The Rising Digital Leader

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Are you a digital (technology) expert who’s dreaming of a thriving career and life? Today’s superstars in cloud, cybersecurity, data science, and the like are tomorrow’s business leaders. It’s time to break free of the crowd — we need you to rise. Welcome to your home for rapidly enhancing your digital leadership abilities — improving your influence, wealth, career potential, and freedom. Your host, Matthew Doan, specializes in developing digital leaders by focusing on human nature. Subscribe to this weekly show to receive a potent elixir of stories, principles, and guests that pack a punch.

Matthew Doan


    • Jun 3, 2025 LATEST EPISODE
    • every other week NEW EPISODES
    • 21m AVG DURATION
    • 159 EPISODES

    Ivy Insights

    The Rising Digital Leader podcast is an incredibly inspiring and motivational show that offers valuable insights and advice for those feeling stuck in their careers. Hosted by Matt, the podcast features guest speakers who share their personal struggles and successes, providing a relatable and captivating experience for listeners. The honesty and vulnerability portrayed in each episode is refreshing, creating a sense of hope and excitement for those looking to break free from the corporate rat race. Matt's stories resonate deeply with listeners, making it a must-listen for anyone seeking motivation and guidance in their career journey.

    One of the best aspects of The Rising Digital Leader podcast is its honest and straightforward approach to discussing career challenges. Matt highlights the reality of corporate America, encouraging listeners to take control of their own destinies rather than settling for unhappiness in their jobs. The emphasis on owning one's 9-5 is both refreshing and much-needed, as it empowers individuals to create their own version of freedom within their careers. The show also provides practical frameworks and examples that listeners can apply to create more freedom and fulfillment in their lives, making it more than just theory.

    While there are many positive aspects to The Rising Digital Leader podcast, one potential drawback is its focus primarily on corporate work. While this may resonate with many professionals, those outside of the corporate world may find some episodes less applicable or relatable. Additionally, while the show offers actionable guidance on how to thrive in the corporate world, it may not provide as much support or advice for those looking to completely escape corporate life.

    In conclusion, The Rising Digital Leader podcast is a powerful resource for anyone feeling stuck or unfulfilled in their career. With its relatable stories, practical advice, and emphasis on personal freedom within corporate America, this show has the potential to ignite change and inspire action in its listeners. Whether you're looking to climb the corporate ladder or find alternative paths to success, this podcast provides valuable insights that can help you define and achieve your own version of freedom.



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    Latest episodes from The Rising Digital Leader

    157: Seek Higher Ground

    Play Episode Listen Later Jun 3, 2025 7:42


    The ground is shifting. Fast. AI isn't just disrupting work — it's demanding that we evolve from doers into designers. Join us as we explore how to stop clinging to what's crumbling and start climbing toward the next version of you — the one built for higher ground.***

    156: Letting Go Is the First Investment

    Play Episode Listen Later May 27, 2025 11:29


    Most people feel stuck not from lack of options — but from holding on too tightly.They keep stacking more work and pressure, without creating space for what matters.This episode breaks down why real freedom starts with subtraction — letting go of the roles, stories, and obligations that no longer fit.It's not about blowing things up. It's about making room to build what's next.***

    155: Freedom Starts With Who, Not How

    Play Episode Listen Later May 20, 2025 12:21


    “Most people think they need a better strategy — but what they actually need is a better internal operating system.”In this episode, I unpack why no tactic or business model will work if the software of the self is outdated.When you upgrade your identity, beliefs, and habits — the "how" finally starts working.This is where real freedom begins.***

    154: The Job Was Never the Dream

    Play Episode Listen Later May 13, 2025 10:03


    You were taught to find the dream job — but no job can give you the life you're truly meant to build.In this episode, I break down why even the “perfect role” can leave you misaligned, and how to quietly start creating a life that actually fits.It's not about quitting — it's about reclaiming your dream, one intentional step at a time.***

    153: Whose Dream Are You Really Building?

    Play Episode Listen Later Apr 29, 2025 8:50


    You're either building their dream — or yours.This episode is a wake-up call to stop postponing your potential and start reclaiming your energy, purpose, and ownership through Corporate Graduation™.***

    152: Corporate Ladders Are Quietly Collapsing

    Play Episode Listen Later Apr 22, 2025 9:19


    You spent your career learning how to climb — but what if the ladder itself is breaking beneath you?This episode isn't about panic. It's about power.Because waiting for the system to save you is the real risk.It's time to stop trusting the climb… and start your Corporate Graduation™.***

    151: I Didn't Want to Work Less — I Wanted to Feel Alive [Voice Note]

    Play Episode Listen Later Apr 15, 2025 6:22


    You don't need less work — you need more meaning.In this short voice note, I share what it's like to trade the corporate grind of disconnection for focused, purposeful effort that fuels you — and everyone around you.A redefinition of work, freedom, and responsibility.***

    150: “Wait…What Business Are We Actually Building Here?”

