By far the most difficult skill I learned as CEO was the ability to manage my own psychology. Organizational design, process design, metrics, hiring, and firing were all relatively straightforward skills to master compared with keeping my mind in check.

When it comes to money, the only skill most people know is to work hard.

By far the most difficult skill I learned as a C.E.O. was the ability to manage my own psychology. Organizational design, process design, metrics, hiring and firing were all relatively straightforward skills to master compared with keeping my mind in check.

The key thing is to force yourself through the work, force the skills to come; that's the hardest phase.

The most difficult thing about Time, I have learned, is doing it.

The most complicated skill is to be simple.

Wealth creation is not a business suited to those whose skill set
consists of voting “present.” It requires decision making, risk taking,
hard information, discipline, insight, and intelligence.

Capitalism is hard. But part of the reason this happens is because getting money and keeping money are two different skills. Getting money requires taking risks, being optimistic, and putting yourself out there. But keeping money requires the opposite of taking risk. It requires humility, and fear that what you’ve made can be taken away from you just as fast. It requires frugality and an acceptance that at least some of what you’ve made is attributable to luck, so past success can’t be relied upon to repeat indefinitely.

because it’s really, really hard. If this was easy, if there was one formula, one way to do it, we’d all be zillionaires. One principle for sure would be get out of anything that falls below the 200-day moving average.

It's hard to grow beyond something if you won't let go of it.

The stock market teaches you the hard way - it's all in the margin.

The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal. The hard thing isn’t hiring great people. The hard thing is when those “great people” develop a sense of entitlement and start demanding unreasonable things. The hard thing isn’t setting up an organizational chart. The hard thing is getting people to communicate within the organization that you just designed. The hard thing isn’t dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare.

One of biggest slaps in the face in pursuit of hard things is that you won't be good at every aspect of the process.

Learn to be difficult when it counts