Hey friend,
Happy Monday 🤗
As a reminder, I’ve moved this newsletter over to Substack (and renamed it!) but in order for you to have full-access, you’ll need to take the following steps:
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I’ve included the Progress Plan 👇 since I know you’re not (yet!) subscribed to Substack and it technically has a paywall over there 🙂
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Progress Plan
7 Days to Break Free from the Execution Trap and Think Like a Strategic Leader
This isn’t about reading leadership books or attending another management seminar—it’s about rewiring your relationship with control, competence, and what it means to add value. Each day targets a specific layer of your professional identity, from surface-level tasks to deep beliefs about worth and productivity. Every exercise takes 20 minutes or less because strategic thinking isn’t about working more—it’s about working differently. By the end of seven days, you’ll have identified your execution addictions, built systems that work without you, and started leading through leverage instead of labor.
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Day 1: The Execution Audit (20 min total)
Morning addiction inventory (15 min): Your execution patterns are data about your deepest fears. Set a timer and excavate your relationship with doing versus directing:
- What’s your earliest memory of being praised for “getting things done”? (First thing that surfaces)
- Growing up, what happened in your family when something wasn’t done “right”? (Who got blamed? Who fixed it?)
- What belief about your value is tied to being the person who “handles things”?
- Name three tasks you do because “it’s faster than explaining it”
- When did you last let something fail that you could have saved? How did it feel?
- What would people discover about you if you stopped being so capable?
Evening energy tracking (5 min): Today, notice your body’s response to different work modes:
- Solving a problem yourself vs. watching someone else struggle through it
- Creating something vs. creating a system for something
- Being needed vs. being unnecessary
- Doing excellent work vs. enabling excellent work
Rate your anxiety level (1-10) when delegating. Note where you feel the urge to jump in. This isn’t about changing yet—just noticing your patterns.
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Day 2: The Competence Trap Investigation (20 min)
Morning archeology (15 min): Your need to execute perfectly didn’t start in this job. Time-travel through your competence story:
Map your “competence heroes”—people you admired growing up:
- What did they never delegate?
- How did they show their value?
- What happened when they weren’t needed?
- What did being “irreplaceable” protect them from?
Now examine your competence origin story:
- When did being “good at things” become your identity?
- What were you avoiding by staying busy?
- Who did you have to be reliable for?
- What chaos were you managing through control?
Evening compassion practice (5 min): Re-read what you wrote. Instead of seeing these as character flaws, see them as brilliant survival strategies that have outlived their usefulness.
Write one sentence of appreciation: “Thank you, younger me, for learning to be so capable because…” Then add: “I’m safe enough now to lead differently because…”
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Day 3: The Leverage Multiplier Exercise (20 min)
Morning calculation (15 min): Pick your three most time-consuming weekly tasks. For each one, calculate:
The Execution Math:
- Hours you spend per week on this task: ___
- Your hourly rate (or approximate value): $___
- Weekly cost of you doing this: $___
- Annual cost of you doing this: $___
The Delegation Math:
- Hours to properly train someone: ___
- Number of times you’ve re-trained this in past year: ___
- Total hours lost to re-training: ___
- Cost of not having a system: $___
The Strategic Question: “What could I build with those hours that would make this task unnecessary?”
Afternoon commitment (5 min): Choose the highest-cost task from your calculation. Write one sentence: “I will stop doing [task] by [date] by creating [system/process/delegation plan].”
Say it out loud. Notice what resistance comes up. That resistance is your growth edge.
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Day 4: The System Builder Challenge (20 min)
Morning recording session (15 min): Today you stop creating knowledge debt. Pick one task you do regularly:
- Start a voice recording or screen capture
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Do the task while narrating:
- Why you make each decision
- What could go wrong at each step
- What patterns you’re noticing
- Where people usually get stuck
- Don’t script it—just talk like you’re training your replacement
- Save it with a clear title: “[Task Name] – Full Process – [Date]”
Evening reflection (5 min): Listen to/watch 2 minutes of your recording. Notice:
- Where you said “I just know” or “you’ll get a feel for it”—these are your unconscious competencies
- How much context you provided vs. just steps
- Whether you explained the why, not just the what
This recording is now your training system. You’ll never explain this from scratch again.
