97. Jason Pickard | The Gloomy Rollercoaster of Seeking Success and Happiness Outside of Oneself

As a successful portfolio manager at a large hedge fund, Jason Pickard reached a tipping point in 2006. At 330 pounds and getting sick often, it hit him how out of balance, depressed, and uncomfortable he was. Despite his physical size, he felt small psychologically, too—finally realizing that success and happiness were not at all the same. Since then, Jason has studied and experienced a multitude of cross-cultural pathways to greater health, higher consciousness, and multi-faceted self-expression. He now guides as a Life Process Coach to assist others along their experience to a more fulfilled Self.

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We grew up in a world we didn’t create. And one idea after the next—whether it was culture or society—we were told how to look, how to feel, and who to be. We were told that if we checked off the “right” boxes (think: career, car, money), we’d feel good, we’d be whole, and—naturally—we’d be set. But, turns out, there’s more to the story. On The Great Unlearn, Cal dives into unlearning and questioning what the world taught us, and—in the process—how to be the truest version of yourself, minus the bullshit. Whether it’s figuring out how to navigate a relationship, dealing with your emotions, diving into spirituality, or just feeling comfortable in your own skin, Cal and friends navigate the choppy waters of what it really takes to unlearn all the ideas we took for granted, and how to be the best version of what, sometimes, can be so hard to be: yourself.