Choose Courage Inc.

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 MentionedThe Walkout (June 3–5) — a 2.5-day experience for UX and tech professionals exploring entrepreneurship and building sustainable businesses.Follow Vivianne on LinkedIn for more reflections on entrepreneurship, courage, and building businesses that actually fit your life.

Show Notes

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.

  • Follow Vivianne on LinkedIn for more reflections on entrepreneurship, courage, and building businesses that actually fit your life.

What is Choose Courage Inc.?

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.