A friend asked me recently what I hoped to receive from this year. The answer tumbled out without effort, and it took me by surprise: “I want to be at peace with myself.” 

“I want to be at peace with myself.” 

As much as I’ve tried, I’ve realized I can’t escape me. I wake up each morning with her, go to bed every night with her. I’m there in her worst moments, and there in her best. It’s a 24/7, 365 relationship, and yet, it’s the easiest one to neglect.

I’m reminded of Truman Capote’s line in “Breakfast at Tiffany’s” when he says, “…no matter where you run, you just end up running into yourself,” and I’m more convinced than ever that nurturing the relationship you have with yourself is key. To deeply know others, you must deeply know yourself. 

“To deeply know others, you must deeply know yourself.”

Big thinkers across history have stressed the sacred importance of taking time for introspection. Aristotle, Benjamin Franklin, and Lao Tzu all encourage a life of neverending self-examination and discovery, echoing the words of Socrates, “To know thyself is the beginning of wisdom.”

Here’s a treasure chest of 99 self-discovery exercises, prompts, and ideas to help you pull back the layers of who you are within and nurture the most important relationship in your life — the one you have with yourself.

If you’re interested in deepening your relationship with others, too, then take a look at our mindful conversation topics and questions for getting to know your partner better. Happy bonding!

Questions and journaling exercises

1. Imagine a day in your life 10 years from today.

This dreaming exercise was originally created by Milton Glaser (described by Debbie Millman here) where you set a timer for 30 minutes and let yourself dream in precise detail, going through your day from start to finish.

“Take time to describe the kind of home you wake up in. Is there someone with you? What’s the environment feel like?”

Take time to describe the kind of home you wake up in. Is there someone with you? What’s the environment feel like? What do you do first? Do you have pets? If yes, what kind? Do you travel often? If so, where? How do you feel in your body?

Once the timer is up, read what you dreamt up. You might be surprised by what you wrote!

2. Pick a type of tree you feel most embodies your personality. 

If you were a tree, what kind of tree would you be? Take time to research the native environment of that particular tree, note its characteristics, and ask yourself how those details translate to who you are, what you like, and what kind of atmosphere you feel most at home in. 

3. Write a script between your past 10-year-old self and your future 90-year-old self. 

What would they say to each other? What would they talk about? What would your 90-year-old self want your kid self to know? 

4. Identify your hard-set boundaries. 

What are five things you’re willing to be disliked for? What is it you see differently from the majority? What do your answers indicate you’re most passionate about?

“What are five things you’re willing to be disliked for?”

5. Get clear on the environments and circumstances where your truest self is the most comfortable.

When was the last time you felt most like myself? What were you doing? Who were you with? What side of you did that experience bring out? 

6. Write a letter to your inner child. 

What would you have wanted someone to tell you at 5, 12, or 18? What difference would it have made in your life if someone had? 

7. Consider the traits you love the most.

If you could keep just five qualities about yourself, what would they be? Why? 

8. Take time to consider the career, relationship, and life paths you didn’t take. 

What if you had gone to a different school, lived in a different city, or taken a different job? What kind of person would you be? What about your present life would you not have today had you traveled down those paths instead of the one you ultimately chose? 

“What if you had gone to a different school, lived in a different city, or taken a different job?”

9. Try this thought experiment about work.

If you had all the money in the world but had to hold down one minimum wage job for the rest of your life, what kind of job would you choose? Why? 

10. If you only had a year left to live, how would your focus change? 

What would take priority? Who would you spend more time with today?  

11. What does “home” mean to you emotionally, physically, and mentally? 

What do you need to feel “at home?” Is it people, a city, familiarity? Explore where you find pockets of the feeling of home in your daily life. 

12. Share your wisdom.

If you could only pass along one life lesson to the next generation, what would it be? 

“If you could only pass along one life lesson to the next generation, what would it be?”

13. Write a high school or college graduation card to your younger self. 

What do you want this person to know about what’s to come? What did that person need to hear at that milestone? 

