F'ing Up

Ashley Chang on F’ing Up

Deanne Rhynard / Ashley Chang Season 3 Episode 11

During this episode with Ashley Chang, we dive deep into the  reality of work, growth, and the constant pressure to prove yourself. From job searches filled with self-doubt to leadership roles that come with unforeseen challenges, this episode unpacks the highs, lows, and everything in between.

Episode Takeaways:

  • The Comparison Trap: How measuring yourself against others—especially polished success stories—can hold you back.
  • Leadership Challenges: Managing through layoffs and navigating the emotional toll of tough decisions.
  • Starting Over: What it really takes to build something from scratch and why it’s never as simple as it seems.
  • The Weight of Expectations: Why success doesn’t always feel like you thought it would and facing not realizing the feelings of success.


About Ashley:

Ashley Chang is the co-founder and CEO of Sundays, an executive assistant service for working parents. She’s on a mission to accelerate parents in their careers while creating more quality time for family. Before starting Sundays, she worked in the technology industry across all stages of companies – she was the first employee at developer tool company ReadMe and helped scale Carta’s Venture Capital business from 10 to $100M+.



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