Assistant OS

EP 1: Why Delegation Feels So Hard - and How to Fix It


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In Episode 1 of the Assistant Operating System, FreedUp co-founder and CEO Aaron Hayslip sets the foundation for the course by unpacking the real reason delegation often fails—and what to do about it. Drawing from Dan Martell’s Buy Back Your Time and his own experience as a founder, husband, and father, Aaron introduces the core problem: most high-performing execs don’t lack talent or assistants - they lack a system.

You’ll learn:

  • Why delegation without systems leads to burnout
  • How to calculate your buyback rate (and why it matters)
  • The difference between teaching vs. leading delegation
  • What it actually feels like to have a fully systematized assistant
  • Why buying back your time isn’t just about money—it’s about joy, family, and presence

This episode is more than just an introduction - it’s a mindset reset. Whether you’ve had an assistant before or are just getting started, this will help you see delegation as a skill worth mastering, and the Assistant OS as your roadmap.

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Assistant OSBy Aaron Hayslip