How Scott Galloway’s Investment Banking Start Reveals True Career Fit Lessons

Gist

Scott Galloway started his career in Morgan Stanley’s analyst program, where he hated investment banking and felt he performed poorly.
Despite the misery, he credits the experience with teaching discipline, attention to detail, and how to function in a high-pressure corporate environment.
He frames such early misfit jobs as valuable “workshop time” that clarifies one’s strengths and preferred roles, rather than as outright failures.
The story underscores that both individuals and firms should prioritize fit, feedback, and flexible career paths over blind pursuit of prestige roles.

The story of Scott Galloway’s start in investment banking provides a case study in finding one’s fit—and extracting value even from discomfort. From his joining Morgan Stanley straight out of college to his rejection of investment banking as a long-term path, Galloway’s reflections reveal not only personal lessons but broader signals for how talent is sourced, developed, and retained.

After UCLA, Galloway entered a two‐year analyst program at Morgan Stanley. He describes this period with a mix of disdain and gratitude: he hated much of it (“I hated investment banking”) and felt he was bad at it, yet recognizes he absorbed discipline, attention to detail, and exposure to a demanding professional environment—all foundational to his later success [2][7].

One major insight is the role of ‘trial work’—early career experiences that are difficult, even misfits—but clarifying: they teach what one dislikes and what one might be good at. Galloway’s statement that “I was terrible at investment banking” becomes less failure and more feedback [7]. This has implications for talent management: that rigid pipelines pushing everyone through prestige roles risk burnout and attrition if individuals are mismatched.

Mental and emotional costs are central in Galloway’s narrative. He describes insecurity—e.g. constantly fearing that meetings were about him—and intolerance of the “little injustices” common in big companies. These are not just psychological quibbles; they impact performance, turnover, and long-term career satisfaction [2][7].

From a strategic standpoint, Galloway’s lessons suggest young professionals should test, iterate, and be willing to abandon paths that are reputationally strong but personally misaligned. For organizations, this calls for more nuanced recruitment and career paths that allow lateral movement, recognize soft-skills alongside prestige achievements, and provide supportive feedback mechanisms.

Open questions remain around how scalable Galloway’s approach becomes: Can institutions realistically allow for investment bankers to self-opt out or rotate roles early on without cost? Also, how many people have the privilege or financial flexibility to walk away from high‐paying but misaligned jobs—and what systems are needed to support them?

Supporting Notes

Galloway’s first job after college was with Morgan Stanley; he participated in a two-year analyst program. He states explicitly that he “hated it” and believed he was “terrible at it” [2][8].
Despite disliking the job, he notes that the experience taught him rigorous attention to detail, how to work under pressure, professionalism (e.g. early mornings, dress norms), and how to navigate large organizations [2][7][8].
Mental and emotional challenges were significant: insecurity about senior people’s presence, sensitivity to perceived status, dislike of large-company environments and their social dynamics [2][7].
Galloway positions this early stage as ‘‘workshop time’’ in one’s 20s—experimentation, failure, and role exploration—as opposed to expecting instant passion or perfection [7].
He suggests strategic career pivots toward roles or skill sets—storytelling, strategy, analytics—where one exhibits comparative advantage, rather than staying in roles that are prestigious but misaligned [7].
Institutional implications: prestige roles (e.g. investment banking) are often oversold without sufficient transparency about emotional costs, and many people eventually leave; organizations should consider this turnover risk and value alignment when hiring and designing career paths [5][8].

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