Miserable Millionaires: Wall Street, Wealth, and the Hedonic Treadmill with Gregg Schoenberg
Money can solve a lot of problems.
But it does not make someone immune to loneliness, burnout, insecurity, relationship strain, career disappointment, or suicide risk.
In this episode of _At Work, Under Pressure_, Jessi Beyer sits down with Gregg Schoenberg, managing partner at Westcott Inc. and an executive coach specializing in the finance industry, to talk about Wall Street, miserable millionaires, wealth, burnout, loneliness, the hedonic treadmill, market pressure, and what successful people often struggle with behind closed doors.
Gregg explains why the outside perception of Wall Street often misses the human reality underneath. Yes, many people in finance make extraordinary money. But they also work in an environment where the markets never really turn off, bosses and circumstances can exercise a “call option” on their time, and success can become normalized until even huge bonuses stop feeling like enough.
Jessi and Gregg discuss:
• Why “miserable millionaires” are more human than the stereotype suggests
• How the hedonic treadmill shows up in Wall Street compensation
• Why being a servant to the market can create a never-off lifestyle
• How wealth can intensify loneliness, comparison, and isolation
• Why high performers can struggle when their identity is tied to a specific career outcome
• How Wall Street’s incentive structures differ from technology and mission-driven companies
• Why arrogance in finance may be more of a persona than a permanent personality trait
• What Gregg would say to leaders who assume successful people are fine because they look fine
This episode is for executives, investors, finance professionals, coaches, HR leaders, founders, and anyone who has ever assumed that money protects people from deep human struggle.
Because wealth can change your circumstances.
But it does not remove your need to be seen, supported, and understood.
CONNECT WITH GREGG
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