Letters to my sons

A collection of thoughts and lessons I've learned along the way for my little men, and anyone else that's interested.

Posts tagged with #Confidence

My sons,

I know I’ve written about empathy in the past, but I’ve been doing a bunch of reading and thinking on the topic, and I wanted to share some more thoughts with you both as I learn more about this beautifully difficult character trait.

When I first encountered the concept of empathy, I believed it to mean putting myself in someone else’s shoes, and trying to determine what I would do in their situation. While I still think that much of that statement is true, I need to make a small tweak. I now believe empathy to mean putting myself in someone else’s shoes, and trying to determine what they would do in their situation, and why.

The fundamental difference here is the focus. My first definition has to do with me; what would I do in their situation. This is entierly determined by me, my background, my experiences, and my context. The choices I make in that frame of empathy then, will reflect my preferences, my value system, and ultimately would, without intention, be self-serving.

Now, since our goal when we apply empathy is to understand the other person and to add strength to the relationship, this definition isn’t as useful to us.

Our new definition is more compelling because it gets at the heart of what the other person needs, what they desire, and what motivations factor in to their decisions. It causes us to not just know about the other person, but to know them.

In his book The Lonely man of Faith, Rabbi Joseph Soloveitchik postis that one of the core needs of man is the need to know and be known. He argues that the need to be known is a universal characteristic across mankind, and that as relational beings, we find much fulfillment and peace in being known.

And so when we want to demonstrate empathy, there is much good that we can do to add to our shared understanding, and to bring fulfillment to the other person.

  1. Remember that empathy is an act of understanding, not of judgment. It is primarily an observational activity, observing and learning about the other person’s motivations, context, and values. It is not applying our own judgment to those things!

  2. Be patient. In our self-centered and self-focused world, it takes time to develop the muscle to break away from that trend and to focus not on our own agenda and goals but on someone else.

  3. Intentionally practice and apply empathy. No change comes without effort. While the desire to have empathy is already a great first step, we need to progress past that and realize that there is real work to be done in order to get us being truly and effectively empathetic.

My hope for you both is that you grow up to be men that are confident in yourselves, and have enough confidence around your own desires and needs that you’re able to set aside yourselves and learn to concern yourselves with the needs of others.


My son,

As a kid, I loved candles. I loved watching them flicker, loved watching the glow that they made. I was always amazed at how much light could come from such a small little flame. I loved the glow; soft, warm, almost magical in nature.

As I grew older, my fascination with candles changed. While I still loved that warm familiar light that they emitted, I became enraptured with how they shone brighter when a small breeze would come through the room. The small, gentle flame would become large and fierce. It would fight to stay alive, would flame up and light up the room more brightly.

The noble human spirit shares this beautiful quality; it is a peaceful glow that flames up fiercely under adversity, fighting to stay lit and illuminating all those around it in the process.

Jesus said that “in this life, you will have trouble. But take heart! I have overcome the world!” - John 16:33

In this life, we are assured trouble, trials, difficulties, struggles. That’s a fact, guaranteed. The true measure of a man is how we handle these trials. When the wind comes, do we carefully nurture that candle so that it gets just enough wind to let it fiercely light up our spirit? Or do we turn that candle straight into the wind, letting it blow out completely?

One of the hardest things a father has to do is to not stop the wind even though he sees it heading straight for his children. I pray for the discernment for you to know how to nurture that candle so that when you need it to, it will shine brightly in the night. There is much darkness all around us, and the world will need more candles to keep us in the light. May yours be one that shines brightly, and may it bring light to all those around you!


My son,

As much as I wish I did, the truth of the matter is that I don’t have all the answers. Nor am I always right. My thoughts in these letters to you are just that; my thoughts. These letters are a culmination of my experiences, my influences, my environment, and my best efforts. But they are just mine.

The reality is that you are your own person, with your own interests, your own designs, your own desires, your own aspirations. If you’re anything like you are at the time of my writing this, then you’ll have so many of these things. Even at this young age, you’ve got a beautiful personality, decisive, confident, and full of passion. My prayer is that over the years, all of those have grown and have molded and shaped you into a wonderful man.

So with that in mind, today’s thought is going to be pretty simple.

“Find something to care about; and then care deeply about it.”

And that’s it. No matter what you do with your life, no matter pursuits you choose for yourself, pursue them strongly and deeply. Your mother and I will love you and support you regardless of what you choose. My charge to you today is that whatever and whomever you choose to care about, care deeply.

I love you, my boy. I can’t wait to see what kind of man you choose to be.


My son,

One of the toughest things that a man must do is to admit when they’re wrong. We are wired for victory, for success - from an early age, we’re taught that it is praiseworthy to succeed and to be victorious. Hopefully by the time you read this, your mother and I will have instilled in you our philosophy that learning, making progress, and improving yourself are more important than winning.

Life is about more than just the destination. The journey is equally - and sometimes even moreso - important.

And so today we’re going to talk about something that every great man knows is the right thing, but many find difficult to do. Taking responsibility for your own actions, especially when things go wrong.

