When Not to Start a Business

There is a lot to consider when starting your own business, and at face value, entrepreneurship can often feel very exciting to someone who has been in a senior leadership role. This is because at this stage, you have already built a successful career, solved complex problems, led teams, and delivered outcomes at scale. But it’s not always the right choice for everyone. In this article, we will explore why it is important to take a few things into consideration when deciding whether or not you will take the leap.

One of the most common triggers for entrepreneurship is dissatisfaction. When you are running away from your current role, burnt out, feel stuck, or tired of constraints, it is not always a great decision to build a business. Unfortunately, entrepreneurship will often amplify the very pressures that you are trying to leave behind because your responsibilities will increase dramatically, and your external support will no longer be there. While feeling stuck or burnt out might just mean it's too early to take the leap, there may be a better foundation for you to start a business once you have a better footing.

Another thing to consider is that expertise does not always conflate with opportunity. Just because you have demonstrated talent and ability in a certain area does not always mean it can be productized or will solve a pressing market need. A strong business usually starts with a clear problem rather than a general skillset. So it is important to make sure you can articulate who has the problem, what the pain point is, how it is currently being solved, and why your solution is better than the current solution. If you are unable to answer these questions right now, it may mean that you still need to explore rather than launch.

When considering entrepreneurship, there is usually an expectation that your day will be less structured, but for some professionals used to clear roles and responsibilities, defined processes, and predictable cycles, it can be a shock to the system. This is because roles are undefined, priorities shift constantly, and progress is ambiguous and uneven. This can feel destabilizing, specifically for individuals who need structure to function effectively, so it is important to evaluate how you have responded to less structure in the past to see if you can tolerate it when starting your own business.

What is interesting is that entrepreneurship doesn’t have to be a black-and-white choice between “corporate job” and “startup”. Fortunately, there are some intermediate paths that might lead to what you are looking for. That includes consulting, fractional executive roles, advisory roles, side businesses, and board positions. These paths allow you to build client relationships, understand your market, and generate income as you explore. They can be great stepping stones to see whether or not you enjoy something with less structure.

Usually, the best step forward before jumping into entrepreneurship is to explore, test, and ask yourself what you can and cannot tolerate. Once you have answers on how to handle uncertainty, you will have a more informed decision to make.