Week two with Thomas goes deeper into the inner mechanics of growth: how confidence gets built (and rebuilt) in real time, how “needing people” can be both a strength and a signal, and what it looks like to stop outsourcing your own decisions. Ryan and Thomas talk candidly about learning to move forward without requiring constant external reassurance—and how that shift changes the way you show up in work and life.
The conversation also hits the human layer underneath the job titles: believing there’s good in the world, the cost of giving too much without replenishing yourself, and the kind of question people rarely ask—because it requires them to actually be ready for the answer. Along the way: a great metaphor about “overflow vs. emptying your cup,” mentorship, ITSM curiosity, and a surprisingly specific Subway order.
Topics Discussed
- Introvert vs. extrovert energy (and what happens when you’re alone too long)
- How Thomas is building confidence in decisions under stress
- “What are you waiting for?” — self-talk and external validation
- Whether people are fundamentally good (and how to live that belief)
- Protecting yourself from over-giving: overflow vs. depletion
- Envy vs. material jealousy: wanting traits, not stuff
- What strong leaders actually have (spoiler: not all the answers)
- ITSM learning: tools, automation, and simplifying messy processes
- The question people should ask more often: “How are you… really?”
- How to connect with Thomas + his sign-off phrase
Connect with Thomas
Email – Thomas.Eastlack@yc.edu
LinkedIn – https://www.linkedin.com/in/thomas-eastlack/
Connect with Ryan
@Ryan_A_Gray
https://www.linkedin.com/in/ryanagray/
ryan@higheredav.com
Voiceover by Chris Dechter
Have feedback or guest ideas? Let us know!
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