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  • Writer's pictureChris

Asking the Right Question - Press Start: Gamify your life and make the world your playground

Updated: Dec 29, 2021

I'm doubling down. Last week I shared chapter one of my new book Press Start: Gamify your life and make the world your playground, and the majority of people who clicked the link bought the book. So, I'm making the same offer to those remaining. Read chapter two, if you like it, buy the book (seems fair to me). If not, let me know. And as always, I appreciate your time.

“Life is a journey, not a destination.”

Ralph Waldo Emerson

Waves crashed against my back as I extended a salty arm through thick tropical air. My shoulder reached past my ear for the other end of a buttery kayak oar. Dragging myself up the jagged island cliffs, I laughed at the waves as they spit on my cheek—the rock’s snarling below, eager for the slightest mistake. Yanking the oar to lift me out of the moonlit ocean with the help of my friend, I gaze beyond the dozen lacerations on my chest, abdomen, and legs. I feel cactus needles impaling my feet as the sun and moon trade places.

At this point, our one bottle of water and apple are a memory. We climbed these rocks for over twelve hours, and our quest still has six hours remaining. Our trials were outflanking a wild boar, bleeding, a death pact, solving a jungle labyrinth, and finally, a treacherous cliff-side taxi with a drunk driver.

Standing on the edge of a massive boulder overhanging the vast ocean, I wonder, what draws me to these messes? I’ve done some stupid deeds in my life, but I’m beat-up on the side of fifty-foot cliffs on a tropical island, and the world thinks I’m sipping on margaritas by a pool. They should know better. I should know better.

Earlier that week, two strangers ferried us to the neighboring island for an epic New Year’s Eve party. A multi-million-dollar bash since yacht week happened to include the New Year. Some boats cost more than houses, and the dinghy we hitched a ride on broke down halfway home. As I think about that adventure and our current state of affairs, fatigue washes my body as fulfillment radiates my soul. Amidst the exhaustion, cold, darkness, and pain, a smile slips in. I am shivering and already lost my gear to the ravenous ocean, but this is the game. This departure from the common is the latest quest of my vigorous life.

Inherit in every quest is a good question. Questions guide us toward our desires. They set us into action. There’s always an underlying theme when writing a story, a thread weaving its parts into a thick band, answering a question by unifying the arcs. A thread that is strengthened as the hero searches for answers.

A complex system is a fancy word for what mythologies refer to as chaos. Chaos or complex systems are unfamiliar elements randomly dispersing, and as interactions emerge between the elements, relationships form. Over time, these connections create larger patterns we call order. The more relationships, the more patterns emerge, and the more efficient order becomes. People emerge from chaos. Human behavior is one of the countless occurrences of complex systems.

All human behavioral traits are heritable. People’s actions live on through generations. Even more so, complex systems in general, not just people, have a “memory.” As systems change, prior states influence present states. Think of life on Earth, language, or free markets. None of which would be what they are without a memory of the past. Your past relationships influence your current. How animals previously living in an area change the landscape influences the animals there now. New lyrics emerge from old verses, and fears of past stock market experiences impede current trends.

This memory inherent in all complex systems has me wondering. What pattern of acting produces the best plot, unifying life’s seemingly random elements into the most exquisite melody? What’s the emergent relationship and meaning that people simultaneously act out yet seek?

Life without a quest is a tragedy. Perhaps you try your whole life, and it’s not working. Perhaps your friends, spouse, boss, or family are in the way. Maybe you have lost what is most important to you. What you need is to go on a quest and create the answers to your questions. You need to experience a rebirth. You need to venture into the darkest part of your life and retrieve the spark that offers it meaning. Then brighten the world by sharing that meaning.

My quest takes me down the road of an adventurer, adrenaline junkie, university lecturer, athlete, researcher, soldier, entrepreneur, and firefighter. All these paths bring me someplace different, and maybe a fraction is planned…maybe. Yet, they all have something in common. As great as they are, they suck. It was that reoccurring pattern of being in the suck that continually emerged (yeah, me). Allow me to explain in more sophisticated and less self-deprecating terms.

