Our goal is simple:
To help you be and feel more free.
The Walkout is a self-paced experience designed to help you get access to the expert guidance, the tools, and the mindset shifts they need to build a business that genuinely inspires them and a life that feels good. You move through it on your own timeline, and it's yours to return to whenever you need it.
Where: Online, always open. Start the moment you're ready.
What's inside: Guidance drawn from legal, financial, and health insurance experts, the stories of entrepreneurs who left corporate and built businesses on their own terms, and a framework built for people who believe there has to be more to life than enduring the corporate grind.
Hosted By: Vivianne Castillo from Choose Courage Inc.
What you'll experience with The Walkout:
-
Access to the expert team most aspiring entrepreneurs don't have.
You'll hear directly from an attorney, an accountant, and a health insurance specialist, to help you make the transition with clarity and confidence.
The mindset shifts that help you heal from corporate.
So you can stop operating from fear, trust your gut again, and approach business-building as creative and restorative.
-
Actionable steps you can start taking immediately
You'll walk away with specific steps and clarity, without feeling like you need to follow a capitalism bro's blueprint or betray who you are in the process.
The confidence to have the hard conversations.
With your manager, your family, and most importantly, yourself … without apologizing for choosing freedom.
-
Permission to leave without guilt.
From people who've done it, don't regret it and won't judge you for wanting something different. Sometimes we just need to be reminded that we're capable and able to enjoy life instead of just survive it.
The ability to spot which corporate narratives are keeping you stuck.
"Just one more year," "I need more experience," and how to reject them without guilt.
This Isn't Your Typical Self-Paced Experience
| Scroll left to right | The Walkout | The Usual Playbook |
|---|---|---|
| Why We Exist |
✔ To help you leave well ... without guilt, fear, or self-abandonment.
|
✖ To help you stay longer ... with more tools to tolerate what’s breaking you.
|
| Focus |
✔ Clarity, courage, and freedom.
|
✖ Inspiration to endure your current situation.
|
| Depth of Experience |
✔ 2 main speakers. Intimate Q&A sessions and customized panels to common questions. No fluff. Real transformation.
|
✖ 15+ speakers. 6+ folks on one panel (15mins of intros). A mile wide and an inch deep.
|
| Who’s Supporting You |
✔ People who’ve actually walked out. They’ve faced the fear, rebuilt from scratch, and won their peace back.
|
✖ People who’ve learned to survive dysfunction and now teach you how to do the same.
|
| Approach to Pricing |
✔ One accessible, transparent price, no scarcity tactics.
|
✖ Tiered pricing & scarcity tactics; priced for profit margins.
|
| Profit with Purpose |
✔ 20% of profits donated to non-profits to support others in need. People > Profit.
|
✖ 0% give-back. Maximize margins.
|
| What You Leave With |
✔ An action plan and the courage to use it, and it's yours to return to whenever you need it.
|
✖ Some notes you won't look at again, a few new LinkedIn connections, and a lingering ache for more.
|
| The Energy |
✔ Designed for nervous systems that crave honesty and hope in equal measure.
|
✖ A cycle of inspiration and exhaustion on repeat.
|
Join The Walkout
Where clarity and courage converge so that you leave corporate design with confidence, build what's actually yours, and reclaim your life in the process.
If this is resonating, keep reading👀
Meet the Walkouts
-
Vivianne Castillo
Founder of Choose Courage Inc. & HmntyCntrd
I help values-led entrepreneurs build businesses that pay well, feel good, and protect their peace without burnout or selling their soul.
-
Rachael Dietkus, LCSW
Founder of Social Workers Who Design
I help designers build meaningful careers that honor care, integrity, and trauma-informed practice.
-
Patrice Perkins, Esq.
Business Attorney
I help visionary creatives protect their genius, own their work, and turn their intellectual property into profitable assets without exploitation or loss of control. -
Ashby Kyhl, EA
Accounting Expert
I help small businesses and individuals build financial clarity and long term security through proactive tax strategy, sharp bookkeeping, and practical accounting systems that make money easier to manage.
-
Behzod Sirjani
Founder of Yet Another Studio
I help high-growth companies build strong research foundations, scale research operations, and turn insights into strategic advantage without rushing to full-time hires.
-
Vincent Brathwaite
Founder of gidens
I help designers and entrepreneurs build clarity and impact by shaping simple, human-centered experiences guided by integrity, kindness, resilience, and courage.
-
Erika Poole
Health Insurance Specialist
I leverage innovative health benefits strategies through user-centered design and flexible plan approaches to make complex insurance work better for real people.
-
Elizabeth Burke
Founder of Collective Expansion
I help purpose-driven practitioners turn their knowledge and experiences into meaningful learning experiences that transform others.
