Looks Like Work

Building a Business That Supports Your Life (with Jasz Joseph)

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In this energizing conversation, Jasz Joseph—founder of Jasz Rae Digital and HubSpot CRM consultant—shares how burnout from tracking billable hours in 0.25 increments led her to build a business centered on time freedom and travel. After calling her CEO to quit and having him become her second client, Jasz has spent four and a half years creating systems that allow her LinkedIn posts, newsletters, and sales campaigns to run while she's exploring coffee shops in Mexico City. The conversation dives into the trap of tying identity to business success, why "business should be boring" might be the best advice she's received, and how asking "why not?" can uncover the people-pleasing tendencies that hold us back. Jasz reveals how she's learned to sit in the discomfort of slow seasons and trust that busy times will return—all while refusing to track a single billable hour.

Key Topics:

  • Why efficient people get penalized in the billable hours model
  • Building systems that work while you're at the beach (or in Mexico City coffee shops)
  • The identity trap: when business struggles feel like personal failure
  • Learning to sit in slow seasons without panicking
  • The eldest daughter to entrepreneur pipeline (it's real)
  • Travel as a business priority: working from everywhere
  • Finding excitement outside the business when it becomes "rinse and repeat"

    • Notable Quotes:

    • "I caught myself one day folding laundry, and I said to myself, 'That took 0.25 of an hour.' And I was like, this is crazy"
    • "Business should be boring. That's when you know you've kind of made it"
    • "My LinkedIn posts are going out, my newsletter is going out, my sales outreach campaigns are going out, and I don't have to move a muscle"
    • "I was like, 'What's next for us?' Revenue was lower...and because my business was so wrapped up in my identity, I took that so personally"
    • "Sometimes your flowery is bigger and sometimes your flowery is too small and you need more of it"
    • "We live in a society that is uncomfortable with quiet, with stillness"
    • "It's one of the cool things about getting older—you start to collect all of these like, 'Wait, I did that' or 'Wait, I can do that'"

      • Jasz's Powerful Question: "Why not?"—Often followed by "What's the worst thing that could happen?" to uncover the people-pleasing tendencies and fears that hold us back.

      Resources Mentioned:

      • Jasz Rae Digital - HubSpot CRM consulting
      • Christina Langdon - Chedva's former coach - on Looks Like Work

        •  

        Key Lessons:

        • Automation should give you time back, not enable more hustle
        • Your business being your whole identity makes failures feel personal
        • Slow seasons are for nourishment, not panic
        • Gateway questions help you approach big, scary decisions
        • The evidence of your resilience already exists—you just need to collect it
        • Travel and business integration creates a life of genuine freedom

          • Retry

          Claude can make mistakes.

          Please double-check responses.

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          Looks Like WorkBy Chedva Ludmir