- Scott Galloway took a prestigious investment banking job at Morgan Stanley after UCLA but quickly realized he hated the work and lacked the temperament and skills for it.
- Leaving banking, he redirected into branding, consulting, and startups like Prophet and L2, using early discomfort and rejection as fuel to find better career fit.
- He argues that success comes from the intersection of what you’re good at, what the market values, and what you can endure, rather than simply following passion.
- Having amassed low nine-figure wealth and “hit his number,” he now prioritizes autonomy, meaning, and joy over chasing further financial status.
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The core insight from Galloway’s reflection lies in the contrast between prestige and personal aptitude. Starting at Morgan Stanley in 1987 after UCLA, he took what many see as a conventional high-status path—but quickly recognized it did not fit. The role was ‘‘soul-crushing,’’ socially and psychologically misaligned, and he felt he lacked the natural skills for it. His exit decision (within ~2½ years) and subsequent hard lean into consulting, branding, startups, and public speaking reflect a willingness to pivot when the trajectory isn’t sustainable. [1][2][3]
Another major lesson is around rejection and early setback. Galloway describes being materially successful early but still deeply discomforted by aspects like insecurity around promotions, reading rooms, and not being naturally gifted. That catalyzed both personal growth and an entrepreneurial turn—founding Prophet in 1992, later startups like L2. The trajectory shows how early professional discomfort can fuel deeper clarity about what work feels like purpose and what simply pays. [1][2][3]
Financially, he draws lines around goals. He considers himself done from a wealth accumulation standpoint: “hit his number” about eight years ago, and now prioritizes spending on joy, giving, and autonomy. This suggests that chasing status or higher financial metrics beyond meaningful thresholds may carry opportunity costs in stress, time, values. [2][3]
Strategic implications for others—investment bankers, early‐career professionals, entrepreneurs:
- Early career choices need not be permanent; the value lies in what skills, experiences, and feedback they deliver.
- Finding intersection of market need + personal competence + enduring interest tends to outperform following passion alone as guiding philosophy.
- Defining wealth or success in personal terms—knowing your number, calibrating risk and reward—can enable more targeted, less tragic decisions.
- Transitioning sectors (banking → startups; corporate → creative) successfully often depends on early recognition of misfit, scaling personal agency, and leveraging transferable skills.
Supporting Notes
- Galloway joined Morgan Stanley in 1987 after getting his BS in economics from UCLA; left a few years later, saying he ‘‘hated it’’ and ‘‘was no good at it’’ while doing it. [1][3]
- He described investment banking as “soul-crushing, awful place for awful people” in 2017; also said that he literally recognized early he lacked the skills for banking and couldn’t handle insecurity or seeing promotions of those he deemed less capable. [2][3]
- He co-founded the brand strategy firm Prophet in 1992 after leaving banking, which was eventually sold; also founded L2 in 2010 which sold in 2017 for over US$100 million. [2][3]
- Galloway estimates his net worth in low nine figures (≈ US$100-150 million), stating he ‘‘hit his number’’ eight years ago and has no desire to be a billionaire. [2]
- He often underlines that the “follow your passion” advice comes only from those who are already wealthy; instead, the practical intersection of what you can do well, what people will pay for, and what you can endure matters more. [4][2]
Sources
- [1] www.cnbc.com (CNBC) — 2019-01-17
- [2] www.benzinga.com (Benzinga) — 2025-08-15
- [3] www.thestreet.com (TheStreet) — 2025-06-04
- [4] www.ft.com (Financial Times) — 2025-07-17