18 Things I Learned From My Run-In With A Hollywood Executive

I didn’t think I’d ever have a run-in with any major Hollywood players, let alone an executive. But a few weeks ago, that’s exactly what happened. I was sitting at my desk when the phone rang and the voicemail said it was someone from Warner Brothers calling.

I called back as soon as I could, knowing it could be a story for The Billfold (I’m still waiting to hear back on that). In the meantime, my encounter with this person taught me some valuable lessons about money and myself. Here are some of them:

Episode 318: Life Lessons From A Hollywood Actor – YouTube
1. The Power of Networking
2. Navigating the Entertainment Industry
3. Importance of Building Meaningful Relationships
4. Insights into Hollywood’s Inner Workings
5. Lessons in Effective Communication
6. Embracing Opportunities for Growth
7. Impact of Persistence and Resilience
8. Recognizing the Value of Expertise
9. Strategies for Personal Development
10. Leveraging the Influence of Industry Insiders

1. Be Prepared To Fail

There’s a lot of pressure in Hollywood to be successful, and it’s easy to get caught up in that mentality. But while we’re always aspiring to new goals and greater accomplishments, it’s important not to forget what you’ve already achieved or take yourself too seriously. 

If you’re going through life without ever failing at anything, then that means you aren’t trying hard enough! Failure is the best way for us to learn from our mistakes and grow as individuals; if everything goes according to plan all the time, how will we ever know what works? 

It’s also important for me not only as an actor but also as someone who has suffered from depression failing isn’t embarrassing or shameful; it’s just part of life! 

If I hadn’t failed at my audition last week (more on this later), then I would never have tried again when another opportunity presented itself later on during my trip out here in LalaLand…

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2. Online Networking Is A Joke

I know, I know: You’re reading this and thinking, “But online networking got me an interview with a Hollywood executive!” Well, I’m sorry to break it to you but that’s not enough. 

If you want to succeed in Hollywood (or anywhere), it has nothing to do with what computer or device you use and everything to do with the people around you. 

The only way for people in LA who don’t already have jobs or aren’t famous for their work outside of LA will get their break is by getting out there and talking to people face-to-face.

Online networking is just another word for sending emails or tweeting about yourself over and over again until someone gives up trying to ignore your existence because they feel bad about being rude.

3. Trust Your Gut

This is something I’ve learned from my time in the world of entertainment, and it’s also a lesson that has come in handy time and time again in my personal life. 

Whether you’re going through something as trivial as needing a new pair of pajamas or as momentous as taking over an entire country, always trust yourself enough to know what’s right for you at any given moment. 

It doesn’t matter if everyone around you thinks otherwise if it feels right to go left instead of right, then do it! Don’t let anyone else tell you how to feel or how to act; consider their thoughts and concerns but never allow them to hold back your true desires. 

And if they don’t like what they see? That’s ok too: just remember that there are plenty more people out there who will love every bit about who YOU are!

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4. Focus On The Long Game

You know how many people there are in the world who have a running start at their dream? Not many. Most of us are just trying to get by day-to-day, and even if we don’t have our dream job, we’re happy with what we do have. 

But for every one of those people who doesn’t feel like they’re living their best life, there’s someone else out there with a vision for their future so big that it feels like too much for them to handle and maybe that person is you!

So when I say “focus on the long game,” what I mean is focus on your end goal and don’t worry about short-term failures (because they will inevitably happen). 

Don’t worry about what other people think or what they’re doing or even what they’ve done this isn’t about them anyway; this is about finding clarity within yourself so that whatever opportunities come your way feels right and true for YOU.

5. Rejection Isn’t Personal

One of the most valuable lessons that I learned from this experience is that rejection isn’t personal. It doesn’t mean you aren’t good enough or that you didn’t do a good job. 

It means that at that moment in time, something about your work wasn’t the right fit for them and their organization.

This is true for many things in life and business: it’s not always about how much talent or skill you have, but rather how well suited an opportunity is for your skillset at any given time. Sometimes you need to be patient before finding an opportunity that does align with where your strengths lie and sometimes it will take a while until something works out perfectly!

Rejection may seem like a difficult thing to get over after having been rejected by someone who holds considerable influence within Hollywood.

But if I hadn’t had this experience then there would have been no way of knowing whether or not rejection was just part of the process or maybe even worse than usual due to my race/gender identity (which did happen very recently).

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6. Test The Waters First

If you’re wondering whether or not it’s a good idea to ask for help, just ask yourself this: “What’s the worst that could happen?” 

The answer is probably nothing, but even if the worst happens and someone says no, it might be better than going through life feeling like you can’t ask for what you want because of some outdated stigma. 

