E13 - Building a Portfolio Career: How To Make Money In Different Ways In Midlife
Release Date: 01/13/2026
REWIND - The Provider Trap: Reinvent Your Career Without Letting Your Family Down
ReInvention
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...
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REWIND - Tired of Being a Lone Wolf? How To Find Collaborators When Reinventing Your Career
ReInvention
While we prep for an incredible Season 2, we're bringing back one of our most impactful episodes and this one on collaboration and community feels more relevant than ever right now. Reinventing your career is exciting — but trying to do it alone is one of the fastest ways to stall, burn out, or second-guess yourself. In this episode, Todd Jason and Chris Thide explore one of the most overlooked accelerators of successful career reinvention: collaboration. This is a grounded, honest conversation about why reinvention isn't a solo journey — and how the right collaborators, mentors, and...
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REWIND - The Jobs AI Won’t Take: How To Future-Proof Your Career
ReInvention
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...
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REWIND - How to Design Your Ideal Future Self (and Retire Your Old Identity)
ReInvention
While we gear up for a powerful Season 2, we're revisiting one of our most impactful episodes and this one's too good not to hear again. If you're staring down "what's next?" after a solid run in corporate, this episode is your invitation to reinvent from the inside out. Todd and Chris unpack the real engine of lasting career change: identity. You'll learn how to define the future-self you want to grow into, gently retire the parts of your old identity that don't serve you, and build daily practices that make reinvention tangible. From 'clarity' weekends and morning pages to self-talk walks,...
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E33 - The Zeitgeist of Career ReInvention is Upon Us! Here’s What You Need To Do
ReInvention
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...
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E32 - Lost Some Confidence? Here’s How to Move Forward And Take Action Anyway
ReInvention
Imposter syndrome hits hardest right when you're trying to reinvent. You've been confident in your craft for years, then suddenly you're starting over, pitching a new path, learning new skills, and your brain decides you're "not ready." In this episode, Todd and Chris break down a practical system for building confidence without waiting for it to magically appear. They unpack why "fake it till you make it" gets misunderstood (and what it should mean), how to turn insecurity into curiosity (the fastest antidote), and why confidence is ultimately not about results, it's about trusting yourself...
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E31 - Creativity Is a Business Skill: How To Crush Imposter Syndrome And Make The Leap!
ReInvention
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...
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E30 - Isolation Is Hurting You: How to Build an Accountability TEAM Around Your Goals
ReInvention
Successfully reinventing your career (or life) isn't challenging because you lack talent. It’s challenging because you try and do it alone. Inspired by the Winter Olympics, Todd and Chris break down the two traits elite performers build their lives around: clarity and accountability. You can have a powerful vision for your next chapter, but without a real accountability system, it stays a dream. In this episode, we dig into the #1 ReInvention killer: isolation - the echo chamber of your own thinking - and how to replace it with a structure that creates momentum, confidence, and...
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E29 - How A Stanford Ph.D. Uses ‘Product Thinking’ To Reinvent Her Career
ReInvention
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...
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E28 - Your Midlife ReInvention Needs a SOCIAL Strategy: Profiles, Posting, and Personal Brand
ReInvention
Are you reinventing your career and not sure how to handle LinkedIn or Social Media in general? In this episode we’ll share a proven game plan for your socials, with specific guidelines for people in professional transition. Todd and Chris break down the biggest mistake midlife professionals make during ReInvention: treating social media like a polished “final reveal” instead of a tool for building momentum, community, and opportunity while you’re in the process. They talk about the mindset shift that wins right now - authenticity over perfection - especially in an era of AI-generated...
info_outlineWhat if your next chapter isn't "one job" - but a mix of things you actually care about that together add up to your income and identity?
In this episode of the ReInvention Podcast, Todd Jason and Chris Thide break down the rise of portfolio careers - designing work around multiple income streams instead of a single, traditional role. They talk honestly about why the old "one job, one ladder" model is breaking down, and why now is the perfect moment to start experimenting with new ways to make money.
You'll hear real stories from their clients and community: former executives turning skills into fractional work, consultants, coaches, creators, and people testing small experiments on the side before they leap. This is not just theory. It's a practical roadmap for reinventing your career in a world of AI, burnout, and massive change.
In this episode, you'll learn:
- What a portfolio career actually is (and what it isn't)
- How to start making a little bit of money in new ways without blowing up your life
- Why your existing skills are way more transferable than you think
- Smart ways to use your network without feeling salesy or weird
- How to handle the emotional side of reinvention when people don't "get" what you're doing
- Why creative projects and "non-money" experiments often lead to real opportunities
- The mindset shift from "I need one perfect job" to "I'm the CEO of my own future"
If you're burned out, bored, or just know you're meant for more than another decade of scrolling job boards, this conversation will help you see new options and give you permission to start small but real experiments now.
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
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