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

Welcome back to The Glass Sessions!

This week, we’re joined by Garri Rivkin, Founder and Executive Director of City Tutors , an organization that has helped more than 8,000 learners access tutoring, mentorship, and career guidance in New York City.

Garri shares his journey from arriving in Queens as a Jewish refugee from Lithuania in 1996, learning English while working at a young age, and finding support through teachers, mentors, and the CUNY system that helped shape his path.

That experience ultimately inspired him to build the kind of support network he once needed. What began in 2013 as a tutoring program at City College later expanded through the Colin Powell School, became an independent 501(c)(3) in 2020, and during the pandemic evolved into a broader mentoring initiative connecting learners with professionals around the world.

We talk about:

• Growing up as a refugee and navigating a new culture
• The mentors and teachers who opened doors
• Starting City Tutors as a small campus project
• Expanding the program during the pandemic
• Why access to information and mentorship changes lives

We close with a new segment, Glassy Insights, summing up some key takeaways from Garri.

If you care about education, mentorship, or creating opportunities for the next generation, this conversation will inspire you.

Timestamps

00:00 Intro and Recommendations
09:35 Meet City Tutors
12:02 Garri's Origin Story
25:53 Finding Purpose In Service
29:22 Finding Home at CUNY
33:31 City Tutors Origin Story
36:32 Pandemic Pivot to Mentors
42:44 Impact Stories and Belonging
47:08 Writing and Identity
51:54 Garri's Good Life
53:05 How to Get Involved
54:45 Glassy Insights Wrap-Up

Links & Resources:

The City Tutors: https://www.thecitytutors.org

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

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

Courtney's Substack: substack.com/@courtneyattheglassadvisory

Welcome back to The Glass Sessions!

This week we’re joined by Jeff Carlson, Head of Education, Strategy, and Advocacy at Clever, whose career has been shaped by a deep commitment to education and the rural communities that raised him.

Jeff grew up in rural Idaho before heading east to attend Georgetown. After graduating, he joined Teach for America and moved to the Bronx to teach middle school, an experience that solidified his commitment to education equity. From there, Jeff spent time working in Washington, DC, including on Capitol Hill, while continuing to deepen his focus on education policy and access.

Over the years, his work has taken him from classrooms to federal policy to graduate programs focused on rural education. Today, Jeff has returned to Idaho with his husband, Ben, and their dogs, continuing to advocate for students and communities through his work at Clever and through local civic engagement.

In this conversation, Jeff reflects on how relationships and networks have shaped his career decisions, why rural identity still plays a defining role in his work, and how everyday people can meaningfully engage in their communities.

We also talk about Jeff’s volunteer work as a guardian ad litem, his involvement in state policy conversations around education and AI, and why maintaining optimism matters when you care deeply about the future.

Jeff’s definition of a good life?

Contributing more than you take, improving the world for the next generation, and allowing space for daily joy, weekly sorrow, and regular self-reflection.

If you’ve ever wondered how your career can connect to something bigger than yourself, this conversation will resonate.

Timestamps:

00:00 Catch up and recommendations

10:37 Intro to Jeff and his story

29:18 Career decisions and networking

35:47 Volunteering and public service

37:28 Getting involved locally

47:14 Everyday community activism

55:40 Defining the good life

Links & Resources:

Jeff Carlson's LinkedIn: https://www.linkedin.com/in/drjeffcarlson

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

Detailed Show Notes⁠⁠⁠:

https://www.theglassadvisory.com/theglasssessionspodcast

Courtney's Substack: substack.com/@courtneyattheglassadvisory