If they say no, they’ll get used to saying it and will start thinking about how helpful they were in the long run (and then maybe they’ll start being more helpful).

If someone tells me I’m asking too much or pushing boundaries too far or being unreasonable… well… let me put it this way: usually, those people are wrong. 

And if they’re right about something? That doesn’t mean I have to listen to them; I’m still allowed my own opinion on things too!

7. Some People Are Just Jerks

The best way to deal with people like this is to not let them get to you. Don’t let their actions or comments get in your head, don’t let them make you feel bad about yourself, and don’t let them get in the way of your goals and dreams. 

If a Hollywood executive thinks that running into you at a restaurant is going to ruin your chances of making it big as an actor, then he just doesn’t know what he’s talking about!

8. Use Your Connections To Your Advantage

It’s not always possible or even advisable to try to use connections in Hollywood to get a job, but if it is, then take advantage of them. If you have any friends who work in the industry, use them as leverage when applying for jobs. 

If your friend knows someone at the company where you’d like to work and can put in a good word for you, that’s great! Make sure to send flowers (or something else thoughtful) when they do this for you because it costs nothing and goes a long way toward cementing their loyalty.

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9. If You Don’t Ask, You Don’t Get

I was blessed with a father who taught me to always ask questions. He told me that if you don’t ask, then you can never get anything. 

He had an old-school mentality where people didn’t have access to Google and so they needed to know how to find things out on their own. In other words: if you want something done right, do it yourself.

That philosophy has served me well as I navigate my way through the entertainment industry as a writer and producer of television shows and movies. 

One of the most important lessons I learned from him is that asking questions creates opportunities for others to open up about themselves in ways that may not be possible otherwise.

Or even worse could lead them away from sharing something important about themselves with us entirely! 

This is especially true now that we live in such an information-heavy era where there are so many different outlets for people’s creativity (and sometimes paranoia) than ever before… 

Which means there are plenty of chances for us all not only learn more about each other but also accept each other’s differences without hesitation!

10. Never Burn Bridges, But Feel Free To Walk Away From Them

You never know when you might need someone in the future, so while it is important to maintain relationships, it is also okay and necessary to sever ties with people who are toxic or unsupportive. 

If someone isn’t going to be a good friend or partner, then they don’t deserve your time. The only way you can find out is by trying it out for yourself.

11. Casting Is What Separates The Amateurs From The Pros

Casting is what separates the amateurs from the pros. Casting is a skill that can be learned, taught, and practiced. There are books on it and classes you can take. It’s something anyone can learn to do well, regardless of their background or education level.

There are indeed casting directors out there who have been doing it for decades, but if you’re starting from scratch then all you need is time and dedication to get good at it yourself.

And I guarantee that once you’ve made some progress in your practice sessions (you will have them).

Then all your hard work will pay off sooner than later because people will start noticing how much better you are at finding talent when compared to other novices who don’t know any better than they do!

12. First Impressions Are Everything

I began this article with the story of my meeting with the Hollywood executive, which happened to be my first professional experience in Los Angeles. The problem with that was that it was also the only one. 

My run-in with him was a success because he remembered me as well as everything he liked about me and what I’d done for him. 

He had a clear impression of me in his mind, so when we crossed paths again at an event a few years later, he immediately recognized me and greeted me warmly something I learned from watching him interact with others around us that night.

The point here is simple: first impressions matter! If you want people to remember you positively after meeting them once or twice, make sure those meetings go well so they can recall your attributes at will (or similar ones). 

Otherwise, all you have left after making an impact on someone’s life is their memory of an awkward handshake or even worse no memory at all!

13. Sometimes You Can’t Change A Jerk Into A Decent Human Being

As you might imagine, I was not pleased with his attitude. To be honest, I was shocked that someone who worked in the entertainment industry would treat their clients so poorly. 

But after some thought and self-reflection, I realized that this jerk of an executive is simply not a decent human being. 

You see, there are some people out there who will do anything for their benefit even if it means stepping on others along the way and they usually have very little regard for other people’s feelings or opinions. So what can you do when you encounter such a person?

It’s simple: walk away from them! No matter how much money or prestige someone has accumulated in their lives, if they have no compassion for others and treat them unfairly (or worse yet) then there is no reason why your life should be affected by their actions or behavior.

14. You Can Phrase Almost Anything Positively, Even If It Sounds Horrible At First

Here’s an example that illustrates this idea. Let’s say you’re trying to lose weight and you’ve been working out three days a week at the gym, but you’re not seeing any results because your diet isn’t good enough. There are two ways to phrase this:

  • “I’m not losing weight because my diet isn’t good enough.”
  • “I’m not losing weight because I’m exercising too little.”

