Self Discovery

We would like to dedicate this book to our
Marriage365 members. You inspire us with your
bravery and vulnerability every single day. Each
and every one of you is making this world a
better place and we’re so glad we’re on this
journey of self-discovery with you all.
Copyright © 2020 by Casey and Meygan Caston
All rights reserved. No part of this book may be reproduced or transmitted in
any form or by any means, electronic or mechanical, including photocopying and
recording, or by any information storage and retrieval system, without permission in
writing from the authors.
Illustration and Design: Sel Thomson
Typesetting: Melanie Etemadi
Back Cover Photography: Haylee Forster
ISBN 978-1-7324358-6-5
Published in 2020 by Marriage365 Media Group

CONTENTS
Introduction .............................................. 09
Feeling Triggered? ...................................... 22
January ....................................................... 27
February ..................................................... 41
March ......................................................... 53
April ............................................................ 67
May ............................................................ 79
June ........................................................... 93
July ........................................................... 105
August ....................................................... 119
September ................................................. 133
October .................................................... 145
November ................................................. 159
December .................................................. 171
Feelings Words List ................................ 185
Index ......................................................... 189
About Marriage365 .................................. 195

HOW TO USE THIS BOOK

WHERE TO USE THIS BOOK

By Date
For each day of the year, there is one question. Turn to the
date of the year and begin your self-discovery journey.
You don’t need to start on January 1st. Any day is great to
start. Some people like to commit to one question a day
while others prefer to binge several questions in one sitting.








By Topic
If there is a specific area you want to focus on, pick a
question by topic using the index (pg. 189) that can be
found in the back of the book. If you’ve had a difficult day,
we recommend choosing a question from the JUST FOR
FUN category.



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A book club
At your workplace
In therapy sessions
With a small group of friends
As a conversation starter with your partner
For parents - with your teenage or adult
children
A daily check-in with yourself

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INTRODUCTION
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Self-discovery is one of the greatest pathways to building
confidence in our lives, but it seems like we are too busy
these days to stop and check in with ourselves. We are
overwhelmed with demanding work commitments, kids’
sport schedules, 24-hour news coverage, the time suck of
video games, friends’ parties to go to, the latest bingeworthy Netflix show, not to mention the family gatherings
and house projects. For most of us, we wake up checking
our phone, move through the day, and fall asleep scrolling
through social media’s endless feeds. These are activities
that crowd out our time that allow us to bounce from one
distraction to another, and it’s killing us. Like a cat with a
laser pointer, we chase after the next shiny object that will
busy our time. We’ve lost the art of reflection, gratitude,
and awareness.
Let’s do a quick exercise to help you reflect, be grateful,
and become even more self-aware. First, I want you to take
a deep breath and then close your eyes so you can pay
attention to what’s around you. (Ok, you can peek to read
ahead first). Now, bring what you hear to the front of your
mind. Is it leaves rustling, music playing, or the not-sofaint noises of children playing in the house? Open your
eyes and take a couple of deep breaths. Look around you.
What do you see? Is there something that catches your
eye that you are grateful for? Now, think about your last
interaction with another person. Was it something you
are proud of where you both listened and engaged with

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mutual respect? Or were there hurt feelings and emotional
disconnection? There... that was easy. That took maybe a
few minutes or less, but you centered yourself, quieted
your mind and moved closer to being proactive in
your life, rather than reactive.

The journey of becoming
self-aware is the process of self-discovery
and that starts by asking great questions
of yourself.
Self-aware people carry themselves with confidence
because they’ve taken the time to explore who they are
and how they want to be known (that is, self-discovery).
These people have done the hard work of asking themselves
tough questions. They have courageously confronted the
lies that they have told themselves like, “I’m not good
enough,” or “Why try if I’m going to fail?” or “I’m just not
smart enough.” They’ve overcome the inevitable childhood
baggage and the fears that hold them back. Because of
their hard work, these brave souls make a tremendous
impact in the lives of those around them.
Insecure and hurting people, on the other hand, often react
to life’s peaks and valleys as each moment comes, rarely

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stopping to think about how they show up in life. They run
from introspection and avoid dealing with interpersonal
conflict for fear that their emotional shallowness could be
revealed. Their life is marked by selfishness and emotional
laziness because they are too afraid to turn on the lights
and expose the fears that have held them back for so long.
Sorry (not sorry) if that sounds harsh, but at the core, it’s
true.

HERE’S HOW SELF-DISCOVERY
BEGAN IN OUR LIFE

Early in our marriage, we got into a huge fight about
being on time versus being late. We were both angry, hurt,
and filled with pride, which meant days of giving each
other the silent treatment. Who would break the silence
first? Who would apologize first? We finally agreed that
we needed to see a counselor since we couldn’t even be
in the same room without wanting to say hateful and
hurtful comments. We sat down on our new counselor’s
couch feeling nervous and a little excited because both of
us were hoping that the neutral party sitting across from
us would call the other one out. But what she said rocked
our worlds. “So Meygan, can you explain to Casey why
being on time is so important to you, where that energy

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comes from, and how it makes you feel when he’s late?
And Casey, after Meygan shares, I will be asking you the
same question, but I want to know how it makes you feel
when she gets upset with you for being late.”
Her questions made us both stop and really think about
why we cared so much about this fight about being on
time versus late. Here were our responses...
Meygan: Growing up, my parents were always on time, which
is a sign of respect when someone is counting on you. Trust
is one of my core values and how do I trust someone who
I can’t rely on?
Casey: My home life was chaos. As an only child raised by a
working single mom, I was often in day care. There were times
I was the last one to be picked up or dropped off late and I
had to get over it. Things happen and I think you should
make your best effort to try and be on time, but there are
bigger problems in the world to worry about.
As we processed where our value systems came from, we
noticed that Meygan’s frustration came from one of her
core values being challenged. For Meygan, something as
simple as Casey being late caused her to feel like he didn’t
respect her and that she couldn’t rely on him, breaking the
trust they had built. And for Casey, he felt frustrated
because it was unfair that Meygan’s negative reaction to a

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5-10 minute delay could and often did spoil the time they
had together. His value of spending time together and
building connection, stemming from abandonment
wounds, was more important than promptness. In this
one instance, we discovered that rarely is one of us
right and the other one wrong, we’re just different
people with differing views that both stem from our
childhood and life experiences.
Our counselor helped us start the journey of selfdiscovery by asking us great questions: what we felt,
why we felt it, where those feelings came from, and
how we responded to life when things didn’t go our way.
It’s this journey that we are still on and now invite
you into. This book will help move you away from your
insecurities into a place of confidence because of
your willingness to become self-aware. We want you
to dig deep--what you put in is what you get out.
We’ve marked the journey for you with questions, but
it’s up to you to find time to take the journey.
It’s funny because we still occasionally argue about
being on time and being late, but at least we know why
it’s an issue. Our goal is that you would recognize that
you have room for improvement because individuals
who practice self-discovery are more aware, and selfaware people tend to be healthier friends, co-workers,
parents, spouses, and siblings.

