Choose Courage Inc.

Vivianne Castillo
  • 5.0 (44)
  • Business

We're reimagining business and workplace experiences with we-aint-afraid-to-go-there conversations. Choose Courage Inc. is an experience designed for leaders, entrepreneurs, and visionaries who are ready to break free from outdated norms and build workplaces, experiences, and businesses where people, creativity and courage come first.

  1. 11h ago

    Ep 66 | The Slow Build: Staying Grounded on the Way (ft Phillip Hunter)

    If you've ever felt that itch to build something of your own but couldn't quite picture the first step, this one's for you. Vivianne sits down with Phillip Hunter, a longtime voice and conversational AI product leader who left corporate life behind to build something new. Together they talk about what it actually looks like to stay steady while you're figuring things out, one small step at a time. YOU WILL LEARN-Why self-approval, not external validation, is often the real fuel behind becoming an entrepreneur-The difference between fearing failure and getting genuinely curious about it-How "hustle harder" culture quietly convinces us that slow progress means no progress-Why a clear, personal why keeps you going when things get dull or hard YOU WILL BE READY TO-Notice when hesitation is just your body catching up, not a red flag-Let a slow season count as real progress-Name your own reason for doing this, instead of borrowing someone else's-Take a step without having the whole map figured out-Give yourself permission to measure success by who you're becoming, not just what you've shipped If this resonated, share it with someone who's got an idea and just needs a nudge to take the first step.💙 Phillip Hunter has spent nearly two decades designing for voice and conversation, from early touch-tone speech recognition systems to leading experience direction for Amazon Alexa Skills. He now runs Conversational Collaborative AI Services, a consultancy focused on AI agents and conversational product design. After stepping away from corporate work, he's building new products at the intersection of his design background and the current generation of language models. Resources Mentioned:Follow Phillip on LinkedIn.Follow Vivianne on LinkedIn for more reflections on courage, entrepreneurship, and building a life that actually fits you.

    Ep 66 | The Slow Build: Staying Grounded on the Way (ft Phillip Hunter)

  2. 15h ago

    Ep 66 | The Slow Build: Staying Grounded on the Way (ft Phillip Hunter)

    If you've ever felt that itch to build something of your own but couldn't quite picture the first step, this one's for you. Vivianne sits down with Phillip Hunter, a longtime voice and conversational AI product leader who left corporate life behind to build something new. Together they talk about what it actually looks like to stay steady while you're figuring things out, one small step at a time. YOU WILL LEARN -Why self-approval, not external validation, is often the real fuel behind becoming an entrepreneur -The difference between fearing failure and getting genuinely curious about it -How "hustle harder" culture quietly convinces us that slow progress means no progress -Why a clear, personal why keeps you going when things get dull or hard YOU WILL BE READY TO -Notice when hesitation is just your body catching up, not a red flag -Let a slow season count as real progress -Name your own reason for doing this, instead of borrowing someone else's -Take a step without having the whole map figured out -Give yourself permission to measure success by who you're becoming, not just what you've shipped If this resonated, share it with someone who's got an idea and just needs a nudge to take the first step.💙 Phillip Hunter has spent nearly two decades designing for voice and conversation, from early touch-tone speech recognition systems to leading experience direction for Amazon Alexa Skills. He now runs Conversational Collaborative AI Services, a consultancy focused on AI agents and conversational product design. After stepping away from corporate work, he's building new products at the intersection of his design background and the current generation of language models. Resources Mentioned: Follow Phillip on LinkedIn (https://www.linkedin.com/in/philliphunter/). Follow Vivianne on LinkedIn for more reflections on courage, entrepreneurship, and building a life that actually fits you (https://www.linkedin.com/in/vccastillo/).

