talking to Sasha Chapin about unconventional career paths and lessons in love

on finding the complexity that you're interested in

Happy Sunday! I recently had to chance to sit down with my friend Sasha, who is, among many other things, an author, entrepreneur, Twitter celebrity, and meditator whose Substack I love.

Some beautiful excerpts from Sasha on the podcast:

“I think I have given up on having one character arc or being able to make sense of it all as a unity. I'm trying to get lost in whatever work presents itself on a given day, and if it doesn't add up to anything coherent, that's fine.”

“One thing I'm trying to do as I get older is to get a more accurate sense for the way my personality and my approach to people distorts situations. Rather than trying to read people based on how I interact with them, I consider [their behavior] a sort of blending between my personality and the world.”

“People often assess someone they're thinking about dating in terms of who they are right now. They take a snapshot of the amount of money somebody's making or where they're living and even what their temperament is like day to day. And they think, that is the person that I'm with. But that's obviously not true. A person is going to change over time. But that doesn't mean you can't make an assessment. I just think when you're assessing people it's really important to look at trajectory. How do they change over their lives? How do they, as our mutual friend Graham says, move through their environment? Do they tend to get better and different over time, or do they get worse?”

“I think complexity is fractal and you can find it anywhere when you become interested in something. I use to associate a complex and varied life with adventure, broadly construed, like travel and drugs and eating different things, pushing yourself in various ways. And now I think complexity can be found anywhere … One of the things that can make a life worth living is finding the complexity that you're interested in and continuing to pursue that.”

Topics we discuss:

• the challenges and joys of being self-employed and having an extremely non-linear career path

• micro-fame and parasocial relationships

• how people’s demeanors affect their lives

• the importance of choosing a partner you admire

• being able to be candid in a romantic relationship

• romanticism and idealism

• truth and beauty

• being a vessel for your creative gifts and other people’s

• couples who work together

• being a person who is drawn to complexity and grappling that; complexity is a natural function of caring about things

Check out his wonderful Substack if you haven’t yet! And DM me if you’re interested in being on the podcast… I want to do more episodes in the new year.