Choose Courage Inc.

Vivianne Castillo

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Courage Inc. is an experience designed for leaders, entrepreneurs, and visionaries who are ready to break free from outdated norms and build workplaces, experiences, and businesses where people, creativity and courage come first.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. Ep 60 | Revisited: Why Leaving Corporate Is a Discipline of Hope

    May 24

    Ep 60 | Revisited: Why Leaving Corporate Is a Discipline of Hope

    In this replay from The Walkout, Vivianne sits with the question underneath so much corporate exhaustion: is the problem you, or the system you're trying to survive? She names the real tension at the center of staying stuck, the difference between what you genuinely can't change and what you've simply stopped believing you can. This is a reframe of what security, hope, and walking out actually mean. In This Episode: •Why most people aren't afraid of leaving, they're experiencing learned helplessness, and why that's something you can work with •The difference between helplessness and powerlessness, and why naming it matters •Why security isn't something you're given, it's something you build •How hope works less like a feeling and more like a discipline, a muscle, a set of choices •What it actually means for hope to need a plan, a path, and people •The hidden cost of mistaking stagnation for stability, paid in identity, skills, time, health, and freedom •Why anger, when it's honest, is information and not something to suppress (and why courage is what it needs next) You're allowed to stop frantically mopping and reach for the plug. You're allowed to treat financial planning as a way to make hope durable, not as a lack of faith. And you're allowed to see grief as a hallway, a transition space, not a place to take up residence. ______________ Resources Mentioned: Join The Walkout — a 2.5-day experience for UX and tech professionals exploring entrepreneurship (https://jointhewalkout.com/). Follow Vivianne on LinkedIn for more reflections on courage, entrepreneurship, and building a life that actually fits you (https://www.linkedin.com/in/vccastillo/).

    42 min
  2. Ep 59 | Revisited: How to Detox from Corporate: 10 Habits You Must Unlearn

    May 17

    Ep 59 | Revisited: How to Detox from Corporate: 10 Habits You Must Unlearn

    If you’ve left corporate but still feel stuck thinking like an employee, this replay is for you. Vivianne breaks down the hidden habits corporate trains into us and how those same patterns quietly sabotage entrepreneurship, creativity, pricing, boundaries, and growth. Because leaving your job is one thing. Detoxing from the mindset is another. In This Episode: The difference between leaving corporate and actually thinking like an entrepreneur.Why so many founders are unknowingly rebuilding another version of the cage they escaped.The 10 toxic corporate habits that quietly sabotage entrepreneurship.How approval-seeking, overworking, and perfectionism follow people into business.Why pricing too low is often a symptom of undervaluing yourself.The danger of measuring success by busyness instead of impact.Why “playing small to stay safe” slowly kills momentum. Vivianne also shares practical reframes and replacement habits to help you start building differently. If you’ve been stuck in overthinking, waiting for permission or trying to build something new with the same habits that burned you out … This episode will resonate. If this replay helped, share it with someone still detoxing from corporate thinking. _____________ ⁠Join The Walkout⁠ — a 2.5-day experience for UX and tech professionals exploring entrepreneurship and building something of their own (https://jointhewalkout.com/). Follow Vivianne on ⁠LinkedIn⁠ for more reflections on courage, entrepreneurship, and designing a life that actually fits you (https://www.linkedin.com/in/vccastillo/).

    39 min
  3. Ep 58 | My Assistant Spills the Tea: Her Real Role, My Real Mistakes, Your Real Questions (ft. Annie)

    May 10

    Ep 58 | My Assistant Spills the Tea: Her Real Role, My Real Mistakes, Your Real Questions (ft. Annie)

    If you’ve ever wondered what it’s actually like to hire support while building a business, this episode is for you. Vivianne sits down with her longtime assistant, Annie, for an honest conversation about delegation, systems, boundaries, and the mistakes founders make when they hire too early. This is a real behind-the-scenes look at what healthy support inside a business can actually look like. In This Episode: •The difference between hiring from clarity vs. overwhelm. •Why delegation fails when founders expect people to read their minds. •What makes a great assistant beyond just technical skills. •How systems, SOPs, and training create trust over time. •The emotional side of letting go and learning to collaborate. •Why assistants shouldn’t just be treated like “admin support.” •The red flags assistants notice in founders (including constant urgency and micromanaging). They also unpack a powerful truth: Hiring support won’t fix chaos, it reveals it. You don’t need an assistant because you’re failing, you need support because you were never meant to carry everything alone. ____________ Resources Mentioned ⁠The Walkout (June 3–5)⁠ — a 2.5-day experience for UX and tech professionals exploring entrepreneurship and building sustainable businesses (https://jointhewalkout.com/). Follow Vivianne on ⁠LinkedIn⁠ for more reflections on entrepreneurship, courage, and building businesses that actually fit your life (https://www.linkedin.com/in/vccastillo/).

