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

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

Taking Time for Yourself during a Workday

This section discusses the importance of taking time for yourself during a workday and explores the concept of the default path in work and life.

Sneaking Out of Work

  • Taking three hours during a workday to do something for yourself.
  • Block off your schedule and find time to sneak out.
  • People can successfully pull this off by going for a walk without a destination or engaging in activities from their childhood.

Reflecting on Work

  • Pay attention to what emerges when you take time for yourself.
  • Explore why you may feel bad about sneaking out of work.
  • Consider your definition of work and what it means to you.
  • Question why you work beyond just money, and how it relates to being a good person.

Getting in Touch with Yourself

  • Create space to understand your true feelings about work.
  • Reconnect with things that bring you alive today.

Introduction to Paul Millard's Book "The Pathless Path"

This section introduces Paul Millard, author of "The Pathless Path," which explores an alternative approach to work and life. The book has gained popularity within the Tech Community.

Exploring a Different Path

  • "The Pathless Path" challenges the default path in work and life.
  • The author shares his personal journey that led him to his current unconventional work.

Understanding the Pathless Path

In this section, Paul Millard explains what the pathless path is and provides insights on exploring one's own unique path.

Defining the Pathless Path

  • The pathless path refers to breaking free from societal expectations and finding one's own way in work and life.
  • It involves questioning the default path and exploring alternative directions.

Exploring Your Own Path

  • Paul Millard shares advice on how to explore your own pathless path.
  • Address fears related to money, prestige, and safety that keep us on the default path.
  • Provides stories, examples, and tactical advice for thinking about a new direction in life.

Sponsor: Sanity - Content Management System

This section features a sponsor message from Sanity, a content management system designed to help teams create and manage content more efficiently.

Introducing Sanity CMS

  • Many content management systems are not built for speed and flexibility.
  • Sanity offers a solution for fast content creation, experimentation, and seamless integration with other tech tools.

Sponsor: Maui Nei Venison - Mission-Based Food Company

This section features a sponsor message from Maui Nei Venison, a mission-based food company that provides nutrient-dense red meat while actively managing invasive deer populations in Hawaii.

Nutrient-Dense Red Meat

  • Maui Nei Venison offers the most nutrient-dense and protein-dense red meat available.
  • Their operation helps restore balance to ecosystems in Hawaii by managing invasive deer populations.
  • The meat is ethically sourced and delicious.

Interview with Paul Millard

In this section, Lenny interviews Paul Millard about his book "The Pathless Path" and its success as a self-published work.

Success of "The Pathless Path"

  • Over 40,000 copies of "The Pathless Path" have been sold.
  • The book's popularity is considered a huge success for self-publishing.

Understanding the Default Path

  • Lenny asks Paul to explain the concept of the default path.
  • The default path refers to the societal expectations and norms that guide people's work and life choices.

The transcript continues beyond this point, but it is not included in this summary.

The Impact of Freelancing in Different Countries

This section discusses how freelancing differs in every country and its impact on individuals.

Freelancing as a Creator Economy

  • Freelancers are independent workers who have income from various sources.
  • The creator economy allows individuals to jump from job to job.
  • Many people face challenges and lose their sense of aliveness, seeking guidance on how to approach their work.

Shared Ethic and Optimism

  • The shared ethic among freelancers is a sense of optimism.
  • Discovering new opportunities and goals is an ongoing process.
  • The goal is not just finding a job or making money but actively and consciously pursuing personal growth.

Redefining Work and Finding Enjoyment

  • Lowering the cost of living can provide the freedom to explore work that brings enjoyment.
  • Building relationships with like-minded individuals can lead to new opportunities for growth.
  • Challenging the assumption that work is inherently unpleasant can lead to a more fulfilling career.

Creating Space for Personal Growth

This section explores the importance of creating space for personal growth and self-discovery.

Making Time for Exploration

  • It is essential to create space and opportunity for personal exploration, even with financial responsibilities.
  • Taking short breaks or dedicating specific hours during the workday can be more attainable than expected.

Shifting Priorities

  • People in their 30s or 40s who have worked for many years may feel trapped in a job-shaped container.
  • Reevaluating priorities can help create space for personal growth and discovering new passions.

