Traditional goal-setting (navigation) fails for life's "wicked problems." Instead, use wayfinding: a prototyping approach of trying things, learning, and adjusting. The jagged, inefficient path is actually the shortest route to an unknown destination.
When you're unsure of your direction, the solution is not more introspection but immediate action. Trying different paths, even if they're wrong, provides valuable data about what you do and don't want. Action creates clarity, not the other way around.
Don't commit to a rigid career plan. Instead, treat your career like a product. Run small-scale experiments or 'MVPs'—like a 20% project, a volunteer role, or a teaching gig—to test your interest and aptitude for new skills before making a full commitment, then iterate based on the results.
When facing obstacles, adopt the mindset of a GPS like Waze. It doesn't tell you to go home when there's a problem ahead; it simply finds a new path to the same destination. This reframes challenges as simple pivots rather than catastrophic failures, keeping you focused on the end goal.
A fixed long-term career plan can be paralyzing. Instead, view your dream future as being on the other side of a lake covered in lily pads. Your job is to leap to the next immediate opportunity that energizes you, creating a flexible, compounding journey without the pressure of a grand vision.
Brett Victor's "Inventing on Principle" concept suggests defining a core principle to guide your life's work rather than setting rigid goals. This allows for flexibility and unexpected opportunities from the periphery, which are often the most significant breakthroughs and lead to a more exciting journey.
Many people find their calling not by pursuing a lifelong dream, but through a process of discernment. This involves engaging in new experiences, reflecting on what provides fulfillment, and then using those insights to inform the next step in a continuous cycle of trial and error.
A complicated system (a Ferrari) has linear steps, while a complex system (a teenager) changes as you interact with it. Your life and career are complex. Instead of fighting for a straight-line path, embrace the "squiggly" nature of growth, treat wrong turns as valuable information, and learn through exploration rather than rigid planning.
To explore a potential life path, move beyond transactional data (e.g., salary, credentials). Instead, have 'prototyping conversations' to immerse yourself in the narrative story of someone already living that life. This provides a deeper, experiential understanding that data alone cannot offer.
Binary (A-B) choices lead to bad decisions over half the time. To generate better options, create three distinct five-year 'Odyssey Plans': 1) your current path succeeding, 2) a backup if that path vanishes, and 3) a 'wild card' plan free from financial or social constraints. The goal is imagination, not selection.
Successful people with unconventional paths ('dark horses') avoid rigid five or ten-year plans. Like early-stage founders, they focus on making the best immediate choice that aligns with their fulfillment, maintaining the agility to pivot. This iterative approach consistently outperforms fixed, long-term roadmaps.