Beyond W-2 Dependency: How to Navigate Corporate Fragility & Reclaim Time Capital

Are you an overachieving sales director, VP, or enterprise tech leader sitting on valuable skill capital, wondering how to build an independent business without risking your steady corporate paycheck?   In this transparent guest conversation, host Billy Keels sits down with Makeda Boehm, an enterprise software professional, Amazon bestselling author, podcast host, and founder of Seed and Society. Makeda details the "lightning bolt" moment she realized that depending on a single corporate income source was a major risk and how she used AI automation to build a thriving side business while managing a 7-figure quota and raising two young children. Discover how to implement Makeda's "Context Training" framework to automate business operations, why taking fast action builds the evidence you need for real confidence, and how to structure your time so your independent assets always serve your family first.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   Reach out, contact and connect with Makeda Boehm: Websites:  https://seedandsociety.com/about  https://makedaboehm.com/  Instagram: https://www.instagram.com/makeda.boehm/  Podcast: https://podcasts.apple.com/us/podcast/seed-and-society/id1816787845    📌 Questions Answered in This Episode: How can a high-performing tech leader start a side business without giving up their day job? What is the "Context Training" framework for using AI to automate business systems? How do you balance a 7-figure corporate quota with raising young children and building an independent asset? Why is taking fast, imperfect action essential for high achievers wanting to break out of perfectionism? How do you ensure your independent side business supports your real lifestyle goals rather than consuming your time?   ⏱️ Episode Chapters: 00:00 - Broadcast Recording Setup: Tuesday, September 22, 2026, with Makeda Boehm 01:05 - Moving at the Speed of Daily: AI in the Enterprise Software Space 01:40 - The Single Income Realization: Why High Performers Need Income Options 03:00 - Balancing a 7-Figure Quota with Raising a 3 and 6-Year-Old 05:00 - Finding Your Passion: Combining Tech Experience with Teaching 08:30 - System Thinking: Using AI Agents and Automation to Save Time Capital 10:45 - From Classroom to Enterprise: How Teaching Elementary School Sharpens Listening Skills 14:15 - Seed and Society & Context Training: Teaching AI Your Specific Business World 18:00 - Don't Tell Yourself No: Overcoming Perfectionism and Borrowing Evidence 22:15 - Keeping It Real: Managing the Time Trade-Offs for Family and Children 26:00 - Solving Real Problems: Why the Market Only Pays for Real Solutions 31:15 - Trough Principles: "I Have Nothing to Prove to Anyone" 33:45 - Connecting with Makeda Boehm and Seed and Society   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets. With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today! Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI   Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you a senior director, VP, or enterprise leader who has experienced the sudden disruption of a new boss, a bad cultural fit, or a sudden corporate restructuring?   In this real-world solo episode, host Billy Keels shares an insightful story from a recent mentee call with a seasoned executive who managed hundreds of millions of dollars in enterprise revenue. Billy breaks down what happens when the leader who hired you leaves and a "wrecking ball" manager steps in, creating instant instability in a role you loved. Discover how this executive pivoted away from traditional W-2 dependency into independent 1099/subcontracting work, taking control of his earning power, reclaiming his schedule sovereignty, and opening up high-value international opportunities without giving up the corporate game.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm 📌 Questions Answered in This Episode: How do you navigate corporate instability when the executive who hired you suddenly leaves?   What is "corporate fragility," and why are large multinational organizations inherently dynamic?   How can a senior leader transition from W-2 employee status to independent 1099/subcontracting control?   What non-negotiables (like health coverage) must you secure when shifting to an independent structure?   How does reclaiming your time capital open up international speaking, consulting, and investment opportunities?   ⏱️ Episode Chapters: 00:00 - The Reality of Corporate Waters: Restructuring, AI, and Imperfect Steps   01:10 - The Mentee Story: Managing $100M+ Operations and Escalating Corporate Roles   02:15 - The Turning Point: When Your Champion Leaves and a "Wrecking Ball" Arrives   03:20 - Corporate Fragility: Why Even Senior Leadership Seats Shift Rapidly   04:10 - The Illusion of Paycheck Safety vs. Dynamic Personality Shifts   05:00 - The 1099 Pivot: Subcontracting Enterprise Skills for Total Time Control   06:15 - Unlocking Options: International Travel, Speaking, and Independent Assets   07:10 - Moving From Theory to Practice Today   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.   With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today! Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you a senior corporate executive, COO, or enterprise leader sitting on multi-billion dollar operational experience, wondering how to channel your skill capital into an independent venture that aligns with your energy?   In this transparent guest conversation, host Billy Keels sits down with Cathy Ward—former Regional COO for SAP Asia Pacific & Japan (an 8,000-person region generating $2.5B in revenue), Operating Partner at Keensight Capital, and founder of The Future Ready Agency. Cathy shares her 30-year journey across 18 roles in 7 companies worldwide, detailing how writing a sabbatical policy in her late 30s allowed her to step off the corporate treadmill and pivot from sales leadership to HR and global operations. Discover how to distinguish between what skills to keep and what to let go, how to align organization, people, and AI into a unified growth system, and why "radical retirement" is actually about continuously retiring old selves to step into greater schedule sovereignty entirely by choice.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   Today's guest Cathy Ward would love to hear from you! Reach out to her via the links below -  Website: https://futurereadyagency.com/  Contact Page: https://futurereadyagency.com/contact  LinkedIn: https://www.linkedin.com/in/cathy-ward-5456aa1/    📌 Questions Answered in This Episode: How can taking a strategic sabbatical help a senior leader realign their career with their core values? What are the most effective ways to transition from multi-billion dollar enterprise operations into founding your own firm? How do high-performing executives determine which skills to keep and which habits to let go of when moving out of corporate life? Why is aligning organization, people, and AI the ultimate system for future business readiness? What does "radical retirement" mean for high achievers who never want to stop contributing? ⏱️ Episode Chapters: 00:00 - Broadcast Recording Setup: Tuesday, September 8, 2026, with Cathy Ward 03:41 - 30 Years and 18 Roles: The $2.5 Billion Regional COO Journey 06:00 - The Sabbatical Pivot: Writing the Policy and Stepping Out of the Relentless Pace 08:15 - Energy Over Orbit: Shifting From Sales Leadership to Global HR and Operations 10:50 - What to Keep and What to Let Go: Sorting Through 30 Years of Corporate Capital 14:00 - The Rule of Three: Simplifying Strategy When Navigating Major Business Shifts 16:45 - The Future Ready Agency: Integrating Organization, People, and AI 20:20 - Writing for Clarity: How Journaling and Coursework Unlocked Written Voice 22:50 - Radical Retirement: Why Re-inventing Yourself Has Nothing to Do with Stopping Work 26:10 - Managing the Transition: Sit with Uncertainty and Embrace the Plunge 29:30 - Trough Principles: Believing Everything Happens for a Reason and Journaling Patterns 33:00 - Connecting with Cathy Ward and Exploring The Future Ready Agency   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets. With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today! Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI    Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you an overachieving director, VP, or enterprise leader holding yourself back from launching a side venture or pitching a new initiative because you feel you lack certain credentials or qualifications?   In this inspiring solo episode, host Billy Keels breaks down a relatable lesson from a rainy summer afternoon at a Chicago White Sox baseball game. Billy shares how his oldest son overcame self-doubt, navigated around the crowds, and used his unique background as an international traveler from Spain to stand out and claim a souvenir foul ball from the ball boy. Discover why focusing on what you don't have is the ultimate limiting belief, how to identify and lean into your unique differentiators, and why taking calculated action during chaotic moments when others retreat is the secret to winning in your career and building independent assets.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   📌 Questions Answered in This Episode: How do limiting beliefs prevent senior corporate leaders from going after new opportunities?   