019: How To Never Take ‘No’ For An Answer (Jolie Guillebeau)

Jolie GuillebeauHow many times could you hear “no” before you gave up? 10, 20, 100? Our guest for episode 19 heard it for decades, but something inside of her wouldn’t allow her to give up her dream of being an artist.

Jolie Guillebeau always dreamt of being an artist and after decades of thwarted attempts, today she is a successful painter.


At the tender age of 7, Jolie announced to the world she intended to be an artist when she grew up. No sooner had she spoken the words then her grandfather told her to go into real estate to make money, she could paint on the weekends he said.

Little did Jolie know but she was to hear some variation of this every time she began to explore art over the next 20 or so years.

As a youngster, Jolie’s family moved around a lot so it wasn’t feasible for her to take art lessons, though she begged and begged. She was always told she could take classes in high school.

When she got to high school, she excitedly took her first year of art and then applied for advanced art for the next year. Her teacher told her to focus on getting an academic scholarship and she, the teacher, was going to give the limited seats in the class to kids who needed art scholarships to get into college.

It seemed yet again someone was steering her away from art, no matter what her heart was telling her.


  • Does she believe in talent when it comes to art?
  • What was the beginning of her daily art practice?
  • How did she feel when she sold her first pieces?
  • Who are her favorite art buyers?
  • How did she get a TEDx Talk?
  • And so much more!

At this point, Jolie began to ponder what she could if she wasn’t an artist. She knew she loved to read and write so perhaps she could be an English teacher. And that’s what she opted to pursue in college.

But not totally deterred from her artistic pursuits, she enrolled in a drawing course to fulfill her one art requirement.

And her art teacher seemed to assume the role like all her previous naysayers: he didn’t want her in the class. His funding came from the number of art majors he generated from his class and since she was an English and education major, she wouldn’t help his bottom line. He discouraged her but she stuck it out, although it was a miserable experience.

After she graduated, she pursued a teaching career. She loathed her first teaching job at her old high school but her artistic love began to blossom when she took an “old lady art class” in her hometown of Hazel Green, Alabama. Her teacher and her fellow pupils, all old enough to be her grandparent, encouraged her and saw her potential.

Her teacher went so far as to talk to a local famous artist about Jolie, Jack Dempsey. One day Jolie saw him sitting at a restaurant by himself and she worked up her courage to approach him. Soon after, she found herself in his class and under his tutelage.

As was par for the course in her artistic life, Jolie’s passion was put on the back burner a mere eight months after meeting Jack. She and her husband had committed to teaching overseas before she began studying with Jack Dempsey, so she had to leave everything behind.

Over the next 4 years, she would teach and enjoy guiding her students. But a seed had been planted and it took root: she couldn’t deny her love of art and began creating a small bit of art daily.

So when they returned home to the States, she and her husband applied to the same school in Seattle and got in. She was about to finally become an artist! Something inside of her had known all along that this was what she was meant to do with her life and after finishing art school, she was finally able to do it.

Though she still experienced challenges in art school (her professors were amazed when she sold two pieces at her senior show), today she has confidently settled into a day to day artistic creation groove. Even when it feels like “slogging”, she has a commitment to paint one painting every day.

Today her paintings mainly sell based on referrals and her newsletter which details the story behind each daily piece she paints. Through an incredible persistence, Jolie has finally settled into her own as a painter and achieved that dream she had as a 7 year old!

If you were touched and inspired by Jolie’s story, please drop her a note in the comments below or send her a Tweet! She was a fun and motivational guest who I loved having on the show.

Tweetable: “Talent is nothing more than pursued passion.” Jolie Guillebeau 



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