What Today's Most Successful Women Were Doing In Their 20s

By: Courtney Connley

In a social media-obsessed world where it seems that no great moment really happened without an Instagram, Facebook or Snapchat picture, it’s easy for someone’s social media page to look like the highlight reel of their life. From the fancy dinners, to the invite-only industry events, job promotions, vacations and more, we’ve all found ourselves scrolling for hours on social media admiring someone’s lifestyle and success wondering how we can achieve just that.

But often times, one high-profile picture has a long story of hard work, sweat and years of labor behind it that is often untold. So what exactly were some of the most successful women who we admire today doing when they were in their 20s trying to figure life out? Check out the list below and know that wherever you are in your career right now is exactly where you’re supposed to be.

Oprah Winfrey: At 22 years old, Winfrey moved to Baltimore from Tennessee to become the news anchor at a local TV station. In an interview with The Baltimore Sun, she describes the ups and downs of her time there, saying “I had no idea what I was in for or that this was going to be the greatest growing period of my adult life.” After less than a year on the job, Winfrey was fired, but she didn’t let her setback stop her from following her purpose. Shortly thereafter, she was recruited to co-host a local talk show, which gave her just the experience she needed to eventually host her own show years later.

Arianna Huffington: Before launching The Huffington Post, Arianna Huffington worked her way up the ranks as an author and journalist. After publishing her book The Female Woman at age 23, she traveled to music festivals around the world as a writer for BBC before moving to New York at 30.

Taraji P. Henson: Before becoming the Hollywood star she is today, Henson was a Howard University student and young mom studying theatre. To help put herself through school, she also worked as a singing waitress on a dinner cruise ship in Washington, DC and didn’t move to Los Angeles to jumpstart her acting career until she was 26.

Ava DuVernay: After studying African American history at UCLA, DuVernay went on to work in journalism and eventually started her own film publicity company. It wasn’t until she was 32 when she directed her first film.

Michelle Obama: After graduating cum laude from Princeton University, Obama went on to earn a degree from Harvard Law School before working at a Chicago law firm where she met her now-husband and former president Barack Obama.

Mindy Kaling: After graduating from Dartmouth College, Kaling moved in with two friends in Brooklyn and worked as a baby sitter and then a production assistant for a cable television psychic. She also started doing stand-up comedy at local clubs, and at age 24, she was hired as a writer for NBC’s show The Office, making her the only woman on a writing staff of eight people.

Sheryl Sandberg: While attending Harvard University, Sandberg took a Public Sector Economics class that was taught by future Treasury Secretary Lawrence Summers. After earning the highest midterm and final grade in the class, Summers eventually became Sandberg’s thesis adviser, and years later, at the age of 29, she became his chief of staff.

Shonda Rhimes: After studying English and creative writing at Dartmouth, Rhimes landed a job working for an advertising firm before realizing that her true passion was in film. She returned to school and earned her MFA in screenwriting, and caught the attention of Will Smith and Jada Pinkett Smith who showed interest in producing a feature she had written called When Willows Touch. But three weeks before production was set to start, actor Omar Epps walked away from the project and the film lost major funding. Rhimes then went on to land a research gig at HBO on the 1995 documentary Hank Aaron: Chasing the Dream.


Courtney Connley is a writer, editor and digital journalist with a sweet spot for storytelling and helping millennials win in the workplace and in life. She considers brunching to be a full-time hobby and enjoys anything that involves avocado or a good book. You can stay up-to-date with her latest work at courtneyconnley.com and follow her latest happenings on social media @classicalycourt.