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.

My Career has Been a Process of Trial & Error – Part 2

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


I chose my major through a process of elimination — I knew I didn’t have the science chops to be a doctor. I was interested in psychology, but when I learned there was a required lab that was out of the question. My father complained about aspects of the legal profession, including the hourly billing model. I’ve always preferred subjects that are clearly applicable to the real world, so I naturally gravitated towards business.

I was fortunate to have a several internships in college, the last of which, at Arthur Andersen, landed me a full-time offer in business consulting. My first day of work was September 10, 2001. After 9/11, the economy took a major hit, and the end of that year brought accounting scandals of epic proportions. Arthur Andersen found itself at the center of the imbroglio, and after 89 years in business, the entire company imploded under the weight of a criminal indictment by the Department of Justice (of which it was later exonerated). KPMG acquired the practice I was part of so my coworkers and I were spared layoffs, but that experience taught me to see risk differently. I learned first hand that the idea that bigger companies are less risky is pure fallacy. While working at those firms, I also realized I didn’t want to be on a 20 year pre-determined path, and found all of the layers of bureaucracy to be uninspiring, to say the least. I realized that ending up in a career I wasn’t inspired by was a different type of risk, to my personal happiness.

I was interested in entrepreneurship, but didn’t have any ideas I deemed worthy of pursuing. I looked into different obvious possibilities, like becoming a franchisee, and other less obvious ones that came about, like importing marble from India. I ended up accepting an offer to work at a smaller consulting firm specializing in market analysis for real estate development projects. I was drawn to real estate because it is a highly fragmented industry, which to me meant opportunities for entrepreneurs. It is also tangible, something I desperately wanted after my immersion in forensic healthcare reimbursement audits. The fact that I could actually help create something that people would use was extremely appealing. I also saw it as a good opportunity to experience working at a smaller firm. Maybe consulting wasn’t the problem, maybe firm size was the variable I needed to test.

My Career has Been a Process of Trial & Error

From the time we are young children we are prompted to start thinking about our careers with the age old question — “what do you want to be when you grow up?”.

The suggested answers are always given in the form of specifics occupations — lawyer, doctor, architect, etc. Most of us struggle to figure this out, not just as a kids, but well into our careers. Having wrestled with this question for a long time myself and now finally finding myself in a job I am happy in, I looked back on the path I took to get here.

Over the course of 20 years (including college) and 12 different jobs and internships, I figured out which variables matter most to me in my career — autonomy, ownership, a good culture, the opportunity for growth, a broad scope, and a location that works. I actually don’t care as much about function or industry which are the two variables people tend to think about most.

When I started thinking about this, the first realization I had is that it’s impossible to know you want to do something before you have tried it, so racking your brain to try to figure it out is mostly a waste of time. You have to jump in and correct course along the way. Nothing has helped me figure out what I want to do more than doing things I don’t.

The second realization I had is that since we tend to evaluate most things, including jobs, in relative terms, it’s essential to have a basis for comparison. Just because I love what I do it doesn’t mean it’s always easy, but having worked in a variety of jobs, in different industries, in different types of organizations, I feel like I have a great basis for comparison. That perspective allows me to put my current challenges and frustrations into proper perspective.

As a kid, I had no idea what I wanted to do when I grew up. My career has been a process of experimentation and trial and error, which I think is the only way it can be. That process ultimately landed in a position I am very happy in. As the CEO of a small business, I get to set the direction, make decisions, decide how I spend my time every day, and work with people I enjoy being around. I’m constantly learning and being challenged. I sacrificed compensation to get here, but what I’ve gained in experience is more than worth it.


Stay Tuned for Part 2 of this post, coming soon!