    Play Episode Listen Later Apr 8, 2025 12:07


    You're a high-achieving professional. You've built success — but it doesn't feel like freedom. You want more time, more presence, more YOU in your work.This is where entrepreneurship starts to make sense.In this raw solo episode, I break down the exact kind of business we help people build inside Uncaged Life Design — and why it works so damn well.You'll learn: What we DON'T build (no fluff, no hustle traps)What a premium online business really looks likeThe inner foundations required before launching anything The full stack of skills you need as an entrepreneurial CEOThe real-world models (coaching, consulting, hybrid) that unlock freedomIf you're craving a business that fuels your income, lifestyle, and sense of purpose — start here.***

    149: Choosing Possibility Over Paycheck (3 Years In)

    Play Episode Listen Later Apr 1, 2025 26:18


    It's been three years since I chose possibility over a steady paycheck, stepping away from corporate "security" into the wild unknown of entrepreneurship. That inevitable "dip" hit hard — where excitement crashes against reality and challenges arrive in forms I never anticipated.Those pressure-filled moments weren't setbacks but transformative catalysts, forcing me to grow beyond what any comfortable role could have demanded. From difficult money conversations at home to finding my tribe of fellow dreamers, everything changed.Here, I share my raw journey where I reveal what true freedom actually costs — and why, despite the harder path, I wake up with an excitement I never knew in corporate life, finally doing exactly what I was meant to do.***

    148: Hidden Tradeoffs In Moving from Corporate to Entrepreneurship [Voice Note]

    Play Episode Listen Later Mar 25, 2025 10:36


    I'm pulling back the curtain on what they don't tell you about leaving corporate America. The status, security, and identity I had to sacrifice felt like losing limbs at first — but what I found on the other side? Game-changing. Listen for 10 minutes of raw truth about the tradeoffs that transformed my life and might do the same for you.***

    147: Your Inner World Creates Your Outer World [Voice Note]

    Play Episode Listen Later Mar 4, 2025 8:50


    Your beliefs shape your reality more than any strategy or tactic.In this episode, I share practical strategies (e.g., morning rituals) that completely transformed my inner world — helping me graduate from corporate life faster than I thought possible and create the freedom I always wanted.***

    146: The Staggering Costs of Not Knowing [Voice Note]

    Play Episode Listen Later Feb 25, 2025 7:53


    We're all paying a hidden "ignorance tax" that's robbing us of the financial freedom and personal fulfillment we crave. I reveal my costly mistakes and the ONE big strategy you can implement today to stop leaving freedom on the table.***

    145: Take a Hard Look At Your Trajectory

    Play Episode Listen Later Feb 18, 2025 11:08


    That "secure" corporate path? It's a ticking time bomb.Between AI, endless restructures, and diminishing returns, your trajectory needs a hard reality check. This raw, unfiltered episode forces you to face what you already know deep down — and what to do about it.***

    144: Will a New Income Stream Set You Free? [Voice Note]

    Play Episode Listen Later Feb 11, 2025 14:35


    If you're in corporate hell, the common logic is to "find a new income stream."Listen closely as to why that's a terrible approach and what to do instead — to create premium freedom in your life now.***

    143: How to Make Your Corporate Graduation Inevitable With Forcing Functions [Voice Note]

    Play Episode Listen Later Feb 4, 2025 7:37


    Break past the fear, apprehension, and doubt. Install forcing functions that make your Corporate Graduation inevitable. ***

    142: Can You Skip the Inner Work and Succeed as an Entrepreneur? [Voice Note]

    Play Episode Listen Later Jan 28, 2025 7:54


    Providing an honest take on the most dominant "failure" point for aspiring entrepreneurs. ***

    141: The End of Employment As We Know It

    Play Episode Listen Later Jan 21, 2025 16:16


    The Industrial Era gave us 100 years of stable employment. 2025 marks the end of that century-long experiment. "Employment" is dead, which means there's new opportunity that's yours for the taking. ***

    140: Top 15 Corporate Graduation Lessons of 2024

    Play Episode Listen Later Jan 7, 2025 22:46


    The corporate landscape is shifting in a hurry, causing many to shift focus on graduating this chapter and building premium freedom online. Massive technology and social forces are changing how people work, earn, and live. Here, we cover the top 15 lessons Corporate Graduation lessons of 2024. ***

