Lenny's Podcast: Product | Growth | Career

Redefining success, money, and belonging | Paul Millerd (The Pathless Path)

Nov 19, 2023

01:04:52

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Paul Millerd, author and host of The Pathless Path Podcast, shares insights on redefining success, finding fulfillment, and taking unconventional career paths. He discusses the default path, signs of being stuck, and how to embrace the pathless path. He advocates for three-month sabbaticals and offers tips on overcoming fear. The podcast explores creating space in life, financial support options, and the importance of reframing. It also tackles the challenges of unenjoyable jobs, constant reinvention, and pursuing unconventional paths in career and life.

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Quick takeaways

The pathless path encourages individuals to question societal expectations and explore their own desires and priorities.

Creating space for self-reflection and exploration, such as through a sabbatical, is crucial for embarking on the pathless path.

Fear is a common obstacle on the pathless path, but it can be managed through ongoing self-reflection and reframing fears around taking action.

Deep dives

Exploring the Default Path and Shifting Away

The default path is the dominant narrative about what one should do in life and work. It usually involves following societal expectations, such as getting a good job, making money, buying a house, and starting a family. However, many people feel unfulfilled and seek an alternative path. The pathless path offers a shift away from the default path, embracing discomfort and uncertainty. It encourages individuals to explore their own desires and priorities, questioning the scripts they have been following. This path allows for greater self-awareness and the discovery of activities that truly bring joy and aliveness.

Exploring New Paths Can Be Hard But Worth It

01:17

Redefining Work and Finding Fulfillment

02:11

Ship, Quit, and Learn

01:35

The Importance of Creativity and Exploration in Finding a Pathless Path

03:09

Introduction

4min

The Default Path and Opting Out

16min

The Benefits of Taking a Sabbatical

5min

Exploring Different Paths and Reinventing Yourself

4min

Tips for Creating Space and Financial Support

17min

Avoiding Unenjoyable Jobs and Embracing Constant Reinvention

4min

Exploring an Unconventional Path

14min

Paul Millerd spent several years working in strategy consulting and on the “default path” before deciding to walk away to work on his own in 2017. His book, The Pathless Path, chronicles his own journey and deep dive into the history of work and has been read by more than 40,000 people. His podcast, The Pathless Path Podcast, highlights conversations with others following unconventional paths. He also runs the online training business StrategyU, helping people learn the skills of consulting without having to work in the industry. In our conversation, Paul shares:

• An explanation of the “default path” and the “pathless path”

• Signs you may be stuck on the default path

• How to inch your way toward the pathless path

• Why Paul suggests everyone should take a three-month sabbatical

• Tips for embracing fear and betting on yourself

• How to work through the fear of losing money and prestige

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Find the full transcript at: https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/

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Where to find Paul Millerd:

• X: https://twitter.com/p_millerd

• LinkedIn: https://www.linkedin.com/in/paulmillerd/

• Website: https://pathlesspath.com/

• Newsletter: https://newsletter.pathlesspath.com

• YouTube: https://www.youtube.com/channel/UCofS_FvauuHc-x6mq7yz6nA

• Podcast: https://think-boundless.com/podcast/

• Email: paul@strategyu.com

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