Hey Reader,

Welcome back to Little Leadership Lessons, my Monday newsletter sharing short but powerful insights from coaching seven-figure creators. Each note is designed to help you grow as a leader so you can grow your business—with more clarity, alignment, and peace of mind.

At some point, every founder realizes the hardest part of growth isn’t strategy. It’s identity. You have to stop being the one who does everything and become the one who builds everything.

Let’s get to it.

The Situation

Again and again, I hear the same story from leaders in transition. They’ve grown beyond being a solo operator. They know they need to think like a CEO. They know leadership means letting go of day-to-day delivery.

And yet, when the next big project shows up, they default to doing it themselves.

On the surface, the reasons sound logical:

• “I have higher standards than anyone I could hire.”
• “There’s no time to delegate. Launch is too close.”
• “No one I know is the right fit.”
• “I’ll just do it now and document the process later.”

But under the surface? These are stories that keep them anchored in their old identity as "the doer," rather than stepping into the CEO they’re becoming.

The Emotional Blocker

The habit of doing runs deep. It’s comforting, familiar, and validating. You know you can deliver at a high level, so when pressure builds, you go back to what feels safe. It’s easy to default to delivering rather than leading, and shifting that pattern takes time, awareness, and practice.

Delegating feels uncertain because it means trusting someone else with the thing that once defined your success. What if the work isn’t good enough? What if the hand-off slows things down? What if I spend more time training than just doing it myself?

In the short term, doing feels faster. And the tension between comfort and capacity is where most leaders stall. But in the long term, it keeps you stuck: busy instead of leading, exhausted instead of expanding.

The Breakthrough

The breakthrough is realizing that leadership is a habit. Every time you choose to hand off, you’re not just freeing up time. You’re reinforcing an identity shift, from producer to builder.

I recently watched a leader face this exact tension. A major project landed on their desk, and every instinct said, "Just do it yourself. It'll be faster and more efficient. You can be resourceful and find the time for it."

Instead, they paused, created structure, and handed it off. They gave clear context to their team, trusted the process, and stepped back.

It wasn’t perfect. But it was progress. And it strengthened their leadership muscle in the process. Every act of delegation is a small vote for the leader you’re becoming. Each one builds capacity, first in others, then in you.

Coaching Questions to Apply This to Your Business

• Where in your business are you still defaulting to doing rather than leading?
• What stories or excuses keep you from handing things off?
• What’s one project you could delegate this month—even if it feels imperfect at first?
• How might trusting others become your next act of leadership?

Every time you choose leadership over delivery, you strengthen the CEO habit. Over time, those choices compound into freedom, clarity, and the ability to scale with intention.

If you're a six- or seven-figure creator facing the opportunity to shift from creator to CEO, let's chat. Hit reply to this email with what you're currently working through and we can get the discussions rolling.

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Much love and respect,