertainment. Know how to set boundaries while always improving and reinventing yourself to an extent. Let your true self shine through, and show your individuality.

Enjoy the small steps of the journey, and you’ll live a happier life.

When I started in this business over 27 years ago, I had no idea how to get from point A to point B. The fact is no one does. You do the best you can to move forward because it’s the small things and the daily habits you do every day that add up to bigger milestones. By doing one thing a day that puts you in alignment with your higher goals, you’ll be setting yourself up for success.

Surround yourself with people who are going to give you constructive criticism but also lift you up.

Having the right team and support system around you can make or break your career before you even get started. Make sure these are like-minded people who support you and encourage you to be your best and help you reach your goals. While the life of an artist is still relatively unpredictable, being overprepared when an opportunity presents itself is the best advice I can give.

It’s essentially an ongoing mix of all of the points stated above. Great timing doesn’t hurt either, but it’s never too late to pursue your dreams. Some of the best people are returning to the industry after leaving other careers that they’ve been in for years. The most important thing is that you start, which brings us back full circle: Showing up is half the battle.


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