How to Have a Thinking Day


The term “Thinking Day” was coined by my mom when she disappeared for hours one day on a family vacation. Naturally, she’s an introvert, so I can expect her to be MIA on a trip to Hawaii, but when my boyfriend and I were walking to the beach from our hotel, I saw my mom’s model strut walking towards us in her bathing suit and big sun hat, sarong wrapped around her waist. It wasn’t until we were only a few feet in front of her and I yelled “mom!” that she even saw or recognized us (lol). I asked her “Where have you been all day?” and her response was “I had a thinking day,” and thus the Thinking Day was created.

What's A Thinking Day?

A Thinking Day is when you set aside a few hours, or a whole day, just to think. But as my mom later explained to us, a thinking day has more structure than just sitting in one place and letting your thoughts run. A thinking day’s purpose is to reflect on your current place in life and check in on different sections of your life that I’ll lay out below. I recommend having a thinking day once in a while when you feel like you need one; it helps to feel like you have your ducks in a row and you’re on a track that’s true to yourself and the life you imagine for yourself. Without further ado, these are the topics I recommend dissecting on a thinking day:

 P.S. I included some thought-provoking questions. But, a thinking day is personalized to you and your life, so if they don’t apply to you, don’t sweat it. The questions are just to get you going. Personalize them as you please.

Also, feel free to skim. I put a lot down, just pay attention to whatever stands out.


  • How do I feel about who I’ve become in the last few years?
  • What are my weaknesses?
  • What are my strengths?
  • How do I feel about how I exist in the world around me? 
  • What does my most beautiful, fun, satisfying self/life look like?
  • Who do I want to be?
    • What steps do I need to take to become that person?
  • Am I satisfied with how I am managing stress, anger, jealousy, past traumas?
  • What am I proud of?
  • What are my values right now?
  • Am I taking care of myself?
  • Would therapy be a useful thing for me?
  • How could I be better/prouder of who I am?
  • What are my goals for the person I want to become? How do I get there?
  • What’s my personal action plan?

Interpersonal Relationships

  • Am I satisfied with my relationships with each of my friends and family members?
  • What kinds of feelings come up when I think about the people closest to me?
  • Do I feel supported and fulfilled by the people around me?
  • Do I want more, less, or new friends?
  • Are any of my relationships unstable or toxic?
  • How can I make my relationships better?
  • How can I be a better friend, sibling, or child?
  • Is there anyone I miss that I should talk to more?
  • What kind of people do I need around me?
  • What kind of person do I want to be to the people around me?
  • Are there any friend or family traumas that I’m avoiding unpacking?
  • What’s my relationship action plan?

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    Sex and Romance

    • Am I satisfied in my relationship(s)?
    • Do I feel like my partner listens, hears, and sees me?
      • If not, does it bother me?
    • Could my communication, temper, or expectations be better?
    • Are my standards too high? (expecting your partner to basically not be human)
    • Are my standards too low?
    • Do I feel used by my sexual partners?
    • Could my sex life use some work?
    • How can I be a better partner/lover?
    • What does my ideal relationship/sex life look like right now? 
      • Is it having no intimacy or relationship at all?
    • Do I feel whole and independent from my partner? Or do I feel whole and independent and ready to enter into a relationship?
    • Are my FWB, one-night stands, or situationships taking more energy out of me than they’re giving me?

    Editor’s Note: Check out our article on casual sex.


    • Do I feel like I’m making strides in the direction of the career I want?
    • How do I feel like I’m doing in school?
    • What aspect of my schooling or career is missing right now that I would feel prouder if I had?
    • Do I know what I want to do for work in the future?
    • How am I doing on accomplishing my school and/or career goals?
    • What are my career goals?
    • Am I satisfied with the work I’m putting into my education and career?
    • What can I do to make this aspect of my life feel better?
    • What’s my career action plan?


    • Do I feel comfortable financially?
    • Do I need to budget more?
    • What can I do to feel like I have enough money? Save more? Spend less? Find another way to make extra money?
    • If employed and paid, do I feel like the work I’m putting in matches my income?
    • How can I plan my expenses better?
    • Do I have enough money to do the things I want to do?
    • Does money stress me out?
    • Do I want to learn more about saving, investing, taxes, or retirement? 
      • How can I begin to learn more about these things?
    • What’s my financial action plan?

    Final Thoughts

    I hope this wasn’t too overwhelming to read through – and maybe you just skimmed it to potentially come back to these questions later. 

    I want to emphasize that your thinking day is unique to you, so if there’s something I missed that largely applies to your life, lean into that. These questions can be formatted differently for everybody. 

    The main takeaway that I want you to get from this is that it’s important to check in with yourself every once in a while to assess your current state of affairs, and a thinking day gives you the structure and intentional time to do that. As a result, you might see yourself, the state of things around you, and your goals/future clearer. 

    A thinking day is done right when, after, you feel like you’ve combed through every section of your life and come face to face with any knots that you might push under the rug in your daily life. I hope this was useful to you and gave you some inspiration to take a step back and reflect, and if you try having a thinking day, I hope it’s productive and allows you to make changes.

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