14. Define your travel style.

Where do you go on your ultimate trip? Who are you with? What kind of activities do you engage in? Are you more of a full relaxation type or do you want to see the sights or is it a mixture of both?

15. What’s the “no” you keep postponing? 

What’s holding you back from setting that boundary or eliminating that obligation? How come? 

16. What’s something you wish people asked you more often? 

“What’s holding you back from setting that boundary or eliminating that obligation?”

Why is that question important to you? Who in your life can you kindly request to ask you that more often?

17. What’s a book you think everyone should read?

What is it about that book that is so important? What does that say about you? 

Crafty and out-of-the-box ideas

18. Give yourself a doodle challenge. 

At the beginning or end of every day for 30 days, doodle the first thing that comes to mind in a journal or on a Post-It note. After you doodle, write your top-of-mind, unfiltered thoughts beside it. At the end of the month, look back on all the unique places your mind wandered. 

19. Create a mood board on Pinterest specifically for the upcoming season. 

What do you want to wear when the weather turns? What recipes do you want to try? What aesthetic feels the most comfortable to you? What are you most excited about doing in the next chapter of the year? 

“What do you want to wear when the weather turns?”

20. Leave yourself a secret reminder for the future. 

Find a puzzle under 500 pieces at the thrift store and, if you can, put it together face-down. When the puzzle’s complete, write a message to yourself a year from now on the back. Include quotes, and meaningful symbols, and paint or draw with colors you like at the moment. 

Piece the puzzle back together a year from now as a reminder that life comes together piece by piece. 

21. Take a look at your home and identify one item or corner where you can inject a little more of your personality. 

Bobby Berk, designer and author of “Right at Home: How Good Design is Good for the Mind,” says, “Create a space that tells a story about who you are and what you love.” 

Is there a creative way you can frame and showcase your travel photos? Is there a family heirloom you could put on display? Could you repaint a piece of furniture in a color that feels more like you?

22. Take yourself on a date to the park with some headphones and a notebook.

Try closing your eyes, listening to an instrumental album, and doodling what you see in your mind’s eye as you let your thoughts wander.

“Try closing your eyes, listening to an instrumental album, and doodling what you see in your mind’s eye as you let your thoughts wander.”

23. Check out the Styled DNA App to identify your body and complexion’s most flattering colors and shapes. 

Dive into your closet to explore what you want to add or subtract from your wardrobe to feel most like you and play around with your new color pallet. Explore styles and colors you’ve always wanted to try. 

24. Go on a hike with a journal and your medium of choice – watercolors, markers, colored pencils, or crayons — and pick a vista to create. 

What about that view captures your interest? What details stand out most? Journal your thoughts. 

25. Explore a medium you’ve never tried but has always intrigued you.

Think pottery, figure drawing, or jewelry-making. Take a class online or at a local studio and see how you like it! 

26. Throw a just-because get-together in your home. 

Have a themed poetry reading or an open mic night. Host a viewing of your favorite series or put on a PowerPoint party. 

When you do, ask yourself how hosting makes you feel. Do you enjoy creating an experience for others? Does the art of hospitality light you up? 

“Do you enjoy creating an experience for others? Does the art of hospitality light you up?”

27. Commit to noticing your own cute quirks. 

Keep an ongoing note in your phone called, “My Weird,” and whenever you do, think, or act in a peculiar way (or someone lovingly points it out), write it down to capture your unique brand of weird. 

28. Use FutureMe to auto-send an email to your future self months or years into the future.

Share your present-day dreams, desires, and feelings and some encouragement for future you.    

29. Start a blog and challenge yourself to a writing sprint for 30 days. 

See where your creativity takes you in a month of daily diligent writing. Use resources like 30 Day Blog Challenge to support you! 

30. Try your hand at drawing a self-portrait. 

Challenge yourself to see beyond the features of your appearance that bother you and honor your beauty, noting the details of your face you admire. Watch this unexpectedly touching Dove ad for inspiration. 