It’s a story as old as storytelling itself - the first sons of the world struggled with this very concept. In Genesis 4, we’re told the story of Cain and Abel, sons of Adam and Eve. Because of his jealousy and his own inadequacies before God, Cain takes Abel’s life out of anger and frustration. That of itself is already quite bad, but when God calls him on it, what is Cain’s response?

“Am I my brother’s keeper?” - Genesis 4:9

I won’t mention that this was already a family trait, as dad had already pulled the same stunt with God, blaming Eve for his eating the apple before the two of them got themselves kicked out of paradise. Oh and so did mom - she passed the blame onto the serpent.

Great start humanity has eh?

Fast forward a bit, and we’ll see that even God’s favorite son struggles with this one. Thankfully for mankind, when the prophet Nathan confronts him, David does in fact repent and fesses up and repents for his actions, but even he needed a kick in the pants to get on the right page.

So what does this mean for us?

I believe there are a few reasons why taking responsibility for your own actions is not just something that we ought to do, but is something that actually gives us strength and adds to our effectiveness. Here’s why.

  • Integrity
    Absolutely the most importat. Having integrity is what makes a man. I don't care what anyone else says. Integrity is in my books one of the most (if not *the* most) important traits a man can have and must guard. It is the quality that brings out the best in you and in those around you because it's the quality that says no matter what the circumstance, no matter who's watching, no matter what the arguments are opposed, I *will* do the right thing.

  • Earnest connection
    By taking responsibility for our actions and admitting when we're wrong, we move ourselves from the adversarial position to an earnest and open one. As a populice, we resonate with leaders that let their guard down and share an apology, a fault, a heart-felt admittance of failure.

    By displaying vulnerability, we remind people that we're all flawed and broken, striving to be better, reaching for that beau ideal of human excellence.

  • Humility
    Taking responsibility also keeps us honest and keeps us humble. It keeps us in a posture of humility where we're able to hear truth being spoken into our lives. It lets us recognize that we need to grow, and lets us see the path ahead.

I love the quote by legendary football coach John Wooden about the topic. He says that “you aren’t a failure until you start to blame”. How true that is!

And so my son, my challenge to you this time is to continue striving for greatness, continue growing and learning and trying new things, and to continue putting yourself out there and going out on a limb for things. As you do that, you’re bound to have set backs, and when you do, my prayer is that you’re able to own up to those too. Claim your losses just as you claim your victories; they both are great opportunities for growth and for deeper connection. And those are great things.


My son,

One of the most sobering realizations that you’ll have in your life is that your life this side of heaven is finite. As I noted last month, time is the only resource in life that we will never get back. Each moment that you spend is one that you’re never going to get back. So how do we make the most of it? And what’s that got to do with self-respect?

Quite a bit actually.

Self-respect is the thing that lets you own your own destiny, that lets you fearlessly choose the path that you want to take. You are beautifully and wonderfully made - own that. Claim it. Run with it.

There are all sorts of benefits from having a strong sense of self-respect, of self-esteem, but the fundamental thing is that it gives you confidence to be your own man, to do things that may not be popular, to stand up against opposition, and to do the things that you believe in.

  • Confidence to fight for the little guy.
    This one is arguably the most important. In this world, there are so many people without voices - the sick, the poor, the scrawny kid in class that gets picked on, the girl on the bus that no one wants to sit with.

    To each of these, Jesus asks us to love them as He loves us. In Matthew 25:40, Jesus tells us that "whatever you did for the least of these, you did for me".

    In my own life, I've found that this one is extremely difficult. It's so hard to step outside the norm, to go against the grain, to put yourself out there to stand up for the little guy. But just think - how much harder is it for them?

  • Confidence to stand up for what you believe.
    We live in an age where the social norm is to not offend, to not have beliefs that could show disapproval to anything that popular culture deems is acceptable. We have axioms like "it's the nail that sticks out that gets hammered".

    Never in the history of our world has there been a need for people to stand firm in what they believe in, to have a deep rooted sense of morality, and to be that light on a hill for all to see.

  • Confidence to be alone.
    It's tough being alone. Whether it's being circumstantial - being home alone for an evening, going to an even like prom alone, or even taking a vacation on your own - or if it's a longer term thing like being single while your friends are coupled off, being alone is tough.

    Having self-respect gives you the confidence and sense of self enough to be not just okay with those situations, but to stop seeing them as inflictions and instead to start seeing them as opportunities.

  • Confidence to strike it out on your own.
    It's a basic human instinct to seek safety, and to seek safety in numbers. Striking out on your own goes against that very nature and by definition isn't easy.

    But so much of life, so much about being a man, so much about an enriching experience is only accomplished and experienced when you strike out on your own. Being your own man isn't easy, but it's absolutely essential.

  • Confidence to ask her to marry you.
    Nothing is more nerve wracking than when you find yourself on one knee holding a little box with a ring that costs 3 months of your salary in it. Nothing.

    And no matter what anyone else tells you, nothing should be.

    Finding a life partner that you can run with, laugh with, celebrate with, and mourn with is so hard, and when you finally find her, asking her to be yours as long as you both shall live is nerve wracking. As it should be.

