Legend Letters

Annual
Reflection
7 questions inspired by legends
that can change your life.

by HOWIE CHAN
 Annual Reflection

2023 is coming to an
end, but our learning
continues.
Dear Legends,

it’s hard to believe the year is almost over. Even though the globally adopted
calendar is arbitrary, our perception and our habits around it gives it meaning.
The end of a phase and the beginning of another - this is a good time to reflect.

“By Three Methods We May Learn Wisdom: First, by

Reflection, Which Is Noblest; Second, by Imitation,
Which Is Easiest; And Third by Experience, Which Is
the Bitterest”
~ CONFUCIUS

To aid in our learning, I’ve pulled together a list of seven questions inspired by
the greats. People who’ve made their mark on the world, I hope that they may in
turn inspire you to gain new insight and add to your wisdom.

Wishing you a wonderful end of year and a strong start to the next year.

Live your legend,

 Annual Reflection

QUESTION 1

WHAT BROUGHT
ME THE MOST JOY
AND PAIN?

Happiness is not something

ready-made. It comes from
your own actions.
~ DALAI LAMA

Review your year and look at all the

activities, projects, or people you’ve
interacted with.
What/ who brought you the most
joy and the most pain?
How can you get more joy and
less pain in 2024?

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 Annual Reflection

QUESTION 1

WHAT BROUGHT ME THE

MOST JOY AND PAIN?
Think activities, projects, and people. Try to be as specific as possible.

Joy:

Pain:

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 Annual Reflection

QUESTION 2

HOW HAVE I
EMBRACED
MYSELF?

“If you are out there and

reading this, yes it’s true, I’m
just as strange as you.”
~ FRIDA KAHLO

Much of life we are trying to shed

what society has placed upon us.
How did you embrace yourself this
year?
What are some things you didn’t
do in fear of being judged?
How can you embrace yourself
more in 2024?

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 Annual Reflection

QUESTION 2

HOW HAVE I EMBRACED

MYSELF?
What were some ways you embraced yourself and defied norms? And for things
you didn’t do for fear of judgement, which are you going to attempt in 2024?

Things I did that defied norms:

Things I didn’t do for fear of being judged:

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 Annual Reflection

QUESTION 3

WHAT AREAS OF
MY LIFE CAN BE
MORE SIMPLE?

“Embellish the soul with

simplicity, with prudence, and
everything which is neither
virtuous nor vicious.”
~ MARCUS AURELIUS

Complication often results in

confusion and inaction
What is particularly complex in
your life? That you have to spend
way more time and attention than
you needed to?
How can you simplify in 2024?

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 Annual Reflection

QUESTION 3

WHAT AREAS OF MY LIFE CAN

BE MORE SIMPLE?

Relationships Home

Work Health (physical, mental, financial)

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 Annual Reflection

QUESTION 4

WHAT AM I
AFRAID OF?

“Nothing in life is to be feared, it

is only to be understood. Now
is the time to understand more,
so that we may fear less.”
~ MARIE CURIE

Sometimes we fear success as much

as we fear failure, we often think
about loss more than about gain.
List all the things you are afraid of
and score them 1 to 5 - the higher
the score, the more you need to
learn about them.
How can you fight fear with
learning in 2024?

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 Annual Reflection

QUESTION 4

WHAT AM I AFRAID OF?

List what you fear, the imagined consequence and score them from 1-5,
5 being your most fearful. The higher the score, the more we need to learn.

Things I fear and why I fear them: #

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 Annual Reflection

QUESTION 5

WHICH DREAMS
BECAME A
REALITY?

“Imagination is everything. It is
the preview of life’s coming
attractions.”
~ ALBERT EINSTEIN

Turning dreams into reality is

powerful, for everything begins in
the mind.
What have you made real in 2023?
What other dreams do you have
that is not real yet?
Which dream(s) is important for
2024?

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 Annual Reflection

QUESTION 5

WHICH DREAMS BECAME

A REALITY?
List out the dreams which became a reality, celebrate them! Then list out those
which are not yet a reality and check which one(s) are a priority for 2024.

Dreams became reality:

Dreams not yet a reality:

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 Annual Reflection

QUESTION 6

WHAT WERE MY
FAILURES & WHAT
DID I LEARN?

“I’ve grown most not from

victories, but setbacks. If
winning is God’s reward, then
losing is how he teaches us.”
~ SERENA WILLIAMS

Either you learn or you succeed.

How have you failed and what have
you learned? What will you do
differently?
With that in mind, how might you
shoot higher and potentially fail
bigger?
What shots will I take in 2024?

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 Annual Reflection

QUESTION 6

WHAT WERE MY FAILURES &

WHAT DID I LEARN?
Failure Failure

Learning Learning

What shot(s) will I take in 2024?

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 Annual Reflection

QUESTION 7

WHAT AM I
HOLDING ON TO?

“As I walked out the door

toward the gate that would
lead to my freedom. I knew if I
didn’t leave my bitterness and
hatred behind I would still be in
prison”
~ NELSON MANDELA

What are you consciously or

subconsciously holding on to that’s
holding you back from more
happiness, success, and health?
Think grudges, beliefs, habits
What can you let go for a freer
2024?

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 Annual Reflection

QUESTION 7

WHAT AM I HOLDING
ON TO?

Grudges/ Relationships Beliefs/ Ideology

Habits

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HERE’S TO A
LEGENDARY 2024.
Remember that these are prompts for
you to reflect. Want more out
There is no right or wrong way to of this exercise?
conduct your reflection.
Try doing this by yourself and
The only thing that matters is that
then share it with you partner or a
you gain insight and chart a course
close group of friends.
that’s better for you next year.

Legend Letters

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HOWIE CHAN
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Brand Strategist | Entrepreneur | Creator