One of my favorite things about open questions is that they can be freely borrowed anywhere you encounter them.

In my course Building a Second Brain, I lead students through an exercise to identify their own favorite problems. They can then serve as a filter for what to capture in their notes, a guide for what material to give their attention to, and a north star as they choose which projects and goals to pursue.

I’ve kept a running list of the most interesting, resonant, and provocative questions my students submitted . Feel free to borrow these questions for yourself as is or tweak and customize them for your own needs. 

I’ve grouped them into high level categories to make discovering interesting ones easier for you.


  • How can I build a good reading habit?
  • What can yoga teach me and move me towards?
  • How do I improve the functionality of my brain including cognitive processing and memory?
  • How can I improve every day by 1%?
  • How can I structure my goals so I increase my chances of achieving them?
  • What are the classics? What are they trying to teach us? And how is it relevant?
  • How can I consistently achieve the goals I set for myself?
  • What facets of my life can I automate?
  • How can I become friends with people that I want to be like?
  • What does systems thinking have to teach us about healing and personal growth?


  • What are ways I can be a more engaged, connected, and playful dancer?
  • What is the most efficient way to learn how to draw?
  • How can I improve my skateboarding skill?
  • How can I use knitting as a means of bringing healing to the world?
  • What kind of music do I want to create?
  • How can I reduce friction to ensure practicing the keyboard is a part of my daily routine?


  • How can I live joyously with menopause and care for the aging female brain?
  • What can I do to switch off and relax from time to time?
  • How can I eat healthy food that is delicious, pescetarian, and gluten-free?
  • How can I better strengthen and soothe the aching muscles in my feet, neck, and jaw?
  • How do I create a body that I am proud of and that serves me well?
  • How can I balance my personal life with my professional life while still feeling productive and fulfilled?
  • How can I achieve regular deep sleep?
  • How can I leverage social media in healthy and productive ways that add value to my personal and professional life?
  • What are the optimum behaviors, habits and tools to mitigate my cognitive challenges (ADD)?


  • How am I my own biggest stumbling block?
  • How do I overcome my personal bottlenecks to be authentic, vulnerable, and risk failure?
  • How do you find your way after losing your faith?
  • What does living in integrity with myself look like?
  • What does celebrating my life, showing gratitude for my life, look like?
  • What can I do to accept myself as I am?
  • What in my past casts a shadow on my present?
  • What are the most simple and universally effective practices to experience and sustain inner peace?
  • What am I missing?
  • What does addiction and recovery have to teach us?


  • How can I become a more natural and effective collaborator?
  • How can I make problem-solving fun and attractive?
  • How can I generate income pursuing my interests?
  • What are the key skills to prepare for the future of music?
  • What other things should I learn/unlearn to be an effective Executive Assistant?
  • What forms of marketing are ethical, profitable for the marketer, and useful for the audience?
  • How do I build a career I don’t want to retire from?
  • How do I create residual streams of income that can buffer my productivity highs and lows?
  • What is the best platform for me as a creator?
  • What should my personal brand be, and how do I get it there?


  • What should I invest my money into so it can work harder for me?
  • How do I catch up building a nest egg midlife?
  • How can we balance investing strategically with spending money on what we love today?


  • How can I improve my leadership skills and consistently support, empower, and challenge those around me?
  • What processes and people should I put in place in order to replace myself in the current business so I can focus on the next phase of the business before IPO?
  • How do we create messages that are unique and persuasive to rural voters in Maine?


  • How do I express myself clearly and more often to my wife to show her that I love her to the moon and beyond?
  • How can we cultivate a romantic relationship of respect, understanding, support, care, affection, and passion as a couple, which will serve as an example to our children so that they grow up to become adults responsible for the reality they live in, respecting themselves and others?
  • How can I curiously explore life together with my life partner?


  • How can we learn to share and manage collective resources?
  • How can we use models from nature to solve our gnarliest problems?
  • How can I make environmental issues and climate justice appealing to Christian congregations?
  • How can we reduce pollution while improving quality of life?
  • How can I travel sustainably without harming the planet or other people?
  • How do I determine the best intervention point in a dynamic but failing system?


  • How can I not lose track of my core values and live up to them?
  • How can I foster greater understanding, equality, and unity without disenfranchising any in the landscape of gender diversity?
  • How do I live a fulfilled life with no regrets in all aspects of my life?
  • How can I deepen my self-awareness and sharpen the values that are most personal to me, so that they permeate all areas of my life?
  • What can I do to get clearer on my purpose?
  • How can people utilize technology in a way that corresponds to their values?