Suppose you want to find an answer to a question as significant as how to act. In that case, you have to study the world's religions from a historical and philosophical perspective. Some of these religions have morphed into mythologies and explain society’s main concerns during a specific period. Problems that are still relevant today. Where science attempts to define and explain the world objectively, religion and mythology explain it through action, as a story, a play.

Themes reoccur throughout religions and mythologies. At first, I thought life’s x-factor is vigor, and that answer still stands strong with me. But it’s deeper than living vigorously. The underlying theme is, play in accord with nature. Your vigor should aim at something meaningful. Make the world better by making yourself useful. The best way to do this is by bringing your best self to the game. Playing in accord with nature is best accomplished when you know yourself and your environment.

What makes that simple phrase so powerful is that the environment is blind to you, yet you are weld to it. Spanning from the Bhagavad-Gita, Aristotle, The Bible, The Lord of The Rings, Star Wars, Harry Potter, and the Avengers, there’s an underlying theme that all things attune to their more extensive system. How we fit the song isn’t given or found, we create it. When people don’t fit their music, they may not know why, but they know they are off their path. What we are going to do together is create that path.

When an author writes a book, most of what they write is junk and gets tossed away because it doesn’t fit the story. Trust me. This book is my third publication searching for answers to my questions. Life is the same way. If you plow through it without paying attention to your uniqueness and how it fits the grand scheme, deleting what you consider meaningless, you may miss your calling. Living vigorously and engaging life is essential, but how you engage is as unique as your DNA.

Famed author Kurt Vonnegut noticed that people’s lives are seldom dictated like a story and are concealed in mystery until the end. You don’t know what is going to be right for you until it’s over. Vonnegut discovered real life is not clean-cut because people do not understand how any event will affect the next. Like any complex system, you never know what will emerge from a new event or relationship. Is getting fired from your job good or bad? Did you marry the right person? Are you raising your children in the best way? You don’t know how it’s all going to play out until the final act. No one does, that’s Vonnegut’s point, and that’s mine.

Yet, when we live as players in a game composed of countless more minor games, we can map our quests. We can measure our progress by framing each situation and its relation to our purpose—the relationship between all our games compounds into one big score. Our allies, foes, acquaintances, and accomplishments provide a picture of how we are progressing.

That score is your character. Imagine every relationship you encounter as enhancing or diminishing your avatar in the game. If you hang around with crappy people, you’re probably a crappy person. Your character reflects your values and reputation. It’s a direct reflection of the questions guiding your life and the paths you choose.

A quest is a series of actions toward a goal. Asking the right questions aims you at meaningful goals. We should focus less on people’s behavior and more on their goals. A behavior is a result, but a goal is a beginning, a why. We can’t do anything without a motive. The word motive comes from the Latin word Movere, to move. Our motives are why we move. All the whys combine to form our personality (personal reality). We bring our story to life through actions aimed at goals.

You build your questions on your values, and if you are not living in alignment with your values, you will not ask the right questions. Without the right questions, you will aim at the wrong goal and go on the wrong quest. Then you will wonder why life has no direction. Let’s not do that. Let’s invest heavily in defining your questions.

When starting an adventure game, you may select your character. As soon as the game begins, you start learning about the character’s traits. Each type of character, wizard, archer, warrior, etc., has different attributes and builds a unique quest upon these attributes. Even if the story is the same, your experiences make it different. The quest is your avatar’s desires. It highlights your values and concerns. It’s an attempt to bring order from disorder by solving life’s problems. A quest is a reflection of your character. If you want to develop your character, you need to ask demanding questions.

Life is a quest during which we level up – a game. We, the players, have to ask the right questions if we want to progress. Regardless of whether philosophy refers to life as a process or hierarchy, these great minds inform us that life’s purpose is to engage in meaningful quests continually and level up by extracting lessons. Anyone can do almost anything if they aim and work for it. Attaining a good life entails being a player in your game, not a spectator. It involves living vigorously and playing your game to its fullest.

