I asked 3 CEOs about their biggest career mistakes — and what they learned
Business Insider
February 28, 2026
AI-Generated Deep Dive Summary
Three CEOs share their biggest career mistakes and the lessons they’ve learned, offering insights that could transform how professionals approach their work. Shlomo Kramer, CEO of Cato Networks, reflects on his tendency to invest in areas outside his expertise, such as AI-based marketing or fintech, driven by excitement rather than deep understanding. He emphasizes the importance of specialized knowledge, which he now recognizes provides clarity and focus. Matt Fitzpatrick, CEO of Invisible Technologies, rejects the notion of mistakes entirely, viewing them instead as decisions that lead to growth. For example, choosing a less conventional path in his early career ultimately redirected him toward tech success. Raina Moskowitz, CEO of The Knot, admits her biggest mistake was not trusting her gut when making hiring decisions, often prioritizing skill over passion for the company’s mission. She now values candidates who align with the brand’s vision, ensuring a motivated and cohesive team.
These leaders highlight the importance of self-awareness, adaptability, and strategic focus in overcoming career challenges. Their stories underscore how even seasoned professionals can learn from missteps, emphasizing growth through reflection and adjustment. By sharing these experiences, they provide actionable lessons for aspiring business leaders, encouraging them to prioritize understanding over excitement, reevaluate decisions with fresh perspective, and build teams that align with their core values.
For anyone interested in business leadership, these insights are invaluable. They demonstrate how mistakes can be turning points rather than
Verticals
businessfinance
Originally published on Business Insider on 2/28/2026