Freedom over Fortune

Sunrise in Mexico can awaken deep thoughts for every man... It was supposed to be a mission statement... Stressed Leaders Newsletter, Volume 40

Growing up in the rural Midwest, small town kids dream of riches, of professional sports, of yachts, of California Dreamin’… but those same cornfed kids don’t typically dream of the frustrations, the grinds, the mindlessly numb, at times, hard work to get near the point of riches.

I never set out to be rich. But on a holiday celebrating freedom, like July 4th, maybe we should celebrate the freedom of controlling our time.

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Recently, I held our 2nd Annual Stressed Leaders Retreat, and we have built a community of like-minded leaders, growing and supporting each other, navigating the tribulations and demands of executive leadership.

However, the reality of leadership is that many are fading out of the shackles of other people’s unrealistic demands, choosing to exit, or even worse, quality leaders being forced out. Forced out by ravenous politicians or ineffective evaluators, faux supporters, or the myriad of personality conflicts that exist in toxic relationships.

I learned from executive leaders who have ascended to the apex of their careers, but have found themselves pushed out or choosing to exit because of people, because of feeling chained down by the politics of executive leadership. This complicated relationship troubles me; the world needs leaders, it needs risk takers, those who choose courage over comfort, or who aren’t afraid to make unpopular decisions.

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I advanced my career in education in a traditional, yet somewhat outside of the norm mode. Ascending from teacher and varsity head coach, to school improvement director, to business manager, and then finally to Superintendent. The pinnacle of my career; the apex of the growth ladder. I grew in financial analysis and was blessed to have one of the best mentors a man could ever ask for. While I enjoyed the pay raises that grew from the promotions, I really learned from multiple mentors about the grind, the work ethic, the long hours, the chasing sunrises and sunsets at work, to get the job done. The work is the work and it must be done…

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But for some people, the wealth grows, and yet, the time fades. The job can become enslavement, both physically and mentally.

That post-it note sits in my office, near my keyboard, a reminder of the power and responsibility I wield within my grip.

But I know, from my work, from my support systems of others, that the gravity and the weight of our jobs is demanding. I choose to decompress with my earned vacation time, while others leave it sitting in a damp vault somewhere, perplexed by the unwritten rule to always be available, their freedom of their time, never to be realized.

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A sunrise run in Mexico, down 5th Avenue in Playa del Carmen, salt from the ocean water singing my nostrils, the quiet still before the bustling shops open, the hustle of those scrambling to get to the early morning Cozumel ferry, racing the Gringo in the opposite direction for the first horn, life suddenly awakens inside of you…

What I discovered in that sticky, sun kissed morning, what I really desperately wanted, in that moment, and in that time, was freedom.

For many, wealth becomes just another kind of confinement—an upgraded cage with sleeker furniture.

It’s the same early mornings, the same inbox full of people who think they own your time.

The same meetings where your body is present, but your spirit is somewhere else, quietly asking, Is this really it?

Money without freedom is just decoration for a life you don’t control.

At some point, you realize: you don’t need a yacht—you need escape velocity. The ability to live on your terms, to design your days, to step out of the noise and into something that feels truly your own.

I look at what two of my friends are currently doing with their career arc and I see them striving for that freedom, building something ALL on their own. I look at my friend, Adam, who took the leap, who built the business, invested in the relationships, and is watching years of motion, of energy, and momentum explode with his new venture.

A quiet part of you already knows this. You weren’t made to be managed. You weren’t designed to spend five days a week in traffic, only to spend your weekend in a fluorescent-lit store asking permission to buy back your own energy.

You were made for something more. Maybe it’s waking up near the ocean, disappearing into the horizon with someone you love, and returning to a life that belongs only to you—one that isn’t dictated by push notifications, google calendar appointments, emailed agendas with no goals, no purpose, and no end time, or performance reviews by someone you might not respect.

Every skill you develop should move you closer to autonomy. Every dollar earned should mean less dependence on approval, less bending to expectations you never agreed to in the first place.

And yet, so many live as if they have no choice. They trade their fire for comfort, their independence for predictability. They call it being responsible. But often, it's just fear—disguised as comfortable maturity.

They obey. They shrink. They endure. And when it becomes too much, they think starting a business or building a “brand” will save them, only to find themselves trapped again—this time by algorithms, banging their head up against a problematic wall that could have been taken down, brick-by-brick just by asking for help, or phony social media applause.

If you're spending most of your days doing what others expect, in ways that drain you, for rewards that feel empty—you haven’t escaped. You’ve just changed uniforms. I see my friends BUILDING something and I’m there to cheer them on these new ventures. I see them in the ARENA taking chances and I cannot wait to celebrate their success.

You don’t need to be a billionaire. You need to wake up without dread. To sleep beside someone who believes in your mission. To make decisions from a place of clarity, not panic.

You need to build a life so honest and self-directed that others question whether it’s even real. That can be found in traditional careers, but we must strive to build a culture so authentic, and so supportive, that we aren’t shackled by these factors. I find myself blessed to be in a leadership position like this, often explaining to people that my school, is a lot like Mars.

You weren’t born to chase raises or soften your voice to make others comfortable. You weren’t put here to survive until retirement and hope Florida feels like freedom, one day…

You were meant to be a sovereign force—skilled, focused, and fiercely alive. Paid to be exactly who you are. Respected not because you followed the rules, but because you had the courage to write your own.

And if that vision stirs something in you—if it makes you feel restless, excited, maybe even a little afraid—that’s good.

It means you’re not numb yet. It means you're still in there.
Because your life doesn’t change when you earn more.

This isn’t a calling to quit what you are doing, because it is hard, because your boss is demanding, or you are simple in a rut, this isn’t some manifesto…

But for the leader out there, who feels like it is unraveling, who feels like they have been pushed too far, under the boot of the people who shackle you, you can take the next step. It doesn’t have to be a grand exit, or even a drop everything, I’m quitting and changing careers, it can just be one step forward…

It changes the moment when you say, I’m done living on someone else’s terms.

36 leaders discovered ways to find support, to take the next step, to grow, in our Stressed Leaders Retreat, more information coming soon to sign up!

www.stressedleaders.com