    50 min
  4. Ep 57 | How to UnF*ck Your AI (ft. Ovetta Sampson)

    Apr 26

    Ep 57 | How to UnF*ck Your AI (ft. Ovetta Sampson)

    If you’ve been using AI but feel like everything it produces sounds generic, flat, or not quite you, this episode is for you. Vivianne sits down with AI expert Ovetta Sampson to break down why AI outputs feel “off,” what it’s actually costing your creativity, and how to take back control so your work reflects your voice and values. Ovetta Sampson is a 15-year veteran of designing intelligent experiences for some of the largest companies in the world and Business Insider named her one of the top 15 people in Enterprise AI. This is a grounded, no-hype conversation about using AI without losing yourself in the process. In This Episode: •Why AI outputs often feel generic, flat, or “off.” •The “median trap” and how AI pulls everything toward mediocrity. •Why AI is optimized for reward and agreement, not truth or quality. •The hidden cost of AI on your voice, trust, and creative identity. •How over-relying on AI can quietly erode what makes your work unique. •The difference between knowledge vs. wisdom (and why AI needs yours). Why better prompts aren’t enough and what actually works instead. Ovetta also reframes AI as a tool you govern, not something you follow. If you’ve been feeling frustrated with AI (or worried it’s flattening your voice), this is your reminder: AI doesn’t replace your creativity but it will dilute it if you let it. ____________ Resources Mentioned: Ovetta Sampson’s Mindful AI Masterclass: frameworks for designing AI that aligns with human values (https://www.ovetta-sampson.com/right-ai). Join The Walkout June 3rd - June 5th: a 2.5-day experience for creatives exploring building something of their own (https://jointhewalkout.com/). ___________ Ovetta Sampson is a 15-year veteran in intelligent experience design and a Business Insider Top 15 leader in Enterprise AI. She’s the founder of Right AI, where she helps organizations implement AI in equitable, sustainable, and ethical ways while calling attention to the Human Engagement Risks of AI.

    53 min
  5. Ep 56 | Leaving Isn’t the Hard Part. This Is. (ft. Rachael Dietkus)

    Apr 19

    Ep 56 | Leaving Isn’t the Hard Part. This Is. (ft. Rachael Dietkus)

    If you think leaving corporate is the hard part … this episode will challenge that. Vivianne sits down with Rachel Dietkus LCSW to unpack what actually happens after you leave: the patterns, grief, and identity shifts no one prepares you for. This is a conversation about what it really takes to heal, rebuild, and trust yourself again. In this episode: •The invisible patterns you carry out of corporate (even after you leave). •Why autonomy can feel uncomfortable after years of seeking permission. •How hypervigilance, overperformance, and people-pleasing follow you into your next chapter. •Why leaving often feels worse before it feels better. •The role of grief, disorientation, and identity loss after you walk away. •How corporate conditioning shapes your nervous system. •What it actually looks like to heal from corporate (beyond surface-level fixes). They also explore a powerful reframe: What if the behaviors you’re judging yourself for… were never flaws, but survival patterns? You didn’t just leave a job, you left a system your body learned how to survive in. So if it feels messy… disorienting… or harder than expected… You’re not doing it wrong, you’re unwinding patterns that took years to build. _______ 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. _______ Resources Mentioned + ⁠The Walkout⁠(https://jointhewalkout.com/) (June 3–5): 2.5 days with an expert team (attorney, accountant, health insurance specialist) and entrepreneurs who left corporate and built something worth leaving for. + ⁠How To Prototype Your Purpose In 30 Days⁠ (free download): https://choosecourageinc.kit.com/362352e7c4 + Book: Time Off by John Fitch and Max Frenzel

