So much of what we identify as suffering stems from our inability to sit still

Every single human being on the planet is flawed. We're all flawed in different ways. We're all imperfect. This idealized state that our culture has created where you have to carry yourself and present yourself in a certain way is actually a massive inhibitor of people being effective and successful.

For many of our friends who are in startup land, the thought of taking a weekend off is as terrifying as my thought of taking two months off—and that's a problem. That's a problem that not only affects them physically, it's a problem that affects them mentally. It's a problem that, actually, I would argue, undermines their leadership capabilities and creates toxic environments.

What am I not saying that needs to be said? What's being said that I'm not hearing? What am I saying that's not being heard?

Behaviors persist because they serve us

Part of what we do, which I think leads to a significant amount of burnout and existential struggle, is we take meaning for motion. We take meaning from performance. And then when I take away the motion, what happens to my meaning?

When one is willing to accept oneself all the way down to one's bones... self-confidence and self-worth grow out organically

Stopping striving is pretty enlightening because our programming as people—and as entrepreneurs especially—is that you must constantly be striving to achieve the next goal or the next outcome. What a load of bullshit. The words themselves make me shrivel up. No, that's not the essence of it; that's the thing we're programmed to do.

It is not failure that annihilates us, but it's when we attach our sense of self-worth and self-esteem to the accomplishment of a goal and then fail to achieve the goal that we are annihilated.

The demon disappears more often than not when you confront it

Until you make the unconscious conscious, it will direct your life and you will call it fate.

One of the most important adulting skills is learning to be with, and be in a relationship with, our conflictual, ambivalent, confusing, and uncomfortable perceptions and feelings

There is no correlation—zero—between happiness and achieving a milestone.

Confronting the existential threat is actually the best way to deal with it. Running away, hiding, and bypassing don't actually help... they only make the situation worse.

I often say that I sit on the meditation cushion during the morning because I need to be able to meditate throughout the day. I need to be able to return to that state of mind ... Go to the mountaintop for a week at a time, so that, in an afternoon while stuck in the middle of Austin, you can go for a bike ride; you can go for a hike; you can go to a park; you can take a dog for a walk; you can do the things that nourish you.

When I reflect back on my early 20s, I wish I had not linked my entire identity to my work. Linking some of my identity to my work—totally healthy. But my entire identity—not healthy for me at all.

No matter what blame or praise or fame or shame that you might feel, don't forget who you are and who you have been

It's all of the emotional load that we put into that notion of productivity that actually exacerbates the stress and tension that causes us to need to take the rest in the first place.

Mental health and mental wellness are just part of our character as humans. They're not something to be ashamed or unduly burdened by in a way where you create this negative reinforcing loop that becomes a personal doom loop when you're in a depressive state and trying to be an entrepreneur or a leader and running a company.

Certainly, there are mental models of leaders out there who seem literally fearless ... The only reason you have courage is actually as a response to fear. You actually do feel fear, but there's something even more noble about overcoming that and still moving towards a goal, but it is not without fear.

When you take that stance and you're in this place of self-acceptance, then self-confidence becomes a natural byproduct

The best mentorship relationships are ones that I call peer mentors—when you have a mentor-mentee relationship, but over time, you both become mentors to each other.

I make my bed every day, because that's what I learned when I was in the mental hospital, was that you make your bed every day. Even if you do nothing else, even if you don't shower, you make your bed every day. And, so, I make my bed still to this day.

When I attach my sense of worthiness to something outside my inherent being, I am subject to the nauseating phenomena of riding an emotional roller coaster.

An open and honest question is one that you couldn't possibly know the answer to