Fighting the 'Should' Gremlins

Rex discusses pressure to do everything, balancing expectations, and coping strategies with Adam's reference.

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Rex Gelb is the Founder/CEO of Summit Chase, a paid media agency serving B2B, SaaS, and professional services companies. Before starting Summit Chase, Rex spent more than 11 years at HubSpot, where he became the company’s Head of Paid Media. He’s also a husband and dad to a daughter who recently turned one.

In this episode, Rex shares what it was like for both him and his wife to quit their jobs within 24 hours of each other right after parental leave, why that leap made sense for their family, and how becoming a dad has changed the way he thinks about ambition, hard work, and presence. We discussed:

Leaving stable jobs right after parental leave: How Rex and his wife both quit their jobs within 24 hours of each other and why that felt like the right move for their family.
The sooner you give up, the better: Why Rex believes fatherhood gets easier when you stop clinging to your old life and allow yourself to evolve into a new season.
Fighting the “should gremlins”: How Rex thinks about the pressure to show up perfectly at work, at home, and for himself, and why letting go of impossible standards matters.
Household systems that reduce friction: The shared notes, walking one-on-ones, and email threads Rex and his wife use to stay aligned and keep family life running smoothly.
Using AI as a parenting tool: How Rex and his wife use monthly “leap alerts” with Gemini to stay on top of milestones, safety considerations, and what’s coming next for their daughter.
Never deprive them of a struggle: Why Rex is already thinking about how to let his daughter work through challenges on her own so he can build confidence instead of accidentally undermining it.

Where to find Rex Gelb