  • Where should I prioritize my time, energy, and attention to make the greatest impact in serving others?
  • How can I empower others to be better leaders and lifelong learners?
  • How might I make academic philosophy feel alive and meaningful for everyone?
  • How can we do better as lawyers when mentoring young lawyers?
  • What are my gifts and how do I share them?
  • How can I make it easier for African content marketers to grow, get paid their worth, and become respected?
  • How can I create a home and safe haven for people like me?
  • How can I take advantage of the capabilities of my Second Brain to improve the quality of the clinical care I provide to my little patients and their families, without neglecting the most human, close and warm aspect of the relationship?
  • How can I build a nonprofit organization to help dogs that are abandoned or part of the meat trade?
  • How can I give back to my community in a way that only I can?
  • How can I develop a course for women struggling with their curly hair that’s enjoyable, and gives them the results they want?


  • How do I speak with more conviction and stand behind my opinions?
  • How do I discover my voice through writing and sharing my ideas with others online?
  • How can I better listen to what others say, reducing the personal interpretation to a minimum?
  • How can I develop my ability to express myself spontaneously, creatively, and authentically?
  • What do I feel is important for me to express?
  • What can I do to launch my YouTube channel?
  • How can I channel my emotions to become a better communicator?
  • What are the key ingredients of global music’s top hits?
  • How can I increase my writing output without taking time away from my family?
  • What would creating look like if it were easy, light, and fun?
  • How do I learn to meet criticism with more acceptance and less resistance?
  • How do I find the time to think and write a book in 12 months?
  • How can I share myself with the world without draining my energy?

Institutions and communities

  • What is the best way to influence change in the school system to turn it into a critical thinking and problem-solving system?
  • What are we unnecessarily tolerating as female attorneys?
  • How can I help people trust democracy and engage more seriously in political debate?
  • How can Indonesia improve its child protection and social welfare system to ensure that all children have equal opportunities to live and thrive?
  • How do I control the negative news cycle while keeping a pulse on all that’s going on around me?
  • How can I improve the state of education in my province?
  • How can we design a better city or society from scratch?
  • How do I balance needed time alone with making time to build community?
  • How do I set aside space for the culturally unique sacred knowledge held in each religion while maintaining egalitarian access to spiritually rich truths in an agnostic digital space or multicultural community center?
  • How can we create more collaborative neighborhoods with sharing economies and alternative currencies?
  • How can imagination and play fuel organizing grassroots movements that uplift the working class and poor?

Family and relationships

  • How can I help my father keep his remaining cognitive capacity and extend his health span as much as possible?
  • How can we prioritize our personal time when we are in demand by so many other people?
  • How can I address sensitive issues after allowing so much time to pass that the only thing I feel is shame?
  • How can I organize realistic/feasible family vacations with a limited budget?
  • How do I raise kids to be loving and empathetic yet understand that not everyone will be that way to them?
  • How do I pass on the love of learning to my kids?
  • What do I want my relationship with my parents to look like moving forward?
  • How can I slow down and enjoy the experiences that life has to offer without impacting my family’s income?
  • How might I become more of an advisor than an authoritarian to my two daughters?
  • How do I create a life of wonder, curiosity, and traveling while still having a family?
  • What can I do to design a career that allows me to see my kids grow up?
  • How do I raise a child into a healthy, whole and contributing adult as a single mother while still being fulfilled and achieving my own fulfillment in life?


  • How can we stay present with our most difficult feelings?
  • How can I recognize the factors that most influence my emotions and express them with disarming frankness?
  • How do I become immune to micro-aggressions and focus on what I can control?
  • How can we deepen a more compassionate life for ourselves, for those around us, and for the rest of humanity?

Personal knowledge management

  • How can I create a system that allows my creativity to flourish?
  • How do I translate my perspective into a meaningful and productive financial endeavor?
  • How should I keep track of my twelve favorite problems?
  • How can I master overwhelm and live meaningfully in chaotic times?
  • How can I live life where I feel independent, free, and unbound by time?
  • Which note-taking tool/task management app should I stick with?
  • How can I use my Second Brain to continue learning throughout life, while bringing experiences, knowledge, and motivation forward that can inspire others?
  • How can I ask better questions?
  • How can I capture, organize, and distill the knowledge and experience from my current and previous projects?
  • What frameworks can I adopt to transform my curiosity into tangible outputs?

The future

  • How can I understand, embrace and use emerging technologies, the internet of things, and cybersecurity while protecting my privacy, autonomy, and sanity?
  • How can we create modes of work so everyone can live by their own definitions of work/life balance?
  • How can I contribute to building up the people of the Basques, in which the daily use of language is a value to be cultivated, preserved, protected, and promoted, in the face of the globalizing and homogenizing threats of the cultures that surround us, as a heritage and unique enriching contribution to this corner of the world?
  • How do we help individuals put out of work by automation?
  • How can I leave a legacy that will serve generations of my family not yet born?
  • What do I want to achieve by the time I am 40?
  • How can I be remembered?

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