perennially great questions to ask

Life is modular, not linear. You don't choose a career at twenty-two and stick with it for forty years like some kind of professional arranged marriage. Instead of hunting for the mythical perfect tree, follow your curiosity. What ideas make you pause while scrolling? What conversations do you find yourself returning to days later? When a friend me... See more

What kind of life do you want to build? What values do you want your work to reflect? What skills do you want to develop? How do you want to contribute to the world around you? What kind of people do you want to work alongside?

And then:

What are you willing to sacrifice for those things? What discomfort are you willing to endure? What would make yo... See more

What aspect of your work is hardest to copy? How can you amplify it?

Describe your ideal self—the qualities you’d most like to embody—in five words. Then, to find your shadow self, locate the opposing qualities of each one. The shadow self describes the parts of ourselves we most ardently reject and repress. I think my ideal self would be: insightful, generous, authentic, funny, discerning. That means my shadow self... See more

Talk about potential mistakes before they happen and people start looking for ways to prevent them.

Talk about actual mistakes after they happen and people start looking for reasons to defend their actions.

What do we need to be talking about now, so we can learn the lessons before we need them?

what do you believe will lead to human flourishing?