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Episode 010: Jeremy Redleaf

Episode 010: Jeremy Redleaf

A Hustler’s Take on “Adulting”

Simply put, Jeremy Redleaf is so goddamn fun. And sweet. And smart. And engaging. He has a unique type of charm to him: an ability to be approachable and unassuming amidst his many successes. When asked how he wants me to introduce him for our interview, Jeremy is quick to erase all four lines of any box that I put him in, reminding me that human beings are not defined by what they do but by who they are. 

Jeremy is 32 years old, recently married, and lives in Brooklyn, New York. Our interview begins with a brief reflection on the idea of “adulting,” which he describes as a conscious awareness of how he spends his time, takes care of himself, and lets go of what no longer serves him. I appreciate how he turns the word “adult” from a noun into a verb. It’s process-oriented, never fully reaching conclusion because there is always more to learn. 

I ask Jeremy about his experience with his partner as they transitioned from dating to marriage. He notes that in his twenties he had a lot of preconceived judgments, such as believing marriage was an archaic institution not in alignment with the current realities of intimate relationships. However, since getting married, he has felt subtle shifts in how he relates to his wife, his relationship, and himself. The rituals of marriage have not only helped Jeremy feel closer to his wife, but they have provided him with the relief in knowing that someone has his back. In The Course of Love author Alain de Botton writes the following about the leap into marriage: 

“Marriage: a hopeful, generous, infinitely kind gamble taken by two people who don’t know yet who they are or who the other might be, binding themselves to a future they cannot conceive of and have carefully omitted to investigate.”

Reading de Botton’s definition and reflecting on Jeremy’s thoughts, I can’t help but think that even amidst the gamble and all of the uncertainty, human beings are programmed to not want to do life all alone. For Jeremy, a long-time freelancer and independent contractor, this feels like an unexpected surprise. After years of being self-reliant and struggling with having to ask for help, marriage is an opportunity for him to strengthen his muscles of trust and vulnerability. These muscles don’t just support his marriage but every other relationship in his life. He is learning to ask for help and be okay if things don’t go the way he wants them to. This part of adulting doesn’t make him a failure, but rather a man bravely stepping into the weak and often helpless spaces of what it means to be human. 

When Jeremy was 22 year old, he created the web series OddJobNation. It was a satire inspired by the 2008 recession, with a couple getting into shenanigan and playfully poking fun at the opportunity to work odd jobs. The project hit big, winning "Best New Web Series" at the Streamy Awards and "Best Writing" at the Chicago International Television Festival as well as being named by CNBC as one of the "10 best things of the recession."

With all of the praise and excitement came numerous offers and opportunities. Before Jeremy knew it, he found himself intoxicated by the throngs of Hollywood, exhaustedly saying yes to everything that was thrown in his direction. What he discovered soon after was that his actions toward and developments with OddJobNation were no longer based on what he wanted but rather what he thought others would like. 

Listening to Jeremy, I can’t help but relate to what he is saying. It’s that part inside all of us that wants to be accepted, validated, and reassured that we are enough. It’s the part that questions our own wholeness and often holds us back from making magic in the world. It’s the gremlin, or the inner critic side of ourselves, that yells so loudly that we can no longer hear our own gut instinct.

We speak briefly on the topic of fame. Jeremy notes that when you are in the public eye, it is easy to muddy your perception of reality and what it is that you really want and desire. He shares an old Hollywood adage that goes something like, “People get into show biz for validation and they survive if they know they don’t need it.” After years of feeling like he needed external validation to be enough, Jeremy has stepped into a new space—a space where he knows that he is enough exactly as he is. He has also come to believe that he has a responsibility to use the power of being known for some form of greater good. 

Jeremy and I discuss the importance of taking risks and hustling to make things happen. He playfully quotes Tony Robbins in saying, “If you always do what you’ve always done, you’ll always get what you’ve always gotten.” (Aside: When I researched this quote, there was a huge internet forum as to where these words actually originated). I love that Jeremy brought these thoughts into our conversation, as it is such an important reminder. If you continue to do the same thing over and over again hoping to get new results, it may be time to take a long, hard look in the mirror. And that doesn’t necessarily mean starting from scratch! As Taylor Pearson, the author of The End of Jobs: Money, Meaning and Freedom Without the 9-to-5, says, 

“While our first instinct is usually attempting to push harder, it’s more valuable to figure out where to push.”

At the end of our conversation, Jeremy offers his sage advice on how to reclaim your instinct. He emphasizes the importance of having a personal and professional mission statement and value system that you constantly check in with to make sure you are living in alignment with those values. He also encourages you to understand your ego’s triggers in order to not fall into the trap of living your life for how others perceive you and to embrace the truth of who you are. Living this way may initially feel like a test to your safety and security because it requires you to unravel old ways of thinking, feeling, and being in the world. However, in the long run, you will free yourself from the shackles of self-protection, allowing you to adult with far greater ease, grace, and the sense of being enough.


Jeremy Redleaf is a Daytime Emmy Award winning voice artist, filmmaker, community builder, co-creator of Cave Day, and entrepreneur who makes things under his [Creative] shingle that remind people they're alive and maybe just maybe, more connected than they think. His first feature film, 3rd Street Blackout, which he not only starred in but also co-wrote, co-directed, and produced is currently available on all digital platforms. He is also the co-creator of Cave Day

Website | Instagram | Facebook| Twitter

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Episode 011: Robert Anton Patterson

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