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Reflection Questions
108 questions. Each one designed to find the thing underneath the thing you tell yourself.
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108 questions. Each one designed to find the thing underneath the thing you tell yourself.
Browse by categoryYou've been circling the same decision for weeks. Not because you lack information. Because every option costs something you're not ready to name.
What is wrong, exactly?
What boundaries can we positively break?
Which part of your work, if it suddenly got much better, would have the biggest impact on the outcome you seek?
What do I want, exactly?
What change do you want to make? Why would this change benefit me?
You've read the books. Done the routines. Tried the frameworks. And you're still here, looking for something none of them addressed. These questions skip the prescription and look at what's actually happening.
What thoughts am I ruminating over?
Can you think of an example of a task you didn't do as well as you would have liked, and what factors may have contributed to that?
Have you taken full advantage of the opportunities offered to you?
Who aligns with your way of thinking?
What tasks or situations do you often procrastinate on, even if they are important or necessary?
How have I embraced change recently?
What kinds of meetings or situations do you find particularly challenging or difficult to handle, and why?
Can you think of a recent activity you enjoy doing that would surprise your younger self?
Looking back, what do you think your younger self could have worried less about and focused on more?
Is there a task or activity that you find yourself fully immersed in and energized when doing?
Is there something you enjoy doing, even though you don't think you will ever become particularly skilled at it?
Is there an activity that you feel particularly drawn to when on an extended vacation?
What boundaries can we positively break?
Have you cleaned up your life?
What have you learned is actually a lot easier than you once thought it was?
Are there any situations or tasks that make you feel anxious or uneasy, causing a physical sensation in your stomach?
Where am I waiting for another person to make the first move?
What activities have you been drawn to since childhood and still find enjoyable?
How can I honor myself today?
What would need to be included in a perfect day?
Are you treating your close ones with dignity and respect?
When was the last time you laughed really hard?
How can I carve out time to replenish?
Have you said what you need to say to your friends and family members?
Do you have habits that are destroying your health and well-being?
What obstacles could arise today?
What was a recent project you enjoyed working on and would be interested in continuing to work on?
Have people who know you well ever mentioned any special strengths that they see in you?
What topic or activity are you particularly passionate about and can't stop talking about?
Are you truly shouldering your responsibilities?
Backward-looking questions for people who sense something shifted but can't pinpoint when. The discomfort of looking back honestly is the point.
What is happiness?
Can you think of an example of a task you didn't do as well as you would have liked, and what factors may have contributed to that?
What do I ignore because it’s too painful to accept?
If I took over my life from scratch today, what would I immediately stop doing?
What is bothering you?
Am I learning new things?
What shall I do with the fact of aging?
Who aligns with your way of thinking?
What is wrong, exactly?
What tasks or situations do you often procrastinate on, even if they are important or necessary?
Where I go through unnecessary struggle?
Where do I feel most at ease? Where do I not?
What time of day can I be least reachable?
What can I do in the next week that will make the rest of the year easier?
What kinds of meetings or situations do you find particularly challenging or difficult to handle, and why?
What makes me proud?
What does wellness look like for me?
What conflicting notions am I oscillating between?
What haven’t I experienced firsthand that leaves me naive to how something works?
Who do I spend time with that pulls me down?
Who do I spend time with that lifts me up?
Looking back, what do you think your younger self could have worried less about and focused on more?
What does success mean to me?
What brings you joy?
Is there a task or activity that you find yourself fully immersed in and energized when doing?
Who am I?
What's something you learned to love about yourself?
What can you do to build trust?
Is there something you enjoy doing, even though you don't think you will ever become particularly skilled at it?
Is there an activity that you feel particularly drawn to when on an extended vacation?
What emotions can I identify that deplete my energy?
How can I maintain trust within myself?
Are there any situations or tasks that make you feel anxious or uneasy, causing a physical sensation in your stomach?
What do I desperately want to be true, so much that I think it’s true when it’s clearly not?
Am I off center?
How can I be my best under the current circumstances?
When could I benefit most from a little lightheartedness?
Am I happy?
How can I calm my thoughts, when I need it?
What do I want, exactly?
When was the last time I did something for the first time?
What are ways I can be gentle to myself?
How are you spending your time?
Do I love well?
Am I living the life I choose for myself?
What am I avoiding?
What do you do when you have nothing to do?
Which of my current views would I disagree with if I were born in a different country or generation?
If I had one year to live, what would I change?
What drains my energy?
