Lesson 87: Conviction
About the Searcher
Nothing inspires me like conviction. Recently, I heard from Eda Henries and Sháka Rasheed. They each built impressive careers on Wall Street, and eventually left the stable infrastructure of name brand banks to pursue their own entrepreneurial journey.
They each shared insights about their professional journey with current Toigo Foundation Fellows. In each conversation, they emphasized that they did not borrow their skills from institutional prestige but rather built capabilities with the platform provided. Eda described focusing on what she contributes: analytical rigor, relationship-building, or strategic thinking. Sháka emphasized defining your own metrics of success. Both mindsets embrace the belief that your value is intrinsic.
As a Searcher, my greatest strength is myself. I spend time reflecting on precisely what I contribute and how I measure success. In my CliftonStrengths results, one of my top five characteristics is Maximizer: “Maximizers see talents and strengths in others, usually before anyone else does.” When I present to investors, sellers, employees, and customers, I offer a specific combination of skills and experience that maximize the talents of people around me; I value bringing the best out of those around me.
About Entrepreneurship Through Acquisition
One of the ways I have unlocked the talents of my classmates is learning from their work experience. The conviction to pursue technical education as a target sector began with imperfect information but has been refined by gathering evidence. This week, I met with Chaq Thomas, a first-year at Chicago Booth, who worked in cloud operations and data center infrastructure at Microsoft and Meta before the MBA. 30 minutes of inquiry into Chaq’s firsthand experience revealed three insights about the potential of technical education for the next generation of data center technicians:
As a Searcher, I do more than analyze data. I have a willingness to leverage a connection, ask thoughtful questions, and synthesize perspectives into an actionable thesis.
About the Bigger Picture
My mission is to increase representation for Black leaders at the executive, investor, and board level. This mission requires the same conviction Eda and Shaka demonstrated—the belief that my leadership is not validated by external credentials but by my intrinsic value. As an executive, I balance conviction with curiosity by remaining aware of my value and the values others bring to the table. Conviction does not mean certainty; it means knowing what you contribute while remaining open to what you can learn. When leaders operate from this mindset, they build organizations that do not just succeed in the marketplace—they create pathways for others to build conviction in their own value.
This is Lesson 87: Reliability. Next week is Lesson 88: Prioritization.
