The first time I met Jonathan was back in 2009. His book Career Renegade: How to Make a Great Living Doing What You Love had just been published. It was also the time in which the personal finance primer for women in their 20s and 30s that I co-authored, On My Own Two Feet: A Modern Girl’s Guide to Personal Finance came out.
Jonathan had learned a great deal about the publishing world—and more specifically, how much of the responsibility for marketing and promoting a book is up to the author. So ever the entrepreneur, he decided to put together a weekend workshop in New York City. There were probably a dozen of us who had flown in from around the country to spend the weekend learning from Jonathan and each other. I recall leaving that weekend thinking I had just witnessed something pretty darn spectacular—a true heart-centered “seeker” with a deep passion for learning and perhaps an even deeper desire to give back. In a world of “shaman gurus,” every single one of us knew we were in the presence of the real thing.
As you’ll hear in this episode, Jonathan offers a fresh outlook on business ventures and life changes. His focus and work have evolved greatly since 2009. Today he is best known for sharing ideas what it means to live “the good life.”
This episode has two threads. The first is Jonathan’s career story from the buttoned-down world of law to the highly creative world of being what he would call being “a maker,” someone who brings a wide array of ideas to life. The second thread contains the tools and tactics Jonathan shares about when and how to hit the “reset” button—be it on an individual project or your entire life. As you’ll hear, Jonathan thinks deeply and articulates what he has found to be the key ingredients that have helped him cook up “the good life.” I have a hunch you will find some delicious morsels in this episode that will help you do the same.
Manisha’s Top Takeaways
- The centuries-old power of self-inquiry
Jonathan makes a beautiful case for an ongoing practice of self-inquiry. In an age of selfies and often self-promotional social media, that may sound like a slippery slope to let your ego slide down. Fear not! As Jonathan points out, self-inquiry in the spirit of the Stoics and the Greeks is an effective means of leading a life that brings both personal joy and at the same time enables a contribution back to the greater good in whatever way one feels called to do so. [8:45]
- The tyranny of technology
We all know that technology, incredible as it is, often keeps us from connecting to each other on a human level. Just look at a line in the grocery store or your local coffee shop, and you will see a majority of heads staring down at a smartphone. In this episode, Jonathan takes it a step further, arguing that technology also makes us so externally focused that we are increasingly disconnected from ourselves. [8:00]
- The freedom of running “projects and experiments”
A full chronology of Jonathan’s entrepreneurial endeavors reveals a shockingly wide range of projects, subjects, and delivery mechanism. Fear of failure is a very common reason many people do not take action on their dreams. In this episode, Jonathan shares how he relieves himself of the pressure of perfectionism by replacing it with an approach of experimentation. In fact, he uses words like “projects” and “experiments” to talk about his creative, entrepreneurial endeavors to reinforce the notion that the goal is not “failure or success,” but in exploring an idea and seeing where it leads. [14:00]
Other Major Topics
- How to think about the role of money when trying to “do good” [11:00]
- What happened when Jonathan experienced burnout and hit reset [15:45]
- The daily practice that has been transformational to Jonathan [19:45]
Resources Cited in the Episode
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