Jonathan Mildenhall: 4 lessons on authenticity

Connection Mentors

The Connection Mentors Series

Healthy relationships are the foundation of well-being, but the strength of our connection to our authentic self creates the blueprint for how we show up in relationships with others. It takes courage to walk the path of authenticity.

This series celebrates the stories of those who live on their terms—honoring their truth, authentic strengths, and deepest desires. Embracing our unique expression as human beings creates a meaningful and impactful life.

May this series inspire you to step closer to your truth—or surrender fully to the wisdom of your inner knowing.

Connection Mentor: Jonathan Mildenhall

"It takes less energy when you come from a place of authenticity because you are very clear about what fuels your sense of authenticity. When you’re clear that, you become incredibly courageous"— Jonathan Mildenhall

Jonathan Mildenhall, the Chief Marketing Officer at Rocket Companies and co-founder and chair of TwentyFirstCenturyBrand, is a marketing icon. Born in Leeds, England, in 1967, he grew up on a council estate in the north of England. He went on to hold prominent roles, such as vice president of global advertising strategy and creative at Coca-Cola and the first chief marketing officer at Airbnb. The life he’s led is a masterclass in what we stand to gain when we live our truth. Embracing his authenticity brought meaning to his life and allowed him to push boundaries in his career.

Here are four powerful lessons on authenticity from the life of Jonathan Mildenhall.

1. Show people who you are from the beginning and risk being rejected from the spaces that aren’t meant for you to thrive in.

   When Jonathan set his sights on advertising, he faced a reality: he didn’t match the profile of the average marketer. A school career counselor told him he’d make a great marketer—but also discouraged him because he wasn’t what the industry typically looked for: a white, upper-middle-class (or upper-class) man from Oxford or Cambridge.

   
   

   Jonathan wasn’t deterred. He spent hundreds of hours preparing applications for his dream agencies. He even attached his photo to his résumé, wanting to be upfront about who he was. That way, whoever called him in for an interview would be aware of who would be showing up.

   
   

   He landed his first job at the McCann advertising agency as their first trainee of color. He wasn’t their usual hire, but they gave him a shot, and he made the most of this stepping stone.

   
   

2. You are fortunate to encounter those who create a safe space that allows you to be your whole self.

   Growing up, Jonathan was one of five boys and the only Black person in a white family. It was challenging for him to feel a sense of belonging. One day, after being bullied at school because of his race, Jonathan’s mom consoled and encouraged him with these words: “You can’t change your packaging. They can never damage what is inside of your packaging—and what’s inside is this beautiful energy.”

   
   

   Another pivotal encounter came during a meeting with his then-boss, the legendary Cindy Gallop—an authentic badass in her own right. Cindy, an award-winning marketer, founded the U.S. branch of the BBH advertising agency.

   
   

   After becoming confident and embracing his Black identity during his teenage years, Jonathan realized he was gay. Still, shame led him to hide that part of himself. He lived a double life in his early twenties: openly gay outside of work, closeted in the office. It became exhausting. So, when he decided to switch agencies, he vowed to walk in his truth.

   
   

   A testing moment presented itself during a conversation with Cindy Gallop, his boss at his new job at BBH. She asked if he was gay, which provided Jonathan with the opportunity to show up as his true self at work for the first time. After replying yes, she handed him an invitation for him and his boyfriend to her birthday party. That moment marked the first time Jonathan introduced himself fully to some of the top players in the marketing world. Cindy told him he could go far in his career if he stood in his authenticity.

   
   

3. Follow curiosity and knock on the doors that lead to the support you need.

   His deep loneliness as the only Black person in his household pushed him to master the art of being likable. As a child on the council estate, Jonathan would knock on the doors of neighboring apartments and spend time with other families.

   
   

   That experience taught him his first lessons about human connection and sparked a curiosity about others’ lives. Those early days shaped his enduring love for people and culture.

   
   

4. Authenticity fuels career success.

   By bringing his authentic self into his work, Jonathan helped create Coca-Cola’s America the Beautiful ad, which featured the first same-sex family in a Super Bowl commercial. He used his influence to advocate for that moment, resulting in a history-making ad on one of the biggest nights in American television.

   
   

   Those who show up as—and work through—their authentic selves may face rejection early in life, but they gain access to unique opportunities made just for them.

   
   

Xx

Carly

Sources/ Resources:

• This is My Why Podcast

• Fearless Creative Leadership