A Career Reinvention Watchlist

As layoffs continue in the wake of a year of ominous headlines about the bots who are replacing us, a recent EY report found that over 70% of employees are reeling from AI anxiety.

That actually sounds low. The idea of having to concoct a new livelihood – one that won’t be taken over by AI – is enough to send everyone’s angst headquarters into overdrive. But headlines about our impending obsolescence are not actually news, and to shed some light on how to survive automation and reinvent your career, we turn to an overlooked professional resource: movies and TV shows.

The Watercooler has compiled a starter watchlist that will offer perspective and hope while sparking new ideas…and some much-needed laughter. A few of these picks can even offer a blueprint for how to start over.

The Career Samplers


One of the challenges of embarking on a career reboot is not knowing where to direct your focus. After graduating from college, Sean Aiken heard the same advice that many grads receive: find something you’re passionate about. Forget for a moment how impractical that advice can be for the vast majority of people trying to pay down student loans or credit card debt while affording record-high rents. Sean didn’t know what he was passionate about. So he pitched himself to try out 52 jobs in 52 weeks, and invited his friend along to film it.

The result is a Whitman’s Career Sampler in the form of a documentary, one that allows viewers to drop into professions they likely never considered before: trade show salesman, cancer fund-raiser, hotel staffer, stock trader, brewery master, fashion buyer, vet assistant, and 44 others.

More recently, Barack Obama traveled the country to interview tech, hospitality, and care employees and bosses about their jobs, their worries, and their motivations for his Netflix docuseries Working: What We Do All Day. The four episodes explore how automation is impacting each sector while also revealing some of the day-to-day of roles like a hotel general manager, a data analyst, a lobbyist, an autonomous truck company founder, and a home care supervisor.

If the idea of job sampling appeals to you as a what-next, several companies do offer rotation programs. Or you could pitch yourself to run one at your current or next employer by sending them these FastCompany and Society for Human Resources Management articles.

          Where to stream Work: What We Do All DayNetflix   One Week Jobs:  Amazon 

Historical Perspective: Modern Times (1936)

United Artists

If it feels like our current moment is unprecedented, Charlie Chaplin’s treasured classic will assure you: our forebears found their way to the other side of ominous “modernizations” nearly a century ago.

One of the 25 films selected by the Library of Congress for preservation, Chaplin wrote and starred in Modern Times as Little Tramp, an assembly line worker who has a meltdown while struggling to keep up with the pace of his factory job – and ends up stuck inside the machine.

The slapstick comedy captured several of the anxieties of the 30s. Little Tramp ultimately ends up in a hospital, followed by jail (after being confused for a communist protester), followed by an accidental ingestion of cocaine. But on the other side of all that, he reinvents himself as a shipbuilder and a department store night watchman, proving that despite the Depression era the film is set in, nothing is gonna keep him down.

         Where to stream Modern Times:  The Criterion Channel

We’re Gonna Make It:  Laverne & Shirley

Paramount Television

In Season 6 of this Happy Days spinoff set in the 50s, best friends and co-workers Laverne and Shirley (Penny Marshall and Cindy Williams) learn that their bottle capping jobs at the Shotz Brewery in Milwaukee are going away; Mr. Shotz is replacing everyone with a machine, he announces over a loudspeaker, and everyone has to take their personal belongings and leave. Instead the twosome grab ketchup and mustard dispensers and deface a painting of their boss.

That doesn’t bode well for finding other work in Milwaukee, so with nothing left to lose, they strike out for LA, where they eventually land work at a department store, a BBQ run by an aunt and uncle, and their buddy Carmine’s singing telegram business. But the best reinvention comes from Lenny and Squiggy, their “greaser” friends and former coworkers at Shotz, who follow them out west and launch the Squignowski Talent Agency. Look for the episode where they crash the live “Golden Circle Awards.” Being replaced by a machine was the best thing that ever happened to this motley crew. – M.R.

          Where to stream Laverne & Shirley: Pluto TV

Special bonus:  In case you don’t recognize him, Lenny is played by Michael McKean – better known today as Chuck from Better Call Saul. For older generations, McKean will forever be the guy from This is Spinal Tap and a staple of Christopher Guest movies – not to mention nearly 100 TV shows.

Faking It Til You Make It:  The Secret of My Success

Universal Pictures

An 80s time capsule that was set to be turned into a 2020 theatrical production (shutdown by Covid), this is the comedy that stars Michael J. Fox as Brantley Foster, a college grad from Kansas who moves to New York after landing a job in finance, only to discover his company got bought and his first job is gone.