In the first case, the issue is with your diet your exercise habits are fine! In the second case, it sounds like working out just isn’t enough for you right now; it’s not going to be effective until you get on a better eating plan. 

The first way is negative (you aren’t getting what you want) while the second way is positive (there’s something else that needs improvement). Both are true, but one feels better than another. 

So next time someone asks why something didn’t work out as planned or why things aren’t going according to plan yet again which happens fairly often in Hollywood! try turning their statement into a positive or negative statement before answering them.

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15. Make Tough Decisions Now, Not Later

This is the toughest thing to do when you’re in the middle of a project and things are not going well. You want to stick with it because you think if you just give it some more time, everything will turn out all right. 

That way of thinking can lead to disaster if you don’t make a decision before things get too far along and your reputation or money are at stake. 

The key is making sure that when you decide to drop something, it’s for good reasons and those reasons should be based on logic rather than emotion (otherwise, we would all be dropping our careers every time someone said something means).

16. Forcing Yourself Can Lead To Huge Growth

When you force yourself to do something, you will learn more about yourself. You’ll discover that you can do things that are outside your comfort zone and realize what kind of person you are. 

For example, I thought I was afraid of speaking in front of a room full of people but as soon as I forced myself to deliver a speech at work, I realized that it wasn’t that bad! 

Now I just need some more practice because it was still early in the morning and everyone else seemed asleep while they listened to me. 😂

By forcing ourselves out of our comfort zone, we become more confident overall with our capabilities in general which can help us succeed later down the road when faced with difficult situations or challenges. 

It also helps us feel less afraid when trying something new because now we know we probably won’t fail at whatever it may be (at least not right away). 

This also gives us an opportunity where if we do fail during our attempts at something new–what’s one more attempt? We’ll keep getting better until eventually succeeding doesn’t seem like such a far-off dream anymore!

17. Know When To Walk Away From Something

Sometimes you have to know when to walk away from something.

You may be going into a meeting with the most powerful person in Hollywood, but if you don’t feel confident about what you’re doing, it’s not worth it. 

Cut your losses and move on. You can’t force yourself into being someone who isn’t true to who they are at least not without completely losing yourself in the process.

18. There Is An End In Sight, I Promise

Do you hear that? That’s The Voice of Experience talking. It’s not going to be easy. It’s not going to be quick. It’s not going to be painless. 

And it might not even go the way you want it to go, but trust me: there is an end in sight, and one day you’ll look back on this whole mess and laugh about it with your friends at brunch over mimosas and egg white omelets with avocado toast on the side (because of #health).


It may seem trivial, but I hope my experience shows you that, in Hollywood, sometimes it’s the little things that make the biggest difference. So remember to look out for all those small opportunities as they come your way, and be sure to take them when you can!

Further Reading

Explore these additional resources for more insights related to the topics discussed:

Lessons From Running a Bookstore: A 2-Year Reflection Short Description: Ryan Holiday shares valuable lessons learned during two years of running his own bookstore, offering insights into entrepreneurship and the world of literature.

Personal Reflections: 18 Things Learned From a Hollywood Executive Short Description: Dive into personal reflections on 18 lessons gained from an encounter with a Hollywood executive, delving into the entertainment industry’s dynamics and personal growth.

Insights from “18 Things I Learned From My Run-in With a Hollywood Executive” Short Description: This resource offers deeper insights and discussions based on the article “18 Things I Learned From My Run-in With a Hollywood Executive,” providing additional perspectives on the subject matter.


How can running a bookstore provide valuable lessons?

Running a bookstore involves various challenges and opportunities that can offer insights into entrepreneurship, customer engagement, and the book industry’s dynamics.

What can personal reflections teach us about encounters with industry professionals?

Personal reflections on interactions with industry professionals like Hollywood executives can provide unique insights into the entertainment world, career growth, and the lessons learned from such experiences.

What are some key takeaways from the encounter with a Hollywood executive?

The encounter with a Hollywood executive can offer valuable lessons about networking, navigating the entertainment industry, understanding the importance of connections, and fostering personal development.

How can personal experiences shape one’s understanding of the entertainment industry?

Personal experiences and encounters in the entertainment industry can shape one’s understanding of its complexities, challenges, and the insights gained from interactions with industry insiders.

What can we learn from reflections on 18 specific things learned from a Hollywood executive?

Reflections on 18 specific lessons learned from a Hollywood executive can provide actionable insights into areas such as negotiation, communication, industry dynamics, career advancement, and the importance of adaptability.