    139: I Was the Ceiling

    Play Episode Listen Later Dec 17, 2024 11:04


    Ever feel like you've maxed out on your current path? Like you're hitting your head on a ceiling of what you can do, earn, and be in your career and life? Harsh truth: the ceiling isn't out there — it's staring at you in the mirror. Let's break through that barrier right now, and soar to new heights. ***

    138: Separating From the Crowd

    Play Episode Listen Later Dec 3, 2024 14:05


    It's time. To separate from: The crowd Mediocrity Your past self All it takes is a decision (not the "how"). I'm not holding back in this episode. Listen closely. ***

    137: Recapping Our First Retreat

    Play Episode Listen Later Nov 19, 2024 14:41


    Matt and Cecilia are broadcasting live from their first-ever coaching retreat! Uncaged clients gathered from multiple countries to learn and grow as a community. They explored mental and practical strategies for graduating from corporate life to entrepreneurial freedom. Tune in for an update on their business and the 5 key takeaways from this private event. ***

    136: Anti-Commodity

    Play Episode Listen Later Nov 12, 2024 13:50


    Tired of being another corporate commodity? This episode is your wake-up call. Learn why "finding your niche" is dead wrong, and how becoming a Category of One transforms everything — from your paycheck to your purpose. Warning: Not for those who love playing it safe. ***

    135: Engineer Your Beliefs, Engineer Your Future

    Play Episode Listen Later Nov 5, 2024 14:22


    What's really holding you back from graduating corporate life? From building entrepreneurial freedom? It's not your skills. It's not your experience. It's not even your circumstances. It's your beliefs. Here, we discuss how to re-engineer your belief system so that you radically improve your future. ***

    134: The Deceptive Allure of Self-Transformation

    Play Episode Listen Later Oct 15, 2024 12:23


    Maybe you've consumed all the books and podcasts. It feels good, and you can point to some results. But traditional self-help often leads you to a frustrating purgatory — "learning" but never truly transforming. Here, we introduce Self-Help 2.0. Discover why true change isn't just about "self," but about embodying new learnings within a transformative community. ***

    133: Unpopular Truths of Going Corporate to Entrepreneur

    Play Episode Listen Later Oct 8, 2024 13:12


    Let's not kid ourselves: entrepreneurial freedom comes at a price. Here are 9 unpopular truths about what it really takes. These are the lessons I wish I had before starting my corporate graduation journey. ***

    132: Space Is the Place (Where Miracles Happen)

    Play Episode Listen Later Oct 1, 2024 14:25


    This episode explores the critical skill of creating "space" — time, energy, and mental capacity. It's the essential first step towards any meaningful personal transformation. Discover how this often-overlooked foundation is crucial for building the career and life you truly desire. Learn practical strategies to create this vital space, even within a demanding job. Gain insights on how to lay the groundwork for future success, whether that's launching an entrepreneurial venture or reimagining your current career path. This isn't about work-life balance — it's about creating the breathing room necessary for real change to take root. ***

    131: Leaving "Safety" (My Wild Journey)

    Play Episode Listen Later Sep 10, 2024 11:15


    In this honest episode, Matt reveals his journey from feeling trapped in a "safe" life to finding purpose through entrepreneurship. Balancing a complex family, financial pressures, and a draining corporate job, he faced the classic struggle between security and fulfillment. Matt shares how he gradually built an online business aligned with his passions, transforming not just his career but his family life too. This isn't a tale of overnight success, but of steady growth and persistence. If you've ever felt pulled towards more meaningful work but held back by responsibilities, Matt's story offers relatable insights and inspiration for taking those first steps towards change. ***

    130: Entrepreneurship Is No Longer Optional For You

    Play Episode Listen Later Sep 3, 2024 18:20


    The corporate landscape is shifting beneath your feet. Job security? It's becoming a myth. But there's an opportunity in this chaos. This episode explores why entrepreneurship (even while keeping your day job) is becoming essential for your growth, financial stability, and family's future. We'll cut through the hype and show you practical steps to leverage your experience into a thriving online business. It's not about quitting tomorrow; it's about future-proofing your career today. Time is of the essence. Learn why waiting is no longer an option, and how to start your entrepreneurial journey without upending your life. ***

    129: Family, Freedom, Fortune

    Play Episode Listen Later Aug 27, 2024 12:45


    Feeling trapped by corporate "success"? This episode explores balancing professional achievement with personal fulfillment. Discover practical strategies for transitioning to entrepreneurship without risking your family's stability. Learn to leverage your skills and methodically build an online business aligned with your values. Listen now for a step-by-step process to break free from the corporate mold and gain actionable insights toward true professional autonomy and personal happiness. ***

