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.