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Why Chasing Success Almost Ruined My Life—and How I Found Clarity at 3:02 AM


At 3:02 am this morning, I was jolted awake by a question that refused to let go:

“What do I want out of life?”

At 37 years old, I’m sitting here in utter confusion, reliving my entire past, trying to dissect where I went wrong, what I got right, and what I should learn from it all so I know how best to move forward.

Doubt is one of those sneaky emotions that can chain us down. It whispers that we’re not ready, not good enough, not worthy. It paralyzes us, leaving us stuck in a loop of inaction, spiraling into deeper pits of doubt, aversion, and lack of confidence. It’s like cutting our Achilles’ heels, robbing us of the strength to move forward and out of pain. Yet, I’ve learned that doubt is also a compass pointing toward growth—if we’re brave enough to face it.

So, after lying in bed with my mind racing, I walked downstairs, opened my journal, and distilled my thoughts into 16 essentials. I now feel a sense of clarity and focus, knowing exactly what I want out of life.

This is what I want to share with you now straight out of my journal…

I’ve had an epiphany throughout this process: answering one profound question can unravel a thousand tangled ones. It’s the simplicity of clarity that cuts through the chaos.

The 16 Dials

This morning, I found myself tearing books off shelves and frantically searching through my Google documents, hunting for those passages that have always sparked something in me. I pored over my Apple iNotes, a treasure trove labeled “My Thoughts On…” where I’ve stashed my insights and learnings for years.

These aren’t just notes; they’re my personal guideposts, my dials. I can adjust these dials—ramping them up or turning them down—depending on how I’m feeling and where I am in life. They’re like the levers on the control panel of my life, each one representing a different facet that I can tweak to find my balance.

Right now, the dial marked Growth and Personal Mission is cranked up.

I’m just six months into growing my new company, The Rainmakers. This start-up phase demands energy and focus, especially as the business’s growth has felt like a rocketship from the start.

In my pursuit of success, I’ve neglected the dials labeled Balance and Harmony—particularly the delicate dance of work-life balance and nurturing my own sense of peace.

That 3:02 a.m. crisis, the one that led me here, hammering away at this keyboard to share my thoughts, was a wake-up call. Once again, the universe was trying to teach me a lesson I’ve been stubbornly refusing to learn: achieving and succeeding mean nothing if they’re at the expense of harmony and well-being.

I’ve found that where distractions are abundant, and expectations are relentless, the question of what one truly desires from life remains a poignant and often elusive inquiry. Understanding what I genuinely want is not just an intellectual exercise; it’s the bedrock for living a life filled with purpose and fulfillment.

And isn’t that what we’re ultimately wanting..?

In today’s society, which often equates success with external achievements, it’s when I’m at my best that I remind myself that true fulfillment arises from within. It comes from understanding and embracing what genuinely matters.

I’m ashamed to admit that I already “knew” that before this morning’s wake-up call.

But clearly, I wasn’t embodying it, so I know I must be and do something different. Knowing the right thing to do yet not having the strength of character to follow it is my definition of foolishness.

And I’ve been foolish.

The dials of my life are in my hands. It’s up to me to fine-tune them, to create the harmony that resonates with my true self, aligning ambition with well-being and external success with inner peace.

As I stared at the words on the page, a sense of clarity washed over me. I realized that the insights I’ve collected over the years aren’t just for me—they’re lessons that can resonate with anyone seeking a life of meaning and purpose.

Instead of complicating things, I will share these raw, unfiltered reflections straight from my journal.

Here’s hoping they offer you the same guidance they’ve provided me.

Existential Inquiry

In my life as an entrepreneur, husband, and father, I’ve learned so far that meaning isn’t something handed to you—it’s something you create.

When I first started each of my businesses, I chased success as society defined it: money, recognition, and growth. However, I quickly realized that true fulfillment comes from aligning my work with my core values and passions.

It’s not about ticking boxes on a societal checklist but about uncovering what resonates deeply with your inner self. For me, that means building something that thrives financially and positively impacts my team, customers, and community.

