Starting Over at 50: Why AI Feels Like Y2K All Over Again

Starting Over at 50: Why AI Feels Like Y2K All Over Again

Have you caught yourself rolling your eyes every time someone brings up AI? Or lost four hours "tinkering" with something that felt productive but didn't move the needle on anything that actually matters? In this unplanned episode (they hit record on a quick catch-up and it turned into something worth keeping), Corey and Mike dig into what it really takes to navigate the messy middle of reinventing your work. They talk about why Corey is pulling back on AI as a talking point — not because it isn't useful, but because the hype has turned into noise — and how to tell the difference between genuine progress and an expensive distraction. If you're a Gen Xer trying to build a business and a life on your own terms — without becoming a "guru" you don't believe in — this conversation is a permission slip to do it as a real person, mid-experiment, with no guarantees. In this episode, we cover: * The "Pain Phase": Why learning AI (or anything new) means getting your hands dirty — and why leaning into that pain separates the people who adapt from the people who get left behind. * The Rabbit Hole Test: How to know whether you're building something valuable or just chasing a cool output that doesn't serve your real priorities. * The Dried-Up Watering Hole: What to do when the strategies that worked for 13 years stop working — and the boats keep showing up. * The Guru Trap: Why Corey refuses to make "make $40k in a week" claims — and the difference between handing someone the keys and riding shotgun pointing things out along the way. * Passion as Fuel: Mike's take on why doing the work that excites you is what makes the boring, necessary stuff sustainable. * The Y2K Parallel: Why this AI moment is starting to feel awfully familiar to anyone who lived through the last "everything's about to change" panic. Resources Mentioned: Get the full resource list: https://redefiningretirement.io/p/gen-x-unplugged-podcast-resources-books-tools-prompts [https://redefiningretirement.io/p/gen-x-unplugged-podcast-resources-books-tools-prompts] Work with Mike Buccialia directly to get unstuck: https://www.mymindworx.com/ [https://www.mymindworx.com/] Subscribe to Corey's Redefining Retirement newsletter and redefine it with us:

Goals vs. Intentions: Why You Should Stop Waiting for January 1st

Are you waiting for the "perfect time" to start your side business, lose the weight, or pivot your career? Do you find yourself stuck in "research mode," telling yourself you’ll start on Monday, or worse—January 1st? In this episode, Corey and Mike break down why "preparation" is often just fear in disguise. They discuss the critical difference between Goals (outcomes you can't control) and Intentions (daily actions you can), and why shifting your focus to the latter is the secret to escaping the corporate grind without burning out. If you are a Gen X professional looking to build a "New Life" rather than just a "New Year's Resolution," this conversation is your permission slip to start imperfectly today. In this episode, we cover: * The "Preparation Trap": Why we delay starting the things that matter most. * Goals vs. Intentions: A framework for building consistency without the pressure of perfection. * The 1700-Day Streak: How Corey tracked his way to health (starting in December, not January). * Environmental Cues: Simple hacks to make your new habits automatic. * The Y2K Panic: A nostalgic look back at why Gen X is so cynical (and resilient). Resources Mentioned: * Get the full resource list + my Gen eXit Playbook here: https://redefiningretirement.io/p/gen-x-unplugged-podcast-resources-books-tools-prompts [https://redefiningretirement.io/p/gen-x-unplugged-podcast-resources-books-tools-prompts] * Work with Mike Buccialia directly to get unstuck: https://www.mymindworx.com/ [https://www.mymindworx.com/] * Subscribe to Corey's Redefining Retirement newsletter and redefine it with us: https://redefiningretirement.io [https://redefiningretirement.io/subscribe]

Midlife Career Pivot: How to Rebrand & "Un-Stick" Yourself (w/ Michelle McKown-Campbell)

You’ve spent 20 years building someone else’s dream, but lately, you feel "invisible" in your own career. You know you have value, but your resume makes you look like a robot, and you feel trapped in the "Corporate Gray Zone." If you’re waiting for permission to pivot, you’ll be waiting forever. In this episode, HR-pro-turned-founder Michelle McKown-Campbell reveals why the standard resume is killing your potential and how to break free from the "Invisible Employee" trap. IN THIS EPISODE, YOU WILL LEARN: * The "Invisible Employee" Syndrome: Why you feel undervalued despite years of hard work. * The Resume Lie: Why your resume is failing to show your true worth (and how to fix it). * The "Awesome Tree" Framework: A practical tool to map your skills and uncover the value you didn't know you had. * Strategic Pivots: Why you shouldn’t "burn the boats" or quit your job tomorrow—and exactly what to do instead. * The HR Secret: How recruiters actually look at your experience. Activate Your Awesome with Michelle here: https://activatetheawesome.com/ [https://activatetheawesome.com/] Subscribe to Corey's newsletter, get the free Gen eXit Playbook and redefine retirement with us: https://redefiningretirement.io/subscribe [https://redefiningretirement.io/subscribe] Liked this episode? Please leave us a review on Apple Podcasts! It helps us reach more Gen Xers ready to bet on themselves.

