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Tess Brigham


When I was in my 20s I was living in Los Angeles working in the entertainment industry. I worked as an assistant at a mid-level talent agency making so little money that I am too ashamed to even mention it today.

The actresses we represented were my age, had killer bodies, and made in a week what it took me an entire year to earn. Everywhere I turned it seemed that there was someone my age who seemed to “made it.”

Even now in my 40s I continue to have to remind myself that achieving great success at a young age is more of a fluke than the norm. For every Beyonce (who just turned 29! Yikes!) there are tons of women who spent their 20s struggling to figure out who they are and what they want to do.

If you are in your 20s and feeling like everyone around you has it “all together” I want to share with you 5 profiles of successful, influential women who didn’t achieve success until they were in their 30s and 40s.

Kristen Wiig

Wiig was born in upstate New York, studied art at the University of Arizona and on a whim moved to Los Angeles after college to become an actress.

Wiig spent her 20s working odd jobs (folding clothes at Anthropologie, selling peaches at the Farmer’s Market, babysitting, and sellinghot dogs at the mall), while honing her acting and improv skills as a member of the Groundlings Troupe.

She was 32 years old when she finally got on Saturday Night Live. She had a lot of small supporting film roles until she wrote and starred in Bridesmaids at age 38.

Suze Orman

Born in Chicago Illinois, Orman was the youngest of three children and had to overcome a speech impediment as a child. Her family struggled with finances while Orman was growing up. She went to the University of Illinois at Urbana-Champaign but dropped out.

Orman spent her 20s waiting tables at a diner in Berkeley, CA (my hometown!). She dreamed of opening her own restaurant. After she shared this dream with one of her regular customers, he gave her $2,000 and asked other customers to help. She was able to raise $50,000.

Orman took her money to Merrill Lynch who told her that she could make $100/week on risky ventures. Orman, knowing nothing of finances, signed a blank document that allowed that broker to completely control her money. She lost it all within 3 months.

After that experience, Orman decided to become a broker and applied for a job at the same Merrill Lynch office where she had lost her earlier investment. Orman discovered that her broker had violated the company's policies. She sued the company, and Merrill Lynch eventually settled with her out of court.

Orman worked hard for her customers and in 1983 she joined another firm as a vice president. Orman went out on her own in 1987. Today she is probably the most well known financial advisor with a regular column in O Magazine and her own TV show.

Jane Lynch

Jane Lynch was 40 when she got her “big break” in the Christopher Guest movie “Best in Show.” She was 49 when she got her role as Sue Sylvester in “Glee.”

Lynch spent her 20s studying acting and working primarily on the stage. She received a Masters Degree from Cornell University and was part of the theatre scene in New York but eventually returned to her hometown, Chicago, to work in theatre there.

She was 28 when she got her first small film role and spent most of her 30s taking small film and TV roles and doing voice-overs for commercials. Lynch met Christopher Guest for the first while shooting a cereal commercial. It was still another couple of years before Guest cast her in “Best in Show.”

Lucille Ball

Did you know that Lucille Ball was 40 years old when “I Love Lucy” premiered? Prior to creating and starring in this iconic show with her then husband, Desi Arnez, she was known as “The Queen of B-Movies.”

Lucy spent her 20s starring in B movies and taking any other acting gigs she could get. Her movie career stalled out when she was in her 30s and in 1942 she dyed her hair red in the hopes of rebranding her career. She walked away from a CBS contract because they refused to cast her husband. Lucy and Desi took their “I Love Lucy” act on the road and it was a huge success, which made CBS reconsider. “I Love Lucy” was the #1 show for 4 years running.

Her production company with her husband, Desilu produced a number of well known TV shows. Lucy bought out Desi’s portion of the studio after their divorce in 1962. At age 52 Lucille Ball was the first woman to run a major television production company.


Sheryl Crowe

Sheryl Crowe was born in Missouri and majored in music education at the University of Missouri. She worked briefly as a music teacher and moved to Los Angeles at age 24.

Crow spent her 20s recording jingles for advertising clients, including McDonald's, and working as a back-up singer. When she was 25-26 she sang on Michael Jackson’s "Bad" world tour. She later sang back-up for Sting, Rod Stewart and Don Henley.

When Crow was 31 she got her big break and recorded an album for A&M Records but it was shelved because it was too “slick.” She was 33 when she first released the album “Tuesday Night Music Club” which included the hit “All I Wanna Do.” It wasn’t until a year later that the song really took off.


You may be wondering how these stories relate to you. These 5 stories represent the norm of how people achieve success. It takes time to figure out what you want to do with your life. Once you start working towards that career goal, it takes years of practice and honing your skills to achieve that “overnight success.”

If you feel like you are floundering, working at random jobs, starting one career only to decide you want to go in a totally different direction: don’t worry. While it feels like you are “lost” you are actually figuring out what you like and what you don’t like. You are eliminating jobs or careers that won’t work for you and you’re understanding yourself better and better.

Don’t give up. None of these women did and they all achieved success, just not in their 20s.