In this step-by-step guide, I’ll share the exact process I use for myself and my students to formulate the most powerful open-ended questions possible. 

In Part 1, I introduced “favorite problems” as a lens through which to filter the immense amount of information we are exposed to every day. A favorite problem is an open-ended question you use to prime your subconscious to notice potential answers in the information you’re consuming.

Each question serves multiple purposes:

  1. Giving you a filter for deciding which information you’re consuming now helps move forward your long-term goals
  2. Focusing your reading and learning where it has the highest chance of making a difference
  3. Reminding you of which interests captivated your attention in the past and may be worth revisiting

But these benefits can only be realized when you make a concrete list of open questions in a trusted place outside your head. You need a list you can revisit, revise, and reflect on without having to wrack your memory. Your digital notes are the perfect home for such a list.

Here’s my current list of favorite problems as an example:

  1. How can I design an effective online learning community that sustains itself?
  2. How can I translate principles from the Theory of Constraints to modern knowledge work?
  3. How can I cook healthy meals for my family every day that don’t take too much time and also taste good?
  4. How can I exercise joyfully every day?
  5. What would the ultimate corporate offering for our Building a Second Brain program look like?
  6. How can I build a bootstrapped company that serves people around the world while still preserving my free time and peace of mind?
  7. How can we create the world’s best free library of content on digital notetaking on YouTube in a way that is financially sustainable?
  8. How can information science be used to enable people’s personal growth?
  9. How can I teach timeless values and principles to my kids when my own are always evolving?
  10. Where in the world do we want to live (and for how long) to inspire a sense of adventure and novelty while also providing stability and lasting friendships for our kids?
  11. How do I support and contribute to the people I care about without interfering in their own learning and growth?
  12. What is the right structure for our company to give everyone freedom and balance while also provoking personal growth and progress?

Notice that these are hard problems without simple answers. The truth is, they aren’t even necessarily designed to be definitively answered.

The value of questions comes from provoking your thinking at deeper and subtler levels, not finding a single “correct” answer. You may even arrive at different answers to the same question in different seasons of your life, depending on what you’re going through and what’s important to you at that time.

Open questions are “serendipity engines” – active generators of possibility to fuel your learning and growth over many months and years.

Here’s my 4-step guide to formulating your own favorite problems. I suggest setting aside a few minutes to make a first pass at your own list using the prompts below, keeping in mind you can always go back and revise them later.

1. Get started with these prompts

Here are some prompts to help you get started identifying your own favorite problems:

  • What were you obsessed with as a child or teenager? (Ask your parents or caregivers)
  • What are the longest running hobbies you’ve had in your life?
  • What common themes or patterns do you notice emerging in your life repeatedly?
  • What kinds of stories, art, or music give you goosebumps, make your hair stand up, or move you to tears?
  • What pursuits that others consider challenging do you find fun and engaging?
  • What do you find your mind wandering to in the in-between moments of your day?
  • If you could wave a magic wand and have the ultimate answer to any question, what question would it be?
  • If you could travel to the future and ask your future self anything, what would it be? What would you ask your past self?
  • If you read all the books and took all the courses you wanted to, what question would you like to have answered after all that?
  • What are your most pressing problems currently?

2. Formulate your own “How/What” questions

Once you have an idea of your long-term interests, I recommend phrasing them as questions that begin with “How…” and “What…” Such questions can’t be answered with a simple yes or no – they invite more subtle, complex answers based on deeper reflection:

  • How can I…?
  • How might we…?
  • How can my team/organization…?
  • How can I help others to…?
  • How does X relate to Y?
  • How do I…?
  • What does it look like to…?
  • What would be possible if…?
  • What do I want with…?
  • What would I do if…?
  • What would happen if…?
  • What would have to be true to…?

Once you’ve made a first draft of your list, save it in your notes (my recommendation is a digital notetaking system, which I call a “Second Brain”). That way they will appear in your searches, can be linked to and tagged with related ideas, and you’ll always be free to edit and change them as your interests evolve.

3. Make your questions specific, counter-intuitive, or cross-disciplinary

Here are some guidelines to help you come up with the most direct, impactful questions possible:

  1. Make them specific
  2. Make them counter-intuitive
  3. Make them cross-disciplinary

Make them specific

Open questions are often profound and a little mysterious, but that doesn’t mean that they can’t be specific as well. The best questions are ones that focus your problem-solving and spur you into action.

For example, instead of “How can I be a better leader?” which is a little broad, try “How can I be a better leader as an introvert?” See how that second version puts a fine point on the question, while also creating constraints to guide your thinking? 

Don’t be afraid to make the question completely unique to you and your circumstances – in fact that is the entire point!

Make them counter-intuitive

The best open questions have an element of surprise – they grab your attention and refuse to let go. Try to include something counterintuitive, unexpected, or paradoxical within the question.

For example, instead of “How can I improve the standard of living in the global south?” try “How can I improve the standard of living in the global south without further contributing to the climate change that threatens those regions the most?” Such a question has a tension between two important but potentially opposing forces, which will force you to come up with more creative solutions.

Asking a question is an art form, and like any art form, there should be a bold element of surprise hidden within.

Make them cross-disciplinary

Open questions don’t have to be contained within one field, industry, or subject. At their best, they cross the usual boundaries between categories to spark unorthodox connections that no one else is likely to look for.

For example, instead of “How can I improve education?” you could ask “How can I improve education by borrowing ideas from video games?” 

With such a framing, you are laying down tracks for your mind to follow. You are purposefully biasing yourself toward certain kinds of answers while drastically reducing the number of options you have to consider.

4. Start capturing information relevant to your favorite problems

Your favorite problems are a powerful complement to digital notetaking, because they tell you what you should be capturing in the first place, i.e., anything that potentially leads to answers.

Instead of doing what most people do – randomly and haphazardly hoarding tons of digital stuff hoping it will all somehow magically lead to an insight – you are taking a far more focused approach. You are detailing precisely in which areas you would like to have breakthroughs, which makes them much more likely to happen.

Think of it this way: If your Second Brain is a problem-solving machine, what kinds of problems do you want it to solve for you? Assuming that you are constantly coming across potential solutions every day, what kinds of problems do you want the solutions for?

A flexible approach to problem-solving

One of the most powerful aspects of open questions is that they are extremely flexible.

It’s not important to have a precise number of them – the idea is to have enough balls in the air and enough potential pathways of interest that should your progress stall in one direction, you can simply set it aside and pursue something else.

It’s not important that they be “career-oriented” or have a practical use case right away. Goal-setting has a place, but favorite problems are also for the mysterious and whimsical musings that captivate you for reasons you may not be able to explain.

It’s not important for them to appear in order of priority – this isn’t a list of tasks or priorities that you have to tackle in a rigid, linear way starting at #1. Their purpose is to give you permission to move toward whatever naturally sparks your curiosity and joy right here and now.

Over time, you’ll begin to view the world through the lens of questions; they will arise spontaneously, unbidden, as a filter telling you what information matters and why.

In Part 3, we’ll return to Richard Feynman’s story and how he used his favorite problems together with a variety of “thinking tools” to produce some of the most profound breakthroughs in 20th century physics.

A big thank you to Rubén García Pérez, Matthew Brandabur, Jeremy Cunningham, Lukas Puris, Julia Saxena, Arno Jansen, and king chan for their feedback and suggestions on this piece.

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