    54 min
  6. Ep 55 | Two Truths and a Lie: The Cost of Staying

    Apr 12

    Ep 55 | Two Truths and a Lie: The Cost of Staying

    If you’ve been telling yourself you just need a little more time, a little more savings, or one more “right moment” before you leave … this episode is for you. Vivianne breaks down the real cost of staying in misaligned work and why the riskiest decision might not be leaving, but waiting. This is a reality check on what your spreadsheet isn’t tracking. In This Episode: •The truth behind the “two truths and a lie” about leaving corporate. •Why spreadsheets track money but miss what actually matters. •The three hidden costs of staying: emotional, financial, and identity. •How resentment turns into numbness (and why that’s dangerous). •Why a salary is a ceiling, not a floor. •How waiting for the “right time” is often fear in disguise. •The difference between familiarity and real safety. Vivianne also shares the truth: Leaving wasn’t the biggest financial risk staying was. You’re not just deciding when to leave.You’re deciding how long you’re willing to delay becoming who you’re meant to be. Because the real cost isn’t just time or money.It’s the version of you that never gets built. ________________ Resources Mentioned: •The Walkout⁠ (https://jointhewalkout.com/)(June 3–5) — a 2.5-day experience to help you build your exit with real support. •Free Live Session: (https://choosecourageinc.kit.com/839640c1c2)⁠( (April 17) 2pm - 3pm EST -⁠Leaving isn’t the hard part. This is. ⁠with ⁠Rachael Dietkus, LCSW

    18 min
  7. Ep 54 | I Got Quiet … and Here's What Came Back

    Apr 5

    Ep 54 | I Got Quiet … and Here's What Came Back

    If you’ve been feeling overwhelmed, distracted, or unsure what to focus on next, this episode is for you. Vivianne shares what happened when she removed the noise, got quiet, and finally created space to hear herself again. What came up wasn’t just clarity, it was grief, honesty, and a different way of building. This is a reset. In This Episode: •What happened when Vivianne deleted social media and removed constant input. •Why most of us are living in a constant state of noise and distraction. •The unexpected emotions that surfaced in the quiet (including grief). •How productivity culture ties your worth to your output. •The difference between doing more vs. doing the right things. •Why clarity only comes when you create space for it. Vivianne also shares what she’s building over the next 90 days, not from pressure, but from clarity. What She’s Building: •A LinkedIn series: Day One - telling the truth about leaving corporate. •A series of free webinars and workshops designed to be genuinely helpful. •The Walkout (June 3–5), a 2.5-day experience for people ready to build something of their own. All rooted in one intention: Not more noise, more good. If you’ve been feeling the pressure to do more… To be everywhere… To keep producing… This is your reminder: You’re allowed to get quiet. You’re allowed to strip things back. And you’re allowed to build from clarity instead of fear. ____________ If this resonated, share it with someone who needs space to hear themselves again. • Follow Vivianne on LinkedIn (https://www.linkedin.com/in/vccastillo/) for more reflections on courage, business, and building something that actually fits your life. • Join The Walkout (https://jointhewalkout.com/) a 2.5-day experience for UX and tech professionals exploring entrepreneurship

    17 min
  8. Ep 53 | The Legal Side of Building Something Real (ft. Patrice Perkins)

    Mar 29

    Ep 53 | The Legal Side of Building Something Real (ft. Patrice Perkins)

    If you’re building something (or even thinking about starting) this episode is for you. Vivianne sits down with her attorney and longtime business partner, Patrice Perkins, to break down the legal side of entrepreneurship in a way that actually feels practical, not overwhelming. From protecting your brand to navigating AI and ownership, this conversation will help you take your work more seriously and more strategically. In This Episode: •The most common legal mistakes entrepreneurs make early on. •Why protecting your brand (trademarks) should be a top priority. •How contracts impact ownership, pricing, and long-term leverage. •The difference between trademarks, copyrights, and trade secrets. •How to protect your IP when working with contractors and collaborators. •What entrepreneurs need to know about AI, ownership, and legal gray areas. •Why many legal issues are actually identity and value problems in disguise. This conversation is a mix of real examples, live Q&A, and practical insights from entrepreneurs building in real time. If you’re creating something, growing something, or protecting something… This is your reminder: Your ideas are valuable. Your work is worth protecting. And how you build matters. ____________ Resources Mentioned: •The Lab (https://creative-genius-law.kit.com/b80be83301) (Patrice’s legal membership community) ongoing legal support, contract guidance, and office hours. _____________ •If this resonated, share it with someone who’s building something of their own. •Follow Vivianne on LinkedIn (https://www.linkedin.com/in/vccastillo/) for more reflections on courage, business, and building something that actually fits your life. •Join The Walkout (https://jointhewalkout.com/) a 2.5-day experience for UX and tech professionals exploring entrepreneurship

    1 hr
See All (60)

5
out of 5
40 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
    60
  • Rating
    Explicit
  • Copyright
    © Choose Courage Inc. | 2025
  • Show Website
    Choose Courage Inc.

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