31. Keep a money diary for a month to learn more about your unique money mindset. 

Utilize Tori Dunlap’s Cash Calendar to track how you spend your money, how it makes you feel, and get curious about the purchases that bring you joy and the ones that don’t.

“Get curious about the purchases that bring you joy and the ones that don’t.”

32. Determine your life-giving and energy-draining tasks. 

Take a look at your repetitive tasks and ask if it’s energizing or draining. 

If it’s draining, consider automating, outsourcing, or eliminating it if possible. If it’s necessary to do it yourself, explore ways you can make doing the task exquisite by rewarding yourself with a treat when you complete it, taking yourself out for a fancy coffee or tea when you sit down to tackle it, or pairing the task with something that delights you. 

33. Begin a travel journal.

Whether it’s a long vacation or a quick day trip, record your travel experiences in a memory-packed travel journal, noting not just what happened on your getaway but what thoughts, feelings, and ideas came about along the way. 

34. Use the chatbot ChatGPT as an interactive journaling guide.

Take a page out of blogger Mandy Nicole Hong’s book and let the bot help you dive deeper into specific areas of life, work, and future plans. 

35. Use journal prompts.

Find a newsletter or resource that gives you prompts to help spark your imagination in unexpected ways. We love author Elizabeth Gilbert’s Substack community, Letters From Love which offers weekly journaling prompts.

“Find a newsletter or resource that gives you prompts to help spark your imagination in unexpected ways.”

36. Find your overarching “why.” 

We love this method (via Simon Sinek) to help put language to the driving force behind what you do and what fulfills you. 

37. Try the Ikigai Method to clarify your purpose. 

Identify the intersection of what you love, what you’re skilled at doing, and what the world needs.

38. Use the FaceApp to see what you might look like as an elder and dream up your retired life. 

Imagine yourself at 70, 80, or 90. What does a typical day look like? Where are you living? What are you giving your time to?

39. Try The Alter Ego Effect.

Use the power of your imagination and lean into your hidden confidence. 

40. Try Warren Buffet’s 25/5 Rule. 

As explained here by James Clear, use this to clarify and prioritize your most important goals. 

41. Explore the traits of those you admire. 

“Explore the traits of those you admire.”

And then find where these traits are within yourself by creating an Inspiration Map. 

42. Go on a personal history deep dive. 

Learn more about your lineage through Ancestry or 23andMe. 

43. Sit down and make yourself a custom playlist for the upcoming season. 

What’s the soundtrack for your next chapter? How come? 

44. Make a nostalgia playlist 

Think of songs you listened to as a teen and take time to think back to where you were when you first heard them. 

“Think of songs you listened to as a teen and take time to think back to where you were when you first heard them.”

How old were you? What did a typical day look like? Who were you hanging out with most? What memories do you want to revisit? 

45. Write a short story depicting the events of your last year like you’re the main character of a book. 

What’s the hero (you) feeling? What was their biggest challenge? What did they learn? Who helped them along the way? Where are they now?

46. If you have them, take time to read through your old journals. 

Highlight the moments where you can see how you were expanding and growing. What revelations did you have? What struggles have you worked through? Pull out the golden threads of your history and acknowledge how you’ve grown. 

47. Freewrite a poem every day for 30 days. 

Try doing this at bedtime to unwind, reflect, and reground yourself. 

48. Record your earliest memories with as much crisp detail as you can remember. 

Doodle the scene and try to remember the feelings you had at the moment. 

49. Film yourself telling your favorite story. 

Watch your video back and take note of your mannerisms, body language, and facial expressions. Make a list of what you like about yourself and how you talk. 

“Make a list of what you like about yourself and how you talk.”

50. Reread your favorite book as a kid. 

Why did this story resonate with you so much? Does the story still strike a chord? What does that say about you? 

51. Forage for flowers or buy an assortment of stems to make yourself a bouquet. 

Put words to why you chose each element of the bouquet. What about the greenery and flower type made you choose them over the other options?  

