October 06, 2025

225: Sahil Bloom | Do You Want this Job, or Do You Want Other People Seeing You Have This Job?

16 minutes

Sahil Bloom is a writer, investor, and former collegiate athlete who is the author of the New York Times bestseller The 5 Types of Wealth. He earned his undergraduate degree in Economics & Sociology and a master’s in public policy from Stanford, where he also played baseball. He also leads SRB Holdings and SRB Ventures, where he invests in early-stage companies. And Sahil has amassed a massive following online, with over 800,000 subscribers to his newsletter and more than 1 million followers on X.

In this episode we discuss the following:

We can’t truly feel successful until we define what success means for ourselves. If we look at the scorecard that is handed to us, which consists of accumulating money, status, titles, and promotions, we will always feel like we need to reach for more, a trap made worse by the arrival fallacy.

Our ability to achieve our goals is influenced by our surroundings. The goal to live a simple life is much easier to accomplish in small town America than New York, where Sahil sees extraordinarily rich people spend their time figuring out ways to impress even more extraordinarily rich people.

To help us reveal how much our decisions are influenced by external validation, we can ask ourself some version of the question, “Do I really want this job, or do I want other people to see me having this job?”

True success is built on five types of wealth (time, social, mental, physical and financial) rather than chasing society’s default measures.

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