Ashley Chang on F’ing Up

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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views, thoughts, and opinions of the companies or individuals referenced during this recording. The material and information presented is for general information purposes only.