When I write, I attempt to do so as if I am a window or a mirror. I share what I see when I gaze through the glass at our industry, your business, or you as an entrepreneur. I write as your reflection, allowing you to see how others view you or your business. I do this in the hope that these words stand out amid all the clutter in your inbox and help you improve your business, entrepreneurship, and perhaps even your life.
Today, I will stand on the other side of the window, step in front of my mirror, and share what I’ve seen in myself and my business. My goal is that you’ll learn from my missteps and frustrations and feel encouraged by my demonstration that there is a way forward.
It hit me as I prepared for a mastermind retreat in Mexico City in a couple of weeks. The facilitator asked me to prepare a talk about the evolution of my business over the past decade. As I worked through the slide deck, I reached the last 24 months. I started with the bullet points I wanted to cover, wrote them down, and then read them back. At the top of the slide, I typed my title: “The Doldrums.” I sat back, and it hit me.
“Shit,” I thought. I’m the guy who helps entrepreneurs and businesses get unstuck. Yet here I was, sucked into the vortex of the status quo, idling on the placid waters of stagnation, feeling unfulfilled, frustrated, and ineffective.
Through my research and experience, one of my most essential discoveries has been fulfillment. I’ve uncovered what drives it and why it’s critical to success. Fulfillment doesn’t come from financial rewards, status, or achievements—it’s simpler than that. We feel fulfilled when we make progress doing meaningful work. Fulfillment delivers focus, energy, and resilience. Without it, we’re lost, adrift at sea without a rudder.
That’s where I had been—rudderless. At TIG Brands, we offer two different programs. The TIG Collective was established to educate, equip, and empower founders by tapping into industry wisdom, peer-to-peer learning, and the collective intelligence of our ecosystem. The second is my one-on-one work with entrepreneurs and their teams. I was working hard. I cared deeply. We were doing good work—but not great work. I want to be transformational. I want our entrepreneurs to achieve their dreams and create all five types of wealth: financial, mental, physical, social, and time. It wasn’t happening, and I felt depleted, frustrated, and—most dangerously—unfulfilled.
I blamed this on the moment in time. It’s been tough out there; these have been challenging years for our industry. But that was just me playing the victim and avoiding the truth. I had built something that wasn’t working, and because of the fear, doubt, and vulnerability that come with radical change, I was being crushed by the weight of sameness. I suffered, the business suffered, and those I serve suffered.
The only way to escape the doldrums is to break free of the status quo’s inertia. It requires recognizing that sameness is no longer an option. You must start asking questions and seeking answers: “Why am I feeling unfulfilled?” “Why am I not doing great work?” “What isn’t working?” “What am I missing?” “How do I get unstuck?”
I lingered in the doldrums for far too long. What finally prompted me to grab the oars and start paddling? Maybe it was the gnawing disquiet in my gut or an unwillingness to stop loving my work. Whatever the reason, I began paddling vigorously.
Once I started asking the questions, the answers came in a flurry. I learned that I wanted to do more meaningful work but less of it. I realized that what energizes me is researching, synthesizing new insights, and turning them into tools that help founders unlock their potential. I saw that I’m at my best when creating and thinking differently. Lastly, I acknowledged that, despite its daunting nature, I’m compelled to write a book—something I’ve relegated to the back burner for years.
With answers in hand, it was time to turn them into action. I’ll save the details of how I did that for another article and skip to the results.
We’ve reimagined the TIG Collective. Its purpose—educating, equipping, and empowering entrepreneurs—remains unchanged, but how we achieve that has shifted significantly. My research led me to the power of mastermind groups. We now curate small groups of five entrepreneurs at similar stages, paired with two to three advisors, to form mastermind groups. These groups meet weekly for a “power hour,” working through an agenda of hot seats, goal setting, and accountability. I’m confident it will be transformative. I hope to have over twenty groups by year’s end.
I’m now focused on high-performance coaching for those I work with one-on-one. I’m bringing new tools and techniques to help them do precisely what I’m doing: making daily progress while pursuing meaningful work and building all five types of wealth.
As for the book, this is the first time I’m putting that commitment in writing: I am writing a book. I’m not yet sure how it will take shape—whether as a “how-to,” a parable, or a novel—but it will come to life, and I ask all of you to hold me accountable.
I hope this article helps. It feels deeply personal and a bit embarrassing. But if it resonates with even one of you and inspires you to start paddling, it’s well worth it. I’ll see you in the tradewinds.
I have two favors to ask. First, I want to hear from you; please share your comments. Second, share this with others who might find it helpful.