    Ep 66 | The Slow Build: Staying Grounded on the Way (ft Phillip Hunter)

  3. Aug 23

    Ep 65 | What to Expect When Negotiating a B2B Contract (ft. Ray Knickmeyer)

    If you've ever sat in the silence between sending a proposal and hearing back, wondering if you did something wrong, this episode is for you. Vivianne sits down with Ray Knickmeyer, a former corporate leader with 20 years at places like Verizon and Capital One, now running their own consulting business, to unpack what three months of B2B procurement actually felt like from the inside and how to hold your terms without turning rigid. YOU WILL LEARN-Why the dead zones between emails are often more anxious than the actual contract terms-The difference between a hard boundary (money down, IP protection) and one you can flex (payment schedule, signature timing)-How "you created your own luck" reframes years of quiet relationship building into real leverage-Why a corporate client's master service agreement almost always leaves wiggle room through the statement of work YOU WILL BE READY TO-Name the difference between catastrophizing silence and an actual red flag-Ask for a non-refundable deposit without apologizing for it-Separate what you're willing to negotiate from what protects your business and your IP-Give yourself permission to walk away from a client who won't respect your terms If this resonated, share it with someone who's still detoxing from corporate thinking💙 Ray is the Founder & Principal Strategist at Knickmeyer Strategic Facilitation where they partner with leadership teams to dismantle broken systems and build the human-centered scaffolding teams need to thrive. Blending architectural rigor with deep empathy, Ray helps organizations stop paying what they call the Misalignment Tax, the hidden cost of circular debates, strategic guesswork, and team friction. Their work replaces the standard corporate offsite with a diagnostic-first methodology that solves the root cause of a team's exhaustion instead of treating the symptoms.---Follow Vivianne on ⁠LinkedIn ⁠for more reflections on courage, entrepreneurship, and building a life that actually fits you.Connect with Ray on LinkedIn

    Ep 65 | What to Expect When Negotiating a B2B Contract (ft. Ray Knickmeyer)

  4. Aug 16

    Ep 64 | The Art of the Pivot: Finding Clarity in Change (ft. Michael J.A. Davis)

    If you've ever wondered whether the second pivot is supposed to feel easier than the first, this episode will complicate that. Vivianne sits down with Michael Davis, founder of Tiny Cup Coffee and author of Coffee Rest Rituals, and a former participant in Choose Courage's From Corporate to Entrepreneurship cohort. This time, the shift isn't about escaping something broken. It's about protecting a vision he already believes in. YOU WILL LEARN-Why a pivot shows up in the body months before it shows up on a calendar (and why overriding that signal is a skill many of us were trained into)-The difference between emotional endurance and just enduring-Why a second pivot can feel harder even when it's easier, because there's no longer an outside villain to blame-How rest quietly turns into payment when it has to be earned first-The role old fear plays in disguising itself as something new YOU WILL BE READY TO-Name what your body has been telling you before your calendar caught up-Recognize when you're crashing out instead of actually in crisis-Question whether you're fighting a villain or just gathering provisions for the next leg of the journey-Separate rest as ritual from rest as reward-Give yourself permission to protect a vision instead of abandoning it If this resonated, share it with someone who's in the meantime season and needs permission to trust it💙 Michael is the founder of Tiny Cup Coffee, built around rest and resistance to grind culture, and the author of Coffee Rest Rituals. After nearly two decades as a designer working at the intersection of design and DEI, he left corporate to found his coffee company and now lives and works between Egypt and the U.S. He's also building Tiny Cup Studio, a creative offshoot supporting food and beverage brands with their identity and storytelling. Resources Mentioned:Tiny Cup Coffee — Michael's coffee company, built around rest and resistance to grind culture.Coffee Rest Rituals by Michael — his book on using the five senses to turn small daily rituals, like making coffee, into real rest. Try the code CHOOSECOURAGE for 15% off.Self-paced The Walkout — for anyone who knows they want something different but doesn't yet know what.Follow Vivianne on LinkedIn for more reflections on courage, entrepreneurship, and building a life that actually.