Embracing Change

  • Achieving impressive milestones such as saving money, owning a house, or getting married may not bring fulfillment.
  • Taking a sabbatical or extended break from work can lead to a realization that change is needed.

The Power of Sabbaticals and Mindfulness

This section discusses the power of sabbaticals and mindfulness in shaping one's career path.

Sabbatical as a Catalyst for Change

  • Taking a sabbatical can create separation from current work and allow individuals to reassess their goals.
  • It provides an opportunity to explore new interests and discover what truly brings fulfillment.

Redefining Work-Life Balance

  • Challenging societal norms around work hours and finding time for personal activities can lead to a more balanced life.
  • Engaging in activities that bring joy, such as painting or playing sports, can help reconnect with one's passions.

Questioning Traditional Scripts

  • Many people grow up with scripts about full-time jobs and limited free time.
  • Creating space for self-discovery involves questioning these scripts and exploring what truly brings fulfillment.

Encouraging Personal Exploration

This section focuses on encouraging personal exploration and providing support for individuals seeking new paths.

Unwinding and Trusting the Uncertain Path

  • It takes time, typically 6 to 8 weeks, to unwind from previous work commitments.
  • Trusting the uncertain path ahead is crucial for discovering new opportunities.

Empowering Individuals to Pursue Their Passions

  • Remote work offers more flexibility, allowing individuals to explore their true passions.
  • Companies should provide opportunities for personal growth, enabling employees to become the best versions of themselves.

Mindfulness and Meeting Others

  • Practicing mindfulness helps uncover feelings about work and identify desired activities.
  • Connecting with like-minded individuals through networking or shared interests can inspire new possibilities.

Path and Taking Time Off

The speaker discusses the importance of taking time off and shares a trick for feeling comfortable about it. They mention setting a budget as a runway to give themselves the freedom to explore new opportunities without worrying about finances.

Taking Time Off and Setting a Budget

  • Taking time off can help in figuring out what one truly wants to do.
  • Setting a budget for the time off provides financial security during this period.
  • Viewing the money spent during this time as an investment in personal growth can help overcome judgment or criticism from others.
  • Considering it as a gift from one's former self or future self can provide positive reframing.

Being Underemployed and Embracing Creativity

The speaker talks about being underemployed as a way to find new paths and embrace creativity. They discuss how people often underestimate their own ingenuity when faced with challenges, and how regrets are often related to missed opportunities rather than mistakes made.

Being Underemployed and Embracing Creativity

  • Being underemployed allows for exploration and discovery of new paths.
  • People are more creative than they give themselves credit for when faced with challenges.
  • Regrets usually stem from not taking action rather than making mistakes.
  • A quote from the book emphasizes that wasting hours can lead to finding new paths.

Eliminating Risks Along the Way

The speaker highlights that transitioning into something new is rarely an all-or-nothing leap. They explain that people often quit jobs after gradually testing changes over time, reducing risks along the way.

Gradual Transitioning and Risk Reduction

  • Transitioning into something new is typically done gradually, after years of awakening and testing changes.
  • By gradually eliminating risks, individuals can make informed decisions and feel more secure in their choices.

Summary

The speaker summarizes the concept of a pathless path and emphasizes that finding a new path is not an all-or-nothing decision. They explain that people often quit jobs after years of awakening and safely testing changes, reducing risks along the way.

Finding a New Path

  • Finding a new path does not require an all-or-nothing leap.
  • People often quit jobs after years of awakening and safely testing changes.
  • Gradually eliminating risks along the way allows for a smoother transition into something new.

The transcript provided does not contain enough content to create additional sections.

Writing for Fun and Overcoming Fear

In this section, the speaker discusses their motivation for writing and the fear they face when pursuing their passion.

Writing for Fun and No Goals

  • The speaker enjoys writing for fun without any specific goals or objectives.

Fear of Inaction

  • The speaker realizes that they are afraid of the consequences of not taking action, such as hiring someone or facing existential risks. They constantly think about these fears but still take action.

Dealing with Fears

  • The speaker acknowledges that fears related to money and existential concerns don't go away. They have learned to have conversations with their fears and accept them as part of their life.
  • Despite the fears, the speaker finds comfort in the fact that what they have been doing has worked so far, giving them confidence to continue.
  • They emphasize the importance of dancing with your fears rather than trying to make them go away completely.

