💭 Journal Prompt

🤔 On “Good Morning”

• What would my greatest day look like today? What is today’s adventure going to be? What is my side quest for today?
• How do I want to feel at the end of the day? Joyful or frustrated? What do I need to do now, so that I can feel this way in the evening?

🤔 On “Good Evening”

• Am I putting myself in good positions and creating the conditions that are impossible to fail and guaranteed for success? ¹
• What excited me? What drained me of energy? Was my attention on loving or on who isn’t loving me?
• Which moments were the most important? Which moments were the most memorable? What major realizations did I have?
• What did I learn? What did I improve? What was my biggest win of the day?
• What’s on the agenda for tomorrow? How will I push the needle forward?
• Am I a little wiser now than I were when I woke up? Am I getting better than yesterday? Did I beat Yesterday Me?

🤔 On “Today”

• Are the results I’m expecting aligned with the actions I took today?
• What am I certain of today that I’ll laugh at in 10 years?
• Am I putting myself in the best position possible today, so that Future Me can play easy mode?
• What was my definition of enoughness 5 years ago and how does it compare to my definition today?
• What am I going to be celebrating one year from today?
• What small action can I take today to make myself slightly better off tomorrow?
• What would future me wish that I had done today?
• Looking back ten years from now and I can probably identify a few blind spots or mistaken beliefs I held at that time. Now, fast forward ten years: What are likely to be my current blind spots? What am I not spending enough time thinking about or perhaps even willfully ignoring?
• What does that ideal future look like? What does that imply about how I need to live today?
• What would I invest in today assuming I had to hold the investment forever?
• What would Tomorrow Me want Today Me to do in the present moment?
• If I repeated every action I took today, every day for a year, where would I end up? Is this the place I want to be?
• What good habit did I perform today that will benefit me in the long term?
• If I knew I would die in 10 years, what would I do today?
• What are the behaviors I want to unlearn? What are the beliefs that are no longer serving me?
• What would my 80-year-old self say about my decisions today?
• What actions am I engaged in today that I will cringe at in 5 years?

🤔 On “Prioritization”

• If XXX were the last day of my life, would I want to do what I am about to do XXX?
• Which undone item, if done XXX, would liberate the most energy for me personally?
• If I could only accomplish one thing XXX, what would make everything else easier or unnecessary?
• What is scarce in my work XXX? How can I leverage it?
• If I had a heart attack and could only work two hours XXX, what would I choose to do?
• What is the biggest bottleneck that holds me back XXX? Am I avoiding it?
• What are the one or two mission-critical tasks I could accomplish XXX that would define the day as a success?
• What is XXX’s biggest and most critical task that’ll render all the rest either easier or completely irrelevant?
• What is the ONE highest-leverage thing I can do XXX that’ll take the largest load off my shoulders?
• What activity I can do XXX that will create the most impact and value to the world?

🤔 On “Productivity”

• What would this look like if it were dead or stupid simple and easy?
• Have I considered whether doing less might actually lead to better results?
• How can I approach this with a little less seriousness and a little more sincerity?
• What would this look like if it were fun?
• Am I being productive or just active/busy?
• Is there a higher leverage, more efficient way to approach this?
• What is the most sensible order of tasks? Which tasks naturally flow into each other? How can I make transitions smoother?
• Am I chasing mice or hunting antelope? ²
• If this is the only thing I accomplish today, will I be satisfied with my day?
• Am I inventing things to do to avoid the important?
• Am I focusing on the big, weighty, important tasks that will provide sufficient reward for my energy? Or am I burning calories chasing the tiny wins that will not move the needle?
• How can the work I am doing accumulate and layer on top of what I did previously?
• How can I win the day by noon?

🤔 On “Miscellaneous”

