102: How to Pivot Your Business When You Feel Trapped by Its Success — with Jason Van Orden

Is pivoting just a way of rebranding failure as NYT writer Jacob Silverman would have us believe? I say no way José. In fact, pivots are often a product of our success. As I shared in the #PivotList newsletter I wrote in response to Silverman's somewhat snarky article, Silicon Valley start-ups do tend to talk about pivoting in response to their initial strategy failing. Or in the case of Ross from Friends, when a couch just won't fit around a tight corner :) 

But the fact is that nothing in business is as stable as it was even ten years ago, and companies (and leaders) of all shapes and sizes are required to navigate micro-changes much more frequently than in the past.

Pivoting is the new crucial skill we must all foster, a far cry from being just another silly PR performance. If you've hit a pivot point or plateau, it means you have outgrown your current career or business and are ready for something new. We should celebrate that, and all the searching and small experiments that follow!

That's why I'm thrilled to bring you this week's conversation with my friend Jason Van Orden, a fascinating guy who was early to the podcasting and internet marketing scene, but who began to feel trapped by that very success, unsure about how to redefine himself from a unique perch atop of his industry. He is chock full of wisdom and systems to help you navigate out from under success that you've outgrown, and I hope you enjoy this conversation as much as I did! 

Check out full show notes from this episode with links to resources mentioned at PivotMethod.com/podcast/jason-van-orden. Enjoying the show? Make my week by donating just $1 and episode at Patreon.com/pivot.

More About Jason Van Orden


Jason helps thought leaders to reach a larger audience with their ideas, create new income streams from their expertise, and build business models that align with their goals. In September of 2005, Jason co-founded the first ever podcast about internet business and online marketing, and it quickly became one of the top business podcasts in the world. His mission is to help visionaries with impactful ideas reach the people they serve best and the problems they are uniquely positioned to solve.

As a consultant, trainer, and strategist, he draws from thirteen years of researching top Internet influencers as well as personal experience gained by launching over 60 online courses, teaching more than 7,000 entrepreneurs, and generating 6 million dollars in online course sales, and 8 million downloads of his podcast.

Topics We Cover

  • What to do when your business feels like a prison

  • His process for taking a sabbatical from your own business

  • Exploring curiosity, following ideas

  • Moment of truth when you know you can’t just continue the way you were

  • Feelings of failure and identity loss - who am I if not this person, the founder of Internet Business Mastery?

  • Entrepreneurship and mental health — anxiety, ADD, stress, depression

  • His experiences with depression; ups and downs, confidence was eroding

  • The power of speaking your truth, your story

  • How 1:1 consulting and creating feedback loops helped him map his new direction

  • The success trifecta: if one or more of these three things is lacking, your progress and growth will slow or even stall completely

  • The three V’s: vision, value and voice

  • Check back in with the audience: relevance, resonance, remarkability

  • Business model: what’s out of alignment with the Three V’s and Three R’s? Messaging

  • How he discovered podcasting in 2005

  • Attention economy: how to maintain attention and not get discouraged by competition

How To Pivot Your Business When You Feel Trapped By Success — With Jason Van Orden

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Resources Mentioned

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