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WHAT IS SELF-DISCOVERY AND
WHY IS IT IMPORTANT?
Personal development has been a growing trend for many
years. More and more people are actively looking for ways
to improve their lives by having a better understanding of
who they are. Many people listen to podcasts, read books,
take online personality assessments, attend retreats, or go
to therapy so that they can become the best version of
themselves.
The self-discovery journey will help you uncover your
passions and guide you to identify your motivations and
drive. A life void of your passions and strengths is a life
without fun, joy, and fulfillment. You will get to dream
about what you want your future to be like and turn your
desires into real-life stories.
A huge part of personal growth is self-discovery and we
believe that it’s a lifelong journey of exploring your
thoughts, feelings, dreams, concerns, trauma, past
experiences, responses, and personality. It’s getting you
to know yourself better, on a more intimate level. We
are always changing and evolving which means that we
need to be constant learners of ourselves, requiring us to
be more aware.

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Becoming more self-aware will also help you discover what
you need and desire in relationships with your friends and
family. With these questions, you will learn which people
bring out the best in you and which bring out the worst.
You will begin to recognize which behaviors make you feel
insecure and which make you feel empowered. You will
discover how to evaluate your expectations of others and
what you want your relationships to look like moving
forward. Practicing self-discovery will help you feel more
confident with and around the people you come across
every day.
Self-discovery gives you a chance to heal from past traumas
and experiences that you’ve been holding onto. Life dishes
up many hardships like illness, death, abandonment, and
heartbreak. Every one of those hurts becomes personal.
While shining light on your past can be very emotionally
draining, it also starts the process of forgiveness and
healing, which you both need and deserve.

WHY DO SO MANY STRUGGLE
WITH SELF-DISCOVERY?

The biggeset hurdle is time. We move at such a pace where
our schedules are filled to the brim, leaving no room for
self-care. Many people move through the motions of

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everyday life without ever stopping to check in with
themselves to see what’s working or how they’re feeling.
Another common thing that gets in the way of selfdiscovery is fear. Fear of the unknown and fear of realizing
that you’re in a toxic relationship. There’s fear of having to
change unhealthy behaviors and fear of going back to
painful memories. There’s fear of disappointment and fear
of failure. There’s fear of exposing your actions and choices
from the past and there’s fear of shedding light on your
thoughts that you feel shame around.
And lastly, oftentimes people have a desire to become
more aware but don’t have the tools, resources, or support
that they need. This is exactly why we wrote this book
and are so glad you picked up a copy. You’re putting aside
your fears, taking the time, and now have a practical tool
to help guide you on this journey of self-discovery.

OUR TOP TIPS FOR MAKING THE
MOST OF THIS BOOK

Tip #1
There are no right or wrong answers. With 7 billion people
in this world, we’re all uniquely made with different
upbringings and personalities and there’s no shame in

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that. Your answers reveal how you feel and what you think
in a given moment. You may ask yourself the same questions
years later and answer differently. Self-discovery isn’t
effective when you worry about how your response sounds
compared to others. We’re all on our own journey of
trying to learn more about who we are, why we do what
we do, and why we think the way we do.
Tip #2
Stay away from minimizing or avoiding pain. A common
survival technique is to stuff away any memory that was
painful (or shameful) by placing it in a box that we seal up
and put away in our attic never to be looked at again. The
problem with this is that the feelings attached to that
memory will eventually bleed out, usually at an unexpected
time and often in an unhealthy way. Stay away from
thinking things like, “It wasn’t that bad compared to others,”
or “I don’t want to bring it up or I’ll open the flood gates.”
Part of self-discovery is leaning into painful experiences to
learn more about how you handled it and how it changed
your view of yourself and others.
Tip #3
Get curious. The people who “master” self-discovery are
those who aren’t afraid to get curious as to why they think,
feel, and do what they do. Getting curious shows that you
desire to know yourself on a deeper level and that you

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want to be an emotionally aware and healthy person.
Getting out of your comfort zone can be draining and
overwhelming at times, but remember to keep making your
emotional and mental health a priority.
Tip #4
Don’t be your worst critic. It’s easy to become the
harshest judge of your life choices, taking away from your
opportunity to grow emotionally. Have you made mistakes?
Of course you have! Because we’re all imperfect, messy
people who struggle with insecurities, pride, and
selfishness. Making yourself feel bad for a choice you’ve
made will only hold you back from moving forward. So,
if at any point you notice that you’re criticizing yourself
and your answers, say any of these statements to yourself:

“Attempting to do this took courage and I’m proud
of myself for trying.”
“I am capable and strong and I will get through this.”
“I can learn from this situation and grow as a person.”
“This was an opportunity for me to learn more about myself
so I can change my future.”

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Tip #5
Take your time and put away distractions. Opening this
book up minutes before you have a big work meeting or
when your kids are tired and hungry is probably not the
best idea. This book is not about finishing in record time
or rushing through each question as if checking off your
weekend to-do list. Self-discovery requires time, patience,
and an open mind to really think, process, and meditate
on your experiences.
Tip #6
Use the ‘Feelings Words List’ often. The questions in this
book are going to ask about how you feel and we encourage
you to expand your emotional vocabulary by using our
handy and convenient Feelings Words List on page 195.
It might be easy at times to answer certain questions
without really getting into it. Don’t be afraid to dive into
the feelings that come up as you share your answers. And
if you don’t know how you feel about a topic or question,
don’t be afraid to explore that either (more on this later).
Tip #7
Have fun! Life is hard enough and self-discovery should also
be fun and bring joy and laughter to your life. Consider
the time you’re spending on yourself as a gift. Each time
you open up this book and answer a question, smile
knowing that you are becoming a smarter, more confident,
happier person.

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I HAVE NO ANSWER TO THE
QUESTION. NOW WHAT?

Here you are, taking time to explore and strengthen
your emotional health. You read a question and nothing
comes to mind. So you take a deep breath hoping that
something will come up, but nothing. It’s okay to not
recall past memories or specific feelings about a certain
topic. Our advice is to skip the question and go to the
next one. Mark each question you skip so that you can
come back to it on a different day when you have more
time, have processed the question on your own, or are
in a different headspace.
Be aware that if you have a lot going on personally
or professionally, whatever you are going through may be
the reason you feel emotionally or mentally stuck. Even
the idea of engaging in conversations around selfdiscovery can be overwhelming and cause stress. If that’s
what you’re feeling, we recommend setting aside time to
rest and reset. Designating time for self-care each day will
help you make the most of your self-discovery journey.
A walk or run, a kid-free cup of coffee, a long shower or
a few chapters of that book you picked up months ago-a little bit can go a long way. Remember, this is a journey,
not a race, and we hope you’re in it for the long haul.

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There are questions that get very specific about sexuality,
politics, religion, racism, and other hot topics. If these
questions feel big to you or this is the first time you’re
approaching the subject, that’s ok. Start with where you’re
at, answer as best as you can, and consider circling back
when you’ve had more time to process the question or
topic. We encourage this! When done in the spirit of
learning and understanding, these potentially sticky
conversations can lead to incredible personal growth.
Bonus tip: Not everyone feels inspired by sitting down,
reading a question, and then writing down their response.
While there are dozens of ways to process and answer
these questions, consider thinking and walking. Think of
it like active meditation centered around a reflective
question. Many people we’ve worked with have found
success taking a walk in nature and repeating the question
a few times out loud as they process. You could do this
alone or with a friend, family member, confidant, etc.

