What's a vacation for anyway?

Vacations are good for managing motivation. The prospect of a vacation after many months of work can drive us to persist until a major project is completed. And then it acts as a reward for all the hard work we've put in.

Vacations also help us manage energy. We have rhythms of work and respite. We can't work all the time without something breaking down. Vacations allow us to rest and recharge.

Given these two objectives of vacations, it makes perfect sense for employees to take time off after a win, such as at the end of a project or after reaching a target.

The following diagram represents the prevailing wisdom about when to take a break:

When Employees Take a Vacation

But it doesn't make sense for an entrepreneur or self-employed individual to follow the same pattern.

Doing so can jeopardize their success. For them, the moment after a win is the absolute worst time to take a vacation.

Why You Shouldn't Take a Break Right After a Win

There are at least three reasons why it's a bad idea for entrepreneurs to take a break after a win:

The first is we don't need a vacation to feel rewarded. Entrepreneurs tend to be intrinsically motivated. For us, working on our businesses and seeing the results are enough reward. (This partly explains why entrepreneurs seem to be working all the time and are happy to do so.)

The second reason is because a vacation can cause entrepreneurs to lose momentum. Think of it: wins create momentum. A success tends to snowball into bigger successes. Taking action after a win heightens that momentum; inaction weakens it.

This makes taking a vacation right after a win a terrible thing for your business.

And third, a vacation can cause entrepreneurs to miss out on opportunities. Wins change everything. Achieving a goal changes you and your business. Suddenly, you see opportunities everywhere, and when you do, you don't go on vacation. You seize the opportunity!

So When Is the Best Time to Take a Vacation?

It's not that vacations are a bad idea, period. It's not that entrepreneurs should work non-stop.

If entrepreneurs can stay motivated even without respite, and if taking a break causes us to lose momentum and miss out on opportunities, then should we go on vacation at all?


We all need vacations to manage our energy. So, the best time to go on vacation is when you're tired.

When you keep trucking on even after you're exhausted, you become less efficient and less effective. You have a harder time focusing. It takes you longer to get things done, and the quality of your work isn't as good as it could be.

With your brain drained, your judgment and decision-making suffer. You get impatient and irritable, which can lead to rash decisions and strained relationships.

Sheer willpower and determination will take you only so far beyond physical exhaustion. Eventually, you get sick. You're forced to take time off, and you don't want this kind of breather, because it doesn't happen on your terms: it can and usually does happen at the most inconvenient time.

Better to take a break when you need it, when you your mind and body are showing signs of fatigue--yes, even when you're in the middle of a big project.

Getting downtime when you're in the process of going for a win gives you the physical energy and mental vigor to go the rest of the way, to complete that big project, and to execute it in the best way possible.

That's the best time to take a vacation:

When Entrepreneurs Take a Vacation

What about the danger of killing your momentum and missing out on opportunities?

This is where you decide what kind of a break you can afford take. A vacation doesn't have to be a month-long cruise in the Mediterranean for it to be effective. Sometimes a 10-minute meditation break is all you can do, and it's enough to get you through the day. Sometimes a half day spent at the spa does wonders.

And sometimes it can't be nothing less than an all-out holiday overseas.

Listen to your mind and body, respect your personal signals, and you'll be a more successful--and happier--entrepreneur.