The Glass Sessions

Is This Actually Good Advice?


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Advice is everywhere.

Friends share what worked for them. Managers guide based on company needs. Family weighs in from a place of security - or fear.

But advice isn’t neutral. It reflects someone else’s experiences, incentives, and worldview.

In this episode, we break down how to tell the difference between advice that helps - and advice that pulls you off your path.

We cover:

  • Who’s actually worth listening to (and what to look for beyond success)
  • Why “do what I did” is often a red flag
  • How to spot hidden incentives from employers, family, and others
  • The role of people-pleasing in bad decision-making
  • The difference between someone giving answers vs. helping you think

At the core: the best advisors don’t tell you what to do. They help you get to your own answer.

Mastering this skill helps you:

  • Make fewer reactive decisions
  • Navigate career pivots more confidently
  • Build stronger judgment


Timestamps:

00:00 Intro and Recommendations

10:02 Episode Topic: Taking Advice

14:18 Advice vs Comfort Boundaries

16:51 Family Advice and Biases

21:38 Bias in Career Advice

25:25 Connector Mentors

27:48 Trust and Challenge Balance

31:12 Red Flags in Advice

36:59 People Pleasing Pitfalls

38:28 The Neutrality of Coaching


Links & Resources:

⁠⁠⁠The Glass Advisory⁠⁠⁠: https://www.theglassadvisory.com

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

Courtney's Substack: substack.com/@courtneyattheglassadvisory

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The Glass SessionsBy The Glass Advisory