Fulfillment doesn’t come from shallow pleasures; it comes from embracing the suck. Appreciating or at least accepting the struggles, hardships, and shortcomings of life as part of the bigger game. If you want to be fulfilled, and find your purpose, understand the questions you ask are dancing around your purpose. Your purpose develops as you play the game, creating meaning through action. Your purpose is the result of who you are, and who you are is the product of your habits. We may never know our purpose until we reach the end, but if we play the game right, does it matter if we know? If you can look back at the end and say, “I lived life my way,” does it matter if you can spit out your purpose as an elevator pitch?

When I was writing my first book, a couple of buddies thought I needed a break. They convinced me to set my work aside and head into the White Mountains to hike the Presidential Traverse. I bought the cheapest pair of hiking boots I could find, thinking I would only go hiking once. Fast forward seven years, and I have a room filled with adventure gear hanging from the ceiling and the walls. I bring clients on wilderness leadership and confidence excursions, traveling by float planes, foot, or boat into remote areas to learn leadership by overcoming adversity as individuals and a team. I now own a gym where I do all of my performance training, flipping tires, yanking chains, and blowing speakers.

I never thought a quick weekend getaway would revolutionize my life. It realigned my values and put me on an entirely new quest. Since that weekend getaway, whenever I need to get serious writing done, I head into the mountains to replace typical distractions with an open sky and creativity. I often set my gear on a summit where I can hang my legs over the edge and take in nature’s vastness and potential. Boredom births creativity, and being in nature slows life, allowing inspiration to catch up to our otherwise racing thoughts. Our potential is born in our imagination. Imagination that needs to be fed moments of silence and opportunity. When we continuously consume, we are not allowing random thoughts to manifest out of free space. It is essential to balance stuffing our brains with information and vacant periods when “aha!” moments can manifest.

Creativity allows us to overcome a lack of resources. An open mind shows us another path through the trees. Sometimes it is better to work your way around something rather than face it head-on. In Homer’s Iliad, the Greeks fight Troy’s walls for ten years without progress before sending in the Trojan horse. They were stuck in endless conflict because they lack imagination.

Every quest is a growing experience. A chance for you to discover who you are and what drives you. Pain and struggle define your quest. The question is, what pains and struggles do you want to outline your life? A creative and open mind allows you to ask better questions. Realize you should have sent in the Trojan horse ten years ago, unlike the Greeks who fought for a decade because they did not slow down and question their actions.

Quests teach us how to overcome obstacles and evolve into your ideal self. Some quests are small, others monumental, some planned, and others unexpected, but all quests play into your ultimate goal, fulfillment. Fulfillment in the quests you chose, fulfillment in the friends you meet along the way, fulfillment in the quests unwarranted and unavoidable, and fulfillment in the distractions and disasters you overcome. All from a question, all for personal growth and a sense of purpose and meaning.

Trials forge some of my sturdiest relationships. An unspoken bond links people when they have a common adversary. That’s why the military, fire service, sports, and adventures mean so much to me. They provide robust bonds that can withstand a storm.

One of the greatest minds in history, Fredrich Nietzsche, knows pain and hardship are how people grow. Nietzsche also understands that these metaphorical quests to mountain tops are where we experience the best views. These views are only for courageous people who have the will to earn them. It is during literal and metaphorical quests up the mountain that character emerges, and you learn who you are and discover your real friends. It is during struggle and discomfort that we realize who is worth our time. The art of personal development is engaging adversity with people with whom we have a strong rapport. People we can relate to because they play a similar game with similar goals.

Over the years, my business evolved from general personal training to a full-scale performance coaching company, blending sport and fitness training with confidence and leadership development. I coach high-performing athletes, C-Level managers, doctors, soldiers, professors, investors, firefighters, and entertainers to strive for more in the things they love. I teach world influencers lessons on how to be better parents, managers, leaders, athletes, doctors, and everything else by taking them on a quest into my Ludus. Here, they may not be aware, but they learn the skills that transfer to everything they do.