52. Take this confidence-building exercise from Emily Nagoski, sex educator and author of Come as You Are.

Nagoski’s exercise calls on participants to stand in front of a mirror “as close to naked as you can tolerate” and write down all the things about your body that you like. Set aside all the swirly negative thoughts that might come in at first glance and simply identify all the details you see that you like about your body and write it down. Do this daily to grow in appreciation for your wild and wonderful body.

53. Take a look at your upcoming calendar and challenge yourself to cancel 5 energy-depleting obligations. 

What in your schedule or routine gives you energy and saps it? What can you subtract from your calendar to make more room for what’s truly important to you? 

“What in your schedule or routine gives you energy and saps it?”

54. Dive into the famous collection of 36 Questions to Fall in Love. 

Originally from the New York Times, these 36 questions are meant to serve as intimacy builders between partners, but try going through them solo and see what happens! 

55. Take up Mel Robbin’s on her High 5 Challenge and learn how to be your own biggest cheerleader. 

Learn the art of seeing and supporting yourself by implementing this stupid-easy habit every morning. Journal your thoughts throughout the challenge, noticing if your inner dialogue, confidence, and perception of yourself begin to shift. 

Personality Tests

56. Learn more about your astrological sign and explore your chart. 

57. Identify your core motivations, perceptions, and how you most naturally operate through the 9 types of the Enneagram. Look into your type’s wings for even more insight. 

“Identify your core motivations, perceptions, and how you most naturally operate through the 9 types of the Enneagram.”

58. Explore your Human Design chart to dive into your purpose, how you can best align with your natural strengths, and identify the unique gifts you have to offer the world. 

59. Gain language around your personality’s preferences and tendencies by looking into your Myers Briggs (MBTI) Personality Type.

60. Learn how your relationship with your primary caregiver might have influenced your Attachment Style and bled into how you navigate relationships today. 

61. Gain insight on your top 5 values by going through this personal values test. 

62. Discover your Big 5 Personality traits and assess your natural levels of Openness, Extroversion, Conscientiousness, Agreeableness, and Neuroticism. 

63. Take a love language test to identify how you most naturally give and receive love. 

64. Have some silly fun with Buzzfeed quizzes.

“Have some silly fun with Buzzfeed quizzes.”

65. Discover your spirit animal and its intrinsic meaning. 

66. Take this Strengths Finder test to uncover your embedded natural talents. 

67. Use the DISC test to gain career-focused insight on how you work best in a professional environment based on your personality. 

68. Build a morning and bedtime routine that serves you by discovering your natural chronotype or sleep type. 

69. Explore The Japanese Field, Cube, Ladder, Horse, and Flower visualization test – each element suggesting a condition of your psyche. 

Spirituality and inner work

70. Visit a local psychic or palm reader 

This is a way to get a fresh take on the state of your life, character, and where your story may be heading. 

71. Undergo a Reiki session. 

Reiki is ideal for assistance in identifying and moving energy through and out of your body. 

“Reiki is ideal for assistance in identifying and moving energy through and out of your body.”

72. Look into somatic experiencing for help in nervous system regulation. 

Somatic experiences help to gain grounding tools as you learn to acknowledge and process your body’s sensations.  

73. Attend a sound bath meditation. 

Do this when you need to look inward, relax, and unwind. 

74. Grab a friend and go to a local Women’s Circle. 

This is where women gather to honor their ancestors, unite in sisterhood, and connect with one another.

75. Develop a daily mindfulness practice. 

Try using the Headspace or Calm apps to grow in greater awareness and peace with your body, mind, and thoughts. 

76. Give manifestation or manifest journaling a go. 

Manifesting is a powerful way to help you get clear about what you really want, break your big dreams into doable steps, and set the path to reaching your goals. 

“Manifesting is a powerful way to help you get clear about what you really want, break your big dreams into doable steps, and set the path to reaching your goals.”

77. Explore equine therapy (a therapeutic method involving horses). 

How could this type of therapy benefit your mental and emotional health and healing?

78. Find a local spiritual retreat. 

Or take yourself on your own private getaway to reflect, recenter, and dream for the future. 

