THE

INSIGHT
JOURNAL

31
THOUGHT-PROVOKING
QUESTIONS FOR GREATER
SELF-AWARENESS
 Welcome!
It’s ironic that the biggest questions in life are often the ones that we never
seem to have time for:

• What are my dreams and aspirations?

• What are my deepest fears and insecurities?

• Why do I keep falling into bad habits or self-sabotaging?

• Why is it so hard to express myself honestly?

In one way or another, these are all questions of self-awareness. And while I
think everyone would agree it’s good to be self-aware, it’s a hard thing to
actually do…

How do I become more self-aware?

I don’t have all the answers, by any means. But over the years working as a
psychologist, I’ve discovered one pretty good place to start:

You can become more self-aware by making a little time each day to ask
yourself good questions.

This journal is a collection of questions designed to help you enrich and

expand your self-awareness and personal insight.

Each page has a main question along with a few follow-up questions for you
to reflect on and consider.

I recommend printing out this journal then spending a few minutes each
day for a month writing down your thoughts about each question.

Enjoy!

—Nick

“At the end of the day, the questions we ask of ourselves

determine the type of people that we will become.”
― Leo Babauta

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 1

What does your perfect day look like?

What sorts of activities or events do you do? Which people do you spend it
with? Where would you like to be? Describe the happiest day you can
remember from your past?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 2

What person has had the biggest influence

on your life so far?
Do you have mentors in your life right now? If yes, what do you appreciate
about them? If no, what would you look for in a mentor?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 3

What does self-esteem mean to you?

Where does healthy self-esteem come from? What types of things lead to low
self-esteem? Can self-esteem be too high?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 4

When was the last time you did something

completely new or unexpected?
How important to you is spontaneity? What role does
adventure play in your life?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 5

Does it make more sense to define yourself

by your past or by your future?
If you were at a cocktail party and someone you didn’t know approached you
to chat, what question would you like them to ask you first? Who’s the most
self-aware person you know? What makes them so self-aware?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 6

When was the last time you felt truly

appreciated?
What person in your life do you appreciate most? What do you appreciate
most about yourself?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 7

What’s you biggest fear?

In what ways does this fear impact your life? Have you ever conquered an
especially difficult fear? What does it mean for a fear to be “conquered”?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 8

What are the top 3 things on

your bucket list?
If you knew you only had 3 years to live, what would you most hope to do,
experience, or accomplish?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 9

What do you think about the common

advice to live life without regrets?
Is it possible to live life without regrets? In what way might the following
statement be true: A life full of regrets is a live well-lived.

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 10
What one-sentence message would you
put on a billboard for thousands of
people to see everyday?
What book do you recommend most often to people and why? If you were to
write a book, what would the topic be?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 11

What role does guilt play in your life?

Do you ever feel guilty even though you’ve technically done nothing wrong?
What do your suppose this means? What’s the difference between guilt and
shame?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 12

What’s one habit you could do each

morning that would make your day easier
and more enjoyable?
Sometimes this is called a “Domino Habit,” a habit which when you do it, it
leads to a lot of other good things falling in place as a result.

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 13

What accomplishment are you most

proud of in your life?
How important are accomplishments? What types of accomplishments matter
most in the long run?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 14
How do you know when you are in love?
Is love a feeling or an action? What does it mean to fall out of love? Is love
something you fall into or cultivate?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 15
What’s the difference between worry,
anxiety, and fear?
Can anxiety be healthy? What would your life look like if you never experienced
fear? What’s the one thing in life you’re most worried about right now?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 16
Is it better to define people by their
actions or their values?
What’s your most important personal value? What’s the difference between a
goal and an aspiration?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 17

What role does creativity play in your life?

If you had expert skills in any creative area, which would it be and why? What’s
an example of something you think of as creative that most people don’t?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 18
What’s one event from your early
childhood that still impacts you today?
How do you remember feeling when that event happened to you? Did you talk
about what happened with anyone? Why or why not?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 19
What are the pros and cons of setting New
Year’s resolutions?
What’s the most common obstacle to you achieving your goals or dreams in
life? What are some examples of self-sabotage in your life?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 20
What’s your biggest flaw?
What would a good friend say your biggest flaw is? Do you see
your flaws as changeable or unchangeable? In either case, where
do you think this view came from?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 21
What traits or qualities do you admire
most in other people?
What traits or qualities bother you most in others? Why do you think those
particular traits bother you especially?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 22
What’s something you believe strongly
that most other people don’t?
What’s the biggest misconception about human nature that most people have?
What would the title of your autobiography be?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 23
What’s one thing you wish you could
change about your upbringing?
What would be your best piece of advice for new parents? What do you wish
you had understood about adults as a child?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 24
What’s one area of your life where you
wish you had more courage?
How would your life be different if you were twice as courageous as you are
now? What’s the difference, between courage and confidence?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 25
If you could choose any line of work and
be guaranteed to be successful and happy
in it, which would it be?
What’s your nightmare job? What are your favorite and least favorite things
about your current work or occupation?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 26
What does “self-care” mean to you?
If you have a hard time practicing self-care, what are the one or two biggest
reasons why? Is it more important to take care of yourself or others?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 27
What qualities do you look for
in a good friend?
Is it important to have a “best friend”? What are you greatest
strengths/weaknesses as a friend?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 28
What is the biggest misconception most
people have about you?
What’s the biggest misconception you have about yourself? Who
is your “true self”?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 29
What’s one area of your life where you wish
you were more productive?
What types of activities do you tend to lose track of time in? What’s
the single biggest source of distraction in your life?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 30
Is it good to trust your intuition?
In what areas of your life does your intuition tend to help you? And
when does it lead you astray? Is it possible to improve your intuition?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

 DAY 31
What’s your favorite thing about yourself?
What would you say is/was your parent’s favorite thing about you? What
do you think your best friend or spouse’s favorite thing about you is?

NickWignall.com The Insight Journal © N UT H YM IA LLC 2 02 0

About the Author

Nick Wignall is a clinical psychologist and author who

writes about personal growth and emotional health.

You can learn more about Nick and his work here:
NickWignall.com

NickWignall.com The Insight Journal © N UT H YM IA LLC 2020