What does a rainy Chicago White Sox game teach us about identifying unique differentiators?   How do you pivot from focusing on what you lack to leveraging what you actually have?   Why is stepping out of your comfort zone essential for gaining long-term confidence?   How can you spot market opportunities and take action when competitors retreat?   ⏱️ Episode Chapters: 00:00 - The White Sox Game Setup: Summer Travels with Family in Chicago   01:10 - The Rain Delay Dilemma: Row 12 Seats and Spotting the Foul Balls   02:15 - Overcoming Self-Doubt: Facing the Fear of Asking   03:20 - Spotting the Opportunity: When the Crowd Retreats Under the Concourse   04:15 - Finding the Differentiator: Showing the Spanish ID to the Ball Boy   05:30 - Walking Away with the Prize: How Action Builds Real Confidence   06:40 - Translating the Lesson: Applying Unique Value to Your Career and Business   07:50 - Moving From Theory to Practice Today   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.   With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!   Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you a senior enterprise executive, VP, or elite sales director performing at the absolute top of your game, yet feeling an inner friction about what your next logical career step should be ?   In this transparent guest conversation, host Billy Keels sits down with Kate Turner, a veteran sales leader with over a decade of corporate experience, including five years executing strategic goals at Salesforce and scaling tech firms like Glassdoor. Kate maps out the profound, direct correlation between professional poker mechanics and elite enterprise execution, showing how she used a cyclical path between multi-billion-dollar brands, scrappy startups, and live card tables to anchor her own definition of lifestyle harmony. Discover how to disarm the external pressures of mainstream career paths, utilize corporate educational resources to fund your skill development, and analyze any professional rut through a simple three-choice framework so you can navigate your career entirely by intention, not obligation.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   Contact and connect with Kate Turner via these Links: Website: https://www.kateturnercoaching.com/  LinkedIn: https://www.linkedin.com/in/kateturner9/  Instagram: https://www.instagram.com/all.in.with.kate/    📌 Questions Answered in This Episode: How do corporate professionals use advanced professional poker strategies to build self-awareness and negotiation skills? What does a healthy professional cycle look like when moving between massive brands and fast-growing startups? How can an enterprise sales director transition their focus from strict quota production to people management and coaching? Why is keeping your inner circle exceptionally small critical when planning a major professional shift? What are the 3 foundational choices an executive has when looking to solve any severe mid-career challenge?   ⏱️ Episode Chapters: 00:00 - Playing the Person, Not the Cards: Merging Corporate DNA with Poker Mechanics 03:29 - The Three-Part Executive Cycle: Large Brands, Startups, and Live Cards 05:55 - Disrupting Mainstream Expectations: Choosing to Stand Out Over Forcing Compatibility 06:56 - The Multicultural Map: Blending Germanic Structure with Latin Flexibility 09:15 - Shifting From Corporate Sales Quotas to High-Impact Leadership Development 12:44 - Guarding Your Inner Circle: Filtering Prescriptive Advice From Outside Your Playing Field 16:15 - Reconnecting with Yourself: Shifting From a Corporate Persona to Authentic Traits 18:44 - Reclaiming Frameworks: Using Big-Brand L&D Structure for Personal Accountability 21:11 - Poker Immunity: Battling Rejection, Overwhelming Uncertainty, and the Corporate Mask 25:06 - Reinvesting Financial Capital: The Trap of Building Everything on Your Own 26:43 - The Shock to the System: Turning Layoffs and Reorgs into Strategic Action 30:25 - The Salesforce Sandbox: Leveraging Enterprise Educational Budgets to Master Transferable Skills 34:59 - Permission Slip Ups: Unpacking Strategic Failures with Impartial Advisors 39:07 - The Three Choices: Leave, Accept, or Change It Now 42:04 - Expanding Your Professional Network and Connecting with Kate Turner   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets. With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today! Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI   Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you an overachieving director, VP, or enterprise executive who has been told your entire career to climb the ladder, hit age 65, and magically "retire" to a quiet beach?   