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Courage Inc. is an experience designed for leaders, entrepreneurs, and visionaries who are ready to break free from outdated norms and build workplaces, experiences, and businesses where people, creativity and courage come first.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 48 | Real Talk: What do you tell folks who feel stuck? (ft. Vincent Brathwaite)

    2D AGO

    Ep 48 | Real Talk: What do you tell folks who feel stuck? (ft. Vincent Brathwaite)

    If you’ve been telling yourself you’re “too deep in” to change, this episode is for you. Vivianne and Vincent unpack the fear hidden inside responsibility, the psychology of sunk costs, and why staying put is often just practiced survival, not alignment. This is a conversation about identity, agency, and what becomes possible when you stop confusing familiarity with safety. In This Episode, We Explore: • Why “too deep in” is usually attachment, not reality. • The sunk cost fallacy and how it distorts your future. • How identity gets fused with your job and why that makes leaving feel like self-erasure. • Why exhaustion shrinks your imagination. • The difference between certainty in place and uncertainty in motion. • How corporate systems quietly train learned helplessness. • Why movement creates clarity that standing still never can. They also explore a simple but confronting shift: Instead of asking what you’ve already invested… ask what you want the next 10–15 years to feel like. If you’ve been waiting to feel ready, calling misalignment “practical” or have been telling yourself you should just endure, this episode is just a friendly reminder that you’re not behind. ____________ •If this episode resonated, share it with an entrepreneur who’s tired of grinding and ready to build something that actually feels good. •Follow Vivianne on LinkedIn ( https://www.linkedin.com/in/vccastillo/ ) for more reflections on courage, creativity, and regenerative entrepreneurship. _______ Resources Mentioned: Vivianne shares two practical tools to help you move from reflection to action: •Life Audit Workbook from Episode 19, designed to help you spot misalignment before burnout and reclaim your agency. (https://choosecourageinc.kit.com/da998c495d) •Prototype Your Purpose (30-Day Framework) from Episode 23, a step-by-step guide to stop “finding” purpose and start experimenting your way toward clarity. (https://choosecourageinc.kit.com/362352e7c4)

    18 min
  2. Ep 47 | Real Talk: What's Keeping You Stuck (ft. Vincent Brathwaite)

    6D AGO

    Ep 47 | Real Talk: What's Keeping You Stuck (ft. Vincent Brathwaite)

    If you’ve been feeling stuck in a career that looks stable on paper but quietly feels misaligned, this episode is for you. Vivianne and her guest Vincent unpack the subtle narratives that keep designers frozen, stories that sound responsible, wise, even grateful… but are often just fear in disguise. In this honest conversation, Vivianne and Vincent explore the hidden beliefs that keep so many designers in place, including: The arrival fallacy: believing you’ll feel ready once you learn one more thing. •How “I just need more information” can mask fear of movement. •Why stability is often labeled responsible, even when it’s draining you. •How gratitude can quietly become a leash. •The fear of “starting over” and having to prove yourself again. •Staying past alignment because leaving feels like failure. •The difference between protecting your comfort and expanding your life. They also challenge a hard question: When you’re afraid of failing… failing in the eyes of whom? Because many designers aren’t lacking courage … they’ve simply been taught that staying still is the responsible choice. If you’ve been carrying quiet dissatisfaction but calling it practicality… If you’ve been waiting to feel “ready”… If you’ve been telling yourself you should just be grateful… This conversation will resonate. You don’t have to endure what no longer fits. And choosing yourself isn’t recklessness, it’s precision. __________ If this episode resonated, share it with an entrepreneur who’s tired of grinding and ready to build something that actually feels good. Follow Vivianne on LinkedIn (https://www.linkedin.com/in/vccastillo/) for more reflections on courage, creativity, and regenerative entrepreneurship.