Many of the questions you’ll find in this book address
topics you may have never asked yourself. Going there
may bring up new emotions that will make you feel
uncomfortable. These emotional triggers are revealing
aspects in your life that are unresolved or frustrating to
you. Some may be traumatic and even confusing, but the
good news is that you’re doing the healthy thing by
drawing them out so you can start to process and heal.
If you experience a trigger when answering one of the
questions, here are some suggestions:





FEELING TRIGGERED?
A trigger is an emotional wound that reminds you of
something you believed to be unfair or unjust in your life.
For example, if your parents neglected your emotional
needs, this can cause you to feel triggered because you
feel that was unfair for them to treat you that way.

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Take deep breaths. Slow and controlled breathing
forces oxygen to the brain and helps calm nerves.
Get active by taking a walk, going to the gym or for a
swim and get your heart pumping. Our bodies produce
endorphins when we move, which can elevate your
state of being.
Start journaling. Don’t limit yourself to what you
should or should not be writing. Journaling is a
proactive way to deal with anxiety and triggers and
can help you get what you’re feeling and thinking out
of your mind and onto paper. When you are writing,
don’t edit or worry about grammar, just be as honest
as possible about what you’re experiencing.
Call a safe friend, mentor, pastor, or your counselor.
Oftentimes we need to verbally process what we’re
going through when we feel emotionally triggered.
Allowing someone who cares about you into that space

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is extremely therapeutic.
If you feel rushed or are around people, it’s ok to
give yourself an adult time-out and go back to the
triggering question at a later time when you have more
space and capacity to dive in.

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SELF-DISCOVERY
IS A JOURNEY OF
QUESTIONING
YOURSELF.

JANUARY

1

1

4

JANUARY 1

JANUARY 4

Do you think that a sense of humor is
essential to a healthy relationship?
Why or why not?

What motivates you when you’re feeling
challenged or stuck?

JANUARY 2

2

JANUARY 5

How can you engage with your
local community in a way that you
are not currently?

Did your family model healthy boundaries
growing up? Why or why not?

JANUARY 3

3

JANUARY 6

If you could write one message on all of
the billboards all over the world for one day,
what message would you choose?

Is it difficult for you to accept compliments
from other people? Why or why not?

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5

6

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JANUARY 7

7

JANUARY 10

Growing up, did you feel safe and secure
most of the time? Why or why not?

What would you change about your
money habits right now and why?

JANUARY 8

8

JANUARY 11

Do you have a desire to learn more about
yourself? Why or why not? What steps are
you taking to become a better person?

What is one behavior that you never
tolerate no matter who it’s coming from?

10

11

JANUARY 9

9

JANUARY 12

What is one thing that people do
not notice about you right away that
you wish they would?

When was the last time you felt
vulnerable? Who were you with and how did
you handle the situation?

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12

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16

JANUARY 13

13

JANUARY 16

What are two of your favorite memories
with your family as a kid? What makes those
memories stand out to you?

Did you ever have an honest lesson about anatomy,
learning about genitalia and its function? If so, who
was the person who taught you? Was it accurate?
Was it harmful or confusing?

JANUARY 14

14

JANUARY 17

Have you ever felt judged, ignored, or
mistreated because of your race? Explain.

Which values do you believe are the
most important to keep in mind when it
comes to voting?

JANUARY 15

15

JANUARY 18

What is one of the nicest things someone
has said to you? How did hearing it make
you feel and why?

Which quote that you’ve read
inspires you and why?

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17

18

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19

22

JANUARY 19

JANUARY 22

Do you express your gratitude
and if so, how often?

What would be your advice to someone
who has lost hope?

JANUARY 20

20

JANUARY 23

Is there anyone in your life you’re
holding a grudge against? What do you
hope happens?

Do you like surprises or do they
unsettle you and why?

JANUARY 21

21

JANUARY 24

What was your first job and
what did it teach you about money
and work ethic?

How much time do you spend on your phone?
Are you content with the amount of time or
do you need to set healthier boundaries?

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23

24

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JANUARY 25

25

JANUARY 28

What emotional baggage do you carry with
you as a result of your childhood?

How do you handle confrontation with
those you care about?

JANUARY 26

26

JANUARY 29

How does stress affect your body?
How can you address this issue?

What is one area in your life that you are
the most proud of and why?

JANUARY 27

27

JANUARY 30

Geographically, where would you like to live
10 years from now and why?

If you were to start a nonprofit organization,
what need would it solve in your community
or in the world?

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28

29

30

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31

JANUARY 31

How important is it that you
always look your best and why?

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STRIVE FOR
PROGRESS, NOT
PERFECTION.

2
FEBRUARY

4

1

FEBRUARY 1

FEBRUARY 4

Who is the first person that comes to mind
if you were asked about the greatest hurt in
your life? What thoughts come up when you
think about that person?

Do you take the time to reflect on
what is happening in and around you?
Why or why not?

5

2

FEBRUARY 2

FEBRUARY 5

Do you think that you are easily influenced
by others? Why or why not?

When it comes to your career, do you
consider yourself someone who is confident?
Why or why not?

6

FEBRUARY 3

3

FEBRUARY 6

Have you ever heard stories about anything
interesting that happened during or soon after
your birth? Explain.

When someone you care about wrongs you,
are you someone who thinks about revenge or
forgiveness or a little of both?

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10

7

FEBRUARY 7

FEBRUARY 10

Who is one famous person, dead or alive,
that you feel like you have the most in
common with and why?

How many close friends do you want and why?

11

FEBRUARY 8

8

FEBRUARY 11

When was the last time you cried?
What did you cry about?

What is the value of practicing hobbies?
Do you have a hobby that you love and never want to give
up? Is there a new hobby you’d like to try?

FEBRUARY 9

9

FEBRUARY 12

Do you consider yourself a sensual person?
Why or why not?

How do you prefer to celebrate your
birthday and with whom?

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12

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16

13

FEBRUARY 13

FEBRUARY 16

How do you deal with negative people?
Do you think your actions towards them
are helpful or harmful? Think of a specific
example to guide you.

Do you enjoy small intimate gatherings with a
couple of close friends or do you prefer larger
events like parties? Explain.

17

14

FEBRUARY 14

FEBRUARY 17

What is the kindest thing you have
ever done for someone?

Did you find it easy to get along
with your peers when you were growing up?
Why or why not?

18

15

FEBRUARY 15

FEBRUARY 18

What is your biggest pet peeve?

In your life, what has been the
biggest blessing in disguise?

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22

FEBRUARY 19

19

FEBRUARY 22

If you had no deadlines or other
obligations, what project or task would
you focus on right now?

Do you feel like you live with purpose
and are intentional about the choices
you make? Explain.

FEBRUARY 20

20

FEBRUARY 23

Who makes you feel anxious? What do they
do that causes you anxiety?

Growing up, did you ever feel let down
by an adult? Explain.

FEBRUARY 21

21

FEBRUARY 24

What are some of the mistakes you made in
past romantic relationships that you regret?

What comes to your mind when you
think about God?

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23

24

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28

FEBRUARY 25

25

FEBRUARY 28

Do you have any toxic friends in your life?
How can you deal with this?

What is your favorite Olympic
sport and why?

26

FEBRUARY 26

In this last month, did you give yourself the
time and resources needed to accomplish your
goals? Why or why not?

27

FEBRUARY 27

Do you believe that a certain amount of
money should be set aside for pleasure, even if
you’re on a tight budget? Explain.

