Building a Business That Supports Your Life - Looks Like Work, Season 3, Ep 19

Looks Like Work

27 Aug

What if your business didn’t just pay the bills—but gave you your time back, too?

In this energizing and honest episode, Jasz Joseph, founder of Jasz Rae Digital and HubSpot CRM consultant, shares how she ditched billable hours (and burnout) to create a life of genuine freedom. After tracking her time down to 0.25 of an hour—and realizing she was mentally invoicing her laundry—Jasz quit her job and built a business that works while she sips coffee in Mexico City.

We talk about slow seasons, quiet wins, and the “business should be boring” mantra that changed everything. Jasz opens up about the emotional weight of tying your identity to your business, and how asking “why not?” has become her best tool for battling people-pleasing and taking brave steps forward.

what we talk about:

Why being efficient in a billable-hour system actually works against you
How Jasz’s former CEO became her second client
Designing systems that run your content, sales, and marketing on autopilot
Navigating the identity trap: when your business becomes you
Embracing slow seasons without spiraling
The real story behind “building a business that supports your life”
The reality of rinse-and-repeat business models—and how to find excitement elsewhere
Travel as a non-negotiable: running the show from coffee shops abroad
Letting yourself be still in a world that fears silence
Jasz’s Powerful Question:
“Why not?”
Often followed by “What’s the worst thing that could happen?”, this deceptively simple question can unravel your fears—and your people-pleasing habits.
Key Lessons:
- Automation = Freedom: Your systems should free you, not trap you
- Untangle your identity from your business: So every low season doesn’t feel like a personal failure
- Stillness is strategic: Slow seasons can be nourishing and clarifying
- Big decisions need gateway questions: “Why not?” opens the door to courage
- You’re already resilient: The proof is in your past wins—you just have to collect it
- You don’t have to choose between business and life: If you build with intention, they can support each other