Who Will Get the Most Out of This
-
Who this isn’t for ❌
❌ You're in active crisis mode (about to be evicted, health emergency, etc.) and need income stability more than exit strategies right now.
❌ You think investing in your business and personal growth is "risky" but staying in corporate is "safe" (hint: you've got the risk calculation backwards).
❌ You're waiting for the "perfect time" to leave and think this experience will tell you when that is (spoiler: there isn't one).
❌ You want to "think about it" for another 6-18 months while staying absolutely miserable because staying stuck feels safer than committing to change.
❌ You're looking for the magic framework that makes leaving feel easy instead of accepting it will be scary and doing it anyway.
❌ You're more afraid of what people will think than you are committed to your own freedom.
-
Who this is for ✅
✅ You're done consuming content about leaving and ready to actually build your exit plan with support.
✅ You're willing to invest in yourself even when it's scary, because staying stuck is more expensive than any conference, coaching program, course, or degree.
✅ You understand that leaving is a process, not a light switch and you're willing to move towards your exit over +3 months.
✅ You're ready to have uncomfortable conversations because freedom matters more than others approving your career path.
✅ You're not running FROM corporate. You want to run TO something specific.
✅ You know you need support and expert guidance and you're ready to explore all three.
Raw Reviews. Real Experiences.
What to Expect
This self-paced experience shows you proven exit paths from corporate so you can stop navigating dysfunction and start building freedom through agency ownership, entrepreneurship, or helping-profession paths.
If you're curious, keep reading (and notice if you catch yourself with goosebumps, fist pumps, and a few audible heck yeah's as you go).
Part 1: Permission
This is focused on building the emotional and philosophical foundation for leaving, with talks from three entrepreneurs who did it and a conversation with a business attorney to start answering the questions you're already afraid to ask.
The Old Way: Wait for the right time. Wait for enough savings. Wait for someone to tell you it's okay. Wait until the fear goes away. Keep waiting.
The Walkout Way: Stop waiting for permission that was never coming. Build the emotional and legal foundation to leave on your own terms, with people who already did it showing you the way.
Your Sessions
Talks + Fireside Chat
-
Talk | With Rachael Dietkus, LCSW
Leaving an unhealthy or misaligned workplace is often framed as a decisive moment: the resignation letter, the final meeting, the relief as you walk out the door.
But leaving is rarely that simple.
The patterns we learned inside those systems – urgency, over-responsibility, and tying our worth to work – often follow us long after we leave.
In many ways, leaving is only the beginning. The habits, expectations, and survival strategies that helped us function inside demanding environments can quietly shape the way we approach our next chapter.
Even as we try to build something new, we may find ourselves recreating the very dynamics we hoped to escape. Together we’ll explore how those patterns shape what comes next, and how awareness, care, and boundaries help us build a more sustainable relationship with work.
Leaving well is not only about departure. It is about learning how to carry forward what matters – and letting go of what no longer serves us.
You'll learn:
- Why leaving a system does not immediately undo the patterns it taught you
- How urgency and over-responsibility follow many of us into our next chapter
- What it means to practice care and boundaries after leaving corporate
- How to rebuild a relationship with work grounded in clarity and purpose
-
Fireside Chat + Live Q&A | With Patrice Perkins, Esq.
Starting and growing your business comes with legal questions most founders quietly worry about but rarely ask. Contracts, liability, intellectual property, partnerships, and risk can feel intimidating or confusing without clear guidance. In this candid fireside conversation, we'll hear from a business attorney as she breaks down common legal concerns founders face and offer practical insight on how to navigate them early!
The session will conclude with an open Q&A so you can ask the questions that usually stay unsaid.
You'll learn:
- Why your business structure matters more than most founders realize early on
- Which contracts and protections you actually need before your first client
- How to protect your name, your work, and your future without overspending
- What legal mistakes cost new business owners the most time and money
- And more!
-
Talk | With Vivianne Castillo
Entrepreneurship is supposed to be the path to freedom but many founders discover a different reality: the business that was meant to liberate them begins to resemble the systems they once tried to escape. The pressure increases, the hours stretch, and the company looks successful on paper while quietly draining the person who built it.
This talk introduces a radically different vision for entrepreneurship.
We'll unpack a framework that reveals how founders unintentionally build businesses that either erode their wellbeing or regenerate it. Through stories, real founder examples, and practical insight, you'll have a deeper understanding of the four paths of entrepreneurship and learn how everyday decisions about time, money, and growth determine the kind of business they are actually building.
Entrepreneurship can become more than a financial pursuit ... it can become a practice of healing, courage, and creative rebellion.
