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Leader’s Playlist Masterclass

The Leader's Playlist masterclass

Reframing ambition & the value of failure (feat. Patrick McKenna)

Jul 7, 2021

Who would you be without your ambition to attain success? 


Is your ambition driven by the need to create financial stability or make your mark on the world? Many leaders would candidly cite those motivators as the reason for their success.


Patrick McKenna was no different. He had built his incredibly successful career as an investor and entrepreneur — motivated by a desire to leave his small hometown and prove to others he could make something of himself. Without this ambition, he didn’t know where he’d be (or who he’d be).


And yet, as he looked deeper, he saw that behind that ambition was a fear of failure.


Three days after selling his shares of the company he cofounded, he had achieved the financial success and prestige he had been working toward his whole life. But that didn’t bring the fulfillment he was actually seeking.  And now, he didn’t know what to do.


How Patrick changed the object of his ambition 


He realized had a choice: he could continue to pursue more material success, or he could look inward and pursue internal happiness instead. He chose the latter, committing to meditation practice, attending meditation retreats, and seeking meaning — despite a worry that letting go of ambition would lead to a loss of motivation.


But something unexpected happened on his journey to find happiness:


He discovered that love for others was an even bigger motivator than fear of failure.



Rather than pursuing success to safeguard himself from failure, Patrick began seeking challenges that were worth failing at. That is, he looked for endeavors that would help others if they succeeded (and thus, were worth trying, even if he failed the first time).


This led to him founding two companies: Facet Wealth and One America Works. Both serve his mission to bridge the geographic opportunity gap, providing capital and support to companies and people outside of major coastal cities.


Facet Wealth is one of the fastest-growing financial planning firms in the country, helping clients go beyond retirement planning and create a detailed financial roadmap for their lives.


One America Works aims to make cities in every state hubs of talent, investment, and opportunity by investing in high-growth tech companies in cities like Pittsburgh, Kansas City, Austin, and Atlanta. Patrick has invested in over 40 startups, raising over $200 million that resulted in over $200 billion in exit returns.


The importance of clarity over certainty


As Patrick shares, trading fear-based ambition for a love-based ambition is not like flipping a switch. It’s a constant commitment bolstered by daily practices and mindset shifts.


For Patrick, one of the biggest mindset shifts was this: maintain a clear vision and be comfortable with the uncertainty of not knowing how to get there. 


At its core, the desire to eliminate uncertainty leads to a fear-based way of pursuing life. And for leaders, this fearful mindset can result in overly controlling behaviors that restrict your team’s potential.


Patrick recommends zeroing in on the few things you can control and releasing everything else. For most, the only aspect you can 100% control is your response to situations. 


Patrick also talks about…

  • Why living in a “love motivation” is a good investment thesis
  • How to use meditation to let go of fear-based ambition
  • The daily practices that help leaders work toward enlightenment


Where to connect with Patrick McKenna:


Interested in more? Here’s another great Enlightened Executive interview about the benefits of a relaxed mindset, featuring John Rampton.

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