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How to turn your corporate exit into a power move
The pivot playbook from a rock & roll mogul and Xbox launch leader
Howie Chan
December 15, 2024
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THIS ISSUE
Feature: Harvey Lee, the rock and roll mogul turned gaming executive, turned consultant and keynote speaker shares the secret behind his legendary pivots.
Key Lesson: Don’t let too much thinking get in the way of epic
❤️ Heartset: Pivoting is Naturally Scary
🧠 Mindset: Shifting From Fear to Opportunity
🧰 Skillset: The Pivot Playbook
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FEATURE
Life just isn’t linear.
No matter how carefully you plan, change will come knocking. Sometimes it’s a whisper, other times, a thunderous, unavoidable BOOM! The difference between those who crumble and those who thrive lies in their mindset during the pivot.
Harvey Lee, former music industry roadie and manager turned corporate leader, embodies this truth. From selling band t-shirts in packed arenas and managing tours to shaping global gaming brand Xbox, his story proves that resilience and adaptability can turn even the sharpest corners into growth trajectories.
Today, we’re diving into the ultimate Pivot Playbook—a guide to mastering your mindset when life demands you change lanes.
THE LESSON
Don’t let too much thinking get in the way of epic
Harvey Lee wasn’t born a corporate strategist. He earned his stripes in the wild world of music, often learning by doing (or failing). When he transitioned from music into video gaming and now into consulting and keynoting, it wasn’t an easy leap. But he approached each pivot with the same mindset: failure is not an option.
"Sometimes, the best thing that can happen to you is just getting thrown in, don’t think—just do."
To successfully pivot, you don’t need a flawless plan. You just need a resilient mindset. Resilience doesn’t eliminate fear; it reframes it as a motivator.
❤️ Heartset: Pivoting Is Naturally Scary
Let’s face it—pivoting is scary. Whether you’re leaving a corporate career, launching a business, or facing unforeseen challenges, it feels like standing at the edge of a cliff. But here’s the thing: the ground you’re leaving isn’t as stable as you think. Staying still is often riskier than moving forward.
This issue of Legend Letters is here to remind you: pivots aren’t detours—they’re accelerators. Never feel like you are starting from scratch. You are starting from experience! Your next legendary chapter depends on the mindset you bring to the leap.
🧠 Mindset: Shifting From Fear to Opportunity
Every pivot starts with one critical choice: will you see change as a threat or an opportunity?
Harvey’s story of going from roadie to corporate marketer is packed with moments where he had no time to overthink. He was handed a bass guitar hours before a show and told to perform—no training, no rehearsal. "There wasn’t time to question it. I had to deliver," he recalls.
The key mindset shift: treat every new challenge as a test of your adaptability. It’s not about being perfect; it’s about showing up, committing fully, and learning on the fly.
🧰 Skillset: The Pivot Playbook
Here’s your step-by-step guide to navigating the leap:
STEP 1 - ASSESS: Understand Your Starting Point
Start by reflecting on where you are now. What’s working? What’s draining you? What do you value most?
Harvey, reflecting on his shift from Xbox to entrepreneurship, shared, "I couldn't grow anymore on the Xbox team... I had outgrown it. So I left." This kind of self-assessment helped him recognize when it was time to pivot.
Do: Spend an afternoon mapping your skills and achievements. Identify three transferable skills you can use in your next venture, such as leadership, project management, or problem-solving.
STEP 2 - ADAPT: Break It Down
Massive change feels overwhelming, but breaking it into steps makes it manageable.
When Harvey moved from music to gaming, he didn’t rebuild his career overnight. He focused on transferable skills, like marketing and relationship-building, that were useful across industries.
Do: Instead of jumping into a new business headfirst, start by consulting in your field of expertise. Use this as a bridge to test ideas, meet potential collaborators, and build confidence in your new role.
STEP 3 - ACT: Burn the Boats
"Every minute you spend on Plan B is a minute you’re stealing from Plan A," Harvey emphasizes. Success comes when you go all in. For Harvey, this meant moving to the U.S. at 18 with nothing but a burning drive to succeed.
Do: Set a date to fully commit to your new path. Maybe it’s quitting your consulting side gig to launch your own brand or stepping into a full-time entrepreneurial role. Share your plan publicly—it adds accountability.
STEP 4 - BUILD: Use Momentum to Your Advantage
Success builds success. Start small, but celebrate every win.
On his first tour, Harvey sold out an entire arena’s worth of merchandise by taking initiative—literally walking up and down the aisles shouting, “T-shirts! T-shirts!” That small victory compounded as he did the same thing show after show. His reputation as a problem-solver became an indispensable asset.
Do: Tackle one quick-win project in your new field, like launching a simple website or hosting a networking event. Momentum boosts confidence.
STEP 5 - REFLECT: Continue to Refine and Optimize
Mistakes are inevitable. The goal is to learn from them, not avoid them.
As Harvey puts it, "The lessons are grounded in failure. Sometimes things crashed badly, but those became great stories and bigger opportunities."
Practical Example: Schedule a weekly review to reflect on what’s working and what isn’t. Ask: What’s the biggest challenge I faced this week? What did I learn from it? What can I improve next week?
May Your Pivots be Epic!
Every pivot holds the potential for something legendary. Harvey’s journey from "the Shekel" (his roadie nickname) to corporate executive and now to independent consultant and keynote speaker shows that no leap is too great if you bring the right mindset.
Whatever change you’re navigating right now, remember: the story of tomorrow hasn’t been written yet. And you’re the author.
Take a deep breath, step forward, and pivot with purpose.
Make your mark, live your legend 🤘🏽,
Howie Chan
Creator of Legend Letters
P.S. In the podcast, Harvey shares some incredible stories from his time as a roadie (Listen to the episode HERE)
P.S.S. Are you a corporate dropout turned business owner? If you I have a gift for you. This past Thursday was my birthday and I’ve put together a FREE 7-Day Mindset Mastery Email course for anyone looking to go from overwhelmed to empowered. Our mind is a muscle and this is course is like taking your mind to the gym! Enroll HERE.
SOURCES
Chan, Howie, Mastering the Pivot: From Touring With Rock Bands to Launching Xbox with Legend Harvey Lee, The Legend Letters Podcast, December 10, 2024 - LINK
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