Laid Off After 50: How to Use AI to Bounce Back Stronger (w/ Fernando Labastida)

After multiple layoffs and a health scare, Fernando Labastida completely reinvented himself — turning his tech sales, content-marketing skills and AI curiosity into a thriving business. In this episode of Redefining Retirement, Corey Koehler and Fernando break down how to pivot after a layoff, find your zone of genius, and build a career that actually fits midlife. See how to connect with Fernando and design your own category: https://startupstrikes.substack.com [https://startupstrikes.substack.com] Check out out theClick AI community that Fernando and Corey are part of that we mentioned: https://community.jointheclick.ai/a/2148180570/8gzvRUpi [https://community.jointheclick.ai/a/2148180570/8gzvRUpi] (affiliate link) Subscribe to Corey's newsletter, get the free Gen eXit Playbook and redefine retirement with us: https://redefiningretirement.io/subscribe [https://redefiningretirement.io/subscribe] We dig into: 00:00:00 Introduction to Reinvention 00:02:46 The Impact of Layoffs and Personal Growth 00:05:42 Career Journey: From Sales to Marketing 00:09:32 The Rise of Content Marketing 00:12:24 Building in Public: The Power of Blogging 00:15:08 Navigating Employment and Entrepreneurship 00:18:30 The Importance of Networking and Community 00:21:23 Lessons Learned from Career Transitions 00:27:33 The Value of Side Projects 00:29:52 Embracing Creativity and Opportunity 00:33:05 The Rise of Older Entrepreneurs 00:35:56 Navigating Career Transitions 00:39:57 The Power of Writing and Self-Publishing 00:52:18 Launching a New Category through Books 00:53:13 Navigating Health Challenges and Career Transitions 00:55:12 The Journey of a Fractional CMO 00:58:29 Innovating Through Virtual Summits 01:03:49 Lessons from the AI Smart Summit 01:11:20 Embracing Boldness and Category Design #genxpodcast #careertransition #laidoff #comebackstory

Leaving Microsoft: How to Escape Corporate Burnout & Build a Personal Brand w/ Eve Enslow

Eve Enslow spent decades climbing the corporate ladder at Microsoft before burnout forced her to rethink success. In this episode, she shares how moving across the country and redefining “wealth” led to a more meaningful life after 50 as an Executive Branding Coach. Connect with Eve: https://www.enslowgroup.com/ [https://www.enslowgroup.com/] Read Eve's book "INSPIRE!: Go Big Without a Corner Office": https://amzn.to/3J1lPyL [https://amzn.to/3J1lPyL] ($) Want the books, tools, and AI prompts we might have mentioned? Get the full resource list, Corey's Newsletter and Gen eXit Playbook here: https://redefiningretirement.io/p/gen-x-unplugged-podcast-resources-books-tools-prompts [https://redefiningretirement.io/p/gen-x-unplugged-podcast-resources-books-tools-prompts] Subscribe to Corey's newsletter, get the free Gen eXit Playbook and redefine retirement with us: https://redefiningretirement.io/subscribe [https://redefiningretirement.io/subscribe] We dig into: 00:00 Introduction 02:51 Eve's Early Career Journey 05:57 Transitioning to Technology and Microsoft 09:04 The Impact of the Internet on Career Opportunities 11:46 Recognizing the Need for Change 14:58 Moving from Seattle to Maine 17:51 Finding Work-Life Balance 20:58 The Shift from Employee to Entrepreneur 23:53 Defining Wealth and Impact 27:10 Conclusion and Final Thoughts 27:51 Redefining Wealth and Wellbeing 30:09 The Journey of Learning and Growth 32:42 Finding Balance in Life and Work 35:20 The Leap of Faith in Career Changes 39:06 Redefining Retirement and Lifelong Learning 43:00 Exploring New Opportunities and Flexibility 46:40 Taking Action to Build Confidence 49:52 Finding Your Unique Path and Purpose #genxpodcast #midlifereinvention #careertransition