Home News Entrepreneurs: Here’s How to Prepare for that Much-Needed Vacation

Entrepreneurs: Here’s How to Prepare for that Much-Needed Vacation

by Jasmyne Moody

Going on vacation should signify rest and relaxation, but for many entrepreneurs, it signifies anxiety and the need to work remotely. In a culture of overwork and “sleep later” mentality, it’s easy to push taking time off by the wayside. In 2015, more than half of American workers left some vacation days unused. The same study found that the number-one reason we don’t take time off is because we’re afraid of returning to a mountain of work.

But taking some time off from your startup baby, possibly leaving it in the hands of someone else, doesn’t have to spell disaster. Hype has stepped in to compile a list of ways you can prepare for that vacation and not have to worry about a mountain of work when you return.


Look at your never-ending list of tasks and imagine trying to get it all done before you leave. Now acknowledge this: you can’t. It’s okay if you can’t complete all of your projects before you set off, so prioritizing is key. If something isn’t due until 3 weeks after your return, it can probably wait. If your client has expectations of you delivering something during vacation time, you should aim to get it done before you leave.

Give plenty of notice

This goes for both employees and clients. It’s important for people who work closely with you to know that you’re skipping town. Give them as much advance notice as possible, allowing them to plan for the delayed replies and general unavailability. The more advance notice you give, the better!

Decide how “away” you’ll really be

Do you want to unplug completely (it’s okay if you do!)? Would you rather be available during certain hours of the day or for certain people? This is something that should be decided, and explained, in advance. There’s a big difference between a reply a few hours later versus a reply a week or two later. You can try allowing only one person to contact you, making that trusted individual the mitigator between what’s priority and what’s not.

Get coverage

It’s important to make sure your tasks that need to keep going while you’re gone are taken care of. If you have a client that needs to meet often, you could pass them off to another employee for the time being. If you send an email blast out every Friday, assign someone to make sure it still goes out. No matter how big or small the task, if it needs to keep going while you’re gone, you should get it covered.  

Prepare for your return

Set a team meeting for when you get back so that you can be debriefed on what you missed and make a priority list to catch up. Finalize most ongoing projects and delegate tasks to be tackled during your absence. And don’t forget to clean your desk! A clean desk can help you be more productive upon your return, according to the Association for Psychological Science.

Change your voicemail and email

Just because you’re not checking them doesn’t mean that voicemails and emails will stop. Some people will forget, others simply won’t care. Changing your voicemail and setting an auto-response for emails will remind people that you’re on a vacation and that’s why they can’t reach you — minimizing the number of people inconvenienced by your time away. Also, no one is likely to be shocked or surprised if you’ve given them proper advance notice.

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