In this provocative solo episode, host Billy Keels breaks down a recurring, honest realization that surfaces during client onboarding: high achievers are simply wired differently. Traditional retirement—sitting around sipping mai tais—is a myth built for someone else's definition of success. Drawing examples from legendary contributors like Warren Buffett and 80-year-old industry leaders who show up to work every day by choice, Billy explains that true career optionality isn't about stopping work. It's about reaching your "Optionality Number" so you can redirect your high-level skill capital into projects, independent assets, and community causes that give you deep personal energy and financial returns entirely on your own terms.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm 📌 Questions Answered in This Episode: Why is the traditional age-65 retirement myth completely misaligned with high-performing corporate leaders? What is the difference between "stopping work" and redirecting your executive skill capital? Why do multi-millionaires in their 80s and 90s continue to show up and contribute every day? How does reaching your "Optionality Number" give you total agency over where you apply your energy? How can you build independent assets today without waiting for an arbitrary corporate timeline? ⏱️ Episode Chapters: 00:00 - The Heartbreaking Relief: Why You Are Never Going to Retire at 65   01:30 - The High-Achiever DNA: Useful Service vs. Sitting on a Beach 03:55 - The Warren Buffett Example: 96-Year-Old Drive and Lifelong Contribution   05:00 - The Optionality Number: Redirecting Your Energy into Assets You Own   06:35 - Wired Differently: Embracing Your Need for Impact and Meaningful Work   08:10 - Operationalizing Contribution: Getting Compensated into Your 80s and 90s   09:30 - Moving From Theory to Practice Today   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.   With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.   This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!   Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you a high-performing corporate leader or tech executive sitting on decades of valuable skill capital, wondering how to channel your energy into projects that create a profound, real-world impact?   In this inspiring guest conversation, host Billy Keels sits down with Tim Lockyear—two-time "Zoogler," former Google global founder advocate, and founder of the Supporting Kids Foundation. Tim shares his 30-year journey through enterprise tech giants like IBM, Sprint, Accenture, and Google, detailing how facing a scary health diagnosis for his young son prompted him to confront survivor's guilt and co-found a 501(c)(3) charity. Discover how the Supporting Kids Foundation raised over $5.6 million to assist more than 1,100 families dealing with pediatric cancer. Learn why true growth always lives on the other side of difficult, how to recognize when a corporate promotion isn't aligned with your personal motivations, and how to build independent, option-driven endeavors by leveraging the execution skills you master in corporate life.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   📌 Questions Answered in This Episode: How can a corporate executive leverage enterprise skill sets to build a high-impact non-profit organization? What does it look like to turn personal family challenges and survivor's guilt into a $5.6M community foundation? How do you evaluate whether a corporate leadership promotion actually aligns with your personal definition of success? Why is financial independence essential for giving leaders the confidence to take calculated risks? How can modern AI platforms help under-resourced non-profits scale their impact and streamline operations? ⏱️ Episode Chapters: 00:00 - Broadcast Recording Setup: Tuesday, September 15, 2026, with Tim Lockyear 03:37 - 30 Years in Enterprise Tech: IBM, Sprint, Accenture, and Two-Time Zoogler 04:47 - The Catalyst: A Son's Diagnosis and the Origins of Supporting Kids Foundation 07:26 - $5.6 Million and 1,100 Families Impacted: Scaling a Community Mission 09:19 - The Corporate Advantage: How Enterprise Leadership Fosters Confidence and Resilience 12:30 - Embracing the MVP: Why Failing and Stumbling Is Essential to Personal Growth 14:45 - Turning Down Promotions: Recognizing That I Want to Be Where the Action Is 19:46 - "I'm Not Coin-Operated": Defining What Really Drives Your Executive Execution 24:18 - Financial Independence as a Tool for Career Options and Risk-Taking 26:55 - "Growth Is on the Other Side of Difficult": Learning Through Scars and Challenges 30:52 - The $19,000 Investment: From a Small Company to an Accenture Acquisition 35:10 - Leveraging AI for Good: Helping Non-Profits Scale and Do More with Less 42:20 - Sharing the Blueprint: How Tim Helps Other Volunteers Start Foundations 45:16 - The Trough Principle: "It's Never as Bad as You Think, and You're Never as Great as You Think" 50:03 - Connecting with Tim Lockyear and Supporting Kids Foundation 📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets.   