Discover with others

79. Connect with an intimate group.

Try a conversation-sparking card deck game like We’re Not Really Strangers or {THE AND} are perfect for a connection-building potluck or wine night. 

80. Call your best friend. 

Ask them what they like most about you. Then tell them what you like most about them!

81. Spend an afternoon with a kiddo.

Spend the day bonding with your own child or that of a close friend or family member. Lose yourself in play and silliness. 

“Spend the day bonding with your own child or that of a close friend or family member. Lose yourself in play and silliness.”

82. Reach out to an old friend. 

Ask them “How have you seen me grow since we met? What about me has stayed the same? How do you think I’ll change in the future?”

83. Reminisce with your partner.

Ask your partner or loved one, “When have you seen me filled with the most joy? What was happening? Where were we? Why do you think I enjoyed that moment so much?”

84. Think of whoever knows you best, and share wishes for each other. 

Ask them, “If you could magically remove one stressor from my life, what would it be and why?” Then return the favor.

85. Be vulnerable with someone you feel emotionally safe with. 

“Be vulnerable with someone you feel emotionally safe with.”

Ask them, “What do you think holds me back the most from living the life I want? What are the blindspots I’m not seeing? I give you full permission to be honest.”

86. Seek wisdom.

Ask a parent figure, elder, or mentor, “What qualities or lessons are you proud you’ve passed down to me? How do you see yourself in me?” 

87. Compare memories with someone you’ve known a long time.

Ask a sibling or old friend, “What’s your favorite memory we’ve shared? Why was that so special?” 

88. Break up the water cooler talk.

Ask a coworker, “What’s the funniest thing you’ve heard me say? What would you say is my type of humor?”  

Get up and out of your head

89. Detox your physical environment the KonMari way, decluttering your space to only include items that “spark joy.” 

What is it about those items that make you happy? What do your answers reveal about what you value deep down?

90. Give back.

Consider what local charities strike a chord with you and look into how you can get involved. 

“Consider what local charities strike a chord with you and look into how you can get involved.”

Get curious about why that cause resonates with you. What is it about the work that you connect with? Use resources like VolunteerMatch to explore volunteer opportunities available.

91. Head to a furniture store for some window shopping and take note of what sparks joy. 

What do you like? What do you dislike? Are there colors or patterns you find yourself gravitating towards more? Take note! 

92. Go to a thrift store and put together a handful of outfits you like but wouldn’t normally wear. 

Try on styles, shapes, and colors you’ve never given a shot just to see what they feel like on. 

93. Create a movie mood board curating your favorite cinematic characters. 

What is it about these characters or their stories that resonate with you? How do you see yourself in them? 

94. Ask a friend to capture candid photos of you for a day. 

When you get the photos, commit to setting your self-judgment aside and instead, list three things you like about each one. 

95. Read a book of poetry and pull out your favorites. 

Try rewriting the essence of your favorite poems in your own words. What sticks out? What impression does the message leave with you? Why does that resonate? 

“Try rewriting the essence of your favorite poems in your own words.”

96. Climb a tree or go to a local overlook in your city. 

While you’re there ask yourself, “What areas of my life do I need a fresh vantage point? What paradigm shifts can I make to help me see my world in a new way?” 

97. Take yourself star-gazing. 

While you’re taking in the night sky, let your mind wander where it needs to without judgment.  

98. Take a solo train trip with a book and a journal.

As you chug along, check in with yourself about the tracks of your story so far. What stops do you hope are ahead for you? What sweetness is available in the in-between as you make your way to your next milestone?

99. Take yourself to a museum and pick your favorite piece of art. 

Spend time letting the art speak to you. If you can, bring along a notebook and doodle what it looks like, journaling your thoughts as you go.  ✨

What’s your favorite mode of self-discovery? What’s a method you keep coming back to over and over? Share with us in the comments!

Cheyanne Solis is a copywriter relieving entrepreneurs to rest and invest more in what they love. She writes on practical wellness and mindful productivity from the perspective of sustainable work-life balance. Explore her work and connect here.