🧾 The UnLoop Dispatch Issue 1

🟩 FIELD NOTES

From job search to clarity work

If you’ve been following along, you know this started as a job search newsletter. But somewhere along the way, it became something else. Not just a change in what I’m doing—but a shift in how I understand the kind of work where I’m most effective.

Over the past few months, more than a few of you have said things like:

“You get to the core faster than anyone I’ve worked with.” 

“You see the system behind the chaos.” 

“You zoom in and out without losing the thread.”

That feedback helped me name what was already happening: I help leaders find clarity in the mess. I spot the pattern behind the pain. And I use lightweight, high-leverage interventions to get things moving again—without burying people in bureaucracy.

So this newsletter is evolving too.

Still personal. Still practical. But now focused on what I’m seeing inside founder-led and mission-driven teams:

• The loops that keep leaders stuck—and how to break them

• The leverage hiding in plain sight

• The work of designing smarter structures that scale

Let’s call it clarity work. And let’s dig in.

🟦 CLARITY DROP

The 3 hidden loops that keep you in the weeds

If you’re a founder or executive doing work two levels below your role, the issue probably isn’t discipline. It’s a loop.

Here are three patterns I see all the time:

🔁 The Competence Loop

“It’s faster if I just do it myself.” You do it → it gets done right → your team learns nothing → you keep doing it.

🔁 The Trust Loop

“They’re not ready yet.” You withhold the real responsibility → they stay unsure → you confirm your doubt → rinse, repeat.

🔁 The Clarity Loop

“They should’ve known what I meant.” You assume shared understanding → they misfire → you get frustrated → you avoid delegation next time.

These aren’t leadership. They’re inertia dressed up as accountability.

To break them, you don’t need more effort. You need better design:

• Name the pattern

• Adjust the inputs

• Build just enough structure to support better outcomes

Staying in the weeds isn’t a sign of commitment. It’s a sign of an unbroken loop.

🟨 CASE IN POINT

From stalled sale to smart internal pitch

A startup founder I’m advising was struggling to close her first customer.

Every time she built momentum with a prospect, the same thing happened:

“I need to take this back to the team.” Then silence. No decision. No deal.

She thought the issue was her go-to-market strategy. But the real problem? Her buyer didn’t know how to sell it internally.

So we paused the deck and focused on what would actually move the deal:

• A plain-language engagement menu built around a “Good, Better, Best” model—three clear, testable offers that made saying “yes” feel safe and simple

• A short script to help her reframe the internal conversations

• Simple tools to help her champion make the case with confidence

Instead of waiting for consensus, she gave her buyer a frictionless “yes.”

Traction doesn’t come from the perfect pitch.It comes from arming the right person with the right words at the right time.

🟪 OPEN THREADS

If someone came to mind while reading this—a founder stuck in the weeds, a team spinning on the same problem, or a smart operator sensing something’s off but can’t quite name it—I’d be grateful for an intro.

I typically work with:

• Founders and CEOs of companies between $5M–$20M in revenue

• Mission-driven orgs trying to scale without losing their soul

• Service businesses where growth has outpaced structure

That stuck point? It’s usually not a people issue. It’s a loop. And loops can be fixed.