    23 min
  3. Ep 46 | The Unspoken Cost Of Staying at Your Job

    FEB 15

    Ep 46 | The Unspoken Cost Of Staying at Your Job

    If you’ve ever felt the slow erosion of staying in a job that looks “good on paper” but feels heavy in your body, this episode is for you. Vivianne shares the real cost of remaining in environments that require self-neglect as a condition of employment and challenges the one-sided way we’ve been taught to think about risk. This isn’t just about leaving a company. It’s about choosing yourself before something essential in you disappears. In this deeply personal episode, Vivianne revisits ⁠the resignation letter⁠ she wrote when she left Salesforce (view here: https://bit.ly/4c0n1yF) and reflects on how the same cultural patterns continue to surface years later. But this episode isn’t a corporate takedown ... it's a broader conversation about: •What it costs to stay in environments that don’t protect you. •How toxic systems require your self-abandonment to function. •The difference between confidence and conviction. •Why the “safe” choice is often just the familiar one. •What it actually means to bet on yourself. If you’ve been carrying a quiet resignation letter in your head, this conversation will resonate and help you choose you. And if you’re in a season of questioning what’s next and want a space to talk it through, Vivianne invites you to book a 30-minute conversation at: https://calendly.com/choosecourageinc/lets-connect-and-vibe Because sometimes choosing yourself starts with simply saying out loud: “There has to be more than this.” __________ If this episode resonated, share it with someone who needs permission to choose themselves and don’t forget to leave a review to help others discover Choose Courage Inc💙

    26 min
  4. Ep 45 | How to Book Your First 10 Discovery Calls

    FEB 7

    Ep 45 | How to Book Your First 10 Discovery Calls

    In this episode of Choose Courage, Inc., Vivianne shares a training from inside her coaching community that helped members feel more confident, less avoidant, and more connected to the possibility of their first sale. Rather than teaching funnels or hype-driven tactics, she offers a grounded framework for booking your first 10 discovery calls through integrity, proximity, and thoughtful outreach. At its core, this episode is about replacing fear-driven avoidance with courageous conversation. Not to close deals but to practice, learn, and build real momentum. From there, she introduces a clear distinction: Inbound is about being found. Outbound is about being willing This episode focuses on outbound, not as chasing or convincing, but as relational courage in action. •The Three-Circle Framework for Aligned Outreach:Rather than starting with strangers, Vivianne encourages entrepreneurs to begin with proximity and trust. •A Different Way to Think About Discovery Calls: This episode challenges the pressure-filled belief that every call must turn into a client. •Outreach Without the Ick: Rather than scripts that manipulate or pressure, Vivianne shares principles behind outreach that feels clean. ______ If this episode resonated and you want support putting it into practice, ⁠download the outreach templates⁠ (https://choosecourageinc.kit.com/69a53b8b31) and choose one message to send this week. You don’t need to do everything. You just need to start.

    25 min
  5. Ep 42 | Why Leaving Corporate Is a Discipline of Hope

    JAN 25

    Ep 42 | Why Leaving Corporate Is a Discipline of Hope

    Welcome to Season 3 of Choose Courage Inc. This season is about movement over motivation. It’s for people who are done enduring, done over-explaining their burnout, and ready to design what comes next with intention, honesty, and support. Episodes this season will alternate between solo reflections and grounded conversations with people who have receipts, not highlight reels. You’ll also hear shorter midweek Real Talk episodes where real questions about leaving corporate, entrepreneurship, money, fear, and identity get answered without fluff or false promises. If you’re questioning your work, your path, or the story you’ve been told about stability and success, you’re in the right place. This season is an invitation to treat hope not as a feeling, but as a practice. ___________________________________ In this powerful panel session from The Walkout (jointhewalkout.com), Vivianne Castillo shares a deeply reflective and practical framework for rethinking work, stability, and entrepreneurship. Drawing from her background in counseling, design, and building a seven-figure consultancy, Vivianne challenges the belief that endurance equals success and invites listeners to stop “frantically mopping” broken systems. She introduces hope not as wishful thinking, but as a discipline supported by three essential elements: a plan, a path, and people. This episode blends storytelling, nervous-system-aware insights, and concrete business guidance for anyone contemplating a move beyond corporate life. Hope as a Discipline: The Three Essentials: •A Plan (Financial Reality) •A Path (Clear Enough to Start) •People (Community as Infrastructure) Redefining Security and Success: •Traditional corporate “stability” is often a false promise dependent on external approval. •True security comes from skills, adaptability, relationships, and self-trust. •Staying solely out of fear can cost you time, health, creativity, and freedom. Who This Episode Is For: •Professionals burned out from corporate environments •High performers questioning whether they’re the problem •Aspiring or early-stage entrepreneurs seeking a grounded exit strategy -Anyone navigating grief, anger, or loss of identity from toxic work experiences Walking out is not about impulsively quitting or burning everything down: it's about choosing yourself with intention. Whether you stay in corporate while building, leave soon, or redefine your path entirely, this episode offers a compassionate and strategic framework for reclaiming agency, rebuilding hope, and designing a life and livelihood that actually support you. _________________________ And if something in this conversation stirred you, I'd like to invite you to honor it. Please consider sharing this episode with someone who might need permission to imagine something different💙And when you’re ready, explore what’s possible at ⁠choosecourageinc.com⁠

