ReInvention

If you're feeling stuck in your career, this episode might be the wake-up call you've been waiting for. Sara O'Connor is the definition of a modern Reinventor - former attorney turned full-time artist, poker industry leader, writer, and entrepreneur. In this conversation, she shares how she walked away from a prestigious legal career, navigated burnout and identity shifts, and built multiple creative income streams on her own terms. This isn't a "burn it all down" story. It's a masterclass in Strategic ReInvention - making a plan, running experiments, and betting on yourself before you feel fully ready. We dive into: Why most people stay stuck (and how to break out) The financial reality of reinventing yourself How to test a new path without blowing up your life Navigating identity, fear, and starting over Why ReInvention isn't one move - it's a lifelong mindset Sara also opens up about neurodivergence, entrepreneurship, and how embracing who you actually are can unlock entirely new paths. If you've ever thought: "How did I get here… and what do I do next?" - this episode is for you. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook, learn more about us, and start creating what's next! https://ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

This is a special Mother's Day show, and it comes along with one of the most important frameworks we'll talk about: Masculine vs. Feminine energy. Most of us have been conditioned into constant "go mode." Push. Achieve. Figure it out. But successful ReInvention doesn't come from more force. It comes from learning how to balance action with awareness. We talk about: What masculine vs. feminine energy actually means (and why everyone has both) Why so many high performers are burned out and misaligned The power of "allow and reflect" as a real strategy, not just a nice idea How creating space leads to better, more aligned decisions This one also gets personal - family, loss, parenting, and how these dynamics shape who we become. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook, learn more about us, and start creating what's next! https://ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

We sat down with Scott Clary, host of the Success Story podcast (100M+ downloads) to break down what it actually takes to reinvent your career. Scott didn't follow the traditional path. He questioned it. In this conversation, we go deep on why curiosity is the starting point for any reinvention - and how most people stay stuck simply because they never stop to ask: is this even what I want? We also get practical. If you're mid-career, successful on paper, but feeling out of alignment, Scott shares how to navigate that tension without making reckless decisions. You'll hear: Why the old career playbook no longer works The "die every night" exercise to get clear on what you actually want Why confidence (and control) matters more than talent How to take action without quitting your job overnight The truth about entrepreneurship: hard, but not complicated This is a grounded, no-BS conversation about what it really looks like to take ownership of your career, and build something that actually fits your life. If you've been thinking about making a change but haven't started yet, this is your push. We are BIG fans of Scott's newsletter and we highly encourage you to click this link and sign up to receive consistent drops of gold from him! If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook, learn more about us, and start creating what's next! https://ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

Season 2 is on its way and while we get ready, we're revisiting this deeply personal episode on the provider trap because feeling stuck as the breadwinner is one of the most common and most solvable challenges in career reinvention. If you're the primary breadwinner or you carry the "provider" identity, Career ReInvention can feel impossible. The fear is real: If I change jobs, the whole system collapses. Mortgage. Bills. Kids. Expectations. Your nervous system starts treating reinvention like a threat. In this episode, Chris and Todd unpack the Provider Trap - the hidden identity that keeps high-achievers locked into misaligned work long after it stops working. They talk about why "providing" is more than a paycheck (presence, energy, relationships, legacy), how fear and scarcity get passed down through generations, and why staying in the wrong career can quietly cost you the very family life you're trying to protect. They also get a bit personal with their own stories. Chris reflects on losing his dad when he was 25 and the conversations they had towards the end. Todd shares some personal challenges he and his wife are currently dealing with when it comes to the question: 'What is a breadwinner - and what are we really providing'. At the end you'll understand why courage is the most important muscle that makes ReInvention possible - even when you feel like you have no room to fail. If you've ever thought, "I can't change - everyone depends on me," this episode is for you. If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. https://ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

