I Want My Career To Be Relationship-Focused ft. Gary Vee & Ryan Holiday

Joel Sigrist
4 min readDec 10, 2021


Gary Vee, Ryan Holiday, and I don’t have a lot in common. Or do we? I want to be driven by peace and love and kindness for those I work with and those around me.

Gary Vaynerchuk on Stoicism, Soft Skills, and Becoming Your Best Selfopen.spotify.com

Ryan talks to entrepreneur Gary Vaynerchuk about his new book Twelve and a Half: Leveraging the Emotional Ingredients Necessary for Business Success, how to get comfortable with vulnerability and emotional development, the best way to maintain long term business success, and more.

The 30-Second Summary

Gary Vee and Ryan Holiday are some of my favorite thinkers in the public sphere. Whereas Gary is often overbearing and can come off aggressively, his core message surrounding empathy, kindness, and vulnerability in business is something that’s shaped my professional philosophy.

For Ryan Holiday, if you’ve spent much time around me, you know he’s someone I respect. His passion for stoicism, level-headed approach to life, and meditation on life’s greatest questions are things that I admire and aim to live out in myself.

Naturally, when I saw a new conversation between these two powerhouses of personality, I made it a priority to listen.

I was not disappointed.

This conversation covered so much wisdom. The two men discussed the definition of stoicism (You don’t control what happens to you, you always control how you respond), how to cultivate self-awareness, and leveraging kindness and radical candor in the workplace.

Why It Matters To Me

As a 23-year old, young in my career and my life, I think a lot about the nature of my career. Where do I want to go? What do I want to accomplish? How do I want to balance my young marriage with my career goals?

I often try to leverage great thinkers to inform my answers to these questions as I journal, pray, and meditate on them.

Gary Vee and Ryan Holiday have two undoubtedly successful careers (they’ve spoken about their goals and achieved them), and they pursue happiness. Gary Vee mentions the idea “crying in my ferrari” as the idea that money and status make up for sadness. As he continues, and I agree, what about having the goal be: Don’t be crying anywhere?

Instead of living into the status games that the world plays, I don’t want to measure my career solely on earnings. Instead, these two talk about measuring careers in terms of impact to their companies. They talk about legacy. Gary measures it by asking “who’s going to show up to my funeral?” and Ryan talks about the idea of Memento Mori in the same vein.

I don’t want my career to be status-focused, I want it to be relationship-focused.

I want to wrap up a pitch, finish a presentation, and then chat it up with the people I pitched to and against. I want to treat the work as a sports game, and then exchange jerseys with my competitors once the game is decided. I want to stay loyal to my relationships and my people, while making an impact with my company.

I want to be relationship-focused and people-driven.

Business doesn’t need to be cut-throat. In fact, it shouldn’t be. Instead, it should be driven by kindness, clarity, love, and understanding. It’s not warfare, it’s connection.

Bite-Sized Philosophy

Episode 43: Have No Fear Of Perfection (Or Imperfection) — Bite-Sized Philosophy | Podcast on Spotifyopen.spotify.com

Have No Fear of Perfection, You’ll never reach it. — Salvador Dali.

Episode 44: That’s It. That’s The Hack — Alex Lieberman — Bite-Sized Philosophy | Podcast on Spotifyopen.spotify.com

There is no substitute for sustained, consistent quality. Showing up regularly for 2 years and producing good, relevant, unique content is the best way to grow a podcast. We’re just 44 episodes into this thing, are you ready for the next 246 episodes to see where this takes us?



Joel Sigrist

Consistent writer since a few weeks ago. Not all published stories are good ones, but that’s getting better. In some cool pubs, too.