In partnership with

Learn how to make every AI investment count.

Successful AI transformation starts with deeply understanding your organization’s most critical use cases. We recommend this practical guide from You.com that walks through a proven framework to identify, prioritize, and document high-value AI opportunities.

In this AI Use Case Discovery Guide, you’ll learn how to:

  • Map internal workflows and customer journeys to pinpoint where AI can drive measurable ROI

  • Ask the right questions when it comes to AI use cases

  • Align cross-functional teams and stakeholders for a unified, scalable approach

The Activated Leader™ | Issue #33

In this issue: Stage 3 (ACTIVATE) deep dive. Why waiting for your work to be perfect is costing you the very thing perfectionism promises to protect.

The Activation Series (Part 3b) - ACTIVATE

Last week: Motion vs. Movement (Are you actually moving?)

This week: Why your first attempt should be embarrassingly bad.

This is Stage 3: ACTIVATE — Shipping before you're ready.

I'm coaching someone who spent three weeks perfecting a LinkedIn post.

Rewritten 14 times. Feedback from five people. Still sitting in drafts.

I asked her: "What happens if it's not good?"

She said: "People will judge me. They'll think I'm not ready."

Here's what I told her: They're already thinking that. Because you haven't posted anything.

The Perfectionism Tax

Perfectionism isn't about quality. It's about control.

If you never ship, you never risk being wrong. You never risk judgment. You never risk failing publicly.

But here's the cost: You also never risk succeeding.

The leaders who move fastest aren't the most talented. They're the ones willing to be embarrassingly bad at first.

Your First Attempt Should Embarrass You

Not because you're aiming for bad work. Because if it doesn't embarrass you, you waited too long.

Version 1 is always awkward. Always incomplete. Always "not quite there yet."

But Version 1 creates Version 2. And Version 2 is where the magic starts.

That post my client was perfecting? I told her: "Post the worst version today. We'll make it better based on what you learn."

She posted it yesterday. Was it her best work? No. But it was real.

47 comments. Three DMs. One became a client conversation.

Real beats perfect. Every time.

One Question

If you selected the first three: Ship it this week. Imperfect. Embarrassing. Done.

Watch It in Action

This Friday on YouTube (2pm PT), I'm walking through the exact framework I use to help perfectionists ship:

  • The 3-question test: Is this perfect or am I stalling?

  • How to set a "good enough" standard

  • The 48-hour shipping rule

Next Week

The Activation Series Part 4: AMPLIFY. Why some success doesn't scale — and what to do about it.

Until then, ship it imperfect.

Ways I Can Support You or Your Team

1:1 Coaching
For perfectionists ready to ship. We build your "good enough" standard together.
Explore here →

2. Keynote Speaking
Teach your team to ship before they're ready. Culture shift starts here.
Book Lilah →

3. Leadership Workshop
Your team practices shipping imperfect work in real time.
Explore here →

Not sure which is right? Reply to this email, and I'll send you personalized guidance (no pitch, just direction).

Keep Reading