When I sold my last company, I scribbled down a list of “rules” I wanted my next ventures to live by. I was determined not to repeat the same mistakes.

Turns out that sticking to these rules has been tougher than I imagined. I see others, even my close peers, breaking the very rules I set for myself. There’s clearly some work to be done on my end to march to the beat of my own drum, even if it sounds off-beat to everyone else.

Personal Mission

Every morning, I want to kick my legs out of bed with a sense of mission—not just to build a company but more importantly, to create a life that matters.

This personal mission extends beyond work to how I show up as a father and husband. Knowing why you wake up every morning transforms your life, infusing it with purpose and energy.

When I focus on my family’s happiness and growth, I find that everything else falls into place. Purpose isn’t just a grand vision; it’s the intention behind every small action.

As I type this, I catch myself in a contradiction.

This section is titled “personal mission,” yet I just said my focus should be on my family. It’s always been easier for me to prioritize others’ well-being over my own.

Right now, I’m not sure if I’m truly being useful or if unresolved issues are preventing me from taking care of myself.

Love

At the heart of my journey is the understanding that life is about loving and being loved. In business, this means building relationships that go beyond transactions. Arthur C. Brooks distinguishes between “real friends” and “deal friends,” and I constantly work to nurture the former.

I strive to offer kindness and show compassion, creating a sense of belonging with my team members and clients. As a father and husband, I’ve learned that the love I give to my family returns tenfold.

Love is a currency that never loses value, and it’s the most precious investment I can make.

Belonging

We humans are social creatures, and finding your tribe is crucial. As an entrepreneur, I’ve learned that success is a team sport. Surrounding myself with people who share my vision and values has been key to my growth.

Being part of a community—whether it’s through family, friends, or a group of like-minded individuals—grounds me. It reminds me that I’m part of something larger than myself, a collective that supports and uplifts each other.

I believe…

You can’t outperform your support network.

You can’t outperform your environment.

I believe in the power of a solid, supportive network. Not just any network, but a handful of great people, sharp as tacks and committed to helping each other rise. It’s about creating a space where you don’t just survive but thrive.

This is why after chatting with one helluva smart cookie or a marketer and having this insight this morning, I said f**k it, let’s cultivate our world-class crew.

I want to create a private mastermind to bring together a small group of great people with the intention of each of us rising the tide for each other.

Self-Knowledge

There are plenty of people who say “Know thyself” is more than a mantra; it’s a lifelong journey.

But what does this actually look like in real life?

How do I best practice and embody this?

As an entrepreneur, father, and husband, understanding my strengths, weaknesses, desires, and fears is foundational to my personal growth. I’ve had to confront uncomfortable truths about myself and embrace them to become a better leader and partner.

Self-awareness is the compass that guides my decisions and interactions, ensuring I remain aligned with my values.

This practice that I’m doing right now with introspection is clearly something I need to be doing more often.

Continuous Learning

Growth doesn’t stop once you reach a milestone. I will stop learning the day I die, and not a second before.

I embrace a mindset of continuous learning, whether through formal education, life experiences, or inner contemplation. This means staying curious and open to new ideas, even when they challenge my beliefs.

As a father and husband, I learn from my children and spouse every day. They teach me patience, empathy, and the importance of being present.

I’m not looking for perfection, I want progression.

Can I be 2% better today compared to the person I was yesterday?

Giving Back

As I’ve grown in my career, I’ve realized that true success is measured by the impact I have on others.

All these books on my shelf stress the importance of service to others.

Contributing to the well-being of others not only helps them but enriches my own life with purpose and satisfaction.

Right now, I get the “good feels” from mentoring younger men and donating to the causes I feel best to reduce suffering. Giving back is a reminder that we rise by lifting others and that the world is richer when we share our gifts.

Legacy

I’m torn on this one…

On one hand, legacy seems like it’s all about caring what others think of you after you’re gone. But on the other hand, could legacy be the lens through which I refine my thoughts and actions to make a greater impact on others?

