Optimizing for the journey.
I’ve decided to quit. I’m not sure when or even how. I’m going to leave my corporate job in Tech to go Indie.
I’m a firm believer in optimizing for the journey, not the destination, so this will be a place for me to share the early, ambiguous, and vulnerable explorations of going out on my own. Or at least, of me stepping out of my traditional path, into the unknown. I value shared learning spaces, and learning by doing and thinking together, so I’m going to learn out in the open, with the garage door up, and share the good, the bad, and the messy in-between.
The pull has finally become stronger than my internal barriers and my internalized fears. I’m starting the work of shedding the stories and scripts I’ve been telling myself. Starting this internal exploration, has been greatly helped by fellow travelers who have been on this path and who publicly share their writings and conversations. They affirm that there are others out there, and that there is indeed a way to make a living while enjoying what you do. They’ve helped me find the language and develop new mental models to set out on a fresh journey for myself. I have gleaned deep insights from Venkatesh’s writing, especially the Art of the gig. I am supported through honest conversations with friends, loved ones and colleagues. And I am inspired by Paul Millerd and his many conversations on the Pathless Path.
While many have shared their stories of non-traditional paths, they mostly do so by looking back at their early stages once they’ve moved beyond them. These are amazing resources, but I’ve been especially interested in a real-time view into the messy early stage as it all unfolds; and all the emotions, stresses, and considerations that come with it. I want to explore openly the scripts that we tell ourselves and the internal battle that happens when we try to negotiate with ourselves. Mind vs heart. Rational worries vs irrational fears. Intuition vs reason…
I’ve made the decision to quit but I don’t know where I’m headed and I have no step-by-step guide for this type of journey. I don’t know where to start or what to pack. I don’t know what tools I need. And I don’t know how to ride the undulations of my mind from the highs of “Heck yeah, I’m gonna do it. I’m going to quit and everything will be amazing,” to the lows of “I’m crazy for doing this - Why would I leave a successful, high-paying corporate job? We are heading into a recession! What if Im not good or smart enough to do this, to succeed? And….how will I define success?”
For me, regular deep dives into various rabbit holes are micro doses of a journey without a destination. A recent rabbit hole led me from the pleasure of train rides to Hunter S. Thompson’s words about goal-setting to Annie Dillard’s reminder that “how we live our days is how we live our lives,” which inspired my own reflections on the urge to start this journey now. I realized that I can no longer wake up in the mornings with my main goal being to make it through the day and to go to bed just to do it over and over again in order to get to some pre-ordained destination.
On the Platform
I like the metaphor of a train journey as I start this experiment and set out on my early explorations. I have committed to the journey. I have a ticket (well at least for the first leg of the trip) but I have no destination.
For now, Im wandering the platform, enjoying the sounds and smells and serendipitous encounters with strangers. I’m savoring the ambiguity. Sitting with my thoughts, planning and researching, writing notes and reflections, music and stories in my headphones. I’ve traveled by train before, but this time is different. This time I don’t have a clear destination. I have no map, no tour guide, no advice or recommendations. I’ve got a ticket to an unknown place, choosing the route by gut, intuition, and more clarity about how I want to spend my days.
For now, I’m documenting this journey, committed to learning out in the open. I hope this can become a space for shared learning - a platform for those of us just setting out on our own adventures. A place to bump into each other and exchange stories and ideas. A warm place to talk about our dreams and fears. Thanks for following along.
Next time, I’ll share a bit more about my point of departure and how I got there.
Sincerely,
Anonymous, for now…