    Ep 64 | The Art of the Pivot: Finding Clarity in Change (ft. Michael J.A. Davis)

  5. Aug 16

    Ep 64 | The Art of the Pivot: Finding Clarity in Change (ft. Michael J.A. Davis)

    If you've ever wondered whether the second pivot is supposed to feel easier than the first, this episode will complicate that. Vivianne sits down with Michael Davis, founder of Tiny Cup Coffee and author of Coffee Rest Rituals, and a former participant in Choose Courage's From Corporate to Entrepreneurship cohort. This time, the shift isn't about escaping something broken. It's about protecting a vision he already believes in. YOU WILL LEARN -Why a pivot shows up in the body months before it shows up on a calendar (and why overriding that signal is a skill many of us were trained into) -The difference between emotional endurance and just enduring -Why a second pivot can feel harder even when it's easier, because there's no longer an outside villain to blame -How rest quietly turns into payment when it has to be earned first -The role old fear plays in disguising itself as something new YOU WILL BE READY TO -Name what your body has been telling you before your calendar caught up -Recognize when you're crashing out instead of actually in crisis -Question whether you're fighting a villain or just gathering provisions for the next leg of the journey -Separate rest as ritual from rest as reward -Give yourself permission to protect a vision instead of abandoning it If this resonated, share it with someone who's in the meantime season and needs permission to trust it💙 Michael is the founder of Tiny Cup Coffee, built around rest and resistance to grind culture, and the author of Coffee Rest Rituals. After nearly two decades as a designer working at the intersection of design and DEI, he left corporate to found his coffee company and now lives and works between Egypt and the U.S. He's also building Tiny Cup Studio, a creative offshoot supporting food and beverage brands with their identity and storytelling. Resources Mentioned: Tiny Cup Coffee — Michael's coffee company, built around rest and resistance to grind culture(https://tinycup.coffee/). Coffee Rest Rituals by Michael — his book on using the five senses to turn small daily rituals, like making coffee, into real rest. Try the code CHOOSECOURAGE for 15% off (https://tinycup.coffee/pages/restrituals). Self-paced The Walkout — for anyone who knows they want something different but doesn't yet know what (https://choosecourageinc.com/pages/the-walkout). Follow Vivianne on LinkedIn for more reflections on courage, entrepreneurship, and building a life that actually (https://www.linkedin.com/in/vccastillo/).

    Ep 64 | The Art of the Pivot: Finding Clarity in Change (ft. Michael J.A. Davis)

  6. Aug 9

    Ep 63 | Betting on Yourself: The First 90 Days After the Leap

    If you've been sitting in that in-between space, numbers pulled up on a spreadsheet, trying to talk yourself into or out of the leap, this episode is for you. Vivianne sits down with Nathaniel Deal, who left a director-level corporate role to bet on himself, to talk through what actually happened in his first 90 days of full-time entrepreneurship. Not the highlight reel. The real math, the real fear, and the healing nobody warns you about. In This Episode: Why "job security" is often just a story you tell yourself to stayThe difference between chasing wealth and building something sustainableHow a $40,000 hiring lesson taught Nate to trust his own decisions againThe role community played in turning stealth-mode grinding into real momentumWhy leaving corporate doesn't automatically mean you leave corporate habits behindWhat it actually means to heal financial trauma, even after you've "made it"The hidden cost of chasing a promotion that was never built for youYou're not just changing your income. You're unwinding a nervous system that was trained to endure. If you've been waiting for permission to trust your own timeline… if you've been quietly doing the math on what freedom might cost… you're allowed to move before you feel ready. You're allowed to bring your whole, unfinished self into the next thing. Resources Mentioned: Atomic Habits by James Clear: the "you don't rise to the level of your goals, you fall to the level of your systems" line referenced in the conversation.The Walkout, self-paced version: explore what Nate worked through in this episode.Follow Vivianne on LinkedIn for more reflections on courage, entrepreneurship, and building a life that actually fits you.Nathaniel Deal spent years as a corporate director before betting on himself and building his own contracting business, now working toward becoming a founder who buys back his own time. Connect with him on LinkedIn.