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Day 5: The Strategic No Practice (20 min)
Morning boundary setting (10 min): List every request you’ve said yes to this week. For each, answer:
- Was this only doable by me? (Y/N)
- Did this move a strategic priority forward? (Y/N)
- Did this develop someone else’s capability? (Y/N)
If you answered No to all three, you’re execution-trapped.
Design your Strategic No template: “I appreciate you thinking of me for [task]. To maintain focus on [strategic priority], I need to decline. However, [alternative person/resource/solution] might be helpful.”
Afternoon implementation (10 min): Use your template once today. Options:
- Decline a meeting where you’re not essential
- Redirect a question you’ve answered before to documentation
- Suggest someone else lead a project you’d normally grab
- Say “Let me think about that” instead of reflexively saying yes
Notice: How does it feel to preserve your energy? What story does your brain tell about being “unhelpful”?
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Day 6: The Uncomfortable Development Day (20 min)
Morning stretch assignment design (10 min): Think of a team member who could grow. Design a contained challenge:
The Assignment Framework:
- Current capability they have: ___
- Stretch capability they need: ___
- Low-stakes project that bridges the gap: ___
- Resources they’ll need (recordings, documents, access): ___
- Success metric that’s clear and measurable: ___
- Your rescue threshold (when you’d step in): ___
Afternoon delegation (10 min): Deliver the assignment with strategic framing:
“I selected you for this because [specific strength]. This will help you develop [capability], which will position you for [future opportunity]. You’ll likely hit obstacles at [predicted challenge points]. When you do, try [suggested approach] before we troubleshoot together.”
Then—and this is crucial—leave them alone. Your discomfort is their growth opportunity.
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Day 7: Integration & New Operating System (20 min)
Morning pattern integration (15 min): Review everything you’ve discovered this week. Create your personal “Strategic Leadership Manual”:
- My Core Execution Pattern: [The main behavior that keeps you tactical]
- Where It Came From: [Historical source of your need to do vs. delegate]
- What It’s Really Protecting: [The fear underneath the competence]
- The Cost of Continuing: [What staying tactical is actually costing you]
- My Strategic Identity: [Who you are as a leader, not a doer]
- My Early Warning System: [Signs you’re sliding back into execution]
- My Strategic Reset: [One question you ask when tempted to just do it yourself]
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Evening commitment ceremony (5 min): Choose ONE system you started this week. Commit to using it for the next 30 days. Put a recurring calendar reminder: “Did I execute or enable today?”
This isn’t about perfect delegation—it’s about consistent movement toward leverage.
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Your First Month Strategic Leadership Toolkit
When you’re tempted to jump in and fix something:
- Pause and ask: “What would happen if I didn’t?”
- Remember: Their struggle is their learning
- Try: “What solutions have you considered?” instead of solving
- Celebrate one thing they figured out without you
When delegation feels like more work:
- Remember: You’re paying off technical debt
- Calculate: The compound cost of not delegating
- Record: Your process while you do it anyway
- Invest: 20% more time now for 80% less time forever
When someone says “you’re so good at this”:
- Hear: “I’m avoiding learning this”
- Respond: “Thank you! And you could be too. Let me show you.”
- Resist: The ego boost of being needed
- Choose: The strategic boost of being unnecessary
When you feel less valuable because you’re not “doing”:
- Remember: Multiplication is more valuable than addition
- Review: What your team accomplished without you
- Notice: The strategic problems you now have space to see
- Ask: “What am I making possible that wasn’t before?”
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The 30-Day Evolution Protocol
Week 1-2: Foundation Building
- Record one process per day (even 5-minute tasks)
- Notice rescue impulses without acting on them
- Practice saying “What have you tried?” before helping
Week 3-4: Leverage Expansion
- Delegate one task you swore only you could do
- Create one system that prevents recurring questions
- Have one “strategic priorities” conversation with your boss
- Run one team capability assessment
Monthly Check-In Questions:
- What got done this month without my direct involvement?
- Which system saved me the most time?
- Where am I still addicted to being needed?
- What strategic opportunity am I now seeing?
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Remember
You’re not abandoning your team—you’re graduating from player to coach. Every time you choose systems over heroics, delegation over doing, and multiplication over addition, you’re literally rewiring decades of conditioning around what makes you valuable. That’s not small work. That’s transformation.
The goal isn’t to become unnecessary. It’s to become exponential.
