3 Shows That Are Realistic About Work in Your 20s – And 2 That Aren't

Issa and Molly


Taylor Tobin
Taylor Tobin1.84k

All of us who have weathered the stressful, exciting, and ever-changing experience of finding your place in the workforce as a 20-something know that TV doesn’t always give the most accurate picture of early career development. Characters with super-flexible work schedules, inflated incomes, and the ability to buy and do whatever they want show up all the time on TV. 

And while there’s a level of escapist fun to watching these unrealistic fantasy situations, it’s satisfying to find a TV show that truly captures the education, the frustration, and the general weirdness of work life in your 20s. We found 6 shows that deliver the goods in an honest way – and 2 that definitely don’t.

The Realistic Shows

1. Insecure

An HBO comedy centered around a pair of Los Angeles friends in their late twenties, “Insecure” offers one of the most on-point perspectives on the challenges and triumphs of working throughout your third decade of life. 

BFFs Issa (showrunner Issa Rae) and Molly (Yvonne Orji) spend each “Insecure” episode struggling with romantic entanglements, drug dalliances, friendship complications, and career problems. Issa, who is African-American, works as a project associate for a non-profit focused on providing support and resources to low-income students, but she finds herself constantly trapped in meetings with out-of-touch white colleagues who have subtly-bigoted views on the kids they’re trying to help. She ultimately disagrees with the organization’s managers to a point where she chooses to quit, and in order to support herself, she moonlights as a Lyft driver and accepts a property management role at an apartment building in exchange for free rent. These less-than-ideal moves are par for the course for a 20-something employee, and “Insecure” depicts Issa’s employment debacles as highly-relatable moves for a young person still trying to find her foothold in the professional world.

On the flip side, Issa’s best friend Molly has a high-powered career as an attorney, and her professional success clearly sets her apart from other characters in her age group. However, she finds herself dealing with a different set of complications, from subtle racism at her majority-white law firm to sexist comments from male colleagues. Like Issa’s exploratory freedom, Molly’s career success comes with strings attached, which definitely checks out in terms of real-world job experiences.

2. Younger

While TVLand’s “Younger” technically centers around a 40-something mother masquerading as a 26-year-old in order to re-enter the workforce after a divorce, the show reveals plenty of truths about moving forward in your career as an ambitious 20-something.

When the show’s protagonist, Liza Miller (Sutton Foster), takes a position as a marketing assistant at Empirical Publishing, she finds herself saddled with a list of responsibilities very typical for an early-career administrator. She fetches coffee for boss Diana Trout (Miriam Shor), takes notes at meetings, and even handles personal errands for Diana. While Diana ultimately proves to have Liza’s best interests at heart, she initially treats her dismissively, an experience plenty of 20-something admins can relate to.

In the show’s second season, Liza and 26-year-old Empirical editor Kelsey (Hilary Duff) earn the chance to run their own imprint, and they suddenly find themselves positioned as bosses rather than subordinates. While “Younger”’s timeline for this promotion feels admittedly fast, the ability to seize opportunities and put oneself forward for advancement even at an early career stage can and should be common practice for talented young employees. 

3. Vanderpump Rules

Okay, we admit it: a Bravo reality show is a surprising place to find an accurate depiction of the working world. But for all its drama, high-octane fights, and romantic debacles, “Vanderpump Rules” actually reveals a very genuine look at the lives of 20-something hospitality workers.

“Real Housewives of Beverly Hills” star Lisa Vanderpump owns several restaurants in the Hollywood area, one of which – the sultry eatery SUR – provides the setting for the hit spinoff known as “Vanderpump Rules”. The show guides viewers through the lives of a youthful group of servers, bartenders, models, musicians, and hosts, all working shifts at SUR to pay the bills while pursuing their dreams of stardom. While few hospitality employees have the benefit of a boss like Lisa (who makes an almost-inappropriate investment in the personal lives of her staff), the constant squabbles about shift switching, the palpable disappointment when one of the SURvers gets turned down for a promising role, and the consistent appearance of “Vanderpump Rules” cast members working the floor at SUR all feels refreshingly honest to creatives taking restaurant jobs to fund their artistic ambitions.

The Not-So-Realistic Shows

1. Friends

Now that the full series can be enjoyed on Netflix, ‘90s TV classic “Friends” has enjoyed a newfound swell in popularity, largely spurred by a younger generation of viewers who missed the show when it originally aired. But while “Friends” boasts one of the finest ensemble casts in TV-comedy history and brought us immortal cultural moments that stand the test of time (“Smelly Cat”, anyone?), the show absolutely dropped the ball on exhibiting realistic career patterns and lifestyles for its 20-something NYC-based characters.

Between Rachel’s fashion work, Ross’s paleontology professorship, Monica’s role as a head chef in a Manhattan restaurant, Joey’s busy acting career, Phoebe’s eclectic freelance pursuits, and Chandler’s intentionally-mysterious office job, the “Friends” already have enviable work situations for their ages. But where the show really diverges from reality involves the amount of free time and flex time that each character enjoys. They’re regularly able to take long lunches, and hour-long coffee breaks at Central Perk, and we as viewers never see any consequences for these behaviors. While it’s certainly possible for a 20-something employee to have a flexible schedule, the “Friends” take this concept to a whole other level. 

Also, it would be messed up if we didn’t mention the ridiculous discrepancy between what Rachel and Monica likely earned as early-career staffers and the market rent for the gargantuan West Village apartment they live in. Yes, the show makes a point of mentioning that Monica inherited the apartment’s lease from her grandmother, but even so: we’re not buying it, “Friends”. 

2. The Bold Type

A major ratings coup for the FreeForm network, “The Bold Type” tells the story of three 20-something staffers at a fashion magazine heavily inspired by Cosmopolitan. These charismatic young employees – writer Jane (Katie Stevens), social media director Kat (Aisha Dee) and fashion assistant Sutton (Meaghann Fahy) – deliver phenomenal performances as go-getters in the editorial world, and we see their characters constantly striving for new challenges, higher positions, and a promising professional future.

However, “The Bold Type” presents the modern-day print magazine sphere in a very rose-colored light, unfortunately out-of-step with the realities of the industry. For instance, Jane receives a position as a full-time staff writer at Scarlet Magazine, a role that’s increasingly rare at publications, particularly those with print editions. While staff writers aren’t extinct yet, even major magazines like Cosmopolitan produce the majority of their content through freelance contributors. Kat’s director-level role would also count as a rarity among employees in their early to mid 20s. Even in a youth-related aspect of the business, like social media, a position that senior would likely go to a more-experienced staff member. On top of that, the “Bold Type” ladies have impeccably-decorated, beautiful apartments, which definitely aren’t the norm for early-career professionals, especially in erratic fields like media.“ The Bold Type” does a lot with its portrayal of editorial culture in 2018, but small details like these diminish the show’s authenticity (but, luckily, not its entertainment value).

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