Season 2 is on its way and while we gear up for it, we're revisiting this critical episode on navigating AI and the future of work because getting ahead of what's coming is everything right now. What careers actually have a future in an AI-driven world? In this episode Todd and Chris get real about the future of work, what AI is actually going to disrupt, and how to build a career that's hard to replace because it is rooted in your uniquely human skills. They discuss the emerging statistics (like 39% of core job skills changing by 2030), why endlessly scrolling LinkedIn for the same old roles has diminishing returns, and why the smartest move right now is to think of yourself as the CEO of your own life and career. You'll hear real client stories: a laid-off designer who turned his expertise plus AI into a new business, a burned-out exec who became a highly paid workshop leader for his former company, and mid-career professionals who are quietly building second careers in coaching, community, and creator work. If you've ever thought, "Who am I to do that? There are already so many people doing it…" this conversation is your invitation to think bigger, experiment more, and start building a future-proof career that actually fits the life you want. You'll learn: Why AI is absolutely going to replace certain tasks and roles… and which parts of your job are most at risk The durable "human skills" that are only becoming more valuable How to honestly audit your current role for what's automatable vs. what's uniquely you Why experimentation beats perfection, and how to treat your next moves like low-risk "life experiments" instead of irreversible bets How to handle the fear of judgment ("who am I to do this?") and start sharing your work or ideas without waiting to be "ready" **Subscribe to our ReInvention Podcast and stay on the cutting-edge with fresh ideas and practical tools to navigate the future of your work!

In the Season 1 finale of ReInvention, Todd and Chris come full circle on the framework they've been pressure-testing with their community: the 6 core tenets of Career ReInvention. This isn't resume-polishing or a quick pivot - it's a practical, human roadmap for mid-career professionals who want more agency, more fulfillment, and a smarter path forward in a rapidly changing world. They unpack why ReInvention starts with clarity and long-term vision, why game-planning reduces anxiety, how to take imperfect action through experiments, and why humility and a growth mindset are the hidden unlock for learning new skills and building what's next. Plus: a look ahead at Season 2 themes like AI, money, and the future of work. In this episode: A practical breakdown of the 6 core practices to reinvent your career FAST Why this is a ZEITGEIST moment for Career ReInvention, and how you can take advantage Practices to become the most charismatic and magnetic version of yourself The real advantage: building a team so you don't reinvent in isolation If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. https://ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

In a world obsessed with productivity and profit, creativity can feel "optional." For reinventors, it's the opposite: creativity is a core business skill, and a survival skill for the future of work. In this episode, Todd and Chris break down why ReInvention is inherently creative (you're literally designing your next chapter), and how to make creativity practical - even if you're coming from a structured corporate life. We cover: Why creativity will matter more as AI transforms jobs and industries The biggest trap reinventors fall into: hiding in busywork instead of creating How to block "creative time" like it's a real pillar of your work (and why the to-do list never ends) The truth about imposter syndrome: why it's normal, and what to do anyway A simple rule for creative output: let it be messy first, edit later If you're building a business, launching a portfolio career, writing, posting, creating offers, or trying to figure out your next move…this is your reminder: your uniqueness is the asset. Time to get weird, and make it real! If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. https://ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

Roxana Heitz is the kind of person who "has it all" on paper: Stanford Ph.D., 15+ years of product leadership, and a career building health and wellness products across the Google/Alphabet health ecosystem, Peloton, and others…. So why reinvent? In this episode, Roxana breaks down a tension so many mid-career high performers feel: the work still matters, but the environment doesn't fit anymore. The gap between insight → action gets slow. The process becomes the job. The misalignment grows. Instead of making one massive leap, Roxana applies product thinking to her own career reinvention: form hypotheses, run experiments, collect data, and iterate. The result is a portfolio approach - building flexibility and momentum while she explores what's next. What we cover: The moment corporate success stops feeling aligned, even when the mission is meaningful How Roxana gave herself "permission" to step off the treadmill Designing a portfolio career: advisory/consulting, fractional product leadership, and founder exploration Why "betting on yourself" is a skill - and how to build it without blowing up your life The ReInvention superpower most people skip: feedback, accountability, and community If you're a high-achiever who's quietly thinking, "I can't keep doing it this way," Roxana's story will help you rethink what's possible - and how to move forward with clarity without needing a perfect 20-year plan. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. www.ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

What if AI isn't the threat - but the greatest ReInvention Accelerator of your lifetime? In this episode, we sit down with Bill Gurley (legendary Benchmark partner; early investor in Uber, Zillow, Grubhub) to talk about his new book Runnin' Down a Dream and the principles behind building a career you actually want. Bill breaks down why so many people feel stuck on the "college-to-safe-job conveyor belt," and why mid-career can be the best time to make a change - if you approach it with the right mindset. We dig into the difference between low agency (AI feels terrifying) and high agency (AI becomes jet fuel), and Bill shares a practical framework for exploring your next chapter without blowing up your life overnight. In this conversation, we cover: Why career regret is so common, and how to reverse it Bill's "Never Too Late" philosophy for mid-career reinvention How to build a "dream job folder" and test your next path before you leap The smartest way to use mentors, peers, and aspirational models Bill's blunt advice on AI: you can't stop it, so learn to wield it If you're navigating burnout, uncertainty, or the feeling that your work isn't you anymore, this episode is a permission slip + a playbook. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. www.ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

