Want a Stress Free Vacation? Follow These 7 Must Do Steps

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Every entrepreneur dreams of enjoying a stress free vacation. If you’re planning a summer vacation, you’re probably also stressing about how much it sucks to go on a vacation and still have to work and check in on the business. It’s like there’s no point going on vacation at all. 

We’re here to tell you that you can actually have a stress free vacation without a ton of exasperating preparation. In this article, we’ll give you Nathan and Connor’s seven must do steps for a stress free vacation this summer. You can trust that their steps work because they’ve been following these steps for the past 10 years, and yes, enjoying stress free vacation time. 

Give Advance Notice

Let your team know at least two weeks in advance when you’re planning to take a break from work. This way, they have some time to prepare for when you’ll be away.

It’s always different when the boss isn’t around. You won’t be there to answer questions or give approval on tasks. They need to know how they are supposed to operate without you as part of the chain of command. Even just knowing that you’ll be away and for how long will get them thinking about how things will go, and give them some ideas about what needs to be cleared up before you leave.

Appoint a Leader

Assign someone to be in full charge of the team while you’re gone. This person becomes the interim owner for the time that you’re gone. This is vital to a stress free vacation because they will be the one who makes sure that everything gets handled properly. 

In choosing this one person who you will put in charge, make sure that they have the ability to make decisions the way that you would. They should also know the difference between issues that they can decide on by themselves and those that they still need to run by you. Make sure that they know if they need to get your say on these issues right away or when you get back. 

To help them cope, explain to this leader the difference between what you would consider to be emergencies for this particular summer trip, and stuff that can wait. Give them specific examples from the projects that will be ongoing while you’re away.

Assign Responsibilities

In the week leading up to your summer vacation, talk to the team and put them in charge of different things that need to be handled. While you’re gone, everyone needs to know what they are taking over for you.

Now, you may not necessarily be passing off all your tasks or spreading them out among the team. But just doing a review of the various responsibilities that each person has will put them at ease and give you a chance to show that you have confidence in them. This goes a long way. Just having you tell them that you are depending on them to take care of this and that will help them to make sure that they bring their A-game every day.

Have a meeting with the team to make sure everyone knows what needs to be done while you’re gone. Go over important deadlines and make sure that everyone has everything that they need to meet those deadlines, and deliver top-notch work, too. 

Go over who’s in charge, as a kind of formal endorsement. They need to know who they are supposed to reach out to for things that they used to come to you for. The team leader you’ve appointed also needs that vote of confidence to help them keep the team on point in your absence.

Establish Communication Protocols

Set communication expectations with the appointed leader and the whole team. Make sure that everyone understands that everything needs to be run by the leader before reaching out to you. This way, the leader can field all questions and make sure that only the urgent stuff gets sent to you. Also, this helps you limit the number of people with whom you will actually be in communication, reducing your time input and level of tension. This is super important for a stress free vacation.

Give the whole team guidelines for how they can reach you in case of an emergency. Share as well how they should be sending you updates on daily work progress while you’re gone. Having a special system for vacation communications is vital especially if you are the type of business owner who usually makes themselves available to the team. The system tells them that you’re still there for them when they need you, but that you are setting boundaries for this period of time.

Set Rules for Yourself

Set rules for yourself for checking on work. You need to discipline yourself to stay away from operations if you want your stress free vacation to work. No one is going to ignore you if you are the one who is reaching out to them, so you need to stop yourself from getting involved if you really want to get away from it all.

If it’s a long weekend, for example, set the rule that you won’t check in with the team until the last day of your vacation. If it’s a week or longer, maybe you can set two or three days and times a week to check in. Remember that these check-ins are just to make sure that everything is going smoothly. You will already have the progress reports that you can review to see that things are going according to plan. You don’t need to get into long conversations with the team about how everything is going. Just keep it casual, simply making your presence known, so the team knows that you have not abandoned them or completely lost interest in the work.

If you absolutely cannot avoid getting sucked into the day to day, make it a rule for yourself to avoid checking on the business at all. Don’t even open your email unless someone calls your attention to a specific message that needs your immediate attention. Anyway, if you have a great team, you will already have someone sorting your inbox and taking care of most of your mail.

Remove Temptations

You can’t expect to have a stress free vacation without the ability to let go a little. But it can be really hard to relinquish control over your business. The temptation to get back in the trenches can be compounded by constant reminders of the daily grind, like apps that you use for work. 

You can’t be expected to leave your phone behind, but you can move any of these work apps to the back of your phone so you don’t keep seeing them. We suggest that you turn off notifications for incoming messages as well, except for the emergency channel that you designated. This way, you don’t get distracted every time someone sends a message to one of your group chats or leaves you an end-of-day report. You can get to all those later at the time that you scheduled to review work progress. 

If you really can’t stop yourself from looking into things five times a day, you are not going to have a chance at a stress free vacation. The solution here is to delete all those work apps. Sure, you could always reinstall them, but that extra step, plus having to sign in to each one, will act as a deterrent.

Leave your work computer at home if possible. You can either not bring any work-related devices with you, or bring an alternative one that you don’t use for work. For instance, you can bring a tablet that doesn’t have any work stuff on it, including any apps like the ones on your phone. This way, you’ll have what you need to make your vacation more enjoyable without the pressure that temptation brings.

Set Up Accountability

If you’re on a trip with other people, pick one person to keep you in check. For example, you can have your significant other keep an eye on you to make sure you’re not working. If they notice that you’re working, give them permission to sanction you in some way. You can also self-sanction, like hand over your phone for confiscation if you are tempted to check in on work at the wrong time.

Make sure that the person you choose to be your accountability partner understands your reasons for setting up rules for yourself. It will be much easier for them to keep you on a tight leash if they know how important it is to you to have a stress free vacation. If they don’t get it, they are more likely to give in to you because they don’t want to bum you out. They need to know that not getting what you want at the moment — i.e. working — is less of a bummer than getting stressed out about work when you’re supposed to be having a good time away from work.

Your Stress Free Vacation is WaitingA stress free vacation is totally possible and not that hard to achieve when you take these steps to prepare in advance. Of course, a lot of this depends on having a solid team behind you — something that you should have set up for your business anyway, even when you’re not taking a summer break.

Use your past experiences as a guide as well. Think about what made your last vacation stressful and prepare to avoid that situation this time around. You may be tempted to conclude that the solution is for you to stay on top of things, but we want you to pick the better solution — get the team set up to operate at peak efficiency in your absence. Getting you out of the trenches is the only real way that you can have the stress free vacation that you need and deserve.


Would you like to know how to be certain who your next hire should be? Or maybe you are having a hard time deciding what parts of your business can be outsourced with virtual assistants, right now. We can help you answer these questions, and help you to discover what new systems you should add to scale your business faster. Set up a free hiring consultation with us at Outsource School today – simply book here!

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