Why Entrepreneurship Always Takes More Time Than You Expect Ever considered how an entrepreneur is like a chess-playing robot?

When you first decide to be an entrepreneur, you typically have a clear picture of how things are going to go. You may imagine yourself sitting back, making occasional decisions, but also going on vacations while your team makes sure your business remains stable.

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Alternatively, you may imagine yourself working hard day in and day out, rarely taking breaks until your project or product has been perfected.

Either way, there are bound to be factors you hadn't considered, and I can personally guarantee that your vision of entrepreneurship won't come true -- at least not exactly.

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

Hofstadter's Law

Hofstadter's Law, a term coined by cognitive science professor Douglas Hofstadter, posits that, "It always takes longer than you expect, even when you take into account Hofstadter's Law." The adage is kind of silly, but there's a bit of objective truth to its message.

Humans -- be they entrepreneurs, other professionals, or workers -- are generally unskilled at estimating time. Hofstadter's Law was first introduced in connection with chess-playing computers, to calculate the amount of time it would take to develop a program capable of surpassing a human in chess-playing ability.

Despite knowing the complexity of that task, even the newest time estimates have continued to be inaccurate. Hofstadter wrote: "In the early days of computer chess, people used to estimate that it would be ten years until a computer (or program) was world champion. But, after ten years had passed, it seemed that the day a computer would become world champion was still more than [another] ten years away."

Though this set of factors isn't specific to entrepreneurs, it does apply to them, as much as to chess-playing robots; for, like, robots, entrepreneurship is almost always more complex than you make it out to be.

Optimism bias

Optimism bias is a psychological principle and an inherent cognitive bias which nearly everyone possesses to some degree. Essentially, it occurs when certain people think that they're more likely to see positive outcomes than do similar people in similar situations.

For example, many individuals believe they are less likely to develop cancer or become crime victims than the national average would suggest. And, again, this isn't specific to entrepreneurs. But it does set the stage for underestimating the amount of time it takes to get something done.

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Specifically, certain entrepreneurs generally believe that they are less likely to be consumed by tasks than are other entrepreneurs in similar situations (whether they're conscious of it or not).

Many hats

"Entrepreneur" isn't a role by itself. If this is a label you apply to yourself, sure, 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, as you work to project your annual revenues, and then a human resources manager the next, as you look for new people to hire. Because you're working in many different contexts and you're almost constantly switching roles, you'll find it almost impossible to correctly estimate the time it takes you to accomplish any specific task.

You can't be an expert at 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 speaking, an unproductive strategy. In fact, it does a lot more harm than good. Still, certain entrepreneurs are especially prone to multitasking, and they don't always have a choice.

Entrepreneurs are decision-makers connected to every part of their businesses, so it's only natural when every worker, vendor, partner, investor or other interested party comes to the entrepreneur for information. This means, however, that entrepreneurs are pulled in many directions, typically unpredictably. The result is 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 and signing documents. Some of these tasks can be handled by assistants or others within an organization, but not all entrepreneurs have those resources available.

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, as an entrepreneur, you'll never find your job boring, stagnant or predictable. 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 think you'll need. And on the off chance that you end up with excess minutes, maybe hours, you can catch up on email and count yourself among the startling minority of entrepreneurs who wind up with more time on their hands than they expected.

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