Issue #
109

The Question That Changed How I Coach (And Why I’m Evolving)

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    “You can’t build a future on a foundation that was meant for someone you used to be.”

    This week, a client said something that made me realize why I need to evolve this newsletter.

    After 8 years of coaching entrepreneurs, I’ve been asking the wrong question. Instead of “How do I help you bounce back?” I should have been asking “Who are you becoming, and does your business reflect that?”

    Here’s what I discovered:

    Most entrepreneurs I work with already know what they need to be doing. They’re not stuck because they lack strategy. They’re stuck because they’re not clear on who they are.

    A client just proved this perfectly. After our clarity work, he said: “I don’t want to do this anymore.” In my head, I was thinking, “Well, that check has already cleared and the money’s been spent in my head.” But what he meant was he realized his business idea was completely wrong for who he’d become. He was bored by the methodology and saw that AI would wipe out his industry within two years.

    Better to discover this in a coaching session than three years into building the wrong business.

    Why This Matters to You:

    How many entrepreneurs do you know who are successful but feel misaligned? Busy but not fulfilled? Growing revenue but losing themselves?

    The problem isn’t their tactics. It’s that they’re building someone else’s definition of success.

    What’s Changing:

    I’m aligning everything under the R³ Method™—my systematic approach to transformation that works when motivation fails: Reclaim your authentic identity, Realign your actions with that truth, then Rebuild systems that make growth inevitable.

    Starting Thursday, this becomes “The Real Work”—a grounded, no-fluff letter for entrepreneurs and high performers rebuilding who they are and how they grow.

    Here’s my question for you:

    If 2025 ended today, what would be your proudest accomplishment? If you can answer that easily, this year is already a win. Now go get your bonus.

    But if you struggled to answer… that’s exactly why this work matters.

    Here’s another one that might hit even deeper:

    When people ask what you do, do you explain your role or share your impact? Most entrepreneurs I meet can recite their services perfectly but struggle to articulate the transformation they create. That gap? That’s the misalignment talking.

    The goal isn’t to feel anxious and behind. It’s to get so clear on who you’re becoming that your next moves become obvious.

    Ready for The Real Work? 

    Terry

    P.S. What’s one area where you feel successful but misaligned? Hit reply and tell me. I read every response.

    P.P.S. If you know an entrepreneur who’s crushing it externally but struggling internally, forward this. They’ll thank you.

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