My Career has Been a Process of Trial & Error – Part 4

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

After business school, I got to work on two development projects — a beautiful 3,000 acre resort project in Napa Valley and a sleek 42-story condominium building on the Dallas skyline. Simultaneously, I was working as the first employee of a startup that my bosses were partners in (one of the benefits of working for a small entrepreneurial firm). Five years in, after the Dallas project finished, and the startup stagnated for a variety of reasons, all of the sudden I found myself in a seemingly perfect situation — I was making good money without much responsibility. I quickly became bored to death. I had no real purpose and I was no longer learning. I realized that being challenged was just as important as making money. I felt the need to take a risk and either start a business or figure out a way to buy one. Going out on my own would expose my weaknesses, but would also give me the opportunity to become a stronger professional. Regardless, just thinking about it made me feel inspired, nervous, and more alive, which I thought was reason enough.

My sister runs a small physical therapy company that her and I contemplated buying on several occasions. We met with the owner a few times, but ultimately decided not to move forward. I had developed a good rapport with him though, and a couple of months later he suggested I reach out to his son, celebrity chef and entrepreneur, Duff Goldman. He was interested in taking on a partner to help manage his businesses. I jumped on a plane to LA for a marathon weekend where he gave me the overview of all his various interests, including TV, appearances, books, license deals, bakeries, and other ventures. We had a common vision for a partnership, felt like we could work well together, and were able to make an agreement fairly quickly. That was two and a half years ago, and so far it has been the best career experience of my life. It checks all my boxes: I’m challenged, I have upside, I’m learning, I have autonomy. I work with an interesting, smart, diverse array of people. I’ve gotten to shape the company and help improve it in tangible ways.

Even though, I am lucky enough to work in a fun industry, it is still work. I hear a lot of people say their dream is to open their own bakery or cake shop. Sometimes I get the impression that people think my job entails sitting around eating and ogling at beautiful cakes. While I do some of that, the other 99% of my time is spent responding to emails and phone calls, sitting in meetings, making to-do lists and spreadsheets; managing investors, employees, lawyers, consultants, and vendors; and dealing with HR problems, legal contracts, insurance, accounting, budgets, and compliance. Most of what I do isn’t very glamorous; in fact, it can be granular, complicated and sometimes boring. Progress doesn’t come easily, but when it does it’s extremely gratifying. I love the process of collaborating with my coworkers to build a better company. Getting on a career path that I’m excited about took a long time, and that’s just the first step. Now, of course, I feel the urgency to make progress.

The most important things I’ve learned about figuring out what to do for a living is that experimentation is key and to put any job in perspective, you need something to compare it to. I would add that beyond thinking about specific functions or roles, it’s worth considering what other variables might be more relevant, like company size, culture, compensation (amount and type), flexibility, stakes (are lives at risk?), status, degree of influence, breadth of responsibility (9 to 5 or 24/7), etc. The list is different for everyone, but the only way to figure out which variables matter most is by exposing yourself to different ones. The best thing I ever did was to get real world exposure to a number of different companies and work environments early on. Not only did it help me figure out what career characteristics would be more likely to make me happy, but it also helped put different positions in perspective. The only way to develop that perspective is through a process of trial and error.

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

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!