As we close out 2025, reflection matters just as much as goal-setting. In this solo episode, Rob looks back on five of the most impactful conversations from Surviving the Side Hustle so far — not tactical how-tos, but core truths about health, identity, effort, and alignment.

Guest: Holly Porter

Holly shared her near-death experience and the health collapse that forced her to stop everything. What stood out most wasn’t just the trauma — it was the clarity that followed.

For years, she succeeded on paper while ignoring the signals her body was sending… until they couldn’t be ignored anymore.

Reflection: Where have you been ignoring physical, mental, or emotional warning signs because slowing down feels uncomfortable?
https://podcasts.apple.com/us/podcast/surviving-the-side-hustle/id1711453767?i=1000713366899

Guest: Kenny Green

This conversation dug deep into identity and belief systems. Most people chase strategies and shortcuts while overlooking the internal narratives driving their decisions.

Those beliefs don’t show up immediately — they reveal themselves through repeated patterns.

Reflection: What belief about yourself quietly guided your biggest decision this year? Was it empowering or limiting?
https://podcasts.apple.com/us/podcast/surviving-the-side-hustle/id1711453767?i=1000712387433

Guest: Zoraida Morales

Zoraida’s story of surviving cancer and corporate burnout reframed success entirely. Healing wasn’t just about treatment — it required trust, intuition, and learning to listen again.

Reflection: What part of your wellbeing did you sacrifice this year in the name of productivity?
https://podcasts.apple.com/us/podcast/surviving-the-side-hustle/id1711453767?i=1000714447262

Guest: Ben LeRose

One of the most popular episodes of the show, this conversation explored ambition, work ethic, and the pride side hustlers take in outworking everyone else — and the cost of doing so without recovery.

Reflection: Where could better systems replace brute force in your life or business?

https://podcasts.apple.com/us/podcast/surviving-the-side-hustle/id1711453767?i=1000639840629

Guests: Meredith & Craig

Meredith and Craig shared the behind-the-scenes story of leaving security, saying yes before certainty, and building a business together without waiting for confidence to show up first.

Reflection: What opportunity did you delay this year because you didn’t feel ready?

https://podcasts.apple.com/us/podcast/surviving-the-side-hustle/id1711453767?i=1000740347869