#108: landscape of possibility

I think of this like a personal Overton window (although I know the analogy doesn’t make perfect sense). A kind of private tunnel vision that rearranges our reality so that our highs and lows are defined by only the most immediate wins and losses, with everything else rendered irrelevant—the hard fought habits we’ve kept, the old lessons that stuck... See more

The world is full of ideas and opportunities to explore, but it takes time outside of structure to even adjust your eyes to the landscape of possibility. You are cramped by your job, unable to make the class of investments that is necessary for a life beyond the existing tracks.

One of the biggest challenges people have when embarking on an unconventional path is disconnecting from extrinsic markers of success and listening to internal motivational cues. On the default path, you can spend an entire career playing other people’s games. At first, people on a pathless path try to fill the lack of extrinsic goals with new ones... See more

Can you learn to enjoy the process as the end in itself, not the means?

In the beginning, the dissonance between the scale of your aspirations and the reality of your days will riddle you with anxiety. You will be tempted to strip the unknown of its surprises and travel to the future: What if my customers churn? What if a competitor introduces a be... See more

couldn’t possibly do this” syndrome only grows stronger with age. It also creates a formidable sense of path dependency, or the narrative that you are on a certain path, and the best—if not only—option is to stay on it. But path dependency prevents you from exploring opportunities that could lead to a better and more fulfilling life. You’ll never k

... See more