Circular black-and-white Choose Courage Inc. logo. "CHOOSE COURAGE" arcs around the top of the ring with "INC" at the bottom, framing a white center disc that holds a paper airplane soaring upward through a scatter of small stars.

Build a business that pays well, feels good, and protects your peace without betraying yourself (or following a capitalism bro's blueprint).

We help creatives, entrepreneurs, and aspiring corporate escape artists break free from the systems that were never built for them and create businesses where people, creativity, and courage come first.

  • ★★★★★
    Choose Courage Inc. helped me overcome blockers in restarting my freelance business, shifting my mindset, and quietly building my confidence.
    Danita Delce
  • ★★★★★
    If there's a quiet whisper in you, something wondering what else might be possible, this space can help you hear it more clearly.
    Shani Jayant
  • ★★★★★
    Viv shares not only the nuts and bolts of running businesses, but coaches you on the mindset needed to set out on your own.
    Emily Springer
  • ★★★★★
    The Entrepreneurship Cohort helped me heal from corporate.
    Michael J.A. Davis
  • ★★★★★
    I'm not sure that there's been a better investment of my time, energy, and money in the last 4 years.
    Tim Rouf

Where are you right now?

Wherever you are, there's a next step.

  • Line illustration of a pair of golden handcuffs broken apart at the chain, with a small leafy vine sprouting upward from the broken link and a tiny paper airplane below, set against a cream background.

    I'm still inside the machine (and want out)😭

    Feeling trapped in corporate, restless, and are quietly planning a way out that doesn't blow up your life.

  • Line illustration of a paper airplane flying through stylized clouds and wind swirls above a small golden seedling sprouting from the ground, on a cream background.

    I just left / I'm building my idea

    Out on your own in the early years or wanting to build your business without a capitalism bro's blueprint.

  • Line illustration of three sprouting plants with leaves above ground and an extensive interconnected golden root system below the soil line, with a small paper airplane among them, on a cream background.

    I have a business (but something's off)

    The business works on paper but still costs you something it shouldn't ... and you're ready to do something about it.

Line illustration of an open mailbox on a post with its gold flag raised and gold door open, a small sprouting seedling growing at its base, and a paper airplane flying past through stylized clouds and wind swirls, on a cream background.

Not sure where to start?

Start with our newsletter, Courage Over Comfort. Every week, one honest question about building work that doesn't cost you yourself. No hustle, no hype, no five-step formulas. Just the questions worth sitting with, and the company of people asking them too.

If you're tired and done pretending the old way was fine ... this is for you.

You don't need another guru telling you to grind harder or manifest your way to freedom. You need a way through that respects your intelligence, your nervous system, and your actual numbers.

Our Approrach to Business is Grounded In

  • Regenerative Commerce

  • Encouraging Community

  • Trauma-Informed Practices

  • Nurturing Creativity

  • No Capitalism Bro Energy

Vivianne smiling in a teal button-up dress resting her chin on her hand, seated at a wooden desk with a laptop, a podcast microphone, an open spiral notebook, and a dark mug, with a leafy olive tree and white textured wall behind her.

Hi, I'm Vivianne👋🏾

I built and scaled a design and culture consultancy that Fast Company named one of the most innovative companies of its year, working with teams like Capital One, Google, and Patagonia. I have a graduate degree in counseling, which is why everything here is trauma-informed rather than hustle-informed.

I've made the leap you're considering, the messy version and the sustainable one. The work here is everything I wish someone had handed me on the way out.

New Episode

On the Choose Courage Inc. Podcast

Ep 72 | When Your Job Exploits Your Childhood Wounds

If you’re the one everybody calls resilient, and you’re tired in a way that sleep doesn’t fix, this episode is for you. Vivianne, a former therapist, names how corporate reward systems feed on childhood wounds. That voice telling you to keep going sounds like strength… but it’s often “a survival reflex that never got updated.”

The Choose Courage Inc. Podcast is available on Spotify, Apple Podcasts, YouTube, and RSS more!

New Podcast

Listen + Read

  • A hole in a chain-link fence frames a blurred city skyline at dusk.

    When Your Job Exploits Your Childhood Wounds

    In Episode 72 of the Choose Courage Inc. podcast, Vivianne Castillo, founder of Choose Courage Inc., leans on her former training as a therapist and unpacks the career advice she wishes she'd given her 20-something self, the four childhood setups...

  • Person walking through a puddle with colorful reflections.

    Leaving Corporate Is the Easy Part of Healing From It

    In this revisited episode, founder Ash Coleman Hynie comes back on the show for an unfiltered conversation about boundaries, guilt, healing from corporate trauma, and why the traditional entrepreneurship blueprint was never drawn with most of us in mind. This...

  • A stack of worn folders and papers on a wooden table in dim light.

    You Can't Protect What You Don't Know You Own

    In Episode 70, I sat down with Patrice Perkins, founder of Creative Genius Law and my business attorney for the last six years, for a fireside chat about who owns work that AI touched, what belongs in your contracts now,...