Legacy isn’t just about tangible achievements; it’s about my intangible impact on others and the world.

As a father, I focus on the lessons and values I pass on to my children.

As a husband, I work towards nurturing a relationship with my wife that I can look back on as I take my last breath, and know that I loved with an open heart.

In business, I aim to create something lasting—not necessarily a company that endures for decades, but a stepping stone that plants seeds for others to improve how they do business.

I want it to stand for more than just profit. I want to be remembered not only for what I accomplished but for how I made people feel and the positive change I sparked. My legacy reflects the values I live by every day.

Mind-Body-Spirit Balance

A healthy life requires nurturing all aspects of your being. In my pursuit of success, I’ve learned that neglecting my physical health, mental well-being, or spiritual nourishment has negative consequences.

I prioritize exercise, meditation, and time for reflection, ensuring that I’m not just productive but also balanced. Harmony in mind, body, and spirit is the foundation of my well-being.

Without this, I’m a shit person.

Period.

Work-Life Harmony

How do I strike the right balance between chasing my professional ambitions and living a fulfilling personal life?

Hell, is that even the right question?

I know I’m aiming for big things—things that most people can’t even dream of achieving.

But I refuse to buy into the idea that I’ve got to sacrifice everything else to get there. The notion that I should just roll over and accept that some parts of my life have to suffer for success?

That’s not just uninspiring—it’s downright depressing.

I look at people who’ve hit the jackpot financially but are out of shape, in poor health, or disconnected from their families, and it’s a cautionary tale I want no part of.

On the flip side, I get that to achieve something truly world-class—like winning a gold medal—you’ve got to go all-in, sometimes at the expense of other areas of life. But that doesn’t mean I’m looking for a perfect 50-50 split.

Life’s not that neat.

It’s about aligning my actions with my values and being fully present with my family, even when business is tugging at me from all sides. The truth is, I’m writing this because I haven’t nailed this balance yet. I need to do better.

I’ve realized that being a successful entrepreneur, father, and husband isn’t about finding some mythical equilibrium—it’s about setting boundaries, knowing when to say no, and constantly recalibrating my priorities.

Harmony isn’t a final destination; it’s an ongoing practice, a daily commitment to making sure my life reflects what truly matters to me.

Get better at this, Chris.

Gratitude

“Pour more energy into valuing what you have than in pursuing what you lack.”

(Honestly, that might be one of the wisest things I’ve said lately.)

Cultivating gratitude isn’t just about shifting your perspective—it’s about transforming your entire experience of life. When you focus on what you have rather than what’s missing, you’re not just settling—you’re unlocking a deeper sense of contentment and joy. Contentment isn’t about ticking off every item on some endless wishlist; it’s about realizing that what you already have is enough to make your life rich and meaningful.

Gratitude isn’t just a box to check off your daily to-do list—it’s a state of being, a mindset that colors every aspect of your day.

Embrace it fully, and it will change how you see everything around you.

Start by making it a priority to express love and appreciation to the people in your life. Those simple acts of acknowledgment can build stronger connections and a sense of fulfillment that no amount of chasing after the next big thing can replicate.

The more you appreciate what’s in front of you, the less you’ll feel the pull of what’s out of reach.

Acceptance of Life’s Impermanence

I remember Josef Goldstein saying this; “Whatever has the nature to arise, will also pass away”.

Life is transient, and embracing this fact brings peace.

Change is inevitable, and I’ve learned to find peace in the present moment rather than clinging to what was or worrying about what might be.

The only constant is change, and by embracing it, I free myself from the burden of trying to control the uncontrollable.

When I’m the mountain—unshakable and resilient—I become the man who can weather any storm with joy. It’s then that I am best to provide and be of true service to my loved ones.

Be True to Yourself

Every time I try to imitate someone else or chase after things that aren’t aligned with my true self, I screw up my life a bit more.

