The Biggest Lessons I Learned Leaving Corporate
Leaving corporate is often framed as a leap or a risk. In reality, the biggest lessons did not show up in the decision to leave but after. With distance came clarity, and with clarity came a better understanding of what actually mattered in building the next chapter. This is not a critique of corporate work. In many ways, my time in corporate was foundational but stepping away revealed lessons that were harder to see while I was inside the structure.
Lesson 1: Don’t Ask for Money, Ask for Advice
I knew I had to raise capital to build HUMN. Initially, I thought I would build a business place and financial model then go into meetings, pitch, and ask for an investment. Boys was I wrong… especially with the audience. It’s such a different conversation between a VC and an angel investor. Instead of asking for money, I started asking for advice.
That change removed pressure immediately. Conversations became more open and more honest. People were willing to share what they had learned, what they would do differently, and where they saw opportunities or risks. Those insights were far more valuable than a pitch meeting.
What surprised me most was that asking for advice often led to investor interest naturally. When people felt respected for their experience and included in the thinking process, the relationship deepened. The capital conversations followed trust, not the other way around.
More importantly, I learned how to think like an operator. Pricing decisions, sequencing, team structure, and long term risk all came into focus through those conversations. Asking for advice did not just expand my network. It expanded my judgment.
Lesson 2: Your Identity Is Bigger Than Your Title
In corporate environments, titles provide structure and validation. You know where you sit, what you own, and how you are measured. When you leave, that framework disappears quickly. At first, that can feel disorienting. Without a title, it becomes harder to anchor your sense of value externally. That discomfort forced me to look inward and take inventory of what I had actually built over time.
Sales taught resilience. Technology roles sharpened problem solving. Gartner taught me how to think strategically, ask better questions, and communicate complex ideas clearly. When I stepped back and looked at those experiences collectively, confidence followed. Leaving corporate helped me realize that the value was never in the title. It was in the skill set, perspective, and relationships built along the way.
Lesson 3: You Don’t Realize How Tired You Are Until You Stop
This lesson was the most subtle and the most important. While working full time, I didn’t feel burned out in an obvious way. I was productive, engaged, and moving forward. It was only after stepping away that I realized how narrow my thinking had become.
Constant motion has a way of masking fatigue. You keep going, solving problems, hitting deadlines, without noticing how little space there is to think deeply. When I finally stopped, my mind slowed down. Ideas connected. Creativity returned. Perspective widened. Rest was not something I consciously optimized for while working. In hindsight, it became clear that rest was what allowed everything else to come into focus.
Final Thoughts
Leaving corporate didn’t suddenly create these lessons. They were forming long before I stepped away. What leaving provided was the space to see them clearly and look… I’m not perfect. I am forever a work in progress.
I am grateful for the structure, training, and experience corporate work gave me. It built the foundation. Stepping away helped me understand how to use it. Sometimes clarity does not come from doing more. It comes from giving yourself the room to stop and reflect.