    45 min
  6. Ep 41 | 6 Rules for Building the Life That You Want

    12/14/2025

    Ep 41 | 6 Rules for Building the Life That You Want

    This episode is a clear-eyed reset for anyone questioning the promises of corporate stability or the romanticized version of entrepreneurship. Vivianne lays out six practical rules to help you reclaim agency, reduce hidden risk, and build real options without reckless leaps. If you feel stuck between burnout and fear, this conversation offers a grounded framework for seeing your situation clearly and making strategic, sustainable moves. In this final episode of 2025, Vivianne dismantles two dominant but broken narratives: the myth of corporate loyalty and the fantasy that entrepreneurship is inherently freeing or less risky. She argues that both employment and entrepreneurship carry risk, but only one is honest about it. From that tension, she introduces six rules designed to help you stop outsourcing your security and start building it yourself, whether you stay employed, start a business, or do both in parallel. This is not about quitting your job tomorrow. It’s about clarity, leverage, and long-term self-trust. The Six Rules: 1. Your Job Is a Loan, Not a Career. Employment is a transaction, not a relationship. Treat your job like capital you’re borrowing to build skills, savings, and insight. 2. Your Side Hustle Should Scare You More Than Your Day Job. If it’s completely safe and comfortable, it’s probably a hobby. A real side hustle carries stakes: emotional, reputational, financial, or temporal. 3. Stop Waiting to Be Ready, You’re Already Overqualified. Many high performers underestimate themselves when working for themselves while confidently handling massive responsibility at work. The gap isn’t skill, it’s conviction. 4. Your Corporate Job Is Teaching You What Not to Build. Every frustration is data. Every inefficiency is market research. Most people vent; strategic thinkers document. 5. Entrepreneurship Isn’t Riskier Than Employment, It’s Just Honest. Employment feels stable because risk is hidden and outsourced. Entrepreneurship feels risky because decisions (and responsibility) are visible. 6. Work Your Job Like a Consultant, Not an Employee. You can keep an employee title while adopting a consultant mindset: clear deliverables, documented impact, firm boundaries, and emotional distance. Vivianne closes the year with a reminder: courage is not one dramatic leap but a series of small, strategic choices. You don’t need permission to build a life with options. You need clarity, honesty about risk, and the willingness to invest in yourself consistently. —-------- If this episode resonated, share it with someone who’s quietly questioning their path! Sometimes clarity is contagious. -Follow Vivianne on ⁠LinkedIn (https://www.linkedin.com/in/vccastillo/)⁠ for grounded insights on courage, work, and building real security in uncertain times. -Download The 6 Rules for Building the Life That You Want (https://choosecourageinc.kit.com/9fd7efb4ae): a practical guide to reclaiming agency, reducing risk, and building what’s yours without dramatic leaps. This guide walks you through the same framework from the episode with clear prompts, exercises, and next steps you can apply immediately, right where you are. -⁠Join ⁠The Walkout⁠⁠ (https://jointhewalkout.com/), an online 2-day experience from January 15th – January 16th for UX professionals interested in building a life and career outside of corporate without regret, guilt, or starting from scratch.

    40 min
5
out of 5
33 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.