Truth & Trust: Letters to My Daughter

Truth & Trust: Letters to My Daughter 


Dearest Winslow,


I love you darling daughter.

I attempted to write a letter about “Truth & Trust” and months later I had not been able to finish it. I had tried multiple times, and the letter never felt authentic. It felt forced. The dead carcass of the letter is below for you to read if you wish, because letting you read my attempt(s) is the 2nd most honest thing I can do. The 1st most honest thing I can do is to tell you why I haven’t been able to write/finish a letter about Truth & Trust.

I’ve struggled with truthfulness nearly my entire life. Until my late 20’s I mainly lied to myself. I lied to myself about who I was. I thought myself to be bursting with qualities I did not possess. I did this because I wanted to be that man and I knew deep down I was not. I also feared I would never become that man or possess any of the qualities I led others to believe I had.

One of the worst feelings in the world is to see polite distrust within the eyes of your loved ones. Just flashes of pity. Glances of disbelief. Their words said otherwise but their eyes never lied.

I cannot go back into the mind of a child and tell you why I lied as a kid. It was probably for normal and very typical reasons. Fear of punishment. Human nature. Selfishness. Mainly because the truth while right is seldom easy. At least that is the faulty thinking we use to rationalize our lies.

In my late 20’s I began to lie after a perfect storm of life events began to effect my career. These life events began my everyday battle with social anxiety. I was afraid to answer the phone, emails, and talk to anyone if I thought they may have a question I did not know the answer too. So, I lied to ease the paralyzing fear these simple tasks brought on.

It was destructive, and … I became hell bent on self-destruction.

It was not until recently I was able to stop lying to myself and see the truth of my crippling fear and my actions to minimize the effects that fear was having on my life. Once I stopped lying to myself, I was then unable to lie to others. It all started with myself.

As a direct result of being able to fully be honest with myself, life has become easier. Problems are shedding away with ease. Challenges I had built up in my head as insurmountable obstacles became hilariously forgettable as I mowed through them with vigor.

The cold hard truth is simple…

The person you hurt the most with lies is yourself.

While the truth may feel hard or uncomfortable at times, it is always loving. Truth is love.

Yes, the truth will hurt sometimes, whether receiving it or giving it, but it will always set you free.

Truth allows you the opportunity for growth. Growth in relationships, understanding, knowledge, assessment, dream-chasing, faith, and life itself.

Live by truth. Live by your word. Live in the reality that truth brings. Do these things and you will experience a life which very few know.

I want this for you. Not for me, but for you. I hope you do not fall prey to the sins of your father. I hope for more in your life. Luckily for me the truth has set me free, and I plan to be free for the rest of my time on this earth and an eternity longer away from this earth.

I love you sweetie, and that will always be true.

Love your ever-learning,



The original (repeated and failed) attempt at the letter:

You cannot hear me, but imagine this was written in my semi-stern “dad voice”. This letter will not be the most fun or entertaining letter, but it might serve you the best while living with your Mom and I.

I can hear this conversation a hundred different ways at a hundred different times from my past. Usually it entailed my Mother and an exasperated look of disbelief that I still could not grasp the concept in which I will write about in this letter.

I guess, the things I wished I had learned in the past, is what most of these letters are.

Unfortunately for you… this is the most parenting lecture infused letter so far. I won’t apologize for it…

Why should you force yourself to read this letter?

It was written with four main reasons at the heart of it. All of which are very important. All of which are my job as a parent.

  1. To help you.
  2. To teach you.
  3. To protect you.
  4. To love you.



Telling the truth is easy if you make being truthful a habit. I hope it comes natural for you. Yet, there is the possibility that telling the truth will not be a natural tendency for you, as it was not for me.

Here is the simple reality to why people are not truthful at times. Fear.

People fear what the truth may cause, and who it will hurt. Rarely are people who lie worried about hurting anyone but themselves. Whether a person thinks a lie will protect someone else or not, the reality is they lie to protect themselves.

When I was younger, I lied often, and always because I feared what would happen when I told the truth.

On the other hand, your mother is a habitual truth teller. Remember how I always say she is a much better person than me? Well, I always mean it.

You should always tell the truth, sweetheart. Do not let fear cloud your judgement. Fear is irrational in most cases.

In the case of truth, fear is it’s mortal enemy. They fight constantly. Fear lies to you about truth, so you won’t overcome the fear. Truth sheds light on fear, exposing fear’s lies, thus leading you to trust.

Fear + lies= destruction

Truth + trust= Freedom

How will being truthful HELP you in life?

  1. Uncomplicated relationships! If everyone knows exactly how you feel, and exactly where you stand then it becomes easier to have a relationship.
  2. Eases drama! If relationships become uncomplicated because of your truth telling, then people that do not like it will escape from it.
  3. Attracts people! When a person is brutally honest, or unapologetic honest in a kind manner, then people flock to the honest person. Why? It’s Rare! That’s why!

What will Truth TEACH you?

  1. The Truth of course! Seriously, truth will give you real knowledge. Truth cannot be changed or manipulated, and is the essence of wisdom.
  2. Humans rarely use it! When you are honest, it becomes easy to spot when others are not being honest. It reveals patterns of deceit woven throughout the fabric of society.

How will Truth PROTECT you?

  1. No lies will hold your heart!

Why is being Truthful a LOVING ACT?

  1. To tell someone the truth is to show them love!

Missed a Letter? Click the link to the one you missed, and get caught up!

A= Amazed & Altered

B= Boys, Boys, Boys

C= Cosmopolitan, Confidence, and Culture

D= Dreamers


F= Friendship

G= God

H= Home Run!

I= Immediate Gratification

J= Just Joking

K= Knowledge

L= Love

M= Mom

N= Needs

O= Optimistic Override

P= Present(s)

Q= Questions

R= Respect


T= Truth & Trust


5 thoughts on “Truth & Trust: Letters to My Daughter

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