Doing even a small experiment is scary, but the payoff can be profound. When I hosted a group coaching session in New York, I was extremely nervous. I had never done anything like it before, but by the end of the night, I knew that bringing together curious people around questions I was excited to explore was something worth being uncomfortable for

Yet when I became self‑employed, I was surprised at how strongly I had internalized a worker identity. As I struggled to find my first project, I felt guilty when I wasn’t working during typical work hours Monday through Friday. When I started working remotely on my first project, I had 100% control over when and how I did the work, but quickly fel

If the culture doesn’t work, don’t buy it. Create your own. This is what the pathless path is all about. It’s having the courage to walk away from an identity that seems to make sense in the context of the default path in order to aspire towards things you don’t understand.

I wish they knew what I know: the longer we spend on a path that isn’t ours, the longer it takes to move towards a path that is. Money might help pay for therapy, time off, and healing retreats, but it won’t help you come to a place where you really trust and know that everything will be okay.

submit that this is what the real, no‑bullshit value of your liberal arts education is supposed to be about: how to keep from going through your comfortable, prosperous, respectable adult life dead, unconscious, a slave to your head and to your natural default setting of being uniquely, completely, imperially alone day in and day out.⁠6 Wallace’s p

I was becoming a hoop-jumper just like Deresiewicz’s students at Yale, internalizing the idea that education is “doing your homework, getting the answers, acing the test.” I had not developed a sense that “something larger is at stake” as Deresiewicz says, and only was playing the game of student, not using my mind.

Behind our money fears are existential fears, like the fear of death or the fear of not being loved, respected, and admired.

When we look to the market to solve all our needs, it leaves us feeling empty. Professor Tim Wu made this point in a widely read essay titled “The Tyranny of Convenience,” where he argues that convenience, “with its promise of smooth, effortless efficiency…threatens to erase the sort of struggles and challenges that help give meaning to life.”⁠16

However, this is the whole point of embracing the gift mindset and practicing generosity. It exposes our default scripts about how we think the world should work and opens us up to new possibilities.