Lessons from Past Failures

In this section, the speaker reflects on past failures and shares insights gained from those experiences.

Jumping from Job to Job

  • In the first 10 years of their career, the speaker kept switching jobs in search of a fulfilling path but couldn't find it. Various circumstances like bosses quitting and layoffs made it challenging.
  • They developed a mindset of "ship, quit, and learn," where they quickly move on from one endeavor to another after gaining valuable experience from each attempt.

Trying New Things

  • The speaker started their podcast as an experiment by committing to five episodes initially. They found it energizing and decided to continue.
  • While some endeavors didn't work out, like certain consulting and advisory roles, the speaker learned from those experiences and avoided repeating them.

Creating a Fulfilling Path

In this section, the speaker discusses the importance of avoiding creating jobs that are not enjoyable and finding what gives you energy.

Avoiding Unenjoyable Jobs

  • The speaker emphasizes the need to pay attention to what you don't enjoy and avoid creating bad jobs for yourself. For example, choosing a niche or topic that doesn't genuinely interest you can lead to dissatisfaction.

Finding Energy

  • The speaker believes it is crucial to pay attention to activities that give you energy. They have created slack in their life by minimizing meetings, having specific roles for contractors, and working asynchronously.

Balancing Multiple Projects

In this section, the speaker talks about managing multiple projects and finding balance.

Juggling Multiple Projects

  • The speaker is currently involved in various projects but feels the need to figure out how to prioritize them effectively. They started by productizing their consulting services into online courses and workshops with companies.

New Section

The speaker expresses their desire to become an operator in the business.

Wants to be an operator on this business

  • The speaker expresses their aspiration to work as an operator in the business.

New Section

The speaker recommends two or three books that they often recommend to others.

Recommended Books

  • "The Great Work of Your Life" is a book about historical figures who designed their lives around work. It provides interesting insights into different eras and people's approach to work.
  • "Wanting" by Luke Burgess is a personal story and deep dive into a nerdy topic. It explores the author's journey in the startup world and offers valuable perspectives from a tech standpoint.

New Section

The speaker shares their favorite recent movie or TV show, as well as a question they like to ask when interviewing contractors or potential hires.

Favorite Movie/TV Show and Interview Question

  • The Anthony Berdan documentary is highly recommended by the speaker for its portrayal of struggle, ups and downs, and inner demons. It tells a powerful story of someone bringing forth what is inside them while grappling with personal challenges.
  • When interviewing contractors or potential hires, the speaker likes to ask what makes them come alive. They value working with individuals who are energized, connected, and inspired in their pursuits. Examples include a podcast producer in Poland with diverse skills and a former finance professional exploring new ideas through self-employment in India.

New Section

The speaker discusses their favorite product discoveries.

Favorite Product Discoveries

  • The Nuna travel stroller is highly recommended for its convenience during travel.
  • The speaker recently got into the EIM (Email Inbox Management) game, which has been amazing. They also mention using Chat GPT to create their own GPT for automatically generating podcast show notes.

New Section

The speaker shares their favorite life motto and reflects on the importance of personal energy over extrinsic outcomes.

Favorite Life Motto

  • The speaker's favorite life motto is "coming alive over getting ahead." They emphasize the significance of personal energy and intrinsic connection in contrast to chasing external achievements.

New Section

The speaker provides advice for those interested in starting or being successful in podcasting.

Advice for Podcasting Success

  • If the goal is to make money through podcasting, it may not be the best avenue unless there is a massive audience. Podcasting is a long game that requires an intrinsic connection to the content and format. It is recommended to start a podcast out of genuine interest rather than solely for financial gain.

New Section

This section discusses the task of creating a comprehensive and informative markdown file from a given transcript. The goal is to structure the markdown file in a clear and concise manner, utilizing timestamps when available to aid in studying the transcript.

Creating Comprehensive Markdown Notes

  • The objective is to summarize the content of the transcript accurately and succinctly.
  • Use bullet points to provide key points and insights from the transcript.
  • Each bullet point should be linked to the corresponding part of the video using timestamps.
  • Ensure that each section has meaningful titles and is not too short.
  • Follow a chronological order while going through the transcript, avoiding mixing sections.

