Struggle Better: The CEO Playbook for Value Creation

Summary

Lee breaks down how to use struggle as a feature, not a bug—at work and at home. He maps three types of struggle (healthy, unhealthy, and intentionally designed), shares his “organize & develop” mantra for calm execution, and shows how to spot and fix value bottlenecks using value-creation funnels. He contrasts happiness vs. fulfillment, explores live resistance (front-line work where value is actually created), and explains when to let go of people and initiatives. Lee also unpacks why every organization needs a Management/Value Creation Operating System and gives a practical path from idea → traction → package → scale.

What you’ll learn

• A practical definition of struggle you can use to grow faster

• How to shift from frustration to organized problem solving

• Building and using value-creation funnels across teams

• The fulfillment > happiness mindset and how to raise emotional energy

• Why live resistance is non-negotiable for leaders and founders

• Clear criteria for when to part ways (people & projects)

• How to implement a Management Operating System that actually increases enterprise value

• Family applications of the Material / Emotional Energy / Spiritual (Connectedness) framework

Key ideas & frameworks

• Three Struggles

  1. Healthy/normal (capability & character building)

  2. Unhealthy (fix fast, don’t make it identity, harvest the lesson)

  3. Intentionally designed (train the hard things on purpose)

• Mantra: Organize & Develop → Map the work, see reality clearly, then develop people, systems, and flow.

• Value-Creation Funnel: From awareness → qualified demand → conversion → delivery → experience/retention. Find the current constraint, fix it, then re-scan.

• Fulfillment vs. Happiness: Aim at rising fulfillment; happiness follows. List what raises/lowers your fulfillment and act accordingly.

• Live Resistance: Most value is created on the front lines—with customers, teammates, suppliers, investors. Don’t shadowbox; spar.

• Letting Go:

  • People: Be explicit about expected outcomes/ROI and “the line.” If performance stays below the line, help them transition—no surprises, no villains.

  • Initiatives: Define success, investment, horizon, and stop/pivot thresholds up front.

• MOS (Value Creation System): A common way the org plans, executes, measures, and improves so every team’s one most important number rolls up to increasing enterprise value.

• Startup/Innovation Stages: Idea → Business model → Package to scale → Scale. Expect pivots; prove scalable traction before you pour fuel.

• Schedule Ownership: You likely control more of it than you think—set focus blocks, team norms, and family roles to protect high-value work.

• Family Application: Build material, emotional energy, and spiritual/connectedness value; hold weekly “dinner table” conversations; give kids age-appropriate budget line items; teach healthy struggle.

Playbook: Struggle Better (Work)

1. Name the struggle. Healthy, unhealthy, or intentional?

2. Organize reality. Visualize the funnel; quantify the constraint (e.g., CAC, conversion, cycle time, churn).

3. Design the experiment. One change per constraint; set a success metric and review cadence.

4. Develop the system. Document, train, and automate what works; move to the next constraint.

5. Decide fast. If people/initiatives stay below the line, pivot or part ways with dignity.

Playbook: Struggle Better (Home)

• Weekly check-in: What raised/lowered family fulfillment?

• Jobs for the family: Clear roles for adults and kids; include a budget line item per person.

• Healthy struggle reps: Age-appropriate responsibilities; no helicoptering.

• Community: Intentionally expand circles that reinforce value creation.

Memorable quotes

• “Struggle is any effort to improve a life condition, develop a character trait, or build capability.”

• “My mantra: Organize & develop—see it clearly, then build capacity.”

• “Most value is created in live resistance, not in slide decks.”

• “Aim for fulfillment; happiness tends to follow.”

• “Everything we do should make things measurably better. Everything else is waste.”

• “Be explicit about the line, for people and projects, so decisions aren’t personal; they’re principled.”

Resources mentioned

• Dinner Table: Community of families raising kids to create value (Lee serves as CEO).

• Management/Value Creation Operating Systems: Principles for a common way of creating value.

• Leadership Value Lab: Equips leaders with practical tools to create value on the front lines, in real time, with their teams. 

Take action

• Write your Fulfillment List: Top 5 that raise it; top 5 that lower it. Change one thing this week.

• Map one funnel (marketing, sales, ops, or CX). Identify the constraint and set a 14-day experiment.

• Define a Stop/Pivot line for one initiative and a Clear Expectations/ROI line for one role.

• Schedule a weekly family value conversation (material, emotional energy, connectedness).