    ⁠​128: From Cubicle to Catamaran (Inspiring My Kids)​⁠

    Play Episode Listen Later Aug 20, 2024 10:09


    From guilt-ridden corporate exec to adventurous entrepreneur. Here's a story about my journey to heal my family. I'll reveal how graduating corporate life for entrepreneurship led to Greek island dreams. Learn why showing my kids a life of freedom mattered more than any gift I could buy. Battling "dad guilt"? Discover how I turned regret into inspiration through bold choices. Listen to learn how redefining success brought my family closer and ignited their dreams. ***

    127: The Golden Cage Illusion

    Play Episode Listen Later Aug 6, 2024 18:13


    “We are all living in cages with the door wide open.”— George Lucas In this episode, we're looking at the 15 invisible shackles binding you to a golden 9-5 prison. Let's be real: you're your own worst enemy. So let's break those shackles. ***

    126: Invisible to Indispensable (Your Entrepreneurial Awakening)

    Play Episode Listen Later Jul 16, 2024 14:52


    Shatter the belief that you have "nothing special to offer." Uncover the unique genius hiding in your average-looking corporate history. Learn to transform your experiences into a business that energizes you and uniquely serves others. Here, we'll explore how to find your "magnetic match" and build a thriving, purpose-driven business. Entrepreneurial freedom is closer than you think. ***

    125: Removing Friction to Accelerate Entrepreneurial Success

    Play Episode Listen Later Jul 9, 2024 9:11


    You want faster progress toward big goals: graduating corporate, building wealth, creating your dream lifestyle. But invisible friction is destroying your momentum. Learn to identify and annihilate this stealth force that's stealing your speed — so you rapidly manifest your ambitious vision. ***

    124: Success in Reverse

    Play Episode Listen Later Jun 25, 2024 11:29


    Our natural inclination is that freedom and happiness come later — after we put in significant work. But what if the opposite were true? This strategy will radically accelerate your path to entrepreneurial freedom. ***

    123: Don't Self-Sabotage Your Entrepreneurial Dream

    Play Episode Listen Later Jun 18, 2024 18:43


    Self-sabotage is the primary reason we remain trapped in our (often self-created) cages. And it's what prevents many from shifting from corporate to entrepreneurship. In this episode, we cover the top 11 dream killers to avoid. Enjoy! ***

    122: Resumes to Riches

    Play Episode Listen Later Jun 11, 2024 17:41


    Your resume: a cage or a key? Roles, skills, and experiences can entrap us if we let them. Here, we discuss a counterintuitive shift that allows you to finally view your resume, not as a qualifier, but as a launchpad to a life of freedom, impact, and fulfillment. ***

    121: The Shadows Our Loved Ones See

    Play Episode Listen Later Jun 4, 2024 10:51


    Our shadows last a lifetime for our kids and loved ones. Nonstop career hustling puts food on the table, but it doesn't instill values we're proud of. It's time we walk our talk and embody our true values, so they grow up with healthy behaviors. Remember, they're always watching. ***

    120: Your Freedom Vehicle (Beyond Corporate)

    Play Episode Listen Later May 28, 2024 13:59


    Feeling caged in corporate life? Passive income isn't the ticket out. To escape the maze, you need to take an active approach. Build your freedom vehicle. Learn exactly how to leverage your current positioning, unlock your inner genius, and create an online business that provides true lifestyle freedom. Stop trading time for money. Discover how to live a self-directed life by monetizing your purpose. ***

    119: The Riskiest Choice of All

    Play Episode Listen Later May 21, 2024 14:00


    Safety. Freedom. Which will you pursue? There's obviously a balance to strike. But if you're "done" with corporate life, you don't want to miss this life-changing perspective. ***

    ​118: My Top Lessons in Graduating Corporate Life​

    Play Episode Listen Later May 14, 2024 22:45


    I've been on this entrepreneurial journey for nearly a decade and have been out of corporate for the last two years. Here, I'm sharing my top 12 lessons learned in shifting from corporate to entrepreneurship. ***

    117: Make Your Employer Your Investor

    Play Episode Listen Later May 7, 2024 13:56


    You've given a lot to your corporate career. Now that you've got a foundation, it's time to change the rules. The job is no longer an asset to be coveted. YOU are the asset. Direct all energy to building your future self. Learn how to make your employer your personal investor. ***

    116: Letting Go of What No Longer Serves You

    Play Episode Listen Later Apr 30, 2024 12:13


    So much of our pain comes from holding on to what no longer serves us: identities, jobs, relationships, etc. “Letting go” is the key. But it's not just a concept. It's a powerful life skill that shortcuts your path to your dreams — collapsing timelines from decades into days. ***