• What kept me sane?
• When does it benefit me to be patient and when does it not?
• What in my field do I think is a law but is actually just a rule?
• Instead of asking, “What could make me feel happy?” Try asking, “What could make the group excited?”
• What does my ideal ordinary Tuesday look like? What am I doing? Who am I with? How am I spending my time? What makes this day perfect for me?
• What do I hope will be different 10 years from now?
• If I do nothing, what will happen? If I act right now, what will happen? ³
• How well am I treating my body and why?
• What would I do even if I knew it was going to fail?
• Where am I allowing my self-protection to become self-rejection? ⁴
• What is holding me back from living my best life?
• What am I working on and why? Does it support my future-self?
• What might I do to accomplish my 10-year goals in the next 6 months, if I had a gun against my head?
• Where would I most like to live?
• How is my behavior and lack of presence contributing negatively to the situation that I don’t want?
• Imagine my life as a novel. What title would I give to the current chapter? If I am going to look back on this chapter after reading the entire novel, what actions would have made this chapter a key inflection point in my life journey?
• Am I gathering more information to get in the way of more action?
• How will my current struggle fuel my future inevitable growth?
• How would I like to die?
• I am attending the TED conference, and everyone in the audience (including me) is deeply moved and inspired by what the speaker is talking about. The speaker is me, 20 years in the future. What is ”Me + 20 Years” talking about, and what is exciting about it?
• What is my greatest extravagance?
• What makes me hopeful?
• What would I attempt if I knew I couldn’t fail?
• What is the quality I most like in a woman?
• What if my path is a spiral? What if I’m not really going in circles, but going upwards?
• When have I felt most joyful this year and what steps can I take to recreate those conditions?
• If I were stuck in a third world prison or on an island, then I had to call someone to bail me out. Who would I call? ⁵
• What would I do if I had a billion dollars?
• What is my greatest fear?
• What are some small things that other people have done that really make my day?
• How can I do less, but better?
• What did I do as a child that made the hours pass like minutes?
• What advantage am I accumulating?
• Half your problems are just your mind making minor things seem like major things: What am I over-emphasizing right now?
• How long will I put off what I am capable of doing just to continue what I am comfortable doing?
• If everything were to stay the same, what’s the one tiny change that would have the greatest positive impact in my life?
• What am I not achieving simply because I haven’t asked?
• If I hired the best CEO in the world to be the CEO of my life, what actions would be on their 100-day plan?
• Am I being the type of person who could achieve my goals? Why or why not?
• Who do I still owe an apology? Can I make one in the next 5 minutes?
• What is the trait I most deplore in myself?
• What are the 20% of activities or people causing 80% of my stress?
• What would I do if I could stop time for two months?
• If I woke up 3 years from now and were living my ideal life, what were the 3 things I did to get me there?
• What are the boring, basic/tiny actions I am avoiding right now?
• What is a boundary that I need to draw and protect in my life?
• What do I believe to be true that is not?
• What is not being said right now that needs to be said? What problems could we avoid in the future, if only we had the courage to talk about them now?
• What have I been told I’m really good or poor at?
• What are the boat anchors or bottlenecks that create drags in my life? What are the things silently holding me back? How can I slowly, methodically cut these lines and unleash my full power?
• What unrealistic grand beliefs should I cultivate more?
• Think of my childhood. What is one area where my parents did a good job? What is one area where they could have done better?
• What are the current habits that are hindering my future progress?
• If someone observed my actions for a week, what would they say my priorities are? Does my actions align with my intention?
• Did I try my best? Did I give absolutely everything I have?
• What keeps working for me once it’s done?
• Am I taking enough risks?
• Who is my best friend?
• Who is the most difficult person in my life? Why?
• What work am I avoiding?
• If I had a $100M in my bank account, what would I do with my time?
• What are the principles that I want to live my life by?
• How is my curiosity being directed? Is it rocket fuel or a roadblock?
• What is the burden that I am still carrying? Perhaps it is time to place them down on the riverbank.
• How am I complicit in creating the conditions I say I don’t want?
• Can my current habits carry me to my desired future?
• What do I hope will be the same 10 years from now?
• What would I advise someone else in my situation?
• What would I work on if I had only six months to live?
• Think about something I am facing right now. Have I been trying to think my way to a solution or act my way to a solution? ⁶
• What advice would I give myself 10 years ago?
• What do I wish I could do more quickly? What do I wish I could do more slowly?
• In what areas of my life do I communicate well? In what areas do I communicate poorly?
• What is my most treasured possession?
• If everything else stays the same, what one variable could create the biggest positive change on my situation?
• Imagine you’re near death and in a coma at the hospital, everybody has gathered around you and you can hear them. But they don’t know that you can hear them and start talking about you. What do you want them to be saying?
• What is the worst scenario that could happen?
• What do I consider my greatest achievement?
• What is my greatest regret?
• Where am I consistently executing the wrong thing?
• What silly story am I telling to myself?
• Which historical figure do I most identify with?
• Who is somebody that I miss? Why?
• Where will my life end up if I have the same lifestyle or keep doing the same thing for 10 years?
• Opportunities in life come through people. Who do you need to connect with to gain access to the opportunities you want?
• If I could change one thing about the world, what would it be and why? How could I contribute to this change?
• What drives the long-term goal for my future-self?
• What is the best compliment I ever received?
• What is the worst thing that could happen?
• What do I believe is true only because believing it puts me in good standing with my tribe?
• If I woke up in 10 years and were in flow, what actions did I take that got me there?
• What was my greatest waste of time?
• What is something that I have a hard time being honest about, even to those I trust the most? Why?
• If I were the main character in a movie of my life, what would the audience be screaming at me to do right now?
• Am I leaning into my unfair advantages?
• What is the quality I most like in a man?
• If I could write my own eulogy, what would it say?
• What thinking patterns or toxic, false beliefs I have now would have to be broken and changed?
• In what area of life am I underestimating or limiting myself?
• Which living person do I most admire?
• What brings me genuine happiness?
• What was a seemingly inconsequential decision that made a big impact in my life?
• How would I accomplish my 5-year goals in the next year?
• Which talent would I most like to have?
• If I could change one thing about myself, what would it be?
