I've had multiple life design resets in my life. The first was when I returned from Japan. I had gone overseas to pursue a dream that ended up not being what I thought it would. So, I came home to my family. The next came after a health scare. That was the impetuous to look at a new career path that included remote work. Then I lost my father and brother within a short period of time. It was a wake-up call that life is short and all you have at the end of the day is your family Unfortunately, each time, I've reverted back to old habits. Working like a beast, grinding away for all the wrong reasons. Now I'm in another reset. Not entirely of my own choosing, but needed none the less. For the past five years I’ve led my company’s largest, and most expensive, product build in it’s 50+ year history. It’s a project that I helped ideate, validate, and pitch to our Board of Directors for funding. I’m leaving behind that project and my entire team, which I built from scratch and that includes two teams that have never existed at my company.
It’s been tough to see this as a step forward. But, a while back, when I was struggling with the career options in front of me, I prayed that God would point me in the right direction.
It looks like he has chosen the pathless path for me.
So, what’s the Pathless Path? Well, it’s concept I recently learned out from reading Paul Millerd’s book by that title.
The Default Path is the traditional, socially-prescribed blueprint for success that many people follow, often unconsciously.
- Definition: It is a predetermined, stable, and predictable career route and life sequence reinforced by societal expectations. This is what I’ve chased most of my professional life.
- The Script: This typically includes studying hard, getting good grades, securing a stable and prestigious job (often in a specific field), climbing the corporate ladder, buying a home, accumulating wealth, and eventually retiring.
The Pathless Path is the alternative that Millerd advocates for, which is a self-directed, more fulfilling journey.
- Definition: It is a career and life without a clear, pre-defined direction, where you prioritize personal fulfillment, curiosity, and meaning over conventional metrics of success.
- The Journey: It involves embracing uncertainty and discomfort, experimenting with different ways of working, and actively creating a life that aligns with your own values and purpose. The path is "paved as you move forward"—each step is a deliberate choice.
- The Goal: The aim is not just to make money or get a job, but to find work that you want to keep doing and to shift from a life built on "getting ahead" to one focused on "coming alive." It is a call to adventure in a world that tells you to conform.
The Pathless Path is what I’ve known intuitively I should do, but only had the courage to pursue in spurts and its what I’m embracing now. There is no perfectly crafted career path for me at this stage of my career. But, that’s ok. I’m finding myself with the space to be creative again and the time to pursue projects I have wanted to work on but never committed to finishing.
If you find yourself in a similar spot and are looking for some guidance here’s a framework for exploring the Pathless Path.
The Pathless Path Career Framework: An Outline for Reinvention This framework provides a structure for moving beyond the "Default Path" by combining deep self-reflection with small, low-risk experiments to find a career aligned with personal values and energy. Phase I: Deconstruct the Default Script (The Awakening) The goal of this phase is to gain clarity by consciously challenging the unexamined assumptions about success, work, and money that society has instilled. A. Define Your Personal Success Metrics
- Identify the "Shoulds" and Scripts: Write down every external expectation for your career (e.g., "I should earn $X," "I should work for a prestigious company"). Trace where these beliefs originated (parents, school, peers).
- Define "Enough": Determine the minimum sustainable income, time, and energy required for you to feel secure and healthy. This acts as your financial floor, giving you permission to reject opportunities that chase "more" for the sake of it.
- Articulate the Cost of Inaction (The Fear Setting): Use a fear-setting exercise (like the one advocated by Tim Ferriss) to outline the exact consequences of not making a change in 3, 6, and 12 months. This reframes fear from paralyzing to motivating. B. Find the Gaps (The Pebbles in Your Shoe)
- Identify Flow & Joy: List moments in your current or past work where you were completely absorbed, felt useful, or experienced genuine joy (the work that "brings you alive").
- Acknowledge the Disconnect: Systematically compare the work/life you are currently living (the Default Path) with the life you truly want, highlighting the specific areas of misalignment (e.g., lack of autonomy, boring work, misaligned values).
- Practice Non-Doing (Leisure): Schedule intentional time (sabbatical, long weekends, daily deep work breaks) with no agenda. True rest and contemplation are necessary to hear your inner voice and allow new ideas to emerge. For example, later today I am taking a back-country hike and then meeting a good friend for lunch. Phase II: Explore Through Small Bets (The Experiments in Living) The goal of this phase is to stop planning your next job and start prototyping your next identity through low-stakes creative work and contribution. A. Prototype Your Next Identity
- Follow Your Curiosity Before Certainty: Instead of looking for a "dream job," look for a conversation—a theme, problem, or question you keep returning to. This conversation is your new "field."
- Create Before You’re Ready: Start small, visible projects related to your conversation. This is the Small Bets approach: ◦ Example: If your curiosity is about sustainability, start a newsletter, a small consulting project for a friend, or a public research document.
- Prioritize Usefulness and Generosity: Focus on being helpful to others through your small experiments, rather than immediately focusing on monetization or prestige. The income will be an optional byproduct of the value you create. B. Build a Freedom Foundation
- Seek Diverse Measures of Success: Stop measuring success purely by salary or title. Instead, track metrics like: ◦ Autonomy (your control over your time) ◦ Learning (new skills developed) ◦ Connection (quality of relationships built through your work)
- Develop Meta-Skills: Focus on reinforcing skills that enhance reinvention, such as learning agility, self-awareness, and resilience, which are valuable in any pathless journey.
- Build Your Tribe ("Find the Others"): Actively seek out mentors, communities, or peers who are also living unconventional lives. This network provides the validation and imagination needed to sustain an uncertain path. Phase III: Commit and Design (The Infinite Game) The final phase is about formalizing the commitment to continuous reinvention and designing a life where work serves your freedom, not the other way around. A. Design from Ideal Life Backward
- Write Your Second Chapter: Imagine your ideal life 10–20 years from now (what does your daily routine look like? Who are you spending time with? What work are you not doing?).
- Work Backward: Use this ideal vision as a "fixed point" and determine the necessary steps (skills, income level, location) required to move toward it, rather than just taking the "next logical step" on the Default Path.
- Plan for Reinvention: Acknowledge that this next move is not permanent. View your new role or business as a prototype that will inevitably evolve, requiring continuous "pathless" thinking. B. Commit to the Infinite Game
- Embrace the Infinite Game Mindset: Commit to finding work you want to keep doing indefinitely (the goal is to keep playing the game, not to win or reach a fixed "retirement" endpoint).
- Choose Aliveness Over Advancement: When faced with a choice (more money vs. more autonomy; more prestige vs. more joy), choose the option that makes you feel more vital and alive.
- Cultivate Trust in Emergence: Understand that the right opportunities rarely appear on a resume or job board. By taking conscious action and following your curiosity (as prototyped in Phase II), the next steps will naturally emerge.
If this resonated with you, please hit reply and let me know.
P.S. You can find the book by clicking here: The Pathless Path by Paul Millerd. I started it two days ago and am loving it. It's a perfect mirror of me, the true me, when I'm not allowing accolades and accomplishments distract me. At the time of writing this, the audiobook version is on sale for $0.99.
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