As I grow, so does my coaching business, Improve with Chris. Adapting and improving is in the very DNA of my brand’s culture. Improvement is the product of continually being challenged and adapting to these challenges. It’s leveling up your avatar for more challenging and rewarding trials. It’s growing; it’s living. I chose improvement as the foundation of my fitness company because fitness is your ability to improve and fit your environment’s demands. Improvement is an essential element of a Ludus. It’s how our character develops from a timid newbie to a courageous master warrior.

Improvement requires flexibility and adaptability to accept the challenges placed before us. And more importantly, it takes an open mind. Improve with Chris is part of my quest, and the lessons I learn are present in the services I provide. My mission may have transformed, but my vision remains the same: improve the quality of life. My journey has been not only to make things better for myself but everyone. In the end, the latter fuels the former.

Remember, life is a quest for personal growth. It’s an exploration wealthy with treasures disguised as stories. These stories guide you forward, carving the path to your mountain’s peak. Upon arriving at your summit, you may not recognize what you intended to find when you started, but you may find more. As you gaze into what lies ahead and glance back at the choices that brought you, old questions will disappear, and new quests will emerge.

I can tell you firsthand that life did not happen as I anticipated. As a child, I was free to roam a 26-acre estate overlooking the ocean of an 18th-century Tudor-style mansion. I lived every little boy’s dream of exploring a 600-acre forest with private ponds. I spent all day crossing rivers and catching frogs with my dog. I would watch the sunrise over the ocean as I went fishing and the salty breeze filled my lungs.

But life is seldom as great as it sounds. We didn’t own the mansion. My dad was the groundskeeper, and my mother was always in the hospital. Dad took me to work and let me roam alone during his workday. I went fishing with my uncle because I was tossed continuously between family members like a hot potato. Whoever was willing to take me was home for the week. My childhood was part enchanted fantasy and part outlandish confusion. I was allowed to live the life of a fairy tale while having very little stability and authority. It was like owning the world’s most profitable Starbucks on top of a volcano. I had some great times, but never knew when the rug was going to be pulled out from under me.

These events unfolded before I was nine. As for my teenage years, dad left, and my mother told me he was dead. Spoiler, he wasn’t, but he did pass away a few years later. I remember it like yesterday, sitting on the edge of my bed playing Nintendo. She walked in, told me he was dead, walked out, and I unpaused my game. I spent my late childhood and early teenage years living with my mother. She had bouts of psychosis (out of touch with reality) and neurosis (low emotional stability, anxiety, depression, and emotional volatility). If I was lucky, I was left alone for weeks on end. I learned how to cook, grocery shop, and do my laundry while my friends were playing Pokémon. And those happy days don’t include her drug use or rotation of boyfriends.

My game became challenging earlier than most. But I’ll tell you what, before my parents’ game was over (they died when I was in my early twenties), they taught me hard lessons that I will share with you. Lessons I will never forget, and anyone with a similar background will agree cannot be understood unless lived.

This book is a strategy guide for your legend. It’s a playbook for life. The scientific research, mythological tales, historical characters, and my anecdotes are reminders that our legend is the result of the questions we ask. Your legend is the life best suited for you. Many people dream of luxury and comfort, but that’s not legendary. That’s not something you look back at and appreciate. You value the effort that got you there. I recommend that your story be one that when you are on your death bed, you can honestly say, “I lived my deepest desires.”

Nested in every quest is a question. People feel more comfortable when they understand the situation. We are rational animals searching for the meaning behind everything. Rationality urges us to make the unknown known and understand what bothers us.

Call to Action

What’s your biggest problem? Write your situation as a question.

List three sub-questions concerning your main problem.




Thanks for reading! I hope you enjoyed chapter two. If so, you can find your copy here.

Always improve,


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