7 Extremely Successful Celebrities And What They Were Doing In Their 20s (Because It’s Okay To Not Have It All Figured Out)

“I’m not as successful as I thought I would be by now.”

Have you ever thought these words to yourself?

The fact is, not everyone is in their peak during their twenties. This is the age where we are still gaining new skills, meeting new people, and figuring out who we will become.

That’s why I’ve put together a list of 7 extremely successful people on what they were doing in their 20s and what major lessons you can take away from each example.

1. Mark Cuban was a bartender after college.

Mark Cuban
Mark Cuban

In 1982, when Cuban first moved to Dallas, Texas, he started off as a bartender and later found a job as a PC software salesperson. But less than a year later, Cuban was fired from his sales job because he wanted to close a deal with a new client instead of opening a new store that day like he was supposed to.

This led him to starting his first business, Microsolutions.

“When I got to Dallas, I was struggling — sleeping on the floor with six guys in a three-bedroom apartment,” Cuban wrote in his book. “I used to drive around, look at the big houses, and imagine what it would be like to live there and use that as motivation.”

Lesson: When you are young and scrappy with the drive to succeed, you can make it!

2. Arianna Huffington was traveling the world with the love of her life.

Ariana Huffington
Arianna Huffington

At age 21, Huffington entered in a relationship with the famous journalist Henry Levin. During her early twenties, they traveled the world together attending music festivals while she worked on her book “The Female Woman” and he wrote for the BBC.

Even though, Huffington broke up with Levin when she turned 30 because he didn’t want to have children, she still regards him as her mentor in her 20s.

Lesson: You can grow and learn a lot while being in a committed relationship in your 20s even if it doesn’t work out

3. Oprah Winfrey was demoted from her job.

Oprah Winfrey
Oprah Winfrey

Before Winfrey was a $3 billion media mogul, she had her humble start as a co-anchor for Baltimore’s WJZ-TV nightly news.

But by age 23, Winfrey suffered one of the biggest career disappointments of her life, a huge demotion.

“I had no idea what I was in for or that this was going to be the greatest growing period of my adult life,” Winfrey said. “It shook me to my very core, and I didn’t even know at the time that I was being shaken.”

This was a stepping stone that would lead Winfrey to becoming the talk show host the world knows her by.

Lesson: What may initially seem like a failure is just a stepping stone to success.

4. Warren Buffett was just getting into investment and sales.

Warren Buffett
Warren Buffett

For several years after college, Buffett put his time as an investment salesman at his dad’s brokerage firm in Omaha.

Afterwards, Buffet did a short stint in New York City as an securities analyst. However, he quickly realized the city wasn’t for him because it’s easy to lose perspective in a big city like that.

At age 26, he went back to Omaha to start Buffett Partnership to do investment partnerships.

Lesson: It’s okay to do the opposite of what everyone is doing and do what feels right to you.

5. J.K. Rowling was daydreaming about Harry Potter during her day job.

JK Rowling
JK Rowling

In 1990, a 25 year old J.K. Rowling was stuck in a delayed train ride when she came up with the idea for Harry Potter. That evening, she started writing the very first book.

During the next 7 years, she would experience being fired from her secretary job at Amnesty International, marriage and divorce, having a daughter, and getting diagnosed with depression.

Even with all the traumatic events in her life, Rowling managed to finish her book in 1995 and get it published in 1997.

Lesson: If you have a will you will find a way no matter what challenging situations life throws at you.

6. Anderson Cooper couldn’t get even get a job answering telephones right after college.

Anderson Cooper
Anderson Cooper

The first job Cooper landed was being a fact-checker for Channel One, a news broadcast show for high schoolers. Even after 6 months of doing this, he wasn’t discouraged and was determined to find a way to becoming a foreign correspondent.

“For me, that was hatching a plan to quit my job as a fact-checker and go overseas to shoot stories by myself. I would make the stories as interesting and dangerous as possible, and then offer them to Channel One for such a low price that the stories would be hard to refuse. I knew I could live so cheaply overseas that it wouldn’t matter how little I earned. A friend agreed to make me a fake press pass and loan me his home video camera. I didn’t really know what I was doing, but I figured I’d learn along the way.” Cooper says to Fast Company.

Channel One bought his videos on a case by case basis, and after a year, they hired him on as a full-time correspondent.

Lesson: If no one hands you an opportunity, then you have to create it for yourself.

7. President Barack Obama was doing a lot of soul searching in his 20s.

Barack Obama
Barack Obama

Decades before he ran for political office, Obama spent his early 20s helping rebuild low income communities in Chicago by setting up a job training program, a tutoring program, and a tenants’ rights organization.

When he was 27, Obama took 5 weeks off to travel to Kenya where he met many of his relatives from his father’s side for the first time.

“For a long time I sat between the two graves and wept,” Obama wrote. “I saw that my life in America — the black life, the white life, the sense of abandonment I felt as a boy, the frustration and hope I’d witnessed in Chicago — all of it was connected with this small plot of earth an ocean away.”

Lesson: It’s important to take some time to do soul searching, figure out your identity, and what are the things you actually care about.

The truth is, we don’t have to have things all figured out in our 20s, but it is a good time to embark on that journey. Thought Catalog Logo Mark

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