I Am The Most Optimistic Pessimist You Will Ever Meet

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I have always lived in that strange middle place between hope and worry, the place where you can see what is possible while simultaneously imagining every worst-case scenario within a ten-mile radius. It is not dramatic. It is not debilitating. It is simply the mental real estate I occupy. I interpret it as a sign of intelligence, although my family might have other interpretations. Either way, it has shaped the way I lead, the way I build, and the way I carry the weight of the things I care about. That tension is loud these days because I am standing inside the largest shift of my entire career, and it has me feeling strangely ancient and strangely new at the same time.

I am fifty years old. Most days I feel younger than that. Some days I feel like an exhausted minor league baseball coach who has been riding buses for decades. Coaching years do not match regular years. People who have spent real time in the trenches know this. One calendar year in coaching feels like four, sometimes six, depending on the number of client emergencies, leadership meltdowns, or late-night Slack messages that begin with something innocent like “Do you have a minute” but then unravel into a multi-hour existential crisis about employees, direction, revenue, or all of the above. By that math, I am closing in on one hundred coaching years, which probably explains why every joint in my body has started filing complaints even though I barely exercise and move far less than any reasonable adult should.

The truth is that I have carried a lot of things on my back for a long time. My own companies. My clients’ companies. My clients’ fears. My teams’ stress. My family’s rhythms. My church responsibilities. My community commitments. I have walked around with an invisible backpack full of other people’s outcomes while convincing myself that I was simply being responsible. If you read last week’s blog, you know that my default response to anything uncertain is to do more work. I could be standing on a cliff with the rope fraying beneath me and my response would still be to tighten my grip.

Last week gave me a different kind of weight to carry, one that was beautiful and tiring all at once.

We had Joseph at our house every day. I had been looking forward to it. We pulled out the trains and the Lego and set the stage for a week of fun. And it was fun. I loved every second of it. There is a certain joy that only a three-year-old can bring, the kind that makes the world feel softer and somehow louder at the same time. But my knees, back, and shoulders have announced their grievances like a committee that suddenly remembered it has voting rights.

I would do it again tomorrow without hesitation, but I may need two days of stretching and possibly a heating pad the size of a small mattress.

Even in the joy, I felt the familiar undercurrent of anxiety I have carried most of my life. I wonder constantly if I am doing enough. Enough for clients. Enough for my family. Enough for my community and my church. Enough for the new venture that has consumed my time and my energy and my hope. I have asked myself if I am failing more times than I would ever admit in public, which I suppose I am admitting right here, so maybe I am growing.

The new venture is not really coaching at all. That is the part that feels both thrilling and terrifying. After decades in this field, I am stepping away from coaching as I have known it. My mind and soul feel one hundred years old, and the old path simply does not fit anymore. But creating more than five hundred training videos, rebuilding everything I teach from the ground up, and reimagining myself at this stage of my career has been a journey that sits somewhere between exhilarating and brutal. I am grateful for it, but I am also very aware of the toll it has quietly taken.

I remember watching the old road warrior consultants in airports, the ones with suits that looked permanently wrinkled and eyes that looked permanently tired. They could fall asleep anywhere. Chairs, floors, leaning against a wall near Gate 32B. I used to watch them and promise myself that I would never become that.

I planned to be the energetic consultant who bounded through airports with purpose and sparkle. And now I catch myself staring at walls, not because anything is wrong, but because my internal hard drive is loading and I am waiting for the next thought to arrive.

So I blew it all up. I redesigned everything.

I built something new that my heart believes in, that my mind respects, and that my soul feels aligned with. I created a system leaders desperately need, a foundation that stabilizes everything else they build. And people are not flocking to it. At least not yet. The pessimist inside me mutters about timing and market noise. The optimist reminds me that revolutions start slowly, and the world has never been quick to recognize something that will actually save it from itself.

Joseph gave me a metaphor I did not expect. At our house, he has enough wooden train tracks to circle the living room like a small suburban commuter system. We got him four battery-powered engines. In my mind, it seemed brilliant to run all four at the same time, pulling long lines of cars in perfect choreography.

I even bought one that looked more realistic, assuming it would be slower and eventually need replacement. I was wrong. That one became his favorite. He now transports it between houses in its own bag. Which means, of course, that I need to buy a backup because toddler logistics are unforgiving and Amazon seems to know it.

I kept trying to add more trains to the track, thinking I knew exactly what would make the moment better. He kept removing them. Not angrily. Just decisively. He knew what he wanted from the experience, and my interventions were getting in the way. I thought the magic was in the details. He just needed the track set up so he could decide how to play.

Leadership works the same way. We think we need more trains on the track. More features. More content. More adjustments. More pressure. But the real win is in the foundation. The structure that gives us room to improvise, explore, learn, and sometimes fail without losing ourselves.

That is what the Impact Shift Training System is, or ISTS, because after a hundred coaching years I need acronyms the way millennials need validation on the internet. It is the foundation leaders keep trying to build on the fly. The part no one sees but everyone feels. It is what allows a company to breathe and grow instead of collapsing inward on whoever is strongest. It is what turns the mental noise into clarity. It is what gives leaders space to be human instead of machines disguised as visionaries.

The optimistic part of me knows that ISTS is exactly what the world needs. I have seen it change companies from the inside out. I have watched leaders recover their energy and their confidence because they finally had a foundation strong enough to carry them. The pessimistic part of me worries that people will not slow down long enough to recognize what is actually saving them. That they will reach for shortcuts, trends, surface level strategies, anything that promises fast relief without doing the deep work that creates lasting stability.

I want to believe people will see it. I also know how many leaders are out there running their companies on the equivalent of a wooden train track that keeps shifting every time someone bumps the coffee table. They are brilliant. They are exhausted. They are improvising their way through problems that should have been solved by structure, not heroics. They deserve better than that. Their teams deserve better too.

The funny part is that even with all this clarity, even with all this experience, I still find myself trying to add more trains to the track. More details. More pressure. More complexity. I still have moments where I think the answer is to push harder instead of stepping back to rebuild the foundation. Old habits do not evaporate just because you outgrow them. They hang around until you consciously replace them.

So here I am, rebuilding my own foundation at fifty years old. Half ancient, half newborn. Carrying a vision that feels bigger than anything I have done before. Carrying fears that feel strangely familiar. Carrying hope that refuses to be quiet even when my mind tries to manage expectations. It is a strange thing to reinvent yourself when people expect you to have everything figured out. Reinvention asks you to become a beginner again. Beginners are messy. Beginners are earnest. Beginners are often wrong before they are right. And it takes a particular kind of humility to be both a leader and a beginner at the same time.

But reinvention also brings you home to yourself. It clears out the noise. It brings back the part of you that remembers why you started. It reminds you that the foundation matters more than the trains, the tracks, or the choreography. It gives you permission to breathe inside the business you built instead of bracing inside the one you inherited from your old self.

ISTS is the foundation leaders have been missing.

It is the part underneath everything else. It is the reason companies stabilize. It is the reason leaders stop feeling like the only adult in the room. It is the reason cultures shift from reactive to intentional. It is the reason the work becomes meaningful again instead of mechanical.

So if you feel tired, or stretched, or oddly disconnected from the company you built, it might not be you. It might just be your foundation. And that is something we can rebuild.

In the meantime, I am going to try to run four trains on the track again. Not because it will work, but because Joseph will laugh when I inevitably misjudge how those engines behave. That laugh is worth every failed experiment. And maybe that is the whole point.

Build the foundation. Let the rest be discovery.