Jenny Blake on Saying “No” to Something Good, Free Time and Pivot | The Pathless Path Podcast

Jenny is an author, international speaker, career and business strategist, and executive coach. She worked in a start-up during her college years and then she worked at Google. Jenny is the author of three books, Life After College, Pivot and Free Time. She runs what she calls a heart-centered business, which resonates so deeply with me. Her core goal is helping people come alive through the pursuit of big ideas.

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What We Talked About

  • Embracing the Unpredictable: Jenny discusses navigating the unpredictable nature of running a business. She emphasizes the importance of staying calm, patient, and curious during times of uncertainty, and how writing provides a form of catharsis for her.
  • Building Personal Assets: Jenny mentions the value of building personal assets rather than creating assets for someone else’s business. She believes that investing time and energy into her own business, even during challenging times, will pay off in the long term.
  • Overcoming Fear of Failure: She shares her experience of overcoming her fear of failure when considering leaving her corporate job, and how she redirected the energy spent worrying about failure towards more productive pursuits.
  • Value of Self-Reliance: The self-reliance and the confidence that comes from earning money independently are invaluable for Jenny. Investing time and energy into her own business helps her create assets and satisfaction.
  • Learning from Corporate Experience: While working at Google, Jenny learned skills that have benefited her entrepreneurial journey. She also discusses the importance of feedback in personal and professional growth.
  • Reinventing Yourself: For her, it is necessary to reinvent oneself and mourn the loss of past identities. She believes that life requires continuous reinvention and adaptation.
  • Serendipity as a Business Strategy: Serendipity plays an important role in her business strategy. She believes in the power of sharing ideas and experiences, which often leads to unexpected opportunities and connections.
  • The Role of Faith: For her, it’s important to have faith in her journey, surrender to the process, and be open to the next step when answers aren’t readily available.
  • The Power of Asynchronous Communication: Asynchronous communication, such as voice memos, allows her to maintain her preferred lifestyle while still engaging in meaningful conversations.
  • The Value of Podcasts: Jenny sees podcasting as a source of inspiration and reassurance for her. She appreciates the wide range of ideas and perspectives that podcasts offer.


Jenny Blake’s Books

Quotes from the Episode

On Reinvention:

When the financial tides recede, I don’t go run toward the ocean trying to catch a wave that has disappeared. I try to be patient and wait and see what washes up on shore. There are new gifts that arrive and so if I can remind myself don’t panic, stay calm, be patient, get curious and all the meanwhile there’s a real sense of aliveness.

On Taking The Leap:

I realized I am willing to spend every penny of my savings to try and I had six months of savings and I finally I just got burnt out enough and frustrated enough that I said all right six months that’s it if I do this six months I don’t earn a penny and I need to go back and get another full-time job somewhere I will but at least I will go to my deathbed knowing that I tried.

On How People Around Us Reinforce Our Fear:

I think sometimes the kind of funny way the universe works is that whatever our inner critics are there will certainly be people in our life who are even close to us who show up and say those things verbatim almost reinforcing or stress testing are you going to listen to that fear.

On Not Seeing Herself As an Entrepreneur:

I never thought of myself as entrepreneurial. I didn’t think that I was cut out to work for myself. I had always been such a good student and a people pleaser and a rule follower that I genuinely did not think I could make it outside of that environment.