Why Entrepreneurs Always Seem To Wind Up Doing A Bit Of Everything


If you take a look at the average entrepreneur’s CV, you’ll notice something interesting. Most of them didn’t take a direct path from college to business. Instead, they moved all over the place, trying their hands at all sorts of things on their way to creating value. In other words, their resumes look nothing like the average graduate career path.

But why is this? Why do entrepreneurs’ CVs meander left and right randomly? 


It’s an interesting question. 


One way to approach this question is to view entrepreneurs as generalists. We know that they tend to be highly open people who continually fill their minds with new information. And for that reason, they never really delve too deeply into any one particular line of thought. Instead, they build rounded knowledge, using the breadth of their understanding to build their businesses. 


Bill Gates, for instance, was a great programmer and software engineer. But he also spent an enormous amount of time just educating himself about the world, putting himself in a position where he could see where his company was heading and how it might create a new type of society. 


Another way to approach the question is to recognize that the places where value lurks are sort of random – and often new. For instance, colleges weren’t teaching students how to design social media platforms in the 1990s to prepare them for entrepreneurship in the early 2000s. Instead, it took a lot of individual learning and smart insights from the people in the field at the time to create these new platforms. 


If you look at the experience of an entrepreneur like Daniel Fung, you can see this effect in action. He started on the technical side of things, but then with MMJ legalization, he soon switched fields. It was a clear direction in which he could go. 


Remember – most entrepreneurs are rank opportunists. If they see a way to make money, they’ll go in that direction, even if it has nothing to do with their previous career experience. Elon Musk started with payment systems and moved onto rockets. There’s no blueprint for the life of an entrepreneur. 

Successful entrepreneurs also wind up doing a little of everything out of necessity. Running a business isn’t just about having a big picture and getting other people to execute it for you. It also requires having a decent understanding of how all the nuts and bolts work together so that you can make good decisions. 


Not understanding accounting isn’t usually a big deal. But if you don’t know how supply chains work, you could make jarring business decisions that don’t really work, even if they seem like the best strategy. 


Entrepreneurs, therefore, build wide experience. They jump from role to role early in their careers so that they can figure out how the whole machine fits together. Then, once they understand it, they feel more confident managing it themselves. Hence, generalism is sort of baked into their DNA and offers them considerable advantages in the marketplace.