When Prestige Clashes With Purpose: Scott Galloway on Investment Banking & Career Fit

Gist

Scott Galloway describes his two years in investment banking at Morgan Stanley as miserable, feeling incompetent, resentful, and ill-suited to big-firm culture.
Despite hating the job, he credits it with teaching him precision, endurance under pressure, and how large organizations operate.
The mismatch between his temperament and banking pushed him toward entrepreneurship, teaching, and investing, where his skills and values aligned better.
His story warns young professionals about blindly chasing prestige careers and reframes success around fit, autonomy, and sustainable well-being rather than maximum earnings.

Scott Galloway’s reflections on his early career in investment banking have been candid and critical—yet also rich in insight. What emerges is a story not of pure disillusionment but of forced learning: by “hating investment banking,” he gained invaluable skills, self-knowledge, and clarity.

First, we see a mismatch between environment and temperament. Galloway admits he was “terrible” at the role, couldn’t handle the interpersonal dynamics, and felt out of place in the corporate hierarchy. [1][5] His intelligence and ambition clashed with the rigid expectations of status and performance. This led him to resent authority figures he felt less smart than, and to struggle with imposter fears in group settings. [1][5]

Despite this, the experience was transformative. He emphasizes that investment banking taught him precision—proofing legal documents, calculating costs, and managing consequences of mistakes. [2][5] He also learned “how to suffer a little bit,” to operate under relentless pressure, and to understand how large organizations move. These are not skills one typically picks up in startup roles or freelance work. [5][10]

The internal conflict between his values and the career’s demands pushed Galloway into entrepreneurship, academia, and investing—arenas where he could set the terms, embrace risk, and align his energy with self-driven projects. [10] He promotes a financial philosophy: disciplined, diversified investing; leveraging the founding and teaching work he enjoys; and recognizing that what makes people “successful” is not earning top dollar but earning insight and autonomy. [4][6]

Strategically, his narrative carries broader implications. First, talent acquisition and retention in investment banking (and similar high-pressure fields) may suffer if firms fail to accommodate different personality types and values. Secondly, young professionals are under growing pressure: prestige positions, high earnings, brand-name employers are alluring, but may be costly if they conflict with personal well-being. Finally, financial advice rooted in lived experience—like Galloway’s—tends to resonate more than that based solely on returns. His story reframes success away from simply “making it” to discovering what fits personally and sustainably.

Open questions remain: Are modern banks evolving in culture enough to retain people like Galloway? How can young professionals assess “fit” more accurately before choosing high-status but high-cost career paths? What systemic financial education supports better decision-making for those attracted to but unsuited for investment banking or similar roles?

Supporting Notes

Galloway said he worked “two years” at Morgan Stanley, was terrible at it, hated the people, the environment, and investment banking itself. [1][3]
He described fearing that whenever more than three people entered a conference room, they’d be talking about him; senior colleagues who seemed less smart than him angered him. [1][5]
He acknowledged genuinely benefiting from the role: learning attention to detail, understanding prospectuses, calculating costs accurately, and enduring pressure. [2][5]
He revealed that he’s “not a cutout for big companies” and found that his insecurities and temperament led him to prefer alternatives like entrepreneurship and teaching. [1][5]
In subsequent ventures, he built a brand strategy firm, sold it for $33 million, and grew into analytics and investing in order to align more closely with his skills and values. [10]
Galloway has an estimated net worth of around $100 million as of 2025; he says he no longer aspires to accumulate excessive wealth, focusing instead on security and purpose. [6]

Sources

www.jordanharbinger.com

Sources

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