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9 Ways to Vacation Stress-Free

Published May 05, 2019

Business Invoice

If you’re north of the equator, vacation (or holiday as they say in the rest of the English speaking world) season is approaching. When we were younger it was the best part of the year. No school. No homework. Going to new places. Hanging out with our closest friends. Plenty of time to relax and forget about the “responsibilities” of life.

For most SME owners, entrepreneurs, and freelancers this is now an unfamiliar concept. The stress and worry can be too much for many to even think about walking away from the business for even a day, much less for a week or two. I’m sure you have all heard the same things over and over again.

If you want some of those voices to quiet down, and be able to actually re-live a little of your childhood bliss, then below are a few ideas that could help you make that happen.


Figure out when you want to go and for how long. You know the times your business is the slowest or you can work remotely. A quick visit to a website like SkyScanner can help you find the cheapest flights to the perfect destination during any given time period. It will help you save money while you’re trying to pinch pennies.


Speaking of pinching pennies. Now is the time for you to start saving and saving as much as possible. If you don’t already budget, we highly recommend the app Wally. There’s a proverb that says, “Either you control your money, or your money controls you” and this app helps you do just that by setting financial goals or obligations. Best of all, it’s completely free!


Business triage. I’m sure you do it even if you weren’t aware of its name (just google it). There is a lot that you could do at your job, but there is only one you and only so much time. Well, to take a break from work, no matter how short, means there’s even less time available so getting an app like ToDoist can help. It integrates with Google, Slack, Dropbox, and 67 other apps letting you optimize and schedule all your tasks.


One of the hardest things about leaving work is making sure that the house doesn’t burn down while you’re away. Todoist does this very well, allowing you to add members to show completed tasks, so you can monitor them while you’re away. Another good app is Trello, but it is better for bigger companies. If you’re self-employed, you should check out Upwork to find someone to fill the void in your absence.


Communication is key to maintaining all relationships. From marriage and family to friends and classmates. Your clients need that same level of communication. Most people know about Salesforce and Hubspot, with their many features available. However, if you want an alternative, and already have Gmail, you already have one of the best free CRM tools on the market. Just make sure it has an up-to-date contact list with the email scheduler set up, and it also integrates perfectly with every other app on this list.


This is the most important step. You need to do your job. It shouldn’t come as a surprise but some people get too distracted with planning for their vacation. In all actuality, people should be working more than they usually do. Not only to compensate for your time off, but also because you'll be spending more money than you usually do. Besides, you will make your clients happy because their projects will be finished earlier than expected.


To keep your clients, or potential clients, happy, you shouldn’t leave any contact unanswered. Setting up an automated response email and text is a necessity. If you have Gmail, here are the instructions for setting up an auto-reply email. To automate replies for your messaging app, we recommend SMS Autoreply for Android users. You can choose specific phone numbers to exempt from receiving the customized SMS, so the messages from your mom or sister can still make it through. (Sorry iOS users, but there is no way to automate SMS.)


It is a fantasy that all entrepreneurs have, that they can step away from their work without there being any problems. We know that it isn’t really true or possible. Things will go wrong, and we can’t let them wait until we get back, but will have to respond to them as they pop up. The goal is to keep these distractions to a minimum so you can focus on your vacation.


You’re a hard worker who needs a break. You’ve been working 40-80 hours a week for the past two years. But you can’t ignore everything from back home. Look up the app OFFTIME, to help you limit the distractions. Schedule when you can and can’t access certain apps. So while you’re on the beach with the kids, or at a bar chatting up a gorgeous brunette, you won’t keep pulling out your phone every 5 minutes to answer an email or client message.

If you need help or have any questions, send an email to

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