If you are a remote worker and/or self-employed, then you more than likely have a flexible schedule. Some people might look at that as a major blessing, and it is in many ways. With that in mind, being a remote warrior/self-employed isn’t always what it is cracked up to be.

There are many reasons why (for example, anything becomes a distraction when you work from home), but let’s focus in on one of the reasons. When you don’t work in an office, or have an employer, you likely don’t have a salary. Not to mention, you probably have to provide your own benefits, which means you aren’t given PTO/vacation time.

When you aren’t working, you aren’t making money. As a result, taking off an entire week of work during the summer will likely mean you won’t make a single penny during that time. Now, your business might be constantly making you money, and you might also invest, but when you work for yourself, you typically don’t have the luxury of PTO. When you take time off, the cash flow stops.

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The good thing about working from home/being self-employed is you get to pick when you want to work, and you can theoretically go on vacation whenever you want. That’s the good news.

Putting this altogether, there is one way self-employed folks can still get paid when going on vacation, and that is by getting ahead. One might be wondering what the easiest way to get ahead when you have a flexible schedule is.

The answer: Doing a little extra here and there.

When a planned vacation is nearing, it might be tempting for a remote worker to do one of these three things: (1) Combine two weeks of work into one week in hopes of taking off an entire week for vacation. (2) Saying you will do some work while on vacation. (3) Catching up when you get back from vacation.


Here’s the problem with the above methods. The first and third method will result in you doing more work than you can likely handle in a week, and that can lead to you burning out, and sloppy work. The second method is tough. It’s so easy to say you will work while you are on vacation … but then vacation actually happens, and you find out you don’t have as much time for work as you expected. Plus, the last thing you want to do while you are on vacation is work.

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The best thing to do, and the easiest way to get ahead while you have a flexible schedule, is planning ahead. More likely than not, you know a one-week vacation is on the horizon, so plan on spending a little extra time each day in hopes of getting ahead. You can even plan on doing the extra work on the nights/weekends. As long as you aren’t doing this for more than a month (sometimes even two to three weeks is too much), you shouldn’t burn out.

Not only will this method help you get ahead, but you will, in theory, be getting paid for your week off since the work for that week will already be accomplished, and the money will be flowing in.

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