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

Participants will have the opportunity to choose one workshop to attend during this session. Each workshop offers a different perspective, set of tools, and conversation designed to practically support you as you choose to bet on yourself.

Trust your gut and pick the workshop that resonates the most with you and your journey.

Option #1 | The A to B Method: How to Build Something People Actually Pay For

With Vivianne Castillo, Founder of Choose Courage Inc.

Most aspiring entrepreneurs talk about what they do. They list their skills, their services, their process. Then they wonder why conversations stall and potential clients disappear.

The issue is rarely the quality of the work. The issue is framing.

In this workshop, you will learn The A to B Method, a practical and simple framework for designing your business and offerings around transformation rather than tasks. Instead of describing what you do, you will learn how to define the change your business creates and build a structure that reliably helps people get there.

During this workshop, you'll:

• Define your client's Point A and Point B so clearly that they feel seen before you ever pitch them
• Map the key milestones between A and B that build momentum and trust
• See the A to B Method in action through a live walkthrough of a real offer built on this framework

If you are someone who knows they have something valuable to offer but wants help turning that into a business people understand, trust, and buy from, then this is for you.

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Option #2 | What You Hold and What You Don’t: Mapping Your Field of Care

With Rachael Dietkus, LCSW, Founder of Social Workers Who Design

You’ve decided to leave, or you’re preparing to. Now what?

In this reflective and hands-on workshop, you’ll explore how to define your ethical stance and emotional boundaries using a framework inspired by social work’s concept of scope of practice. 

Through guided reflection and conversation, you’ll map your personal Field of Care – the space between what you are responsible for, what you can influence, and what is beyond your control – and begin shaping a practice that protects your energy while sustaining the work you care about.

During this workshop, you’ll:

• Examine inherited work patterns that shape how you show up in professional roles
• Translate scope of practice into clear boundaries, responsibilities, and limits
• Create a personalized Field of Care Map to guide future decisions

Note for participants from the January Walkout event: This workshop has been refined since then and is an opportunity to revisit the reflections you made six months ago and see what has shifted as you continue shaping the work ahead.

If you're a designer, researcher, or knowledge worker leaving corporate and want to build work with more care, integrity, and sustainability, then this is for you.

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!

Participants will have the opportunity to choose one workshop to attend during this session. Each workshop offers a different perspective, set of tools, and conversation designed to practically support you as you choose to bet on yourself.

Trust your gut and pick the workshop that resonates the most with you and your journey.

Option #1 | How to Productize Your Expertise 

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 workshop is for you.

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Option #2 | What You Hold and What You Don’t: Mapping Your Field of Care

With Rachael Dietkus, LCSW, Founder of Social Workers Who Design

You’ve decided to leave, or you’re preparing to. Now what?

In this reflective and hands-on workshop, you’ll explore how to define your ethical stance and emotional boundaries using a framework inspired by social work’s concept of scope of practice. 

Through guided reflection and conversation, you’ll map your personal Field of Care – the space between what you are responsible for, what you can influence, and what is beyond your control – and begin shaping a practice that protects your energy while sustaining the work you care about.

During this workshop, you’ll:

• Examine inherited work patterns that shape how you show up in professional roles
• Translate scope of practice into clear boundaries, responsibilities, and limits
• Create a personalized Field of Care Map to guide future decisions

Note for participants from the January Walkout event: This workshop has been refined since then and is an opportunity to revisit the reflections you made six months ago and see what has shifted as you continue shaping the work ahead.

If you're a designer, researcher, or knowledge worker leaving corporate and want to build work with more care, integrity, and sustainability, then this is for you.

Panel + Live Q&A | With Vivianne Castillo, Rachael Dietkus, Behzod Sirjani, and Vincent Brathwaite

Four UXers-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.

Whether you register today or the day before the event, you pay the same price.

We're not manufacturing urgency through pricing tricks because the urgency is already real: it's the years you're losing staying in a job that's dimming your light.

And unlike a lot of design conference, we believe it's important to practice the values that the UX industry prides itself on ... like being human-centered💙

Whether you register today or the day before the event, you pay the same price. We're not manufacturing urgency through pricing tricks because the urgency is already real: it's the years you're losing staying in a job that's dimming your light.

Why $195?

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.

$195 is less than:

• One day 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.

We believe that choosing yourself shouldn’t come at the expense of others ... it should create more possibility for everyone. That’s why 20% of every ticket goes directly to two organizations doing life-changing work in these unprecedented times:

💙 Kids in Need of Defense (KIND): Provides free legal representation to unaccompanied immigrant children navigating the U.S. immigration system alone, ensuring no child faces deportation proceedings without an advocate in their corner.

💙 Hogares Providencia de Querétaro, A.C.: a long-standing children’s group home in Querétaro focused on protecting and developing the potential of children affected by violence and neglect.

This is what regenerative commerce looks like: care that circulates. Your investment fuels not just your next chapter, but someone else’s chance to either continue or begin theirs.

❌ 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. Community so you're not alone. Permission to want something different.

• Three talks from people who've already walked out successfully
• Three fireside chats and Q&A sessions with an accountant, an attorney, and a health insurance specialist
• Two intensive 1.5hr workshops to support your path
• Direct access to your workshop leader
• An honest panel Q&A addressing your biggest fears and questions
• A room full of people who get it and are bringing good, hopeful energy

The real cost isn't $195.

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.

$195 to stop wondering and start planning.

That's not an expense. That's an investment in the life on the other side of this decision.