Forced to get resourceful, he talks his way into a mailroom job and uses the low level role to learn everything he can about his new company, then creates a new identity to land a second role as a suited-up executive. Next thing you know he’s in a palatial estate being pursued by the big boss’s wife.

The screenplay took some inspiration from the early Hollywood experience of none other than Steven Spielberg, who snuck onto the Universal Studios lot at a young age, found an empty office, and used it as his “production company” – something Brantley does in the film.

While it might not offer the most replicable how-to-reinvent story, the quick pivots, the company research tactics, and the networking he pulls off might just inspire some can-do attitude in the face of your own misfortunes. – C.G.

         Where to stream The Secret of My Success:  Apple TV

The Do-Over: Younger

As a 40-something divorced mom living in the suburbs, Liza has been out of the workforce for over a decade, and no one is giving her a chance to get back in. So she changes up her resume to pretend she’s 26 and lands a job in book publishing – a profession she left 15 years prior.

Warner Bros Television

To keep her new post, Liza has to stay up on all the latest trends and build relationships with her colleagues without revealing her true identity – a balancing act that becomes more challenging with each passing day.

Necessity is the mother of Liza’s invention, and, to a greater extent, reinvention. Despite the implausibility of the premise, the show is grounded in actual age-gap and publishing world realities (there’s a story arc involving an author that Game of Thrones fans will appreciate), and there are actual tips to be gleaned for anyone starting over in a new field mid-life – or wishing they could.

Younger also works as a fun escape watch, as it’s full of love triangles, the twinkly lights of Manhattan nightlife, and groovy, massive Brooklyn artist lofts. As the Watercooler’s Cindy White describes it, the addictive comedy “gives flight to the fantasy of getting a do-over to relive your 20s, albeit with the wisdom and gratitude of midlife.”  Check out her review.  – C.G.

        Where to stream Younger:  Hulu    

Worth noting:  Several companies have created “Returnships” for people who are looking to get back into the working world after a significant career gap. Look up “returner” on Indeed – or look for a Returnship here.  

A Work-Life Comeback:  Chef 

Walt Disney Pictures

Jon Favreau wrote, directed and stars in this underappreciated comedy about a head chef who reaches the top of the LA food pyramid — only to blow up his career with a public altercation with a restaurant critic. Adding to his woes, he’s estranged from his wife and son.

Hitting rock bottom gives him the idea to launch a food truck business and re-discover his passion for cooking, and he invites his family to join him for a road trip in the truck.

Co-starring Scarlett Johansson, John Leguizamo, Robert Downey Jr, and Sofia Vergara, there are details to be borrowed from Chef, from the how-tos of launching your own business to the ways that experimentation can pay off to the roles that both your known networks and social media can play in getting the word out. But this one is also a feel-good film about rediscovering work-life balance and the upsides of a big career loss.  – M.R.

         Where to stream Chef: Hulu

         Worth exploring:  Forbes on How to Start a Business in 2024.

A related Watercooler read:  Laid off? 10 Movies to help you cope.

How to Crash Big Tech:  The Internship

Universal Pictures

The pitch for this movie was surely “Wedding Crashers but set at Google,” as The Internship brings back the mischievous twosome of Vince Vaughn and Owen Wilson, this time as old school watch salesmen Billy and Nick. As watches were largely replaced by cell phones, they’re out of work. So they cook up a plan to reboot their careers: Infiltrate Google’s state-of-the-art internship program and crush the competition with their obsolete methods and outdated charms.

The comedy got some backing from the behemoth, and, “Yes, you get a peek behind the chocolate factory,” Vaughn shared with Australia’s The Age. “But it’s really about wanting to start over, and I wanted to pick an industry that authentically felt like there was a future there.”

To land their roles, they turn their lack of preparation into an asset – delivering wildly out-there answers to the out-there interview questions. Once inside, they have to compete in a Battle Royale with the tech geniuses – Billy and Nick rising to the challenge with teamwork and people skills as their younger counterparts spend all their energies competing against each other.

You’d think that Google would have capitalized on the film and created a legendary mid-career reinvention program – given how much the company could actually learn from the insights, skills, and networks of more seasoned workers. But according to their AI assistant, there is no such thing. Keep hope alive! Other organizations are using their human brains and offering (paid) mid-career internships. Idealist has some advice – C.G.   

