Gen X is Being Forced to Hustle. This Time with a New Career Plan
Inside their fight to keep rising as immovable boomers and contraction stand in their way: ‘Most people I know out of work are in their 50s’

I write about TV from L.A. My Summer Sellers’ Guide reveals what shows they’re buying at Apple TV+, Amazon and HBO & HBO Max, and I reported on the boom in microdramas and how L.A. sound stages are scrambling as production dwindles. I’m at elaine@theankler.com. As a paid subscriber to Series Business, you’ll receive dispatches from Elaine, Lesley Goldberg and Manori Ravindran on the TV business. This is a standalone subscription separate from The Ankler. For access to Series Business and everything The Ankler publishes, including Sean McNulty’s The Wakeup and Richard Rushfield, subscribe here.
Everyone thinks about death every so often, but it’s a curious thing to consider your professional mortality. It’s a bit like being able to plan and even attend your own funeral — what does the home stretch of my career look like? How have my ambitions met reality? What is my legacy in my chosen industry? Have all those years of work paid off?
Gen Xers who work in entertainment are pondering these questions right now as they experience a collective Sliding Doors moment in their careers.
“I’m at an age now where I have friends that are, like, federal judges,” says writer David H. Steinberg (American Pie 2, Slackers, No Good Nick), who pivoted away from an early career in law to pursue screenwriting. “I have a friend from high school who is the head of cardiothoracic surgery at a top university. I saw him back in January, and I was trying to explain to him what it’s like being a 55-year-old who doesn’t think they’re really an expert at anything and not sure if they’re going to keep working the next day.”
Steinberg is currently in pre-production on a pilot and feels “pretty content” with his career, but many fellow creatives from his cohort, born between 1965 and 1980, are in the throes of a “career meltdown,” as the New York Times put it — boxed in by AI, consolidation, the death of cable TV, the death of Peak TV, the writers strike, ambitious millennials who make less and boomers who never leave. The squeeze is hitting right when most of Gen X is squarely in their peak earning years of 45 to 54.
For today’s newsletter, I spoke to nearly a dozen 40- and 50-somethings, including programming and development executives, writers, showrunners, agents and people working in production.
Keep reading to dive into:
How to assess your choices: Pivot to a second act? Move? Scrimp and survive until 65?
How Hollywood boomers “still extremely hungry to keep rising” are stalling Gen X
Why even successful Gen X execs lack the power of previous generations
Why so many in Hollywood who “skyrocketed” early in the ’90s and ’00s have hit a plateau
How Gen X women are getting hit particularly hard
What Gen Xers learned on the way up about negotiating and fighting for creative projects
How even 30 years on, “you have to look the part,” and it costs “a shit-ton” and the female bosses who pressured them to keep up
Why Ozempic is “hugely prevalent” among execs now
The “awkward” dance of the Gen Xer’s job interview with execs way less experienced
One Hollywood role that may be immune to ageism