Authenticity means living in alignment with your true values and beliefs, not bending to external expectations. In a world that pressures us to conform, I’m at my best when I have the courage to be true to myself.

Whether in business or personal life, authenticity means making choices that reflect who I truly am, not who others expect me to be. It’s about embracing my quirks, passions, and unique voice, knowing that I offer my best to the world when I march to the beat of my own drum.

Integrity

“Integrity is doing the right thing, even when no one is watching.”C.S. Lewis

Integrity involves making choices that reflect your principles and holding myself accountable to high ethical standards. Acting with integrity means making decisions that align with my principles, even when it’s challenging.

As an entrepreneur, father, and husband, integrity isn’t just something I talk about—it’s something I strive to embody in every aspect of my life. It’s easy to be honest when things are smooth, but true integrity shows up when the waters get rough. That’s when the real test comes, and that’s when your principles either hold firm or crumble.

Integrity builds trust, and trust isn’t just another feel-good word—it’s the currency of all meaningful relationships, both personal and professional. Without it, everything falls apart. Trust is what allows people to believe in you, to follow you, and to depend on you. It’s the foundation of a solid family, a thriving business, and a life that you can look back on without regret.

Acting with integrity isn’t always easy. And neither should it be.

Sometimes, doing the right thing feels like walking uphill with a boulder on your back.

But I don’t choose integrity because it’s easy—I choose it because it’s who I am.

It’s about staying true to yourself, even when no one’s watching, even when it costs you something in the short term. It’s the quiet assurance that, at the end of the day, you did right by your values, and that’s a reward in itself.

Integrity also means holding yourself accountable. It’s about being honest not just with others but with yourself—owning up to your mistakes, learning from them, and striving to do better. It’s about modeling the kind of behavior you want to see in your children, your team, and those who look up to you. It’s about leading by example, not by words alone.

In the end, integrity is what defines my character.

Pursuit of Joy

This is the second dial I’m lacking most in right now.

Life isn’t just about serious pursuits.

Find joy in the small things and make room for fun and playfulness. Amidst the demands of entrepreneurship and family life, I’ve learned the importance of finding joy in the small things.

“The small things are the big things”

Whether it’s laughing with my daughters or taking a moment to enjoy squeezing my wife’s arse, joy is a vital ingredient for a fulfilling life. It’s a reminder that life is not just about achievement but about savoring the journey with a light heart.

Why the f@#k am I working so hard anyway, Chris?

Embrace Simplicity

Sometimes, the simple pleasures in life bring the most joy.

Yesterday, sitting around a fire with three friends, bantering about the highs and lows of life, was profoundly nourishing.

Strive for simplicity and appreciate the beauty in everyday moments.

In a world obsessed with more, I’ve found embracing simplicity helps me focus on what truly brings happiness and fulfillment. It’s about appreciating the small joys in everyday life and prioritizing what really matters.

As I wrap this and reflect on the journey that began at 3:02 am, I realize that the essence of a meaningful life is not hidden in some distant future but crafted in the choices we make each day.

Each lesson, each dial, and each moment of introspection has taught me that life is about consciously aligning who I am with who I strive to become. It’s about building a life that feels authentic and purposeful, whether it’s in the boardroom, the living room, or in my quiet moments of solitude.

I’ve learned that to be truly alive, I must embrace the chaos and clarity, the doubts and dreams, the successes and setbacks. Life isn’t waiting for the perfect moment to arrive; it’s about making this moment perfect by living fully in it.

This isn’t just an essay; it’s a kick up the arse for how I choose to live—a call to continually refine the dials of my life until they resonate with my true self. It’s a commitment to grow, love, learn, and serve in ways that honor my values and ignite my spirit.

Take control of your dials.

Listen to what truly matters in your heart and have the courage to pursue it relentlessly.

Don’t wait for life to happen to you.

Make it happen for you.

Be a little better, a little kinder, a little more aligned with the person you want to be.

Embrace the uncertainties, cherish the simplicities, and stand as your own unshakable mountain.

The world needs the best version of you, and so do you.