078 – Waypoints Over Destinations

Photo by Mael BALLAND on Unsplash

Why do we make decisions solely based on a projected final destination? A nearly impossible effort because one tends to arrive at a destination a much different person than they were when they set off on the journey. How can you predict who you will be when you get there? It’s hard enough trying to figure out what to eat for dinner on a Tuesday night.

I often get asked by young entrepreneurs or students how I came into my profession. My story was more emergent and experimental in nature instead of planning and mapping a course backward from a destination. By emergent, I mean that it has been colored through various stages like a patina on the rear fender of a 1973 Landcrusier FJ40. It has also morphed over time through experience so much so that the latter version hardly resembles or recognizes the former. Experimental refers to the way I let my curiosity drive my learning to try new things out. Most of those things, including a food hub and marketplace for ideas and investors landed squarely in the trash bin. A few others led me to more refined experiments and amazing relationships. Even fewer led to something somewhat successful. All of them left me with the desire to keep experimenting. It feeds my malleable foundational knowledge, which is my version of (natural) general intelligence. It is an ego-shedding system that fosters a tolerance for not knowing the answers and feeds an inquisitive beginner’s mind.

One of my favorite things about writing for a number of publications and hosting a podcast is diving deep into things I don’t know about only to emerge on the other side of synthesis with a new understanding. I love jumping into something so far out of my prior knowledge base that I am forced to challenge my desire to escape it. For example, I’m obsessed with quantum mechanics, but I’m not savvy enough to build Feynman Diagrams for groupings of hadrons and their associated quarks. I also am not a scientist. I do find the underlying idea of small things as the foundational elements for larger things fascinating, which is a concept that extends from quantum mechanics into every other discipline. While I produce music for television shows, I haven’t developed the expertise to compose a four part fugue and conduct an orchestra in its performance of it. All of these interests feed my idea generation and critical problem solving in various domains. Clearly my method has been to chase down what excites me, synthesize each experience, connect them with previous experiences while being open to new ones.

A traditional path is more linear and driven by meeting milestones at certain stations and progressing through a predetermined pipeline. Factories use specialization and linear processes to build a large amount of one kind of thing. Specialization creates experts and the world needs experts. I just don’t happen to be one. Maybe I’m not focused enough to be one.

Back to the original question, what if instead of buying a ticket to a destination, you navigated waypoints just like a pilot traveling from England to Australia? Pilots travel using a series of beacons that generate signals creating a virtual roadmap in the sky. Flight paths are defined and tracked through this series of checkpoints throughout the journey. These waypoints could change based on external influences like air traffic and weather. Eventually, they lead somewhere, but a successful journey is rooted in the awareness and adherence to the waypoints.

Think about the dots in the image above and focus on the left-most dot in the arrangement. There are a few closely connected options that could make for an interesting first step. The jump from the first dot to one of these options is relatively small, which when compared to the straight line below the group of dots, can make the decision a little less stressful. You can still see the first dot, and there still are other dots in the ecosystem if you find the one you landed on to be uninspiring. Life is a series of small interactions, exchanges and connections that coalesce into a larger experience. Many small jumps over time can lead to a deep and rich journey. With each small step, you learn more about yourself and what inspires you without having to go all in with something that you hope might be right for a future version of yourself. These virtual points in the system create spontaneous one-to-one relationships leading to exponentially grand and diverse routes through life.

In his book, The Lean Startup, Eric Ries elevated the concept of pivoting, which sparked a trend of agile scrum, sprint development cycles and the idea of building, testing and iterating. Ries describes that moment in time for a startup that entrepreneurs learn that their current strategy may not yield their desired result. Many strong-willed self-starters will stay the course even with the insight that suggests a high probability of failure. The reason they don’t change their strategy is they feel that they’ve invested too much time, energy and resources to cut bait. Pivoting is not giving up. It is the fine tuning of a process based on the most accurate information you have at that moment. This concept translates well to how people become so attached to their beliefs that they resist and defend in the face of new crystal-clear information presenting a valid counter-perspective. Time can add a stickiness to these personal beliefs and entrepreneurial strategies that can be physically painful to disconnect.

How many experiences in your day are actually beacons? How open are you to receiving those signals if you are merely focused on the destination? These signals are present in the world around us. They could be a hunch to take a different way home, a snippet of information from a podcast, tying two ideas together on a long walk or a wonderfully crazy idea from a friend. Being open to these signals is a critical piece of the puzzle. If your radar is jammed or you live in a constant barrage of noise over signals, you may never process the transmission that could lead to a life-changing insight.

The discovery and selection of the next waypoint is the victory rather than your position relative to a projected destination. Whether you are tasked with a problem to solve, a new idea to develop, or something as big as a career choice, you don’t always need to know the exact direction or end tactic. You just need the next waypoint that uncovers a better question or new perspective. The next turn, the next exit, the next step is all you need to keep momentum. We can become frozen by the gravity of trying to decide an ultimate destination. The weight of that kind of decision is paralyzing. What if you approached it a little differently? What are your current waypoints? The immediate choice will not define you, it merely helps you iterate and evolve.

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