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T H E R E I S A LWAY S
SOMETHING TO
B E G R AT E F U L F O R
WHEN YOU ALLOW
YOURSELF TO BE
F U L LY P R E S E N T I N
T H E M O M E N T.

3
MARCH

4

MARCH 1

1

MARCH 4

Have any past experiences shaped the fears
and anxieties you have today? Explain.

Do you lack energy? If so, what do
you think is the cause?

MARCH 2

2

MARCH 5

Do you consider yourself an open-minded or
closed-minded person? Explain.

Do you know which unhealthy behaviors
trigger you and why? Examples: interrupting,
eye-rolling, closed-mindedness, laziness, etc.

5

6

MARCH 3

3

MARCH 6

Have you ever loved someone who didn’t love
you back? How did that make you feel?

When was a time when you were generous with
either your money or time? Explain.

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10

7

MARCH 7

MARCH 10

What is something you really did not want to
do that turned out to be a terrific experience?

Who do you feel safe to be yourself with?
Is there any way you can spend more time
with this person/these people?

11

8

MARCH 8

MARCH 11

What are your thoughts about plastic surgery?
Do you think you will ever make any cosmetic
changes to your body? Why or why not?

Is there anything in your life that makes you
feel ashamed? Explain.

12

9

MARCH 9

MARCH 12

What kind of person do you want to be five
years from now and why?

At what age do you think it’s appropriate to
teach children about sex and their anatomy?
Explain.

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16

MARCH 13

13

MARCH 16

Do you believe what you read and see in the
news, or do you question where information is
coming from and the media’s true agenda?

What is your history (past or present) with
health issues? Are you concerned about
having health issues in your future? Explain.

MARCH 14

14

MARCH 17

If you could pick one year of your life to do
over, which would it be and why?

What was your favorite holiday
as a kid and why?

MARCH 15

15

MARCH 18

Have you ever been called a workaholic by
your friends or family members? What are
signs that someone is a workaholic?

Which person in your life is your exact
opposite? What makes you so different
from one another?

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17

18

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22

MARCH 19

19

MARCH 22

When was the last time you laughed out loud?
Who were you with and what happened?

What is the best financial decision you made
in the past? What made it so great?

MARCH 20

20

MARCH 23

Did your mother, father, or other family
members abuse each other or you in any way?
Examples: sexual, emotional, physical, etc.

Do people often ask for your help with
something specific? What is that thing and
why do you think they ask you and not
someone else?

23

24

21

MARCH 21

MARCH 24

Would you ever be willing to go to counseling
if you or the people in your life felt like you
needed it? Why or why not?

What is the worst piece of advice
anyone has ever given you?

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28

25

MARCH 25

MARCH 28

Have you ever experienced any sexual
trauma in your childhood or adult life? If so,
have you reached out to someone for help?
Why or why not?

What is your go-to response when someone
you care about hurts your feelings?

29

MARCH 26

26

MARCH 29

Which political issues do you
care about, if any?

Are you someone who likes to set goals?
Why or why not?

MARCH 27

27

MARCH 30

Have you ever heard the story of how
your parents met? If so, what stands
out to you about it?

Have you been emotionally lazy in any of
your relationships? If so, have you apologized?
Why or why not?

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30

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31

MARCH 31

If you could change one thing about the way
you looked, what would it be and why?

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Y O U M AY N O T B E
ABLE TO CONTROL
E V E R Y S I T U AT I O N
AND ITS OUTCOME,
BUT YOU CAN
CONTROL YOUR
AT T I T U D E A N D H O W
Y O U D E A L W I T H I T.

4
APRIL

4

1

APRIL 1

APRIL 4

Do you think telling the truth is always right,
even if it hurts someone’s feelings? Explain.

Do you feel comfortable agreeing to
disagree with your friends and family?
Why or why not?

5

APRIL 2

2

APRIL 5

What are two positive lessons that your
parents taught you as a child?

Are you proud of your job and what you
do for work? Why or why not?

APRIL 3

3

APRIL 6

Are vacations an important part of your yearly
planning? Why or why not?

Do you think you are more of a thinker
or a feeler or a little of both? Do you wish
you were different?

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6

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10

7

APRIL 7

APRIL 10

What does self-care look like to you?
How well do you incorporate self-care
into your life?

Why do you think it is important for children
and adults to have role models in their lives?

11

APRIL 8

8

APRIL 11

What do you do really, really well?
Does it come naturally or have you
had to work hard at it?

If you had to choose to live without
one of your five senses, which one would
you give up and why?

APRIL 9

9

APRIL 12

In your opinion, what is something
that never ends well?

In regards to past romantic relationships,
what would you do differently if you could do
things all over again?

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12

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16

13

APRIL 13

APRIL 16

Do you have a difficult time setting
limits and boundaries with your family?
Why or why not?

If you got something tattooed on your body,
what would you choose and why?

17

14

APRIL 14

APRIL 17

When you go somewhere new, do you
have an organized plan already mapped out
before you go or do you like to be spontaneous?
Do you like this about yourself? Explain.

Which of your friends do you like spending
time with the most and why?

18

APRIL 15

15

APRIL 18

How important is it for you to live
debt-free and why?

What is something you totally geek out
about and are proud to say that you do?

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22

19

APRIL 19

APRIL 22

Are you afraid of death? Why or why not?

What is your favorite way to relax
when things are chaotic?

23

20

APRIL 20

APRIL 23

Has anyone ever made you feel
uncomfortable sexually? If so, what happened
and how did you feel?

What goal have you been putting off
lately and why?

24

APRIL 21

21

APRIL 24

Are you someone who gets easily offended by
others? Why or why not?

Would you ever walk up to a stranger and start
a conversation? Why or why not?

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28

25

APRIL 25

APRIL 28

What book has had the greatest impact
on your life and why?

If you stayed at the same job for the next
10 years, would you be okay with that?
Why or why not?

29

26

APRIL 26

APRIL 29

Growing up, did your parents listen to your
ideas, fears, stories, and feelings? Either way,
how did that make you feel?

Why do you think so many couples experience
infidelity and why do you think people cheat?

30

APRIL 27

27

APRIL 30

What is the best part and the worst part about
getting older?

What is one personality type that you
typically don’t get along with and why?

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NEVER BE AFRAID
OF CHANGE.
Y O U M AY L O S E
S O M E T H I N G G O O D,
B U T Y O U M AY G A I N
SOMETHING EVEN
BETTER.

5
M AY

4

1

MAY 1

MAY 4

What do you enjoy about being out
in nature and why?

What are the qualities of a good listener?

5

2

MAY 5

MAY 2

When someone you care about is upset, what
is the first thing you do? Examples: give them
a hug, listen, help fix the problem, give them
time alone, etc.

Is there something you need to give up or cut
down on and why? Examples: smoking, drinking,
TV, phone usage, junk food, etc.

6

3

MAY 3

MAY 6

Is there anyone you work with that makes you
feel jealous? Why or why not?

What is something you want to do in the next
few months to improve your emotional and/or
mental health?

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10

MAY 7

7

MAY 10

What do you need to do to feel a sense of
accomplishment in life?

Were any of your past romantic relationships
unhealthy or toxic? Explain.

MAY 8

8

MAY 11

What is one failure that has turned
into a great lesson?

What do you believe is the purpose of sex
in a romantic relationship?

MAY 9

9

MAY 12

Growing up, when you got into trouble, how
did your parents discipline you?

