To gain certainty, we must embrace fuzziness. Where the operationally driven leader manufactures an artificial sense of certainty — often in the form of clear targets and goals — the pioneering leader feels no such need. As such a leader, you're comfortable making progress while only having a fuzzy sense of the potential destination. You don't wait

TO MAKE PROGRESS, WE MUST AVOID SUCCESS. It's tempting to declare victory, and to feel as though we have ‘made it'. But pioneering leaders know this is an infinite game we're playing — one with no finish line. You always have more opportunities to learn, grow and develop to stay relevant. Sure — you'll have small wins along the way. But constructiv

TO BUILD CONVICTION, WE MUST EMBRACE DOUBT. German philosopher Johann Wolfgang von Goethe once said that ‘doubt grows with knowledge'. And Aristotle is said to have once quipped, ‘the more you know, the more you know you don't know'. Whereas some might claim to have all of the right answers, pioneering leaders instead value asking the right questio

Everything has its season,
all exists in oscillation.

"Let’s assume that you think you have a choice of eight paths to follow (all pre-defined paths, of course). And let’s assume that you can’t see any real purpose in any of the eight. THEN— and here is the essence of all I’ve said— you MUST FIND A NINTH PATH...I’m not trying to send you out 'on the road' in search of Valhalla, but merely pointing out

"I am not a fool, but I respect your sincerity in asking my advice. I ask you though, in listening to what I say, to remember that all advice can only be a product of the man who gives it. What is truth to one may be disaster to another. I do not see life through your eyes, nor you through mine. If I were to attempt to give you specific a

When giving or receiving advice, focus on the general, not the specific.

This is exactly how I navigate the perils of advice in my own writing: I try to provide the general principles, ideas, frameworks, and questions that you can take, mold, and leverage in your own way.

“What gets measured gets done,” Peter Drucker once famously said. But the terrible thing is that this often translates to the only things getting done being the things easily measured. And much of the richness, meaning, and fulfilment in life come from the things that can’t be measured easily

Define Your Way of Life

"But beware of looking for goals: look for a way of life. Decide how you want to live and then see what you can do to make a living WITHIN that way of life."

This is my favorite insight from the letter: Identify how you want to live, not what you want to achieve.

So often people focus all their energy on the summits—but complet

When hiring, look for people with the right attitude. Skills can be taught. Attitude changes require a brain transplant.

from Elon Musk by Walter Isaacson