Ashley Levy, Senior Director of Brand Marketing at LinkedIn, joins Chase Jarvis to discuss the transformative power of risk-taking. They explore how scrapping a nearly finished book led to a bolder narrative and why living authentically is crucial for personal fulfillment. The conversation highlights the #1 trait among top performers and the importance of attention over time as a creative asset. They also touch on the balance between human creativity and AI's growing role, encouraging listeners to embrace discomfort and pursue their true passions.
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question_answer ANECDOTE
Scrapping Safe for Authenticity
Chase Jarvis scrapped a nearly finished book because it felt too safe and inauthentic to him.
He rewrote it inspired by a sticky note saying "don't play it safe," leading to a bolder, truer manuscript.
insights INSIGHT
Playing It Safe Is Riskier
Playing it safe is the riskiest move because it leads to a life designed by others' expectations.
The number one regret of the dying is living a life that other people wanted for them.
volunteer_activism ADVICE
Master Your Attention
Master your attention since your experience depends on where you place it.
Practice mindfulness or meditation daily to strengthen focus and awareness.
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In 'Tribe of Mentors', Tim Ferriss collects and shares deep, meaningful, and life-changing tips and hacks from a diverse group of mentors. These mentors include iconic entrepreneurs, elite athletes, artists, and billionaire investors. The book is structured around a set of 11 questions that Ferriss asked these mentors, covering topics such as morning routines, overcoming failure, achieving work-life balance, and reassessing priorities. It offers a rich tapestry of experiences and viewpoints, ensuring there is something valuable for readers from all walks of life.
Man's Search for Meaning
Viktor Frankl
The book is divided into two parts. The first part recounts Frankl's harrowing experiences as a prisoner in Nazi concentration camps, including Auschwitz, between 1942 and 1945. He describes the inhumane conditions and the psychological and emotional struggles of the prisoners. The second part introduces Frankl's theory of logotherapy, which posits that the primary human drive is the search for meaning, rather than pleasure. Frankl argues that meaning can be found through three main avenues: work (doing something significant), love (caring for another), and suffering (finding meaning in one's own suffering). The book emphasizes the importance of finding purpose and meaning in life, even in the most adverse conditions, as a key factor in survival and personal growth.
Never Play It Safe
A Practical Guide to Freedom, Creativity, and a Life You Love
Chase Jarvis
In 'Never Play It Safe,' Chase Jarvis argues that safety is an illusion that holds us back from true fulfillment and extraordinary success. The book is structured around seven core 'levers': attention, time, intuition, constraints, play, failure, and practice. Jarvis draws from his own transformative experiences and insights from top entrepreneurs, artists, athletes, and performers to help readers break free from the comfort of playing it safe. He provides practical techniques to train attention, unlock potential, and achieve a life filled with freedom, creativity, and fulfillment.
In this episode, I share how not playing it safe can be the most powerful decision you make—for your creativity, your career, and your life. I open up about scrapping a nearly finished book to write something bolder and truer, and why embracing discomfort is the path to fulfillment and impact.
This is a syndicate episode from the LinkedIn Speaker Series, where I sit down with Ashley Levy, Senior Director of Brand Marketing at LinkedIn, for a deep conversation about my latest book Never Play It Safe. We talk about trusting intuition, the myth of the linear career path, and the hidden cost of living by someone else’s script. If you’ve ever felt stuck in “shoulds” or worried that taking a leap is too risky, this one’s for you.
Some highlights we explore:
The yellow sticky note that sparked the idea behind Never Play It Safe.
Why playing it safe is actually the riskiest move you can make.
The #1 shared trait of top performers from my 1,000+ podcast interviews.
How attention, not time, is your most valuable creative asset.
The Chase Jarvis LIVE Show 
