Why Entrepreneurship Always Takes More Time Than You Think

Photo by Nathan Dumlao on Unsplash

When you first decide to be an entrepreneur, you typically have a clear picture of how things are going to go. You might imagine sitting back, making occasional decisions, and going on vacation while your team makes sure your business remains stable, or you might imagine working hard day in and day out, rarely taking breaks until your project has been perfected. Either way, there are bound to be factors you haven’t considered, and I can personally guarantee your vision of entrepreneurship won’t come true — at least not exactly.

One of the most severe and common miscalculations associated with entrepreneurship is an underestimation of the amount of time it takes to actually lead a business. No matter how carefully you consider your roles and responsibilities, it seems that almost every entrepreneur consistently underestimates the amount of time it takes to get things done. So why is this, exactly?

Hofstadter’s Law

A term coined by Douglas Hofstadter, Hofstadter’s law is that “it always takes longer than you expect, even when you take into account Hofstadter’s Law.” It’s kind of a silly, humorous adage, but there’s a bit of objective truth to its message. Applicable to entrepreneurs, professionals, and individuals of all shapes and sizes, humans are generally unskilled at estimating time. Originally, the term was used by programmers estimating the time it would take to develop a program capable of surpassing a human in chess-playing ability. Despite knowing the complexity of the task, even newer estimates continued to be inaccurate. Though this reason isn’t specific to entrepreneurs, it does affect entrepreneurs innately, as entrepreneurship is almost always more complex than you make it out to be.

Optimism Bias

The optimism bias is a psychological principle and inherent cognitive bias that nearly everyone possesses to some degree. Essentially, it makes people think that they are more likely to see positive outcomes than similar people in a similar situation. For example, many people believe themselves to be less likely to develop cancer or be the victim of a crime than the national average would suggest. Again, this isn’t specific to entrepreneurs, but it does set the mental stage for underestimating the amount of time it takes to get something done — entrepreneurs generally believe themselves less likely to be consumed by tasks than similar entrepreneurs in similar situations (whether they’re conscious of it or not).

Many Hats

“Entrepreneur” isn’t a role by itself. You might generate more ideas than others or make more decisions than others, but entrepreneurship is actually a melding of many different roles in one. You might act like a financial expert one day, trying to project your annual revenues, and human resources manager the next, looking for new people to hire. Because you’re working in many different contexts and you’re almost constantly switching roles, it’s almost impossible to correctly estimate the time it takes you to accomplish any specific task. You can’t be an expert in everything all at once, so your lack of expertise in specific areas results in weaker estimates for completion in those areas.

The Inevitable Pull of Multitasking

By now, we should all know that multitasking is objectively an unproductive strategy. In fact, it does a lot more harm than good. Still, entrepreneurs are especially prone to multitasking, and they don’t always have a choice. Entrepreneurs are decision makers connected to every part of the business, so it’s only natural that every worker, vendor, partner, investor, or other interested party comes to the entrepreneur for information. This means entrepreneurs are pulled in many directions, typically unpredictably, resulting in tied-up hours every day that can’t possibly be accounted for in advance.

The Devil in the Paperwork

Finally, entrepreneurs have a tendency to forget the existence of administrative tasks, such as entering data, following up on conversations, or signing documents. Some of these can be handled by assistants or others within an organization, but not all entrepreneurs have those resources available to them. As a result, many entrepreneurs only estimate the time it will take to accomplish a core task — forgetting to also estimate the administrative responsibilities surrounding it, and eventually landing on an incomplete estimate.

You’ll never quite get the hang of estimating your time because your job will never be boring, stagnant, or predictable as an entrepreneur. This is a blessing more than a curse, so be grateful for your inability to properly estimate the work ahead of you. When it comes to scheduling meetings, planning vacations, or just organizing your day, be sure to give yourself way more time than you actually need — and in the off chance you end up with excess, you can catch up on some emails and count yourself among the startling minority of entrepreneurs who wind up with more time on their hands than they expected.

CEO of EmailAnalytics (emailanalytics.com), a productivity tool that visualizes team email activity, and measures email response time. Check out the free trial!

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store