Are you someone who can stay relatively calm
under pressure? Explain.

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11

12

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16

13

MAY 13

MAY 16

If you could be a photographer for a day, what
would you take pictures of and why?

When you don’t forgive someone who has
hurt you, how does it affect you? How does it
affect the other person?

17

14

MAY 14

MAY 17

How important is it to you to share the same
religious beliefs with your friends, family, and
romantic relationships? Explain.

Have you ever felt judged, ignored, or
mistreated because of your gender? Explain.

18

MAY 15

15

MAY 18

When and how did you begin your financial
life independent from your parents?

How did you find out there was no Santa
Claus, Easter Bunny, or Tooth Fairy?

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22

19

MAY 19

MAY 22

What do you think is the first
impression people have meeting you?
Do you think it’s accurate?

Have you ever made a decision that you regret?
What happened?

23

20

MAY 20

MAY 23

When you were a teenager, did you
have a solid group of friends or were you
more of a loner?

Have you ever set an unrealistic goal?
What happened?

24

MAY 21

21

MAY 24

In your opinion, what is the best way a person
can spend their free time?

What do you wish you could tell
yourself five years ago?

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28

25

MAY 25

MAY 28

Do you think you are reliable in relationships
with others? Why or why not?

Have you ever shown a stranger
generosity? If so, what did you do and
how did it make you feel?

29

26

MAY 26

MAY 29

Are you someone who is usually early, on
time, or late? Do you like this about yourself?

What activity in your life brings you joy?

30

MAY 27

27

MAY 30

Do you ever struggle with understanding why
certain people feel the way they feel? Explain.

Why do you think that some people struggle
with their sexual identity?

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31

MAY 31

Growing up, when you got hurt or felt scared,
how did your parents comfort you?

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TRUE SELFDISCOVERY
BEGINS WHERE
YOUR COMFORT
ZONE ENDS.

6
JUNE

4

JUNE 1

1

JUNE 4

Growing up, were you someone who enjoyed
attending school or did you dread it? Explain.

What is one financial decision you made in the
past that you regret?

JUNE 2

2

JUNE 5

Does thinking about the future scare
or excite you? Explain.

How important is it for you to be involved in
your local community and why?

JUNE 3

3

JUNE 6

If your past boyfriends/girlfriends listed
your most negative characteristics, what
would they say?

When it comes to your physical health,
what is one thing you can work on this year?
What can you do to make it happen?

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5

6

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10

JUNE 7

7

JUNE 10

Do you make decisions based on how you
feel? Why or why not?

If you could talk to your teenage self,
what would you say?

JUNE 8

8

JUNE 11

Have you ever witnessed anything in
the past that you wish you hadn’t?
What happened?

Do respect and trust have to be earned in
relationships? Why or why not?

11

12

9

JUNE 9

JUNE 12

Would you rather have a housekeeper
or a chef and why?

Think about your first sexual experience.
What sort of feelings did you have? Examples:
safe, loved, abused, awkward, painful,
respected, confusing, etc.

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16

JUNE 13

13

JUNE 16

Do you believe that your parents did the best
they could raising you? Why or why not?

What would you do with ten million dollars to
impact the most amount of people?

JUNE 14

14

JUNE 17

Do you ever struggle with oversharing on
social media? Why or why not?

If you could change anything about politics,
what would it be and why?

JUNE 15

15

JUNE 18

Are you more of a details person or a big
picture person? Explain.

Do you think of yourself as someone who is
emotionally competent? Why or why not?

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17

18

99

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22

JUNE 19

19

JUNE 22

Do you ever feel taken advantage of by the
people in your life? Explain.

Do you feel comfortable asking family or
friends for money? Why or why not?

JUNE 20

20

JUNE 23

Do you remember a time when you
laughed harder than you’ve ever laughed?
What happened?

When conflict arises in relationships,
do you tend to want to face it head-on or
avoid it? Explain.

JUNE 21

21

JUNE 24

Are you a rule breaker or a rule follower?
Have you always been this way? Explain.

What kind of legacy do you want to
leave behind?

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23

24

101

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28

JUNE 25

25

JUNE 28

What is one specific goal you can work
towards this week and what is the first step
you will take to make it happen?

Think about your first crush. Were your
feelings towards him/her intense or more
mild? Explain.

JUNE 26

26

JUNE 29

When you feel hurt by someone you love, how
do you handle that feeling of pain?

In your opinion, what qualities does a healthy,
romantic relationship practice?

JUNE 27

27

JUNE 30

On a scale of 1-10, how much stuff do you
tend to keep around (1= a minimalist and 10=
a hoarder)? Explain.

Who is your favorite musician, singer, or
band? What do you love about their music?

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29

30

103

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YOU CAN HONOR
Y O U R PA S T A N D
HONOR WHO YOU
ARE BECOMING
F R O M I T.

7
J U LY

4

1

JULY 1

JULY 4

What are some negative thoughts you have
about yourself? When did they start?

Who are your core friends and how
much time do you think is important to
spend with them?

5

JULY 2

2

JULY 5

What is one goal you have for this year that
you want to accomplish?

What are some highlights of your
adolescent years?

JULY 3

3

JULY 6

In your opinion, which characteristics make
someone reliable?

If you see a homeless person on the side of
the street, do you think you should give him/
her money? Why or why not?

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6

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JULY 7

7

JULY 10

10

What are some of your talents? Are you
utilizing them? How can you use them more?

What are some technology boundaries you
want to have in your life and why?

JULY 8

8

JULY 11

If you became a teacher for a day, what
subject would you feel most confident
teaching about and why?

Who is someone you look up to as a mentor
or role model and why?

11

JULY 9

9

JULY 12

Do you consider yourself a patient person
often, sometimes, or rarely? When do you feel
the most impatient?

When was the first time you felt like you were
in love with another person? What happened
in that relationship?

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12

109

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16

13

JULY 13

JULY 16

If you could meet anyone, dead or alive, who
would it be and why?

Has anyone every gossiped about
you that you’re aware of? If so, how did
it make you feel?

JULY 14

14

JULY 17

Do you consider yourself more of a risktaker or someone who plays it safe? Have you
always been that way? Explain.

Do you struggle with comparing yourself to
others? Who do you compare yourself to and
how does that impact you?

JULY 15

15

JULY 18

What is your first childhood memory?

In your opinion, what does it look like to be
financially prepared for an emergency?

110

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17

18

111

- 365 S E L F - D I S COV E RY Q U E S T I O N S

22

19

JULY 19

JULY 22

When things change all of the sudden, do you
struggle to be flexible? Why or why not?

When you argue with co-workers,
friends, or family members, what do you
do to try and resolve it?

23

JULY 20

20

JULY 23

What is one country you would like
to travel to and why?

How would you feel if your life looked exactly
the same one year from now?

JULY 21

21

JULY 24

Do you tend to think back on the choices
you made and wonder if you could have done
something different? Why or why not?

Do you remember your first time viewing pornography?
What did you feel physically or emotionally?

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24

113

- 365 S E L F - D I S COV E RY Q U E S T I O N S

28

25

JULY 25

JULY 28

What is one personality type that you’re
typically drawn to? Explain.

What are your family’s views on
race and ethnicity? Do you agree with
their views? Why or why not?

29

JULY 26

26

JULY 29

When was a time that you felt creative? What
ended up happening?