How much have things outside of my control contributed to things I take credit for?
What shall I do when greed consumes me?
There are so many emotions to be felt. What am I feeling right now?
Am I playing the right game?
Have you lately felt flow moments?
What time of day am I most productive?
What do I desperately want to be true, so much that I think it’s true when it’s clearly not?
What was a recent project you enjoyed working on and would be interested in continuing to work on?
What do you wish more people asked you about?
Have people who know you well ever mentioned any special strengths that they see in you?
What gives me energy?
Which of my current views would I disagree with if I were born in a different country or generation?
What topic or activity are you particularly passionate about and can't stop talking about?
What are we ignoring today that will seem shockingly obvious in a year?
The career questions nobody asks in a performance review. Not where you're going. Where you actually are, and whether the scoreboard you're using still measures anything real.
Can you think of an example of a task you didn't do as well as you would have liked, and what factors may have contributed to that?
Have you taken full advantage of the opportunities offered to you?
What kinds of tasks or situations would make you consider a change in jobs or career path?
Have I gotten any recognition of my work lately?
What talents do you possess?
What tasks or situations do you often procrastinate on, even if they are important or necessary?
What’s most important to you in your career?
What trends are happening right now?
What time of day can I be least reachable?
What kinds of meetings or situations do you find particularly challenging or difficult to handle, and why?
Can you think of a recent activity you enjoy doing that would surprise your younger self?
Does my job give me a chance to develop?
Looking back, what do you think your younger self could have worried less about and focused on more?
What does success mean to me?
Why am I actually doing my work?
Is there a task or activity that you find yourself fully immersed in and energized when doing?
Is there something you enjoy doing, even though you don't think you will ever become particularly skilled at it?
Is there an activity that you feel particularly drawn to when on an extended vacation?
What boundaries can we positively break?
Which part of your work, if it suddenly got much better, would have the biggest impact on the outcome you seek?
Are there any situations or tasks that make you feel anxious or uneasy, causing a physical sensation in your stomach?
Am I off center?
What activities have you been drawn to since childhood and still find enjoyable?
How are you spending your time?
Is my work meaningful to me?
What is the much more ambitious version of that?
Are you working hard on your career, or even your job, or are you letting bitterness and resentment hold you back and drag you down?
Am I playing the right game?
Have you lately felt flow moments?
How can I find happiness in my career?
What change do you want to make? Why would this change benefit me?
How do you make sure you’re heading in the right direction?
What time of day am I most productive?
What was a recent project you enjoyed working on and would be interested in continuing to work on?
Have people who know you well ever mentioned any special strengths that they see in you?
What topic or activity are you particularly passionate about and can't stop talking about?
Goals are easy. Knowing which ones are yours and which ones you inherited from someone else's scoreboard: that's the hard part. These questions separate the two.
What can I do in the next week that will make the rest of the year easier?
What boundaries can we positively break?
If I had one year to live, what would I change?
What change do you want to make? Why would this change benefit me?
How do you make sure you’re heading in the right direction?
For when resting feels like failing and doing feels like drowning. These questions sit in that gap. Not to fix it. To name what's actually happening there.
Most problems aren't what they look like on the surface. You're solving the visible one while the real one runs underneath. These questions find the one underneath.
What is wrong, exactly?
What can you do to build trust?
If we took at look at your calendar, how much time is spent reacting or responding to incoming, how much is under your control, and how much is focused on the hard part?
What change do you want to make? Why would this change benefit me?
Not the 'become your best self' version. The version where you look at who you actually are right now, without the aspirational filter, and figure out what's true.
If I took over my life from scratch today, what would I immediately stop doing?
Have you taken full advantage of the opportunities offered to you?
Am I learning new things?
What talents do you possess?
What does success mean to me?
What's something you learned to love about yourself?
What boundaries can we positively break?
Have you cleaned up your life?
Where am I waiting for another person to make the first move?
Am I off center?
When was the last time I did something for the first time?
How are you spending your time?
Are you treating your close ones with dignity and respect?
What is the much more ambitious version of that?
Which of my current views would I disagree with if I were born in a different country or generation?
Have you lately felt flow moments?
Have you said what you need to say to your friends and family members?
How do you make sure you’re heading in the right direction?
Do you have habits that are destroying your health and well-being?
What do I desperately want to be true, so much that I think it’s true when it’s clearly not?
Who would you like to help?
Are you truly shouldering your responsibilities?
The interview asks follow-ups you'd avoid on your own, and names the patterns underneath.
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