[Flash] When John Stewart Mentored John Oliver

Higgins could have easily been describing John Stewart mentoring John Oliver.

In 2006, Oliver joined Stewart’s The Daily Show on Comedy Central.

For eight years, Oliver created and delivered comedic content alongside Stewart. Oliver won three Emmy Awards for his writing for The Daily Show, and when he guest-hosted for two months, audiences loved him.

“The Daily Show was my dream job. It was an incredible experience.”

And then in 2013, as Stewart was heading out on summer break, he said to Oliver, “When I come back, we need to talk about what you’re going to do next.”

That was a gut punch.

Oliver reflected, “It was horrible to hear. I never wanted to leave. I wanted to stay forever and for nothing to ever change.”

When Stewart returned, he encouraged Oliver to consider an offer from HBO to launch his own show.

“I hesitated. It was massively terrifying and incredibly intimidating to strike out on my own without Stewart protecting me. Comedy Central was my safe place.”

But safe places don’t foster growth, and Stewart knew that. He saw what Oliver couldn’t – a comedy powerhouse.

Since 2014, Oliver has hosted the HBO series Last Week Tonight, winning 16 Emmy Awards and two Peabody Awards.

And that’s what great mentors do – they unearth potential. They nudge their mentees out of the proverbial nest, challenging them to see and experience more.

Mentors twist the mentee’s kaleidoscope, urging, “Look what’s possible!”

Great mentors don’t abandon or discard their mentees. Instead, their relationships get redefined as their mentees pursue fresh paths and gutsy goals.

Mentoring is about growing and evolving. And sometimes, mentees need a push to stretch and progress, even if that frightens the mentee and unsettles the mentor. 

No one can grow and stagnate at the same time.

When I boarded the plane after law school to move to California for my first job, my mom – my first mentor – tucked a handwritten note into my bag.

It read, “I did my job. You belong to the world now.” 

© 2024. Ann Tardy and MentorLead. www.mentorlead.com. All Rights Reserved.