Do you feel like you can be assertive with
others? Why or why not?

JULY 27

27

JULY 30

When was the most difficult time of your life
and how has that affected you?

What are two tangible career goals that you
can set for yourself this coming month?

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30

115

- 365 S E L F - D I S COV E RY Q U E S T I O N S

31

JULY 31

In this last month, what is one thing you
wished you hadn’t committed to and why?

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T R E AT Y O U R S E L F
WITH LOVE AND
RESPECT AND YOU
W I L L AT T R A C T
PEOPLE WHO SHOW
YOU LOVE AND
R E S P E C T.

8
AUGUST

4

AUGUST 1

1

AUGUST 4

What is something about yourself or your life
that might surprise others to learn?

If you could choose any career other than
what you do now, what would it be and why?

AUGUST 2

2

AUGUST 5

What were some of the challenges you faced
during your adolescent years?

Do you consider yourself a physically
affectionate person? Why or why not?

AUGUST 3

3

AUGUST 6

Do you believe in life after death? If so,
what do you think it’s like?

Do you ever struggle with blaming others for
your mistakes? Why or why not?

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5

6

121

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10

AUGUST 7

7

AUGUST 10

What causes or movements are you passionate
about and why?

When you think about your future, what is
one thing that worries or concerns you?

AUGUST 8

8

AUGUST 11

How would you rank all the priorities in your life:
work, family, significant other, friends, hobbies,
church, self, school, etc.? Does your ranking reflect
the amount of time you spend on each?

What memories do you have of your
family having fun together?

11

12

AUGUST 9

9

AUGUST 12

What is the difference between failing
and being a failure?

Do you have any fears of abandonment?
Why or why not?

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16

AUGUST 13

13

AUGUST 16

What is your most selfish character
trait or habit? What could you do to
change this behavior?

Overall, do you believe people tend to be
more generous or more stingy with their
money? Explain.

AUGUST 14

14

AUGUST 17

What is something you did or didn’t do today
that you would love to do every day?

Have you ever been jealous of someone or
something in your life? Explain.

AUGUST 15

15

AUGUST 18

Do you tend to be more of an internal
or verbal processor? Have you always
been this way? Explain.

What are ways you prefer to spend quality time
with the people in your life? Examples: parties,
one-on-one, exercising, having dinner together, etc.

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17

18

125

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22

19

AUGUST 19

AUGUST 22

Have you been minimizing or
stuffing away any memories from your past?
If so, what are you afraid of feeling if you face
those memories?

When you make mistakes, are you hard
on yourself or do you give yourself grace?
Explain.

23

AUGUST 20

20

AUGUST 23

What are your thoughts about mental illness?
Do you think they are treatable?

In your opinion, what makes someone
a good sexual partner?

AUGUST 21

21

AUGUST 24

Are you someone who is self-motivated
or do you need accountability? What makes
you this way?

In your opinion, what does the world need
more of and why?

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24

127

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28

AUGUST 25

25

AUGUST 28

If you had an opportunity to go back to
school, what subjects would you want to learn
about and why?

What is one small change you can
make this week that will help you feel in
control of your life?

AUGUST 26

26

AUGUST 29

Do you ever feel down and sad for long
periods of time? Explain.

What does being financially comfortable
look like to you?

AUGUST 27

27

AUGUST 30

Were you aware of any feuds or family
grudges growing up? Explain.

In your opinion, what’s the difference between
an insincere and a sincere apology?

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29

30

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31

AUGUST 31

When it comes to making
life-changing choices, do you use your
head or your heart and why?

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9
SEPTEMBER

L E T G O O F W H AT
YOU CANNOT
CHANGE AND
F O C U S O N W H AT
YOU CAN.

4

SEPTEMBER 1

1

SEPTEMBER 4

Do you consider yourself an animal lover?
What is your favorite kind of animal?

What is the biggest challenge you face when
you try to set personal goals?

SEPTEMBER 2

2

SEPTEMBER 5

What excites you about your job and why?

Do you get embarrassed easily?
Why do you think that is?

5

6

SEPTEMBER 3

3

SEPTEMBER 6

What is one bad habit you need to break, but
can’t seem to change the behavior? How long
has this been a habit?

Who is someone from your childhood that
showed you a lot of love? What is an example
of what he/she did that made you feel loved?

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10

7

SEPTEMBER 7

SEPTEMBER 10

In the last few weeks, did you take
time to practice self-care, rest, and fun?
Why or why not?

What do you miss about being a kid and why?

11

8

SEPTEMBER 8

SEPTEMBER 11

How does it feel when someone you care
about lies to you?

Do you ever pray? If so, how often?

12

9

SEPTEMBER 9

SEPTEMBER 12

On a scale from 1-10, what is the
highest level of pain you have ever been in?
What happened?

Do you consider yourself a generous person most
of the time, some of the time, or rarely? Explain.

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16

SEPTEMBER 13

13

SEPTEMBER 16

Do you believe crying is a healthy
outlet for negative and positive emotions?
What makes you cry?

What is your favorite way to learn? Examples:
listen to podcasts, read, watch documentaries,
go to seminars, take classes, etc.

SEPTEMBER 14

14

SEPTEMBER 17

Do you feel like you have realistic
expectations of others? Why or why not?

Do you feel like you can confide
in your friends about important issues?
Why or why not?

17

18

SEPTEMBER 15

15

SEPTEMBER 18

Why do you think human sex trafficking has
become a worldwide issue?

When you were a teenager, did you feel more
insecure or more confident? Explain.

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22

19

SEPTEMBER 19

SEPTEMBER 22

Why do you believe some people get stuck in
their ways, never changing their behaviors?

When it comes to your emotional
health, what is one thing you want to focus
on this month and why?

23

SEPTEMBER 20

20

SEPTEMBER 23

If you could invent an app, what would it do?
What would you call it?

If you could change anything about religion,
what would it be and why?

SEPTEMBER 21

21

SEPTEMBER 24

When you face challenges, do you feel
overwhelmed and hopeless or empowered and
excited? Explain.

Do you ever have mood swings or moments
when you tend to be more emotional? Is it
triggered by anything specific?

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24

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28

25

SEPTEMBER 28

SEPTEMBER 25
Is social media bringing you closer to your friends
and family or making you more isolated and alone?
Explain.

What is the difference between
someone who complains and someone
who wants to see change?

29

26

SEPTEMBER 26

SEPTEMBER 29

When you are going through a difficult time, who
can you go to that will give you objective feedback to
help you process what you are going through? Is there
something you need to discuss with that person now?

What do you love about your
personality and why?

30

27

SEPTEMBER 27

SEPTEMBER 30

At what age do you want to
retire and what type of lifestyle do you
want to lead in retirement?

What are your family’s views on politics?
Do you agree with their views? Explain.

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HAPPINESS IS
JUST A WORD Y O U C R E AT E T H E
DEFINITION.

OCTOBER

10

4

1

OCTOBER 1

OCTOBER 4

When do you feel the most stubborn and why?

What is something you always love doing, even
when you are tired or overwhelmed?

5

OCTOBER 2

2

OCTOBER 5

How do you feel about your work schedule
last month? Was it too busy, not busy enough,
or just right? Explain.

When you go to your family’s house, is there
something they do that makes you feel safe
and loved? Explain.

