My Career has Been a Process of Trial & Error – Part 3

Click here to read part two of “My Career has Been a Process of Trail and Error”


I learned a lot in that job, including the fact that consulting wasn’t what I wanted to do with my life and that, instead, I wanted to be in a principal role. I wanted to be in position to drive the process, not just advise on it. I wanted to make decisions and live with the results. I switched to a small real estate private equity fund. I was learning, the atmosphere was casual, and the people were smart, but down to earth. There was little to no bureaucracy. I felt at home in a company culture for the first time in my career. Among other things, I learned the importance of fit.

Although it was a great experience, I realized that working directly for the two fund managers, there wasn’t much potential for growth so a couple of years in I applied to business school. I wasn’t sure if I wanted to go, but I also didn’t know what I wanted to do long term, so I thought having an MBA would create options. My world broadened. I met great people. I was reevaluating my career path yet again — career panels, interviews, conversations with classmates, around and around. The truth is, most people in business school don’t know what they want to do for a living, which is exactly why they go to business school to begin with.

I had a great professor in college that emphasized the importance of ownership. That stuck with me. I liked the idea of running a business. Of having more control over my work life, getting to set the priorities, and living with the consequences of my decisions. Living with results has always been more palatable than living with the subjective assessments of other people. I also liked the idea of building something, something that could continue to exist (and I could make money on) even after I was no longer involved with it (the opposite of billing for your time). I also knew I wasn’t an “expert personality”, I would never be able to compete with the quants and engineers. I am much more interested in how the parts fit together, seeing the big picture, and thinking about where to go next and how to get there.

After looking into several different paths, I once again concluded I wanted to be an entrepreneur, but didn’t have any great ideas. So, once again, I decided that the real estate industry would offer the best opportunity for me to continue moving in an entrepreneurial direction as an employee.