        Where to stream The Internship: Hulu

The Five-Career Plan: Julia

Imagine Entertainment

The first celebrity chef had several novel-worthy careers before she first appeared on television at 51 years old. The woman who would become Julia Child lost her first post-college job in advertising, so she threw her name into the hat at the Office of Strategic Services, the WWII-era precursor to the CIA. As the story goes, her first job required cooking up concoctions that would repel sharks from explosives that were targeting German U-Boats.

She must have succeeded, because she rose up to become Chief of the OSS Registry and was assigned to posts in China and Sri Lanka. It was only after she followed her husband to France that she decided to take up classes at Le Cordon Bleu, which led to her cookbook writing career, which launched her TV career as The French Chef. Child reinvented yet again in her 70s when she founded the American Institute of Wine and Food.

To see how she pulled it all off, well you’ll have to read her memoir. But the best film to watch is the 2021 documentary Julia, which will likely intrigue you enough to follow it with the scripted HBO/Max series of the same name. As the Guardian’s Rebecca Nicholson describes the drama, which just released a second season, “it’s a uniquely indulgent watch, erudite and gorgeous and heady.” – M.R.

          Where to stream Julia the documentary: Apple 

          Where to stream Julia the scripted series: Max 

Grandfathered In: The Intern 

Warner Bros Pictures

When a 70-year-old widower (Robert De Niro) realizes that retirement isn’t all it’s cracked up to be, he jumps at the opportunity to become a “Senior Intern” at a burgeoning e-commerce fashion startup founded by Jules (Anne Hathaway), a driven young boss who’s in over her head. Standing out like a sore thumb in his suit, he ultimately becomes a mentor to Jules, helping her navigate the pressures of her CEO role while teaching the other employees some timeless lessons about business.

Before you dismiss this one, you should know it was one of Quentin Tarantino’s favorites the year it was released. The film is also rooted in some realism, particularly in how it depicts the generational divide and ways to surmount it. Opening minds, listening more than talking, and considering other people’s emotional needs are part of how the Silent Generation and the Millennials realize they have more similarities than differences.

It’s an uplifting film about fresh starts and finding fulfillment during the golden years. But more importantly, in a rapidly changing world where institutional ageism impacts people earlier in their careers than ever before, seeing the benefits of pairing older workers with younger ones is more relevant than ever – and will hopefully inspire some other CEOs to take note. – C.G.

         Where to stream The Intern: Netflix  

Worth exploring: 29 Companies with Flexible Jobs for Older Workers.  And The Case for Why Companies Should Hire Older Workers.

The Midlife Crisis: The Rookie


Inspired by a true story – and inspiring more true stories like it – cord cutters might have missed this ABC dramedy about a middle-aged business owner (Castle’s Nathan Fillion) who decides to leave his comfortable life to become an LAPD officer.  His kid has left home, his marriage has imploded, and he’s trying to embrace what he wanted to be when he was younger – which was a Chippendales dancer and an NFL player, but after that, a cop.

As the department’s oldest rookie, he has to overcome the skepticism of his peers and taunting by his commanding officer, who introduces him as “born before disco died” and describes him as “a walking midlife crisis.” But he makes it clear that he has skills and wisdom to spare and, most importantly, he brings the fresh enthusiasm of someone who has finally found a purpose. While it can be as far-fetched as any network comedy-drama amping up the entertainment value, the series makes the big life pivot seem perfectly attainable.  – C.G.

           Where to stream The Rookie: Hulu

The Accidental Activist: Erin Brokovich

Universal Pictures

Many people know her name and associate her with her environmental activism. But this Oscar-winning 2000 movie tells the story of how Erin Brokovich made the leap from unemployed single mom without a law degree to a job as a clerk at an L.A. law firm.  As her story unfolds, it becomes clear that her lack of legal expertise – and lack of decorum – contributed to what became a major discovery. It’s a riveting David vs. Goliath tale about corporate greed and its cost to human health, and the improbable victory she helped secure comes in a hefty court settlement in the hundreds of millions.

But the real reason to watch Erin Brokovich is to witness her reinvention. The movie makes a case for the need to be relentless, which comes easier when the quest is for the truth – and a much larger purpose.  – C.G. 

             Where to stream Erin Brokovich: Netflix   

As reflections of their times, films and TV shows are reminders that we have collectively survived many rock bottoms, technological transformations, and forced reinventions. There’s company in the struggle and wisdom to be found in the stories of the “resilient stock” we all come from. But take some added inspiration from the people who created these films and series, and turn your own anxieties into the next generation’s lessons from our times.

Looking for more stories about fresh starts?  Try the Watercooler’s Beta “Stream Search” and scroll down to Interests – then click on “Starting Over” and whatever else you’re in the mood for.

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