With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day.   This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today!   Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI   Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you an overachieving director, VP, or enterprise leader who is constantly presented with new promotions, side deals, and business opportunities, yet feels completely paralyzed and overwhelmed by having too many choices?   In this practical solo episode, host Billy Keels addresses the hidden challenge that high performers rarely talk about: being "drowned in success." When you excel in corporate life and simultaneously build a side business, your challenge isn't finding leads or opportunities; it's learning how to sequence them without exhausting your 168 hours in a week. Billy shares the exact 3-question framework he uses with private coaching clients to help them filter out noise, strategically say "no," and focus strictly on projects that generate high energy, long-term fulfillment, and real financial impact.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   📌 Questions Answered in This Episode: Why do high achievers struggle with having too many opportunities rather than too few? What are the 3 core questions you must ask to evaluate any new business or career opportunity? How do you differentiate between short-term "dopamine" projects and sustainable long-term ventures? Why is it essential to demand a positive financial return alongside personal passion projects? How does learning to say "no" protect your schedule sovereignty and family time capital?   ⏱️ Episode Chapters: 00:00 - The Hidden Executive Problem: Drowning in Success and Opportunity 01:10 - Scrapping the Surface: Why Side Assets Are About Impact, Not Just Paychecks 02:15 - The 168-Hour Equalizer: Balancing Enterprise Growth with Family Milestones 03:20 - Question 1: Does This Opportunity Positively Spike Your Energy? 04:15 - Question 2: Is This Something You Would Prepare to Do Forever? 05:00 - Question 3: Is It Delivering Real Individual and Financial Impact? 06:10 - The Comfort Trap: Shifting From Saying "Yes" to Mastering the Focus of "No" 07:05 - Moving From Theory to Practice Today   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets. With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today! Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI   Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you an overachieving sales director, VP, or enterprise leader wondering how to channel your day-to-day client execution and operational discipline into high-impact independent assets?   In this transparent guest conversation, host Billy Keels sits down with Kevin Devanney—founder and president of Incentive Travel Solutions and the Devanney Hospitality Group. Kevin shares his 27-year trajectory, detailing how the high-stakes lessons taught by his early corporate mentors laid the foundation for managing luxury group trips to Moscow's Kremlin and the Louvre in Paris. Discover how Kevin navigated the sudden, full-stop impact of COVID-19 by pivoting his team into local real estate and restaurant revitalization, why true entrepreneurs wait for real problems to solve rather than chasing trends, and how managing your "fitness, finances, and family" triangle creates absolute resilience when facing high-stakes business shifts.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   Connect with Kevin Devanney via these links: Website: https://www.incentivetravelsolutions.com/  LinkedIn: https://www.linkedin.com/in/kevin-devanney-5916762  Instagram: https://www.instagram.com/kevindevanney/  Email: [email protected]    📌 Questions Answered in This Episode: How do you translate meticulous corporate customer service habits into an independent asset? What does it look like to pivot an entire company when an unexpected event completely stops your industry? Why is chasing cash bonuses inferior to creating unforgettable, experience-based incentive rewards? How do you build a local real estate footprint that revitalizes a town and creates family legacy options? What is the "Fitness, Finance, and Family" triangle, and how does it help executives navigate low moments?   ⏱️ Episode Chapters: 00:00 - Broadcast Recording Setup: Tuesday, September 15, 2026, with Kevin Devanney 02:04 - The Train at 365 MPH: How Incentive Travel Solutions Navigated the COVID-19 Full Stop 04:35 - Old-School Mentorship: Smacks in the Head, Kremlin Dinners, and Meticulous Details 07:15 - Pivoting Forward: Embracing Mistakes as the Most Critical Part of Growth 11:00 - The Path Chose Me: Why True Opportunities Present Themselves When You Master Your Craft 14:50 - Cash is a Satisfier, Travel is Unforgettable: Redefining High-Performer Rewards 18:25 - Staying in Your Lane: Refusing to Dilute Your Core Niche Expertise 21:28 - Local Revitalization: Turning One Dust-Filled Building into Pineville's Main Street Revival 25:40 - Ethical Entrepreneurship: Never Stealing Clients from Your Previous Employer 28:05 - Legacy Engineering: Deciding Between Selling Out or Passing the Torch to Your Kids 33:10 - The Triangle Framework: Balancing Fitness, Finances, and Family in the Trough 36:30 - Connecting with Kevin Devanney and Exploring Incentive Travel Solutions   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets. With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL Day - today! Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI   Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels  

Are you a high-performing corporate director, VP, or enterprise leader who genuinely enjoys your job, yet feels a quiet, unshakeable urge to see what else you're capable of building on the side?   In this reflective solo episode, host Billy Keels shares a relatable, real-life story about his youngest son's decision to leave a comfortable, winning basketball team to try out for a higher-level squad. Drawing a direct parallel to the corporate world, Billy breaks down why true high performers aren't trying to escape their day-to-day work, they are simply competing against the best version of themselves. Discover how to test your business ideas in the open market without abandoning the safety and steady income of your corporate career, why feeling uncomfortable is a required sign of real growth, and how exploring your natural curiosity gives you total schedule sovereignty and long-term peace of mind.   🚀 Want to make your corporate role optional? Grab your FREE copy of Billy's 3-Step Process eBook here: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm   📌 Questions Answered in This Episode: How can a corporate executive test new business ideas without leaving their current job? Why do high achievers feel the urge to step outside their comfort zone even when they're already winning? How do you overcome the fear of uncertainty and potential failure when starting a side venture? What does it mean to compete against the "best version of yourself" rather than comparing yourself to others? How do you move from passive contemplation into concrete, real-world action?   ⏱️ Episode Chapters: 00:00 - The Energy of Choice: Learning Career Lessons from Family Dynamics 01:10 - Staying in the Safe Zone: Staying on the Winning Team vs. Wanting More 02:25 - Competing Against Your Best Version: Moving Past Surface-Level Metrics 03:45 - The Decision to Try Out: Testing Skills in the Open Market Without Guarantees 05:10 - Navigating the Discomfort: New Systems, New Drills, and Building Confidence 06:30 - Keeping the Foundation: Growing a Side Asset While Enjoying Your Corporate Role 07:45 - Eliminating the "What-Ifs": Moving From Theory to Action Today   📘 About Billy Keels & Corporate Optionality If you're a corporate executive who wants to make your role optional, learn how to achieve true control over your career and turn your corporate skills into personal assets. With 26 years of experience in corporate sales leadership, Billy Keels achieved true optionality through multiple income streams. Today, he has helped dozens of executives build a predictable path to take control of their time and start living their ideal day. This free ebook gives you everything you need to identify, plan, and take control of your career while building financial optionality, leveraging your skills, and starting to live your IDEAL day - today! Get the Free eBook: https://www.makeitoptional.com/?utm_source=youtube&utm_medium=social&utm_campaign=p2olm How to Leave a Review for The Going Long Podcast: https://youtu.be/qfRqLVcf8UI   Be sure to connect with Billy: Website: https://www.billykeels.com YouTube: https://www.youtube.com/@billykeels LinkedIn: https://www.linkedin.com/in/billykeels Instagram: https://www.instagram.com/billykeels Facebook: https://www.facebook.com/BillyKeelsFanPage Twitter/X: https://www.twitter.com/billykeels