Some questions stop me in my tracks and force me to examine my assumptions about the world. As mental models, I think they are very valuable tools in enabling one to step back from the default processes running in our heads and consider other perspectives. This is a running list of questions that have done that for me. Often, this is the only thing I take away from the books I consume, no matter what else the book is about.

When thinking about where you’re going, really look around at who you’ve been, who you are now, where you are now.
To begin to figure those things out, it’s helpful to reflect on questions like, “Have I been and am I being kind? Am I being curious? Am I leaning into difficult places?” That’s where I think our opportunity is.

Jerry Colonna, Reboot

A great commonality we all share is that we only have today to invest in what could outlive us. After today, there are no guarantees. As Mark taught me, every hour you devote to answering the question “What are you doing for others?” becomes something that gets to live on. Every morning, wake up and remind yourself: it’s not about me. Then ask yourself: How can I contribute to another person’s life today?

Tom Rath, It’s Not About You

The questions you ask shape the answers you find. “How much can we give?” was not the end of Dr. V’s querying. A journal entry from the 1980s, written in a series of eclectic questions (and with his trademark absence of question marks), illustrates how intertwined matters of service delivery, leadership, and spirituality are to Dr. V. It opens with the magnificent obsession he is known for: How to organize and build more hospitals like McDonalds. And then with no warning, it shifts to, How was Buddha able to organize in those days a religion that millions follow. This question dramatically changes the plane of inquiry. Other searching questions swiftly follow: Who were the leaders. How were they shaped. How did the disciples of Christ spread their mission around the world. And then a final question that he would ask in a thousand different ways: How do I become a perfect instrument.

Dr.V, Infinite Vision

What Should You Spend Less Time Doing:

  1. What do I spend too much time doing?
  2. What bores me? What do I dread doing?
  3. What do I do that other people could do?
  4. Where do I procrastinate?
  5. What time-consuming activities do I repeat?
  6. Where do I usually make mistakes?

David Perrell

What You Should Spend More Time Doing:

  1. What gives me energy?
  2. What are my unique gifts in the world?
  3. What makes me feel alive?
  4. What puts me into a flow state?
  5. What feels like play to me, but looks like work to others?

David Perrell

We dabbled in enterprise, and we sucked at it. This is a humbling business. It’s really hard to be good. We asked ourselves, and every startup should ask itself, ‘What do you do better than others, and how does that concentration work in your favor? What do you do well?’

Dan Levitan, A Dozen Lessons for Entrepreneurs

The thing that worked best for me is to be relentlessly driven by the desire to solve problems I really care about, and to be open to changing my mind along the way when I learn new things. A lot of successful entrepreneurs do this. They pick a vision of something that’s important, and work as hard as they can to make it happen. Act as if you already know that you won’t fail. What would you do if you knew that you wouldn’t fail?

Sebastian Thurn, some reddit AMA

“How would you compete against yourself?” Every business should be thinking about what could threaten them since their competitors are almost certainly doing so. The mental exercise I am suggesting here is essentially a stress test: Ask yourself, “What would we do if we were our competitors?”

Vinod Khosla, A Dozen Lessons for Entrepreneurs

How will you measure you life?

Clayton Christensen