If you're the primary breadwinner or you carry the "provider" identity, Career ReInvention can feel impossible. The fear is real: If I change jobs, the whole system collapses. Mortgage. Bills. Kids. Expectations. Your nervous system starts treating reinvention like a threat. In this episode, Chris and Todd unpack the Provider Trap - the hidden identity that keeps high-achievers locked into misaligned work long after it stops working. They talk about why "providing" is more than a paycheck (presence, energy, relationships, legacy), how fear and scarcity get passed down through generations, and why staying in the wrong career can quietly cost you the very family life you're trying to protect. They also get a bit personal with their own stories. Chris reflects on losing his dad when he was 25 and the conversations they had towards the end. Todd shares some personal challenges he and his wife are currently dealing with when it comes to the question: 'What is a breadwinner - and what are we really providing'. At the end you'll understand why courage is the most important muscle that makes ReInvention possible - even when you feel like you have no room to fail. If you've ever thought, "I can't change - everyone depends on me," this episode is for you. If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. www.ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

If you're building a consulting practice, doing some fractional work, or starting any kind of entrepreneurial / "hang-my-shingle" venture, here's the truth: your results won't matter if you can't sell. In this episode, Todd and Chris break down sales in a way that's clean, human, and repeatable - especially if you've spent years in corporate and the word "selling" makes you tense up. You'll learn why the best sales conversations aren't about pitching harder, they're about listening deeper. In this conversation, we cover: The 4 key Pillars within any business - and a way to identity your strong suits and weak areas The shift that changes everything: you're not selling a product - you're selling a future outcome Why "deep curiosity" beats persuasion (and how it makes closing feel natural) The moment most people avoid: asking directly for the sale (and how to do it without getting weird) The power of silence after the ask - and how to handle objections without spiraling A key skill most people skip: expertise in the manner by which you actually sell (online vs. phone vs. face-to-face, for example) If you've ever thought, "I'm great at what I do… I just don't know how to sell it," this is your episode. If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. www.ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

Fear. Doubt. Anxiety. The mental spiral that makes everything feel heavier than it actually is. In this episode, Todd and Chris go straight into the "real stuff" that shows up when you're in transition or uncertainty - especially when you're trying to make a big change and your nervous system starts writing worst-case stories. We break down a simple truth: your emotions can feel urgent… without being supported by objective reality. And we give you practical tools to stop the spiral, separate facts from fear, and turn "negative" emotions into forward motion. In this conversation, you'll learn: Why your nervous system can react like the world is ending - even when the numbers say you're okay How to tell the difference between real fear and "rollercoaster fear" A simple method to sort what's valid vs. imagined The "control the controllables" mindset shift (and why it saves massive energy) Why numbing out (Netflix, distractions, checking out) keeps you stuck - and what to do instead The Allow & Reflect practice Todd uses to process fear and generate solutions If you've been feeling stuck, frozen, or caught in old conditioning… this episode will give you a framework to work with fear - without letting it drive the car. If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. www.ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

What happens when you finally start building something new…and your old world suddenly comes knocking? In this episode, Todd Jason and Chris Thide talk about one of the most confusing - and most common - moments in career change: unexpected opportunities from your old professional life showing up just as you begin to reinvent yourself. This is almost a predictable phenomenon, and they'll unpack why these moments are so tempting, how identity and nervous system conditioning pull us back toward certainty, and why this phase is actually a test of your long-term vision. You'll learn: How to evaluate new job offers without panic or reactivity The difference between conscious choice and defaulting to safety How to set boundaries around time, energy, and availability When it makes sense to go back - and how to do it without killing your vision Why clarity around your future self changes every decision The GOAL: to help you make the best decisions possible for your long-term future. So this episode isn't about burning bridges or forcing bold moves, but about slowing down, staying aligned, and making wise, intentional decisions when things get noisy. If you're building something new - and feeling pulled back toward the familiar - this episode will help you stay grounded and choose well. If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next. www.ReInvention.biz **Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.