You'll learn:
- The four paths of entrepreneurship and how to recognize whether your business is quietly draining you or actively sustaining you
- The hidden ways founders recreate the systems they once tried to escape, even when their intentions are good
- What your calendar, business model, and growth strategy reveal about the real values shaping your company
- How to redesign your business around courage, care, and creativity so it supports both your livelihood and your wellbeing
Part 2: Preparation
We'll lean heavily into with the practical as we work through the financial, tax, and health insurance realities of leaving corporate so you can make a clear-eyed decision instead of a fearful one.
The Old Way: Stay in corporate another year because you don't know what leaving actually costs. Then another year because you still don't know. Build a career on financial fog and call it being responsible.
The Walkout Way: Get more clear on the real numbers (aka your runway, your tax picture, your healthcare options) so you can make the decision from solid ground instead of fear. Clarity is what makes a strategic exit possible.
Your Sessions
Talk + Fireside Chats + Case Study
-
Talk | With Vivianne Castillo
For many people, money is not just a practical tool. It's deeply emotional and often carries stories about survival, worth, safety, power, and belonging.
In this talk, we'll get into the real stuff: how financial trauma shows up in your body, your business, and your decision-making. Why you can know exactly what to do with money and still not be able to do it or how scarcity thinking follows you out of corporate and into entrepreneurship if you don't address it directly. And what it actually looks like to build a healthier relationship with money, not by hustling harder, but by healing first.
This session is for anyone who's tired of white-knuckling their finances and ready to understand why their nervous system has been running the show.
You'll learn:
- Language for the money patterns you've been living but couldn't name
- An understanding of how trauma, shame, and scarcity wire your financial behavior
- A new foundation for making financial decisions from clarity instead of fear
- Tools for rebuilding confidence around earning, pricing, and financial boundaries
- Practical strategies for developing a more resilient and values-aligned approach to money
This isn't financial advice. This is the conversation about money that nobody in corporate ever had with you.
-
Fireside Chat + Live Q&A | With Ashby Kyhl
The corporate paycheck came with a system (e.g. taxes were withheld, retirement withdrawals were automatic, etc) but when you leave, all of that disappears and nobody hands you a manual for what comes next. And most new entrepreneurs are left to figure out the financial side reactively (and more times than not, after something goes wrong).
We'll be joined by an accountant (with the highest credential awarded by the IRS) who specializes in helping small business owners build financial clarity through proactive tax strategy, practical bookkeeping, and systems designed for real life. In this fireside chat, he'll break down what you actually need to know and creates space for the questions you have been carrying.You'll learn:
- How to build clearer financial systems for your business
- What entrepreneurs often misunderstand about taxes and bookkeeping
- How stronger financial visibility helps you plan and grow
- Practical ways to create more stability in your business finances
- And more!
-
Fireside Chat + Live Q&A | With Erika Poole
Health insurance is one of the biggest reasons people stay in jobs they want to leave.
The system is confusing by design, and most of us only understand our options through whatever HR handed us during open enrollment. And when you start thinking about going out on your own, insurance is often the first question and the last one to get a real answer.
Join a licensed insurance broker, who is also the founder of health insurance company and a former UX Director at the parent company of the largest Blue Cross Blue Shield plan in the country. She has spent over fifteen years making complex insurance systems work better for real people and in this fireside chat, she'll bring that expertise directly to you and answers the coverage questions that have been quietly holding you back.
You'll learn:
- What health insurance options exist for self-employed and small business owners
- How to find coverage that fits your life without overspending
- Why the insurance question is more solvable than most people think
- How to make a plan for coverage before you make your next career move
- And more!
-
Case Study | With Vivianne Castillo, Founder of Choose Courage Inc. AND Elizabeth Burke, Founder of Collective Expansion
Many professionals have deep expertise (aka years of experience, insight that others could genuinely benefit from) yet when they try to turn that knowledge into a business, it often stays trapped in one-to-one conversations, custom work, or endless explaining.
The issue is rarely the expertise, the issue is often the packaging.In this case study-discussion, you’ll learn how to productize your expertise by turning what you know into a structured offering that can live asynchronously and within a community. Instead of trading hours for impact, you’ll begin to see how your knowledge can be packaged into something repeatable, accessible, and valuable.
During this case study-discussion, you’ll:
• Be able to identify the core insights or expertise you already have
• Learn the key elements that turn expertise into a structured, productized offering
• See this process in action through a live case study showing how one area of expertise was turned into an asynchronous or community-based offering
If you are someone who knows you have valuable knowledge or experience but wants to turn it into something scalable, structured, and accessible to more people, then this case study is for you.
Part 3: Possibility
We'll end The Walkout on proof aka with a panel and Q&A with four folks who left corporate and built something worth leaving for.
The Old Way: Keep your questions to yourself. Assume everyone else has it figured out. Try to reverse engineer freedom alone. Stay stuck between curiosity and fear.