• When you’re told that something is impossible, is that the end of the conversation, or does that start a second dialogue in your mind? ^{7 8}
• Imagine, at the end of a long life when you’ve passed away, you’re at the pearly gates of heaven, and the angels have allowed you back to your life for just one moment, and right now is that time. How do you respond?
• What does “ready” feel like to me? How did I know I were ready for a major step that I have taken in my life?
• Think about a “what if?” or worst-case scenario and work your way through the problem. What are my options if it were to happen?
• Why do I get out of bed in the morning?
• Do I make it default to focus on deep work that creates value in the world and is difficult to replicate?
• What is my most marked characteristic?
• What are the small habits that could lead to big changes in my life?
• Is this relationship making me fulfilled or just less lonely?
• In what ways am I currently self-sabotaging or holding myself back?
• What do I need to say no to, so that I have space for what I really want to say yes to?
• What do you want your obituary or tombstone to say?
• What is one habit I have formed that had a significant impact on my life?
• How can I collaborate with people in my field who enjoy unfair advantages?
• If I could only spend 2 hours a week working on my business, what would I do that most moves the needle? And why am I not just focusing on doing that with the rest of my time too?
• What is my motto?
• What are my core values, and how did my daily actions align with them?
• What do people frequently misunderstand about me?
• What do I find painful but worth doing?
• What is the core elements of my ideal day and week?
• What is the 2-minute version of the task I am avoiding?
• What is the luckiest thing that happened to me?
• Would the idea of living my current life on repeat perpetually be horrifying or affirming?
• What assumptions am I currently making that could be incorrect?
• Why do I dress the way that I do?
• Which responsibilities, relationships, or projects have been weighing heavily on me and can I give myself permission to let one of them go right now?
• What biases do I need to work on?
• Which decisions and actions would the Ideal Me make and take?
• In my own work and life, are there any areas where I am at risk of optimizing the fun out of them?
• What is a reminder that I would like to tell myself next time I am in a downward spiral?
• What is the trait I most deplore in others?
• Am I spending my time in alignment with my goals and priorities?
• How did I bond with one of the best friends I’ve ever had?
• What project, if successful, will make the rest of my career look like a footnote?
• What is one dream I have always had but never pursued? Why is it a dream for me? What has stopped me from pursuing it?
• What would I do if I had 6 months to live?
• Do I know the game I am playing? Do I want the prize for winning this game? Is the game worth winning?
• What do I most dislike about my appearance?
• Imagine I am living my ideal day in the future, what am I doing? How does it differ from my current typical day?
• When and where was I happiest?
• What part of my work do I most enjoy? What part do I least enjoy? Why?
• What do I consider the lowest depth of misery?
• Who or what is the greatest love of my life?
• What lie have I repeated to myself so many times that it feels like the truth?
• Which bad habit am I struggling with, and what is the root cause?
• How can I make sure I actually commit to the experience, rather than retreating back to the safety of my comfort zone?
• What action(s) can I take that would force me to fully commit to a path I have been thinking about for a while?
• Where am I inconsistently executing the right thing?
• What is the tiny first step that will move me closer to my big, scary goal?
• What sacrifices am I willing to make to get the things I want?
• Who are the people I most admire, and why? What qualities do they possess that I wish to emulate?
• Who is my hero of fiction?
• What is one thing I can do this week that is different than what I do on a normal week?
• What kind of game am I playing? Is this a game I can win?
• You have a plan. A time-traveller from 2030 appears and tells you your plan failed. Which part of your plan do you think is the one that fails?
• What would I like to do if money were no object? How would I like to spend my time?
• What am I afraid of? How is that fear holding me back?
• What happens when I am angry?
• Where am I avoiding a hard conversation that I need to have?
• What annoys me about other people that I sometimes do myself?
• If I woke up in 10 years and everything were broken, what went wrong?
• In my professional life, who do I admire most? In my personal life, who do I admire most?
• Where, in my life, should I consider burning the ships?
• What might I be able to spend more time on if I find an easier way to do this?
• What do I consider the most overrated virtue?
• What do I most value in my friends?
• How can I design incentives and an environment that will naturally bring about my desired change?
• What do I need to give myself more credit for?
• What can I serve for the world? How am I making the world a little bit better? How the world will be different without me?
• Whose life do I admire that is secretly miserable?
• How can I change my outlook by changing my perspective?
• If myself 10-20 years from now was to give me some advice, what would that be?
• What do I really want?
• When was the last time I allowed myself to celebrate good and sufficient enough?
• Think about the last time you cried. If those tears could talk, what would they have said?
• What accomplishments do I want to recognize and celebrate?
• How can I make myself an outsider/outlier?
• Would I treat my best friend the way I am treating myself?
• What is something I would be proud to fail on, if I had the courage to attempt it?
• What are some things that frustrate me? Can I find any values or truth that explain why they bug me so much?
• How did I end up with such a blessed life?
• If I could give everyone in the world one gift, what would it be?
• Do I actually need more information, or do I simply need to act on the information I already have?
• What is my idea of perfect happiness?
• Who am I spending time with and why?
• How can I be more present in my daily activities?
• Would I be happy with this result if no one other than me and my family could see it, and I didn’t compare the result to the appearance of other people’s success?
• How quickly can I get started? How quickly can I learn from my mistakes?
• Imagine I have achieved everything I have ever wanted. How have I changed as a person? What qualities and achievements define this future version of myself?
• If I had all the money and time in the world, how would I use my talents to serve others?
• On what occasion do I lie?
• How is cheap becoming expensive in my life?
• How can I bring the after into the before?
• Do I want to be liked or loved?
• 沒了名片，我還剩下什麼？如果拔掉所有身份地位和職業頭銜，我是誰？我跟別人又有什麼差別？
• What’s something I used to believe that I no longer subscribe to?
• Am I aware of the finite, impermanent nature of my time?
• What are my strongest beliefs and what would it take for me to change my mind on them?
• What do I need to let go of to create space for what I really want?
• Am I holding onto something that I no longer need?
• If I had 10x the agency I have, what would I do?
• What system can I create that will make the goal inevitable?
• What did I gain by not having what I needed?
• What mastery or gift have I developed that I can offer to the world?
• What mastery or gift have I developed that I can offer to the world? ⁹