OCTOBER 3

3

OCTOBER 6

Have you ever taken the time to
stand in front of a mirror and explore
your body? What are your thoughts and
feelings about doing this?

When you think about the future, what is one
thing that excites you and why?

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6

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10

7

OCTOBER 7

OCTOBER 10

Are you typically someone who is quick
to accept apologies or do you hold grudges?
Why do you think that is?

If you were the richest person in the world,
what would you do with your time and money?

11

8

OCTOBER 11

OCTOBER 8
Do you tend to meet others’ needs
before your own? Explain.

When do you feel the most insecure? Who are
you with and what is going on?

12

9

OCTOBER 9

OCTOBER 12

When is a time in your life when you felt
misunderstood by someone? What happened?

Growing up, were you ever left out, bullied,
or teased by your peers or family members?
How did that make you feel?

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16

13

OCTOBER 13

OCTOBER 16

If you had to be on a reality TV show, which
one would you chose and why?

How would your best friend describe you?
Do you think you’d agree with his/her
perspective?

17

14

OCTOBER 14

OCTOBER 17

When have you given up on something or
someone? Why did you give up?

What are some things that stress you out
during the holiday season and why? Is there
a way you can better manage or prevent this
stress from happening?

18

15

OCTOBER 15

OCTOBER 18

What is the most amazing true story
you have ever heard?

What is your favorite season and why?

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22

19

OCTOBER 19

OCTOBER 22

How often do you consider how your actions might
affect other people before doing something? All of
the time, sometimes, or rarely?

What is the biggest challenge you face when
you try to set career goals?

23

OCTOBER 20

20

OCTOBER 23

What are your thoughts about
one-night stands?

Is there anything you need to change or give
up that would help your relationships thrive?

OCTOBER 21

21

OCTOBER 24

How often do you need alone time?
How much alone time is too much alone time
for you and why?

If you knew you couldn’t fail, what
would you do?

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24

153

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28

25

OCTOBER 25

OCTOBER 28

Do you believe that implementing boundaries
into your life is a form of self-care?
Why or why not?

What are some behaviors that are
unacceptable during an argument?

29

OCTOBER 26

26

OCTOBER 29

Are you currently taking anything, or anyone,
for granted? Explain.

Do you think that the more money someone
has, the happier they are? Why or why not?

OCTOBER 27

27

OCTOBER 30

When you were a child, were you
complimented or shamed about your looks?
Explain.

Do you find yourself distracted easily? Why?

15 4

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30

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31

OCTOBER 31

What is a new holiday tradition you would
like to start this year?

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PAY M O R E
AT T E N T I O N
TO YOUR
INTENTIONS.

NOVEMBER

11

4

1

NOVEMBER 1

NOVEMBER 4

What is your number one financial priority
this month and why?

Have you ever made a bucket list of all the
things you want to do before you die? Either
way, what are some things on your bucket list?

5

2

NOVEMBER 2

NOVEMBER 5

When it comes to your family, have you ever
made excuses for their unhealthy behavior(s)?
Why or why not?

If you were president for the week, what is
one thing you would do differently?

6

NOVEMBER 3

3

NOVEMBER 6

What measures do you think our government
and society could do to help end racism?

Would you rather have nosy neighbors or
noisy neighbors and why?

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10

7

NOVEMBER 7

NOVEMBER 10

When have you dealt with a conflict
with someone else successfully? What
made it successful?

Would you rather win $50,000 or let your
best friend win $500,000 and why?

11

8

NOVEMBER 8

NOVEMBER 11

Have you ever felt scared or embarrassed to
bring up any questions you had regarding sex and
intimacy to your friends? Why or why not?

What is the most challenging thing
about your job and why?

12

NOVEMBER 9

9

NOVEMBER 12

How can you tell if someone is really listening
to what you’re saying?

What habits and behaviors do you
do when you feel sad?

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16

13

NOVEMBER 13

NOVEMBER 16

Which of your family members are you closest
to and why? Explain whether you think it’s a
healthy relationship or not.

How do your differences help balance out
your relationships with others in your life?

17

14

NOVEMBER 14

NOVEMBER 17

What are your views on and experiences
with meditation?

What are two areas of your life that you are
insecure about? What is something that you can
do to build more confidence in those areas?

18

15

NOVEMBER 15

NOVEMBER 18

Have your goals in life changed recently?
Why or why not?

How do your parents handle their money? Do
you think they set a good example
for you growing up?

16 4

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22

NOVEMBER 19

19

NOVEMBER 22

What is one characteristic you received from
your parents that you want to keep and one
you wish you could change?

Are you someone who believes that miracles
happen? Have you ever experienced or heard
of a miraculous story?

NOVEMBER 20

20

NOVEMBER 23

When it comes to alcohol, what do you think
is a healthy amount to drink and why?

Have you spent time reflecting on your past
to help you understand who you are today?
Explain.

23

24

21

NOVEMBER 21

NOVEMBER 24

Do you feel comfortable asking for help from
your friends and family when you feel unsure
of something? Why or why not?

Which do you think should have the final say
in decision making: logic or emotions? Explain.

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28

NOVEMBER 25

25

NOVEMBER 28

What is your favorite way to celebrate the
holiday season?

Do you view boundaries as more restrictive or
more protective? Explain.

NOVEMBER 26

26

NOVEMBER 29

When someone disrespects you, how do you
typically respond? Is your response healthy?

Which one of your friends is the most
opinionated? Do you butt heads or do you
enjoy hearing their opinions?

29

30

NOVEMBER 27

27

NOVEMBER 30

Do you ever find yourself minimizing your
feelings or the feelings of others? If so, why?

In this last month, do you think you spent
your free time wisely? Why or why not?

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WHEN THINGS
CHANGE INSIDE
O F Y O U, T H I N G S
CHANGE AROUND
Y O U.

12
DECEMBER

4

1

DECEMBER 1

DECEMBER 4

Do you ever struggle with communicating your needs in
relationships? Why or why not?

What is a charity or non-profit that you
would like to give financially to at some point
in your life and why?

5

2

DECEMBER 2

DECEMBER 5

What habits or addictions have been passed down in
your family from previous generations? How has that
impacted your life? Examples: alcoholism, mental
illness, drug abuse, etc.

In your personal life, are you more of a
realist or dreamer and why? Does it differ
in your work life?

6

DECEMBER 3

3

DECEMBER 6

In what specific instances have you acted
stubbornly? Do you think your stubbornness
helped or harmed the situation and why?

When you create boundaries in relationships,
do you have a hard time following through?
Why or why not?

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7

10

DECEMBER 7

DECEMBER 10

Do you believe in God? What does your
relationship with God look like?

Empathy is feeling with someone else. Overall,
do you consider yourself an empathetic person?
Why or why not?

8

11

DECEMBER 8

DECEMBER 11

Would you rather be poor and work at a job you
are passionate about or rich and work at a job
you absolutely cannot stand? Explain.

Do your friends and family members support
your goals? Why or why not?

9

12

DECEMBER 9

DECEMBER 12

Is there an argument that you’ve had with
someone that was never resolved? What can
you do to make it better?

In your opinion, is there anything that
should be sexually off-limits?

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16

DECEMBER 13

13

DECEMBER 16

What is a good thing happening in your life
right now? What makes it good?

To your best knowledge, how do other
people perceive you?