The Walkout Way: Sit in the room with people who already made the leap. Hear what it actually took. Ask the questions you have been carrying in private. Study real timelines, tradeoffs, and revenue paths. Prepare with proof, not fantasy.
Your Final Session
Panel and Q&A
-
Panel + Live Q&A | With Vivianne Castillo, Rachael Dietkus, Behzod Sirjani, and Vincent Brathwaite
Four Employees-to-Entrepreneurs go there and are answering your unspoken questions. You know the questions: the ones you Google at 2am and the ones you feel like you can't ask your manager, your partner, or your colleagues. And we’ll answer them honestly.
No corporate speak.
No toxic positivity.
No "just believe in yourself" hoopla.
Questions like:
- How should I be thinking about money and how much to have in savings before I leave? What's realistic vs. what's just fear talking?
- How do you stop feeling like a fraud when you charge clients more than your old hourly rate as an employee?
- I grew up poor/working class. Leaving a stable paycheck feels like betraying my family's sacrifices. How do you reconcile that?
- Do I quit first and then build, or build on the side until I can quit? What did you do and what would you do differently?
- I'm terrified of being seen as a failure. How did you deal with the fear of leaving a “good job”?
- How do you handle health insurance? That's the thing keeping me stuck more than anything.
- I've invested X years building my design career. If I leave now, doesn't that mean I wasted all that time?
This isn't a sanitized Q&A, this is the conversation you wish you could have with someone who's been exactly where you are: terrified, stuck, and wondering if wanting something different makes you weak or brave.
We'll tell you what worked, what didn't, what we'd do differently and what we'd do exactly the same.
And we'll tell you the truth: leaving is scary, staying is scarier, and you're not crazy for wanting out.
💙 Our Giving Pledge
The Walkout exists because people deserve to leave what isn't working and step into something better. That belief doesn't stop at career transitions. It extends to anyone navigating an uncertain crossing toward a safer, more dignified life 💙
That's why 20% of every purchase goes directly to the children our organization sponsors at Hogares Providencia de Querétaro, a long-standing group home in Mexico protecting and developing the potential of children affected by violence and neglect.
Join us, and be part of something bigger than yourself 🫶🏾
Why This Experience is Different (and Works)💙
Most courses motivate you. We equip you.
Most courses teach theory. We help you build the plan.
Most courses leave you inspired. We leave you with your next 3 weeks mapped.
That's what The Walkout does differently.
You come away with clarity and confidence, and a plan you'll actually execute instead of a notebook full of ideas you never open again.
Your Investment: $149
Find the most frequently asked questions below :) If you don't find an answer for a question you have, please email us at hello@choosecourageinc.com and we'll get back to you!
-
Because we remember what it's like to be stuck: wanting out so badly but feeling like every "investment in yourself" is another luxury you can't justify while golden-handcuffed to a corporate salary you resent.
$149 is less than:
- A few hours of your salary
- The Figma subscription your company pays for so you can make buttons slightly better
- What you spend not thinking about it for another month
For us, this isn't about money or pricing tickets so that we make as much money as possible.
It's about creating a safe space for you to bet on yourself.
We priced this so that if you're seriously considering leaving (even if you're scared, even if you're not sure when) you can say yes without agonizing.
-
Absolutely. While The Walkout was built with UX and Tech professionals in mind, the lessons, frameworks, and conversations apply to anyone navigating a values misalignment in corporate life and wondering what’s next.
You’ll still benefit if you resonate with any of the following:
- A creative, strategist, marketer, or leader who’s outgrown the corporate way of working.
- Someone who knows they want to leave but doesn’t want to start from zero or burn bridges doing it.
- Curious about building a business, agency, or consulting practice rooted in your skills and your values.
-
That’s exactly why we built The Walkout.
Leaving corporate doesn’t mean walking out tomorrow, it means preparing to walk out with clarity and confidence.
This weekend gives you the roadmap, tools, and support to know when and how to do it ... not just the pep talk to try. -
Perfect. This will help you refine and strengthen your next chapter. Whether that means stabilizing your business, redefining your consulting niche, or reconnecting with purpose after the chaos of leaving.
-
Please send us an email at hello@choosecourageinc.com.
Here's to choosing courage over comfort.
$149 to stop wondering and start planning.
❌ Here's what we're not offering: Motivation that fades by Monday. Magic frameworks that remove fear. Guarantees that leaving will be easy.
✅ Here's what we are offering: Clarity on your path forward. Tools to build your exit plan. Proof that other people did it without regret. Permission to want something different.
The real cost isn't $149.
The real cost is another year of Sunday scaries. Another year pretending the next reorg will be different. Another year of 2am Google searches for "how to leave corporate." Another year optimizing someone else's product instead of building your own freedom.