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How to Prepare for an Outstanding Working Vacation

Have you ever taken a working vacation?

For almost my entire working life, going vacation has always been tricky. Of course, I’m SO, SO grateful when I get to even go on vacation. I feel lucky to get a chance to spend time with my family (we’re all spread out all over the country) and, of course, for an opportunity to take a break from work and recharge.

But taking a break from work is tricky.

I’ve never had a paid vacation, so vacations mean I lose out on income that I definitely do need.

This year, for the first time in my adult life, I managed to sort of give myself a paid vacation. How?

Working ahead on all my projects. It was an intense couple of weeks, let me tell you, but I managed to get blog posts, social media, and other projects scheduled or completed early. There is SOME work that can’t be done ahead of time, and I will be working on those projects while away, but I’m happy not to lose the income.  I’m very curious how this will go. If anybody out there has done this before and succeeded, I’d LOVE to hear your tips! I’ll share my plan for making this work:

However, there is some work that just can’t be done ahead of time and need to be looked after on a daily basis.

In this post, I share some tips I used to balance enjoying my vacation with maintaining my cash flow.

Wake up earlier than everybody else and work first thing.

This way, you can enjoy the day ahead of you. Part of the fun of a vacation can be spontaneity, just seeing where the day takes you. This is wonderful, but could very easily result in never getting to your work, so just  sit down with your coffee (or mimosa? It’s vacation. No judgment!) and laptop very soon after your eyes open.

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Make completely sure you’ll actually be able to work.

First things first, call ahead or check online to see about the internet connectivity at wherever you’ll be staying. If there’s no internet or spotty internet, better find out before leaving! Getting a mobile hotspot could be an option or look into using your phone, assuming cell service is okay. Maybe check on that too.

Don’t plan too much work.

Try to work no more than an hour or two a day if possible, leaving plenty of time to rest, rejuvenate, and explore your surroundings.

Set up email notifications and alert all clients to limited connectivity.

It’s important to have boundaries and to keep people in the know. Hopefully, this will keep clients from having “urgent” projects and needs for this period of time. And speaking of boundaries…

Set boundaries with your loved ones.

You’ll all have a better time if you set up some ground rules from the beginning. Let them know ahead of time that your mornings are off limits or that you might need to skip one or two activities.

Try to soak it all in.

I feel like trying to be productive all the time only ends up hurting our work in the long run. Seeing new things can inspire new projects or programs and help us all be happier in our jobs. Lazing about lets new ideas percolate and take shape. It’s good for us!

There’s a part of me that kind of is against the whole idea of working on vacation and sees it as a symptom of being an overworked American, but at the same time, I feel so grateful that I can take them every once in a while. I’m conflicted, I guess.

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What’s your take on working vacations? Have you ever taken one or are you against the whole concept?

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