Formatting Tips

  • Keep each section limited to 4 bullet points, with no more than 25 words per bullet point.
  • Use [] for timestamps and () to link them to specific parts of the video.
  • Organize notes using subheadings and bullet points for clarity.
  • Include relevant timestamps within blocks using format, especially for bullet points.

Summary Tips

  • Only include content from the transcript; do not add any additional information.
  • Titles should be informative or pose questions answered by the video.
  • Avoid drawing conclusions since only a small part of the video may be covered in these notes.
  • Cite relevant timestamps by linking them within blocks using format, especially for bullet points.
  • Be concise and avoid excessive sectioning.

The language used in this summary follows that of the original transcript.

Video description

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 — Brought to you by Sanity—The most customizable content layer to power your growth engine: https://www.sanity.io/lenny | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door: https://mauinuivenison.com/discount/LENNY?utm_medium=podcast&utm_source=show_notes&utm_campaign=lenny | Wix Studio—The web creation platform built for agencies: https://www.wix.com/studio?utm_source=Lennyspodcast&utm_medium=Podcastad&utm_campaign=SL Find the transcript for this episode and all past episodes at: https://www.lennyspodcast.com/episodes/. Today’s transcript will be live by 8 a.m. PT. Where to find Paul Millerd: • X: https://twitter.com/p_millerd • LinkedIn: https://www.linkedin.com/in/paulmillerd/ • Website: https://pathlesspath.com/ • Podcast: https://think-boundless.com/podcast/ • Newsletter: https://newsletter.pathlesspath.com • YouTube: https://www.youtube.com/channel/UCofS_FvauuHc-x6mq7yz6nA • Email: paul@strategyu.com Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Paul’s background (04:33) An explanation of the “default path” (06:32) Questions to help clarify which path you are on (07:35) Paul’s thoughts on “remixing your path” (09:57) An explanation of the “pathless path”  (12:06) Examples of the pathless path (13:54) Why meaning is hard to find and sustain on a traditional career path  (16:05) A case for the three-month sabbatical  (18:16) A mindfulness and self-reflection exercise (20:18) Why Paul recommends three months (22:28) Advice to founders on offering sabbaticals (23:40) Other tactics for self-discovery (27:08) The variability of income in self-employed roles  (29:12) Methods for staying afloat after leaving your job (30:42) Tips for reframing your thoughts around money (33:19) Why betting on yourself usually works out (34:46) The importance of setting aside time for creative pursuits (36:22) How to dip your toes in and find your path  (37:53) Lenny’s personal journey (39:27) Advice on dealing with the naysayers  (40:22) How to acknowledge and tame your fears (44:52) The “ship, quit, and learn” framework (46:39) Why the pathless path is one of constant reinvention (51:27) Paul’s response to criticism  (58:02) First steps for getting started on your journey (55:42) Lightning round Referenced: • The Pathless Path: Imagining a New Story for Work and Life: https://www.amazon.com/Pathless-Path-Imagining-Story-Work/dp/B09QF6Q421 • David Autor on X: https://twitter.com/davidautor • Tim Ferriss’s blog: https://tim.blog/ • Why you should define your fears instead of your goals | Tim Ferriss: https://www.youtube.com/watch?v=5J6jAC6XxAI • How Lenny Rachitsky Got 531,000 Substack Subscribers: https://www.youtube.com/watch?v=DMZem1NYfpM • The Lindy effect: https://en.wikipedia.org/wiki/Lindy_effect • StrategyU: https://strategyu.co/ • David Deming’s website: https://www.daviddeming.com/nyt-columns • The Great Work of Your Life: A Guide for the Journey to Your True Calling: https://www.amazon.com/Great-Work-Your-Life-Journey/dp/0553386077 • Wanting: The Power of Mimetic Desire in Everyday Life: https://www.amazon.com/Wanting-Power-Mimetic-Desire-Everyday/dp/1250262488 • Roadrunner: A Film About Anthony Bourdain: https://www.hbo.com/movies/roadrunner-a-film-about-anthony-bourdain • Nuna travel stroller: https://nunababy.com/usa/trvl-easy-fold-compact-stroller • Build Your Own Chatbot with OpenAI GPT-3 and Streamlit: https://medium.com/@avra42/build-your-own-chatbot-with-openai-gpt-3-and-streamlit-6f1330876846 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.