🤔 On “Life”

• Imagine, at the end of a long life when you’ve passed away, you’re at the pearly gates of heaven, and the angels have allowed you back to your life for just one moment, and right now is that time. How do you respond?
• What season am I in right now? What am I optimizing for?
• Close the eyes, look within. Am I satisfied with the life I’m living?
• Which distractions in my life have become disguised as priorities?
• If a competent CEO got to run my life for a day, what is the first thing they would eliminate?
• What hard lesson keeps repeating itself in my life because I refuse to learn it?

🤔 On “Year In Review”

• Which habits have become more important and I need to double down on next year? Which habits are no longer serving me and need to be replaced next year?
• 今年有哪裡做得好的地方? 今年有哪裡可以做得更好的地方?
• What did/didn’t I change my mind on this year?
• What were my greatest hits and worst misses this year?
• How far have I come this year? Who do I want to become next year?
• What achievements am I most proud of this year? What was my biggest failure and hardest aspect this year?
• What people/activities added the most energy to my life this year?
• What did I learn (武裝) this year, and what did I unlearn (卸裝)?
• What got too much of my attention this year, and what didn’t get enough?
• What did I do this year that I’d never done before? What did I not do this year because of fear?
• Where did I take risks this year, and where did I hold myself back?
• Did anyone close to me give birth this year? Did anyone close to me die this year?
• What cities/states/countries did I visit this year?
• What date(s) from this year will remain etched upon my memory, and why?
• What were my best days this year, and how can I create more of them?
• What was the best thing I bought this year? Where did most of my money go this year?
• What did I get really, really, really excited about this year?
• Compared to this time last year, am I: happier or sadder? Thinner or fatter? Richer or poorer?
• What was the best book I read this year?
• What was my favorite meal this year?
• What did I do on my birthday this year?
• Who was the best new person I met this year?
• What did I learn about myself this year?
• What valuable life lesson did I learn this year?
• What is a quote that sums up my year?

🤔 On “Self-Reflection”

• Better waves make better surfers. Am I on the right beach?
• Who do I secretly envy—and what does that reveal about what I truly value?
• Am I prepared for my moment? ¹⁰
• What would happen if I gave just a little bit more?
• What is something I really want, but haven’t actually asked for?
• Am I allowing their narrative to impact my life? ¹¹
• What will I regret not having done or learned 10 years from now?
• What trade-offs am I willing to make — or no longer willing to make?
• What is something I deeply believe but rarely live out?
• Where am I outsourcing responsibility for my happiness? How can I start taking it back?
• What self-imposed sentence are you serving that you need to let go of?
• What would I ask for if I wasn’t afraid of hearing no?