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

Nov 19, 2023 1h 4m 16 insights Episode Page ↗
Guest Paul Millard, author of "The Pathless Path," discusses breaking free from the "default path" of work and life. He shares tactical advice on creating space for self-discovery, taming fears, and exploring unconventional career paths to find work that truly brings you alive.
Actionable Insights

1. Take a Workday “Sneak Out”

Block off three hours during a workday to go for a walk without a destination or engage in a childhood hobby. This helps you practice work mindfulness, understand your feelings about work, and reconnect with what brings you alive.

2. Plan a Three-Month Sabbatical

Consider taking a three-month sabbatical, as companies are increasingly open to this to retain talent. This duration is vital for creating space, unwinding (which takes 6-8 weeks), and exploring new possibilities to reconnect with yourself.

3. Invest in a “Life MBA”

Reframe the money and time spent on exploring new paths as an investment in a “life MBA.” This perspective helps to counter self-judgment and external criticism, similar to how people view the cost of business school as a valuable investment.

4. Define Your “Exploration Runway”

Set a budget for your time off, viewing it as a calculated amount of money you’re willing to spend with the expectation that it will lead to valuable discoveries. This approach helps you feel more comfortable and committed to the exploration period.

5. Transition to a Contract Role

Explore converting your current full-time job into a contract position, potentially working fewer days a week. Many employers are open to this for known employees, offering more flexibility and control over your work environment.

6. Track Your Energy Levels

Pay close attention to activities that energize you versus those that drain your energy, whether it’s calls, hobbies, or creative work. The strategy is to consciously do more of what energizes you and less of what de-energizes you to guide your path.

7. Practice Fear Setting

Utilize Tim Ferriss’s fear-setting exercise by writing down your fears, how you could mitigate them, and, crucially, the costs of inaction. This process helps expose hidden costs of your current situation and empowers you to take decisive action.

8. Acknowledge Persistent Fears

When facing existential fears (e.g., about money, health, or significance), acknowledge them as ongoing parts of your journey rather than trying to eliminate them. Develop a mindset of having a conversation with your fears and continuing forward despite their presence.

9. Adopt “Ship, Quit, Learn”

Embrace a framework of quickly shipping something with the intention to quit it, using the experience to learn and inform your next steps. This encourages experimentation without long-term commitment, allowing for rapid discovery of what works.

10. Avoid Unenjoyable “Self-Jobs”

Be vigilant about not creating new work for yourself that you don’t genuinely enjoy, even if it seems like an opportunity. The purpose of the pathless path is to find work you love, and taking on unenjoyable tasks defeats this goal.

11. Commit to Constant Reinvention

Understand that the pathless path is a commitment to continuous reinvention, requiring ongoing personal reflection, adaptation, and a willingness to outsource, eliminate, or restart projects. This approach helps protect your time and creative space.

12. Explore “Something More”

If you have an intuitive sense that there’s ‘something more’ for you in work or life, commit to exploring it, even if the journey is challenging. The potential for no regrets and greater fulfillment makes the exploration worthwhile.

13. Connect with Path Experts

Reach out to individuals who are a few years ahead of you on a similar unconventional path, sending a thoughtful message to ask questions or pick their brain. Additionally, seek out a diverse range of people (‘weirdos’) outside your professional bubble to normalize different life and work arrangements.

14. Manage External Perceptions

When asked about your unconventional path, use phrases like ‘I’m just tinkering’ to make it sound delightful and deflect intense questioning. For older generations, provide a ‘Boomer-compatible story’ like ‘I’m an entrepreneur’ to resonate with their understanding of work.

15. Hire for Aliveness & Asynchronicity

When building a team or hiring contractors, prioritize individuals who are energized, connected, and inspired, and optimize for asynchronous work. This approach helps protect your own creative energy and time while fostering productive collaborations.

16. Podcast for Intrinsic Joy

If considering starting a podcast, do so primarily for the intrinsic connection to the conversations or the creative act itself, rather than for financial gain. Podcasting is a long game, and intrinsic motivation is key to its sustainability and enjoyment.