Career/Life Advice — What I’ve Learned…


Over the years, I’ve gathered career/life advice from many sources: My podcast, 1 on 1 conversations, books, twitter, etc… Here it is (I will update this list regularly — Please add great pieces of wisdom you’ve learned in the comments below):

John Krasinski got advice from the legendary Robin Williams early in his career.  Robin told him, “You’re going to go far in this business.  And one day, you’re going to be #1 on the call sheet (meaning the lead actor of a movie).  Just know that it’s not a luxury, it’s a responsibility.  Your job is to carry a set.  You have to be the most energetic, be the kindest, take responsibility.  That is a huge honor.  Don’t ever forget it.”  And John followed, “We were down in Jamaica filming a scene and the air conditioning went out.  And Robin said to me, ‘I’m hot, but I’m not going to complain and say I’m hot.  Because if I’m hot, then the entire crew is hot and then it all goes down hill.’  It’s an amazing responsibility to be the leader.  As my dad has always said, “It is your duty to be in a good mood when you’re the leader.”

“Identify the tasks or knowledge that are just out of your reach, strive to upgrade your performance, monitor your progress, and revise accordingly.” – Susan Cain

“You have to apply yourself each day to becoming a little better. By applying yourself to the task of becoming a little better each and every day over a period of time, you will become a lot better.” – Carol Dweck

“Following your genuine intellectual curiosity is a better foundation for a career than following whatever is making money right now.” – Naval Ravikant

“Ability to focus for long periods of time to become great at something, coupled with the ability to cold call your way to anyone can get you a really long way in this world.” – Garry Tan

From Ryan Caldbeck: “We have crystallized what we look for in a person to hire.”

  • Horsepower – intelligence over experience
  • Integrity – don’t talk negatively about others. Do what you say you will do.
  • Work ethic – must be willing to work hard
  • Teamwork – need to work well with others
  • Pride – care

From Kim Malone Scott: Hiring is the most important decision you will make as a leader:

  • “If you’re not dying to work with that person, don’t hire them”
  • Steve Jobs – “It’s better to have a hole than an asshole”
  • Dick Costolo – “You can’t just hire great people and get out of their way. You must invest time in helping them, develop them even more.” 

“No skill more essential than knowing how to spend more energy on the stuff that matters and less on the stuff that doesn’t. the seduction to do the opposite only increases over time.” – Scott Belsky

From Ben Horowitz: Managerial intelligence, being an excellent manager comes down to two things:

  • Systems thinking – “most people cannot think, ‘If I change this here, it impacts that over there.’  The ability to understand how each tweak or change in one place, how it impacts the rest of the organization (or world).  (Example: How changing minimum wage impacts the rest of the economy)
  • Really seeing the people in your organization for who they are. Knowing everything about their makeup, their motivation, why they do what they do, how they think, why they think that way, how they will respond to decisions made by you and others. Can you interpret them well enough even when they aren’t there?  It’s as if they were there even when they aren’t. Can you understand the implications for them?  See it through their eyes.  Most people don’t have that.  A great manager is extremely perceptive of people.

“Take the stairs and not the escalator. The escalator’s for cowards. We’re going to take the stairs. It’s going to be … one … step … at a time and we’re going to get there.” – Kevin Ollie. Choose voluntary hardship. You don’t know what you’re capable of unless you force yourself to do it.

“Do not seek to follow in the footsteps of the wise; seek what they sought” – Matsuo Bashō

Most success comes from repetition, not new things. “My whole system of life is keeping at it. The task of life is not to see clearly in the distance but to do the task at hand.” – Charlie Munger

“Compounding creates success in almost anything. Always ask better questions and obsess over that. Take wherever you’re at and just try to push your understanding deeper. Focus on being great at what is scare. What is scarce? Intellectual property, or good ideas about what should be produce. Quality labor with unique skills.” — Tyler Cowen

“Learn to sell. Every job is a sales job, especially as you move up the ladder.” – Sam Altman

“You may not control all the events that happen to you, but you can decide not to be reduced by them. Try to be a rainbow in someone else’s cloud. Do not complain. Make every effort to change things you do not like. If you cannot make a change, change the way you have been thinking. You might find a new solution.” – Maya Angelou (power in reflection. It’s how we learn from experiences, zoom out our perspectives to appreciate that life has all manner of ebbs and flows. We can’t learn without reflection)

“Run towards trouble. Have a process. Focus on strengths. Accept responsibility. Pass on wisdom and advice. Work with the world as you find it, not as you want it.” – Shane Parrish

“Genghis Khan was not born a genius. Instead, as one biographer put it, his was a persistent cycle of pragmatic learning, experimental adaptation, and constant revision driven by his uniquely disciplined and focused will.” He was the greatest conqueror the world ever knew because he was more open to learning than any other conqueror has even been. Each victory and advancement that made Khan smarter also bumped against new situations he’d never encountered before. It takes a special kind of humility to grasp that you know less, even as you know and grasp more and more.” – Ryan Holiday

“Monotony collapses time; novelty unfolds it. You can exercise daily and eat healthily and live a long life, while experiencing a short one. If you spend your life sitting in a cubicle and passing papers, one day is bound to blend unmemorably into the next – and disappear. That’s why it’s so important to change routines regularly, and take vacations to exotic locales, and have as many new experiences as possible that can serve to anchor our memories. Creating new memories stretches out psychological time, and lengthens our perception of our lives.” – Joshua Foer

“It is not the strongest of the species that survives, nor the most intelligent, but the one most responsive to change.” – Charles Darwin

“Meaningful = Hard: If something worthwhile appears easy, it means I got lucky. Or, I’ve never done it. Crucial to setting opportunity costs, evoking gratitude, suppressing envy, and cheering others on. Serving vs. Served: The great paradox of life is self-sacrificial service. More I give, with no expectation of reciprocity, the better life goes for others and me. Counter-intuitive and counter-cultural.” – Brent Beshore


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