Millennial Careers are Breaking Down: ‘I’m Just Trying to Survive’

Stalled careers, rising costs and the quiet calculation of how long this still works in part two of The Disappearing Ladder

(Ankler illustration)

This is part two of The Disappearing Ladder, my series about how each generation is navigating Hollywood’s narrowing path (check out Gen Z). I host the Ankler Agenda podcast and wrote about Taylor Frankie Paul and Disney’s Bachelorette mess.

Jessica* had spent seven years clawing her way up from assistant to executive at a major television studio, navigating a corporate climate she describes as “chaotic.” She had considered leaving, but stayed for the benefits as she planned to start a family.

Then, she was laid off — during her maternity leave, no less.

“Between Covid, the strikes and mergers, that was essentially five years of my career straight, and I was repeatedly held back from promotions,” the 33-year-old tells me, pointing to hiring freezes and layoffs that stymied her career goals. (She and several others spoke to me on the condition of anonymity, given concerns about professional repercussions.)

“I’m not the only one I know that has been in a situation like that, where it wasn’t a product of the work they were doing,” she adds. “These larger, major economic factors were getting in the way of moving forward in our careers.”

She is far from alone.

For this installment of The Disappearing Ladder, I spoke to 10 millennials across the business — studio executives, writers and creatives — whose careers have all hit some version of the same wall. They’ve made it past the bottom rung, but can’t see where the ladder leads.

Now in their 30s and early 40s, many are balancing young children and aging parents while feeling frustrated that they are behind where they thought they would be professionally. The careers they spent years building seem liable to blow away with the whims of their next corporate overlords. Yet fanciful professional shifts no longer feel like an option this deep into the game.

“One challenge of our generation is that you have so much more responsibility than Gen Zs,” says Juilliard-trained playwright turned TV writer Hilary Bettis (The Americans, The Dropout), who is in her early 40s. “You also have a mortgage and kids and life insurance and all of this adult stuff that you have to pay for.”

What emerged from these conversations isn’t a single story but a pattern of stalled careers, rising costs and quiet, constant calculations about how much longer this all works — and where the breaking point is.

Read on for personal confessions about:

• The breaking point: when the math stops working — dual-industry households, childcare, mortgages and careers that no longer add up

• The bottleneck: why the path up has stalled, as Gen X bosses block advancement and raises

• Success without stability: how even award-winning writers and working creatives can feel one layoff — or one killed project — away from collapse

• The workarounds: global gigs, constant travel and cross-border hustles as Hollywood work dries up at home

• The new paths: microdramas and alternative pipelines emerging as the traditional ladder disappears

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