Welcome back to the Good Trouble Newsletter. Each issue I share a key learning from the interviews I do with the inspiring individuals doing things on their own terms.

Serial Entrepreneur & Chairman of VaynerX, Gary Vaynerchuk, joined me in the studio for the latest episode of the Good Trouble show.

In this week’s issue: Embracing Your Good Trouble

Thanks for reading! —NK

Embracing Your Good Trouble

“There’s no way to succeed without causing [Good Trouble].” - Gary Vee.

I love his definition and definitely resonate with it. I’ve always gone against the grain and asked “why?”, whether it was to my coaches in childhood or to the fashion overlords (😅)at Wimbledon in 2022.

Asking why to authority almost always seems to cause some trouble initially. After my conversation with Gary, I’ve realized asking why causes Good Trouble. It’s courageous trouble. Asking why has always led me closer to my true self, and it’s only recently that I’ve started to embrace it.

I loved listening to Gary talk about his early business days in 2009 when he would curse in videos and wear casual clothes. People told him he could be the biggest speaker in the world if he just spoke cleanly and wore a suit. But he was unwilling to compromise on his true self, his Good Trouble.

Which leads me to my key takeaway from our conversation: Embracing your Good Trouble involves sacrifice. Gary lost out on tons of business in the early days because he refused to be anyone but himself. Yet what he sacrificed in potential money in the short term, he gained 10 fold in happiness and agency. Ironically, now it’s kind of weird to see keynote speakers in full business suits.

I can’t tell you how many times coaches or fans or the media have told me I could be the best tennis player in the world if I just did X, Y, and Z. I can’t tell you how much slander (online and to my face!) I’ve endured. Who knows how many championships I’ve potentially sacrificed.

Similar to Gary, I’ve never quite been able to be anyone but myself. I’m starting to embrace that more fully.

In Gary’s words, “Is a red fucking hat that serious?”

Make sure to watch the full interview below and let me know what you think!