In this episode of How to Be a Person, Giuliano sits down with Jake Kennington for a wide-ranging conversation about seasons of life, selfishness (the honest kind), and what it really means to play the infinite game.

Jake is a licensed structural engineer turned personal development coach and founder of Actively Human. For years, he was designing $100M buildings, leading complex projects, and doing everything that looks like success on paper. But underneath it, something felt off. As a husband and father of four, the cost of staying on autopilot became impossible to ignore. His health slipped, his relationships felt strained, and the work that once gave him pride no longer felt aligned with who he was becoming.

This conversation explores the moment many high-functioning adults hit quietly… when life is “working,” but not working for them anymore. Giuliano and Jake talk about why certain seasons demand different rules, why selfishness is often misunderstood (and sometimes necessary), and how redefining success can feel terrifying and freeing at the same time.

They also dig into the idea of the infinite game. Not optimizing for quick wins, titles, or external validation, but building a life that can actually be sustained. One where growth, curiosity, and presence matter more than checking the next box. Jake shares how his engineering mindset helped him deconstruct his own life, rebuild his habits, repair relationships, and design something that finally felt honest.

The episode touches on fatherhood, identity shifts, entrepreneurship, and the subtle ways people abandon themselves in the name of responsibility. It’s a grounded, thoughtful conversation for anyone who has followed the “right” path and quietly wondered if there’s another way to live… one that feels as good on the inside as it looks on the outside.

https://activelyhuman.com/#playbook

How to Be a Person: https://howtobeaperson.co/

Business funding: https://funding.howtobeaperson.co/

Want to be a guest on How to Be a Person? Send Giuliano Grimaudo a message on PodMatch, here: https://www.podmatch.com/hostdetailpreview/17374246500089236b5dfbb6b