    Ep 63 | Betting on Yourself: The First 90 Days After the Leap

  7. Aug 2

    Ep 62 | The 5 Words Keeping You Stuck in Corporate

    If you've been stuck on "what would I even do?" every time you think about leaving corporate, this episode is for you. Vivianne opens season four by naming the advice everyone gives before you leave, pick your niche first, and why that sequence keeps good people frozen instead of moving. She traces her own path across three careers, counseling, UX research, and Choose Courage Inc., to show that clarity was never the starting point. In This Episode:-Why "pick your niche first" turns a career question into an entry exam-How a frozen nervous system gets mistaken for a lack of direction-The difference between introspecting and gathering real data-Why paid attention tells you something polite attention never will-What "motion" actually means, and why it's not hustle-How the sunk cost pull shows up disguised as strategy-The one weekly practice that starts direction work with zero financial risk Direction isn't something you find by thinking harder about it: it's something you build by making contact with real work and letting the results tell you something. -----------------Resources Mentioned:⁠The Walkout⁠: Vivianne's self-paced program for corporate professionals in UX, design, and tech working through the exit, including the direction, readiness, and money pieces (https://choosecourage.samcart.com/products/sp-the-walkout).Follow Vivianne on⁠ LinkedIn⁠ for more reflections on courage, entrepreneurship, and building a life that actually fits you. If this resonated, share it with someone who's been waiting to feel certain before they'll let themselves move💙

    Ep 62 | The 5 Words Keeping You Stuck in Corporate

  8. Jun 7

    Ep 61 | The Questions You're Afraid to Ask (ft. Rachael Dietkus, Behzod Sirjani and Vincent Brathwaite)

    This is the season three finale of Choose Courage Inc., and it's a live panel recording from The Walkout. Vivianne sits down with Rachael Dietkus, Behzod Sirjani, and Vincent Brathwaite to move through the questions people were too afraid to ask out loud: about fear and risk, about readiness, about money, about identity, and about the weight of where we come from. This is a conversation that ends the season the way it was meant to: together. In This Episode: Why fear that's warning you tends to get more specific when you look directly at it, and what to do with that list.The difference between uncertainty and risk, and why we keep collapsing them into the same feeling.Why "I wasn't ready" is almost always the honest answer, and why that doesn't mean you shouldn't go.What happens between day 30 and 60 after leaving, and why that emotional unraveling is actually a sign your body finally feels safe.How to price your work when your entire sense of worth has been shaped by institutions that underpaid you.The hidden cost of borrowed identity, and what it means when the panic of losing a logo tells you how much of yourself you quietly handed over.Why grief can do bad math for us, and the only way to find out those years were ever really yours to begin with.What it looks like to break generational chains, not by rejecting where you came from, but by moving with the same boldness your parents had to survive.You don't build a self from scratch.The company just rented you the storefront and let you forget that you're you. Clarity comes through doing, not waiting.And this journey was never meant to be a solo one. _________ •Follow Vivianne on LinkedIn for more reflections on courage, entrepreneurship, and building a life that actually fits you. •More on Rachael Dietkus LCSW: Rachael is an internationally recognized leader in trauma-informed design, civic tech ethics, and care-centered public interest technology. As founder of Social Workers Who Design, she works at the intersection of design, social work, and systems change, helping organizations build ethical, sustainable, and trauma-responsive practices that support both people and impact. •Vincent Brathwaite is a Caribbean American multi-disciplinary design leader, educator, and speaker. For the past two decades, he has worked to transform communities through disruptive design thinking. Driven by integrity, empathy, kindness, courage, and resilience, his mission is to design experiences that help leaders positively impact the world. •Behzod Sirjani is a consultant who is regularly sought out to navigate complex challenges, whether that's helping a fast-growing startup drive growth or a large public company restructure their innovation practice. Through Yet Another Studio, Behzod partners with companies ranging from small startups to industry leaders like Figma and Dropbox to build and scale research practices that drive better decision-making and growth. He is also a Program Partner at Reforge, where he built the "User Insights for Product Decisions" and "Effective Customer Conversations" programs and a venture partner at el cap.

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5
out of 5
44 Ratings

About

We're reimagining business and workplace experiences with we-aint-afraid-to-go-there conversations. Choose Courage Inc. is an experience designed for leaders, entrepreneurs, and visionaries who are ready to break free from outdated norms and build workplaces, experiences, and businesses where people, creativity and courage come first.

Information

  • Creator
    Vivianne Castillo
  • Years Active
    2025 - 2026
  • Episodes
    72
  • Rating
    Clean
  • Copyright
    © Choose Courage Inc.
  • Show Website
    Choose Courage Inc.

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