    115: Your Genius Defies Logic

    Play Episode Listen Later Apr 23, 2024 10:05


    You've made logical bets your whole life. That served you well with career "success" and building a lifestyle foundation. But that time is over. "Logic" means you're just playing the odds while denying your highest self and true aspirations. It eats away at your soul. Ready to activate entrepreneurial freedom and do what lights you up? That means you need to finally choose your genius. ***

    114: Magnetic Match (Your Key to Business Success)

    Play Episode Listen Later Apr 2, 2024 17:24


    The key to entrepreneurial success is magnetism. You want a Magnetic Match between your business and the person (problem) you aim to serve. The business and client should feel a two-way connection — on both emotional and logical levels. Without magnetism, your business becomes a commodity. With magnetism, clients perceive you as "1 of 1." Listen to learn how to find your Magnetic Match. ***

    113: Building Uncaged 2.0

    Play Episode Listen Later Feb 6, 2024 18:55


    I've grown more in the last 2 years than in the previous 20. This includes: The growing pains of starting a business Constant experimentation to be of service Investing in my own growth at profound levels From a personal and professional viewpoint, I now have crystal clarity on my purpose and transformational value for others. And with that, I'm bursting at the seams with insights and strategies I'm ready to share with you. That's what I'm bubbling over with excitement as I prepare for the imminent launch of Uncaged 2.0. This means I'm rolling out massive upgrades to my two coaching programs that are actively transforming dozens of lives at any moment. If you're ready to “graduate” corporate, listen closely. ***

    112: "Work" Half, Double Your Impact (The Double Count Time System)

    Play Episode Listen Later Jan 31, 2024 13:21


    Act like average people and you'll get average results. Like Einstein, we need to reimagine "time." And in tandem, we need to redefine "work." This is how we achieve more impact (professional and personal) with far less effort. Whether you're still in corporate or you're already on your own, this episode presents a critical mental shift you need to hear. Learn the art of the "double count." Install this time system immediately. ***

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    111: The Exponential Career

    Play Episode Listen Later Jan 23, 2024 10:48


    Is your career stuck on an Incremental path? Salary bumps can't keep pace with inflation...let alone your dreams. It's time to make the hyper-jump to an Exponential Career. Learn to: Minimize time at your job Use it to fund a new leveraged business Create exponential gains in your lifestyle Break free from the corporate hamster wheel. Create the freedom, fulfillment, and financial abundance you desire. It's not overnight or easy. But with concentrated effort, you can transition to working on your own terms. So, will you continue the rat race? Or boldly step into an Exponential Career and life? The choice is yours. ***

    110: Centralize Your Genius

    Play Episode Listen Later Jan 16, 2024 13:54


    Far too many professionals conform to one-size-fits-all corporate success criteria. This stifles their natural gifts. Though they deliver results and earn good money, they feel dead inside as their genius gets suppressed. The solution is to harness your Zone of Genius (ZoG) — the intersection of your: Talents Interests Perspectives Centralize and lead from your ZoG. Make it the hub of everything. Stop conforming and gap-filling weaknesses. Start expressing your superpowers. This unlocks freedom, income, and impact. You have a choice: Squander your talents fitting molds Centralize your genius and come alive The key is identifying and then centrally expressing your unique genius, both in corporate and entrepreneurial ventures. It's time to unlock your full career potential and a bigger life. ***

    109: Your Future Self Is Begging You to Act

    Play Episode Listen Later Jan 9, 2024 18:12


    If the corporate grind has worn you down, there's another path to freedom in the new year: Rapidly re-engineer your job to buy back time (keeping income and family safe) Invest in mentors to experiment with opportunities and take daily action toward your dream Build a scalable online business aligned with your superpowers The right system helps you leverage your corporate past to aggressively create the entrepreneurial freedom you and your family deserve. Don't cling to familiarity and fear — craft your next chapter now. ***

    108: Turn Your Faith Inward

    Play Episode Listen Later Dec 26, 2023 14:21


    I was raised to put faith in external systems: religion, school, and corporate systems. And while external systems gave me some value and perspective, I eventually became empty inside. I lacked faith in my inner wisdom and potential. Life skyrocketed when I learned to turn my faith inward. New creative energies awakened, and a brand new life of freedom opened up. ***

    107: Brutally Honest Reflections Since Leaving Corporate

    Play Episode Listen Later Dec 19, 2023 15:14


    "Burn mental boats before real ones." Just one of my 11 reflections since ditching the corporate ladder one-and-a-half years ago. If you have big life responsibilities yet dream of entrepreneurial freedom, you need to listen to this episode. ***

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