DECEMBER 14

14

DECEMBER 17

Who is the most generous person you’ve ever
met? Why do you think he/she is so generous?

In your opinion, what makes someone a loyal
friend? Would you consider yourself a loyal
friend? Why or why not?

17

18

DECEMBER 15

15

DECEMBER 18

What makes you angry and what do you do
when you feel angry?

What would you like said at your funeral?
How do you want to be remembered?

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17 7

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22

DECEMBER 19

19

DECEMBER 22

When you were a child and your parents got
angry, either with each other or with you, how
did it make you feel?

If you were given ten thousand dollars to
spend in the next 30 days, how would you
spend the money?

DECEMBER 20

20

DECEMBER 23

What are some activities or people that
make you feel young again?

What three things can you do regularly
to reduce stress in your life?

DECEMBER 21

21

DECEMBER 24

When making decisions, do you find yourself
being more impulsive or cautious and why?

What is the biggest way you’ve changed
since you were a child? In what way(s) are you
still the same?

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23

24

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28

25

DECEMBER 25

DECEMBER 28

What is the best gift you have ever received?
What made it so special?

Are you aware of any unhealthy or toxic behaviors that
you practiced in your family? Have you implemented
boundaries to protect yourself from getting hurt?
Why or why not?

29

26

DECEMBER 26

DECEMBER 29

What is something you want to do to improve
your physical health and why?

Do you always need to be in control?
How do you feel when you have no control
over a situation?

30

DECEMBER 27

27

DECEMBER 30

What one thing do you really want to
purchase but can’t afford?

Do you consider yourself more of a leader or
more of a follower and why?

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31

DECEMBER 31

Have you ever made a New Year’s resolution?
Why or why not? What was your experience?

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FEELINGS
WORDS LIST

USE THIS LIST TO HELP YOU EXPLORE
YOUR FEELINGS

alone

-

abandoned

-

isolated

-

disconnected

angry - controlled - grumpy - irritated - bitter
loved - romantic - appreciative - refreshed - comforted
confused - misunderstood - deceived - skeptical
peaceful - relieved - confident - relaxed - protected
exhausted - depressed - withdrawn - lazy - beaten down
secure - positive - assertive - self-assured - happy
overwhelmed - burdened - guarded - tense - confused
elated - joyful - satisfied - optimistic - delighted

excited - playful - determined - talkative - rejuvenated

ashamed - guilty - embarrassed - stupid - exposed

sad - hopeless - unhappy - crushed - desperate

anxious - uneasy - worried - fearful - indecisive

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INDEX

BOUNDARIES

12, 15, 22, 26, 31 // Sep 5, 13, 21, 24, 29 // Oct 1, 11, 17, 19, 30
// Nov 12, 17, 24, 27 // Dec 3, 5, 10, 13, 15, 21, 23, 29

Jan 5, 24 // Feb 10 // Mar 4 // Apr 7 // May 5 // Jun 19 // Jul
10, 31 // Aug 8 // Sep 7, 25 // Oct 8, 25 // Nov 20, 28 // Dec

GOALS & DREAMS

6
Jan 4, 27 // Feb 26 // Apr 3, 23 // May 7, 23 // Jun 6, 25 //

CHARACTER & VALUES

Jul 2, 20 // Aug 10, 21 // Sep 4, 22 // Oct 6, 22 // Nov 4, 15 //
Dec 11, 31

Jan 8, 11, 14, 17, 19, 22, 29 // Feb 4, 6, 11, 14, 18, 22, 24 // Mar
2, 8, 13, 16, 21, 23, 26 // Apr 1, 8, 10, 22, 27 // May 6, 8, 14,

JUST FOR FUN

17, 21, 24, 29 // Jun 5, 10, 14, 17, 24 // Jul 3, 7, 11, 14, 17, 23,
27 // Aug 9, 15, 17, 20, 24, 27, 28 // Sep 3, 9, 11, 16, 19, 23, 26

Jan 3, 9, 18, 30 // Feb 7, 12, 15, 28 // Mar 7, 14, 24 // Apr 9,

// Oct 4, 9, 14, 16, 19, 23, 26 // Nov 3, 9, 14, 19, 22, 26, 30 //

11, 16, 18, 25 // May 1, 13, 18 // Jun 9, 20, 30 // Jul 8, 13, 26

Dec 7, 16, 18, 26, 30

// Aug 3, 14, 25 // Sep 1, 10, 20 // Oct 13, 15, 18, 31 // Nov 5,
6, 10, 25 // Dec 8, 20, 25

CHILDHOOD & FAMILY
MONEY & CAREER
Jan 7, 13, 25 // Feb 3, 17, 23 // Mar 1, 17, 20, 27 // Apr 2, 13,
26 // May 9, 20, 31 // Jun 1, 13, 28 // Jul 5, 15, 28 // Aug 2, 11,
19, 27 // Sep 6, 18, 30 // Oct 5, 12, 27 // Nov 2, 13, 23 // Dec
2, 19, 24, 28

Jan 2, 10, 21 // Feb 5, 19, 27 // Mar 6, 15, 22 // Apr 5,
15, 28 // May 3, 15, 28 // Jun 4, 16, 22 // Jul 6, 18, 30 //
Aug 4, 16, 29 // Sep 2, 12, 27 // Oct 1, 10, 29 // Nov 1, 11,
18 // Dec 4, 14, 22, 27

FEELINGS & PERSONALIT Y
Jan 6, 12, 20, 23, 26, 31 // Feb 1, 8, 16, 20 // Mar 5, 11, 19, 28,
31 // Apr 6, 14, 19, 21, 24, 30 // May 2, 12, 19, 22, 26, 27 //
Jun 2, 7, 8, 15, 18, 21, 26, 27 // Jul 1, 9, 16, 19, 21, 25 // Aug 1,

190

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REL ATIONSHIPS
Jan 1, 15, 28 // Feb 2, 13, 21, 25 // Mar 3, 10, 18, 30 // Apr 4,
12, 17, 29 // May 4, 10, 16, 25 // Jun 3, 11, 23, 29 // Jul 4, 12,
22, 29 // Aug 6, 18, 30 // Sep 8, 14, 17, 28 // Oct 7, 23, 28 //
Nov 7, 13, 23, 28 // Dec 1, 9, 17

SEXUALIT Y
Jan 16 // Feb 9 // Mar 12, 25 // Apr 20 // May 11, 30 // Jun 12
// Jul 24 // Aug 5, 23 // Sep 15 // Oct 3, 20 // Nov 8 // Dec 12

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ABOUT
M A R R I A G E 365

We have a dream that one day happy connected couples
will be the norm. Until that day comes, we will continue
to work hard to build healthy relationships and bring hope
to those who desire to live life to the fullest. That is what
gets us up every morning!
That’s a lot coming from us, named the couple least likely
to succeed in marriage, with a 1.3% chance of making it.
By year three of our marriage, we hated each other.
Walking our marriage back from the brink of divorce was
the most courageous act we have taken. It all started
when we stopped waiting for each other to change and
instead began the process of self-discovery. We tell every
couple that if you want a better relationship, it starts by
making a better you.
Our restored marriage was the inspiration to help other
couples that were feeling stuck, lost, and confused about
what to do next. Today, Marriage365 reaches millions of
couples around the world, providing practical advice,
resources, and inspiration. You can find all of our resources
by visiting www.marriage365.com.

Casey and Meygan

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