Why Scott Galloway’s Failed Start in Investment Banking Shaped His Career Strategy

Scott Galloway’s reflections on his early career combine personal candor with strategic lessons for individuals and institutions. Although the Wall Street Journal article is behind a paywall and its detailed content is inaccessible for confirmation, his more public accounts provide a consistent core narrative.

This narrative starts with failure and discomfort. Galloway began in investment banking at Morgan Stanley after college. He describes himself as “terrible” at the work, socially insecure and constantly anxious about how he measured up, emotionally and intellectually. He hated it, and feels deeply sure he lacked the temperament for it. The decision to leave wasn’t out of confidence so much as realizing he was miserable—and not naturally suited to thrive in that environment [3].

Yet, he finds value in what that experience taught him. The misery of investment banking came with discipline: attention to detail, early mornings, tight deadlines, exposure to hierarchy, and learning by suffering. These are traits he credits with helping him later on as an entrepreneur, speaker, writer and professor [3]. He views banking not as a long-term calling but as a rigorous training ground that provided a baseline of resilience and exposure to structure and scale [3].

Third, the career lesson: trial and error. Galloway repeatedly shares the idea that one’s 20s should be spent experimenting—trying on roles, tolerating failure, and staying curious—until you identify what you might be great at. He rejects the ‘follow your passion’ cliché if it obscures the hard work needed to excel. More realistic, he says, is to find where you can win, invest heavily, and build excellence [3].

Strategic implications: For talent development, businesses could offer more exposure to variance—expecting people to try multiple roles, fail, and learn—rather than pushing people into rigid tracks early. Universities could better prepare graduates for the emotional realities of early careers: discomfort, comparison, and instability. For individuals, Galloway’s story suggests building self-knowledge quickly, and being ready to exit paths—even prestigious ones—that are misaligned. Avoid getting stuck chasing prestige or peer approval at the cost of long-term fit.

Open questions:

• How much of early-career ‘misfit’ is due to current market forcing everyone into overcompetitive, high-pressure roles?
• Are there structured ways firms can help young people recognize when they should stay or exit with less stigma?
• Given Galloway’s later success, how much was due to luck or external factors (network, timing, external market shifts) rather than resilience and discernment alone?
• How scalable is this model for people without safety nets, personal capital, or flexibility to fail?

In sum, Galloway’s story reinforces that early-career suffering does not equal long-term success, but discomfort and failure are indispensable to building strategic clarity. High-prestige roles aren’t always the right fit—recognizing this early and using the opportunity to learn can be far more valuable than staying for status alone.