    Having confidence in yourself lets you realize that it's just as hard for her, and that it's just as big of a commitment for her as it is for you. And that's a good place to be.

So my prayer is that as you grow into a young man that you would have confidence in the man that God is created you to be, and that out of that understanding of self, of self-worth, of self-respect and self-esteem can come a heart for the world that is kind, considerate, protective, bold, and courageous. I love you, my boy.


My son,

It’s human nature to reminisce, to think back to days gone by, and to romanticize the days gone by. While I certainly don’t support living in the past and not being able to live in the present (that’s another topic for another day), I do believe there is value on occasionally reminiscing about your past.

Reminiscing reminds you of your values
One excellent outcome of reminiscing is that it reminds you about your values. The things that are absolutely core to your being, the things that you care about, are driven by, and are unwilling to compromise - reminiscing reminds you of those things.

One of the prerequisites of living a full life is to know what you’re living for, what you’re loving for. And the only way to know that is to know thyself intimately enough to know your motivators, your passions, and the values that define your very being.

The things that we reminisce about are clues to what we truly care about.

Reminiscing shifts your mindset
One of the great things about the human mind is the ability to transcend the immediate and be immersed in something greater, something bigger than ourselves.

When we take the time to thoughtfully consider the victories and mountaintop experiences of the past, our mindset shifts to adapt. By recalling and reliving those great moments, we’re able to put ourselves in that environment again, and are able to focus on how we felt, how we reacted, how we anticipated, and how we thought in that moment. We’re able to adopt the mindset of our experience and apply it to our current existence, and respond accordingly.

Reminiscing brings your current path into focus
By remembering where we’ve come from and noting where we are, we’re able to extrapolate the path that we’re on so that we can course correct as needed. In looking back on our past experiences, we’re able to see the growth that we’ve had since, and are able to focus on the path and see where we’re headed.

So my challenge to you is not to be afraid to look at where you’ve been, but to deliberately do so in a manner that helps you be more confident in who you are, where you’ve come from, and where you’re headed. Don’t get stuck in the past, but rather learn from it. Draw strength from it, and use it to channel and direct your energy where you want it to go.


My son,

As much as we'd occasionally like life to run entirely on our schedule, the reality is that it doesn't and it won't. And so this entry, while on the one hand is about being dressed well, on the other hand is really about being prepared for the unexpected to happen, and to be able to gracefully handle those situations.

The face value of the title here is very true - you should dress every day like you're going to meet the love of your life. Because who knows, you just might meet her some day, and you'd ideally want your appearance to give you the confidence to be on your best foot. Like we discussed last time, appearances matter, if only to give you an extra boost of confidence - and every man knows that when you first see that face, first encounter that angel that you'll want to spend the rest of your days with, every ounce of confidence is going to be welcomed.

The underlying point here is that life won't go according to your schedule.

That's not to say you shouldn't plan - no, definitely make your plans, and lay out the course that you want to take. But be flexible on that course. Often, the best times in life - the most memorable, the most impactful, the most exhilarating - will come when you least expect it. And if you're dressed and ready for the occasion, you set yourself up for a much better experience.

And so my advice here is to be ready for that. When you're ready and expecting the unexpected, you're able to take things in stride and handle the situation with more grace. When you're ready for life to throw its curveballs at you, you're best equipped to knock that sucker if not out of the park, than at least out to the right field corner for a double. So be prepared. Be dressed for the occasion. Plan, but be flexible. Let life take you where it will.

And who knows, you might just meet the love of your life along the way.


My son,

There are all sorts of proverbs out there about what's on the inside being what counts, that appearances shouldn't matter, that you should never judge a book by its cover, that what you look like isn't as important as who you are on the inside. All of these proverbs - while motivating and comforting - shouldn't be taken entirely literally.

Make no mistake; appearances matter.

I don't mean that they are of central importance; no, in that respect, I agree with those proverbs. What's on the inside is more important. That's why we have all these talks about character, about integrity, about honor; no, without a doubt, what's on the inside is more important.

However, that doesn't mean that appearances don't matter. Here are a few reasons why.

  1. First impressions stick. Whether we like it or not, not only do our first impressions of others generally stick, but certainly their first impression of us does. And unfortunately, much of that first impression will be based on appearance.
  2. Being underdressed puts you at a disadvantage. If not in your eyes, than certainly in theirs. Being underdressed demonstrates to others a lack of care at best, a lack of respect at worst.
  3. When you look your best, you feel that way too. When you take care to look presentable and professional, it sets you in the right frame of reference to feel presentable and professional, and it gives you the confidence to behave as such.

That last one is the real kicker. When you are confident in your appearance, you don't have to spend energy being worried about whether or not you look like you fit; you are confident that you appear like you do. And that gives you the confidence to actually do so.

And that's the real reason appearances matter. Not because they should be used as a yard stick or as a means of judgment, but because they empower you to feel your best. They give you confidence, and put you on an even playing field so that you can be the best version of you there is. And that's not a bad thing.


Archive