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Richard Rushfield

How-To H’wood: Say Goodbye to Your Career the Right Way

The art of the transition: my final guide on industry survival

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Richard Rushfield
Aug 15, 2025
∙ Paid
(The Ankler illustration; Kolae/Getty Images)

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Welcome back to How-To H’wood week, where I solve the great issues surrounding the most labyrinthine and treacherous of industries. So far, I’ve explained how to ask a favor, make a friend and go to lunch.

In the previous How-To H’wood guides, I looked at various strategies for surviving and navigating this industry. Today, it’s time to ask the big question. It’s the one that, sooner or later, comes for us all. But unfortunately, this question is coming for a lot of people much sooner than they thought it would; sooner than they would like.

I speak of the dilemma of how to leave Hollywood.



The first draft of this entry was titled: How to Leave with Dignity. But frankly, at this moment in Hollywood history, I think we’re all well past that. What we’re talking about now isn’t riding out with a ticker-tape parade and an airport renamed in our honor. It’s about when it’s time to go, how do you do it with your best foot forward and your head held high, more excited about the road ahead than regretful about the road behind.

And for those for whom it hasn’t been made completely clear by outside forces that the time to leave might be today — more or less right now, if you would — for those who still can eke out a few more years, or who might float by indefinitely, when is the moment? What can we learn from those who have done it and those who have failed to do it?


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Those are the questions I’ll answer today, along with naming names about who has done it right (always model yourselves after Sherry Lansing and Richard Plepler); the Tony Vinciquerra model; what to learn from the careers of Peter Chernin, Amy Pascal and Barry Diller; others who did it all wrong and, quite literally, died in embarrassment and shame, and what to do when leaving is not your choice, the current scourge of the industry:

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