Upgrade Your Story Pt. 1

Man jumping off cliff


It’s better to be in the arena, getting stomped by the bull, than to be up in the stands or out in the parking lot.

― Steven Pressfield, The War of Art

I know not all fathers are heroic.

This is unfortunate, as I’m unmovable in my conviction they are all meant to be. I’m blessed to have a father who, despite his imperfections, came through in modeling for me how to be a good man in the old fashioned way, with a hard work ethic and a handshake stronger than a signature.

It is a helpful fact to know, despite what moms, teachers and motivational speakers often tell us, we are not able to become anything we want. We all have God-given limitations, but there is nothing stopping us from choosing a better story and sucking the marrow out of the life He gives us. However, to upgrade your story will require both vision and courage.

My father showed me something about this as well.

“Son, should I do it?”

I was in high school and riding shotgun beside my dad on the interstate. Out of the moment’s silence he asked me if he should leave his job and build an entirely new career from scratch. He had recently discovered some technology he felt could disrupt the mining industry in a very needed way, much like Dauber will with dump trucks. It was a complete surprise to me, but he had obviously been wrestling with it a lot on his own and now he needed an opinion, even if it was from a boy. I was far too immature to discern that he was wrestling with more than a career change. His life and heart were hanging in the balance.

His idea was a bit crazy and by no means a sure thing.  It would exhaust our family’s finances and require sacrifice from us all.  And there were so many things he didn’t yet know. It was a very big risk, but my dad, after years of security in the same job, with a little retirement put away and a son about to enter college, was dreaming again.

He had been treated well at the same company for 17 years and already had a level career path laid out for him into retirement. In fact he’d just been given a promotion with pay raise. But he desired more than an income. He wanted the freedom to make his own decisions without “death by committee” meetings or the “paralysis by analysis” that prevents organizations from moving swiftly and acting boldly. He wanted to trade in his “security” for an adventure. It’s no surprise he was internally wrestling with what most men would consider “irresponsible” behavior. If you’re reading this, it’s likely you’re on a similar hunt for a lifehack that will make waking up each day more fun.

After filling me in on the details, I asked him bluntly “You’re not gonna be a coward and not do this, are you?

Teenagers, right? Looking back it’s really hard to believe that was my response.

But to hear him talk about that conversation today, it turned out to be one of those “finest hours” for us both. His life changed course as a result of that conversation and he delights today that his son, young as I was, invited him to drink again from the fountain of youth and take a risk.

But why did I say that? Maybe the young bear cub in me was wrestling with the Papa Bear, a healthy little teenage rebellion. Maybe I thought my dad was boring and I was daring him to do something unpredictable. Maybe I needed to see that it’s not all downhill after 30.

As a young man of probably 17 I had suffered little, the world still felt totally safe and the actual risks to my father and family were invisible. I think I just saw that my dad was unhappy and he was looking to me for encouragement, and maybe even some validation. Thank God, despite my immaturity I somehow passed along the words he needed to hear.

What’s miraculous is that while he was surrounded by “successful” men with big houses and bank accounts who were exchanging their dreams for the appearance of security, he dared boldly to pursue adventure and possibility. He was willing to go against the grain to invest in an upgrade of his life.

Most men, as much as they need a life with more excitement, would never seriously consider a disruption of this magnitude. It’s absolutely true.

And why not?

Behind the mask every man wears are two looming fears: “I don’t have what it takes,” and “I will be exposed“. And so to explore a new frontier is to risk public failure and exposure. The adventure we most need to be satisfied is, in a very real way, opposed from inception.

So what do we do with those deeper desires that would require us to risk more? Mostly we play it safe, take the predictable road, and ultimately end up bored and unhappy, a symptom that bears bad fruit in other areas of our lives. It’s the dark truth Thoreau exposed with his famous line,

Most men lead lives of quiet desperation and die with their song still inside them.

I was privileged to watch my dad sing, and as with most men who find the courage to do so, he was redefined by a single courageous act, which gave him the courage to risk a lifetime of subsequent courageous acts. He has become a man of wisdom and faith while maintaining the best kind of childlikeness. It’s made him a mentor and a sage. And this because he chose to risk.

Safety Kills.

That was 30 years ago. Today I have a son of my own in high school along with a beautiful wife and daughter. They deserve my protection and provision, so to keep my promises and ensure security I am tempted to keep my own song locked inside.

I now know the weight a good man must bear to fulfill his obligations, leaving me even more proud of my father for his mid-life leap into the unknown. He did what was needed to avert the early demise of his heart. Ultimately he did what was best for us all by choosing the adventure.  The wisest of men once said, “He who would seek to save his life will lose it.” It’s like I tell my son, “You cannot become a true man until you let the boy die“, the boy who always chooses safety, comfort and gratification without delay.

Fact is, we weren’t meant for safe. “Safe” can be deadly. We don’t develop mastery without tension. We don’t grow stronger without adversity, or wiser without problems to solve.

I’m 47 years old now. I have felt suffering, been betrayed, felt the sting of failure, and known many men over the years whose lives have been compromised by paralysis in the face of fear of the unknown.


This is the name of your arch-enemy. Fear is the Berlin wall standing between the “you” as you know yourself today and the “you” you would clearly rather be. When I find myself making excuses for my inaction, if I will be completely honest with myself, at the top of the mountain of actual obstacles is fear. Like a lit cherry bomb on top of an ice cream sundae, it must be dealt with if you’re going to enjoy something really good.

Fear is the most real villain in your upgraded story, whether you are considering pursuit of passion, career, relationship or any new idea that feels kinda crazy. And fear comes in many flavors and varieties that can be easy to miss.

It is these fears I want to discuss over the next few posts.

Face Your Enemy.

Maybe I’m writing for my own protection, to prevent myself from taking the broad road—that path of least resistance. I’m discovering through my own story that what I love most, whether with Dauber or elsewhere, is helping people live a better story, and that a better story is actually not nearly as hard to begin as we are tempted to believe. My father is living proof. And so are the men I work with who saw a problem in the dump trucking industry we thought would be really fun to solve.

So what would make a better story for you? How could you upgrade right where you are?

The direction to a better story always starts with desire, which is something many of us refuse to entertain for fear of disappointment and in the service of “security”. What do you go to bed thinking about? And waking up with? Chances are you can find the trail pretty quickly. Another way to get to that desire is to consider what is frustrating you, and then asking “Why am I frustrated? What desire of mine is being blocked?

Your dream, your calling, your gift is already under assault and so you must protect it at all costs. All talent, growth, creativity, genius and industry are prime targets for an opposition Stephen Pressfield calls simply “the Resistance”:

Resistance is experienced as fear; the degree of fear equates to the strength of Resistance. Therefore the more fear we feel about a specific enterprise, the more certain we can be that that enterprise is important to us and to the growth of our soul. That’s why we feel so much Resistance. If it meant nothing to us, there’d be no Resistance.”
― Steven Pressfield, The War of Art: Break Through the Blocks & Win Your Inner Creative Battles

So what upgrades to your life have you considered in secret? What risk would test your character and push the boundaries of your current skill set? If you are a fleet manager or owner-operator, what would make going to work more fun?

What challenge would make you better if you were to face it?

To desire a better life doesn’t make us selfish. It makes us human.

To pursue that life, in spite of our fears, is the beginning of the life we want.