Are you compulsively nice? When has being nice been unhelpful, and when would being disagreeable have been better?
What has your fear of embarrassment held you back from doing, and what would you do if you simply didn't care?
Do you really want help or do you seek attention and validation? When helping others, do you also seek attention and validation?
Where in your life do you doubt yourself, and does this self-doubt hold you back? Why, and what's the worst thing that could happen if you didn't let it?
How can you be more patient, empathetic, and graceful with someone close to you who maybe rubs you the wrong way? What would your relationship look like without drama, and what would that require?
What are you grateful for, and what could you be more grateful for?
What emotions do you feel you must apologize for, and how has this affected your life, decisions, and relationships?
In what ways have you overestimated your emotions and let them dictate your behavior and worldview? Where has this led you?
What have you read that changed your perspective on life, and what could you read that might change it further?
In what areas of your life have you felt pressured to be normal, and how has this pressure caused problems for you?
Are the people in your life there for the right reasons? If not, why are they there?
When have you pretended to know something you didn't, spoken out of turn, or tried to impress someone unnecessarily?
Reflect on your biggest mistakes and opportunities. Did they seem like good or risky ideas at the time? How does this compare to your current situation?
How many things are you doing in your life right now to get back at someone or prove them wrong? What would happen if you stopped?
What extraordinary thing do you want to achieve this year? What small steps can you take this week, and what realistic expectations can you set to prevent burnout?
What hard things have you practiced doing, and in what areas could you lean more into doing hard things?
What's one area of your life you keep trying to solve instead of understanding? Consider both relationships and other personal challenges.
What are you waiting for certainty on before acting? Is that certainty realistically going to come without action?
In what areas of your life have you felt inferior, and why do you think that happened?
When have you apologized for your own happiness or compromised your best self to avoid disappointing someone? How did that go?
How much unnecessary drama have you tolerated to feel needed? What would happen if you stopped tolerating it, and how would it make you feel?
Do you overcompensate with negativity? How's that working for you?
Are you making unrealistic comparisons with others? Are you fully aware of their internal struggles, and are you sure you're better or worse off than they are?
Do you believe you are a person of character? Can you do the right thing or something well when no one is looking or when there is nothing to gain?
In what ways have you sacrificed your self-respect for validation from others? What have been the results?
What are you most afraid of doing that would probably be good for you? What possibilities make you uncomfortable, and what ideas are you avoiding or rejecting?
If you're afraid of criticism, why do you care about the opinions of those too timid to do it themselves? If you are the criticizer, does tearing down someone with courage make you better?
What do you have fun failing at, and how has that paid off for you? What do you try to excel at but hate failing at, and how has that held you back?
What simple lifestyle habits are potentially holding you back? What are your justifications for them, and what simple changes can you make to start undoing them?
In what ways are you overestimating how much people care about what you do or don't do? How has this affected your life?
Are you caught in an echo chamber with your informational diet? How can you challenge your own ideas and assumptions regularly by seeking out differing viewpoints?
If harming yourself earns approval from others, what does that say about them? If helping yourself upsets them, what does that say?
What would you do if you had zero risk of failure? How have you short-changed yourself by avoiding failure?
Are you viewing any relationships as power struggles or competitions? Is this making both of you happier?
In what ways have you allowed others' limitations to hold you back, and why do you think you let it happen?
Where have you gained wisdom through failure and pain? Where do you likely have the least amount of wisdom today?
Are your expectations of your partner in line with your expectations of yourself? Are these expectations realistic?
What problem in your life could improve if you stopped meddling with it? Like a scab that would heal if left alone, what problem could you stop picking at to see if it gets better on its own?
Where in your life do you struggle due to an inability to be bored? Is this inability perhaps distracting you from something uncomfortable?
