In the US, there are almost 30 million small and home-based businesses. This means that over 30 million small entrepreneurs worry about taking a vacation during the holiday season. Traveling while running a business can be a stressful endeavor. Although once your business is established, it becomes easier. The first few travel sessions while the company is still taking off can be a bit challenging. 

A small business owner cannot take one day off without their phone buzzing with messages or laptop overflowing with emails. Despite being hard is hard; it doesn’t mean that you shouldn’t take any vacation for the next 20 years. Or until your tiny little endeavor becomes a multi-million enterprises. 

If you are struggling, don’t consider yourself alone. There are many people willing to give away a chunk of their time and money to have a sound vacation. Fortunately, with a few simple steps, you can take an enjoyable holiday with your loved ones – or just by yourself. 

Let’s discuss some handy tips to take a fun vacation as a young entrepreneur: 

Alert Your Clients 

Your customers and employees depend on this startup, so you need to inform/prepare them in advance of the vacation. Some businesses work with independent clients. You must notify them in advance of your plans so that they can cover all the professional requirements needed from your end. Other than this, they must also be informed about your availability hours and the time you will be completely unavailable. This will help your clients contact you at a reasonable time that does not bother you or your vacation time with the fam.

Sometimes clients wait for the last minute to get some work done – especially if you are a freelancer. In this case, let them know several days – even weeks prior to your departure, so they are able to manage any last moment work requirements without the need to bother you. 

Give Them an Arrival Date 

Suppose you are exploring Stone Mountain attractions all the way in Atlanta, Georgia. It is a beautiful adrenaline-pumping vacation that actually results in an intense amount of physical activity. The point of having a break is to have fun, so you are bound to get tired after the trip. Instead of giving your employees the actual arrival date, we suggest that you tell them that you will be back after 2 to 3 three days of the actual arrival. This will give you a stress-free chance to sleep and just catch up with rest. 

Delay Anything Big Until After Arrival 

Your mind will be hooked on the vacation so instead of scheduling anything significant like a grand meeting with a client or a social media campaign, wait till you return. Other than your mind being hooked on the exciting trip waiting for you, a rushed job can lead to last-minute problems and poor performance. Other than this, you really don’t want potential clients to contact the company while you are away and unreachable. This is why all your megaprojects and plans related to the business should be postponed until after your arrival.

Keep Your Contacts at Your Convenience 

Your smartphone obviously has all the contacts you need and more (thanks Google), but it is always a good idea to keep backups. It’s a good idea to have a printed version in case your electronic device breaks, is stolen, or the battery dies while you’re not near a charging station. Keeping this list on hand will save you time if you need to contact anyone on the list to manage an issue while you’re gone. To keep your phone charged at all times, invest in an excellent power bank that can give you a few rounds of complete charging throughout the day before it dies.

Create A Contingency Plan 

You may be aware of how to get the phone to work or reset the internet if it goes down, but John, who is working in the typing department, may not. Before you leave, we suggest taking a day out and give your employees training on everything they need to know. Most business owners also devise a written contingency plan for their employees in case of any inconvenience. A list of all the important contacts like the phone repairing, internet issues, tech guy should be on the contingency plan. 

Set Time to Check Up On the Business 

Nothing in this whole wide world can help you if you allow yourself to get diverted and start checking up with the employees after a while. Understand that while your business is your baby, your employees are also highly professional individuals who are there to only help you reach your business goals. Avoid constantly ringing up at the office or sending everyone emails about what they are doing and how it’s going. A three-day limit works wonders when it comes to contacting the office. If you are on a long vacation, set a time after three days to contact the company. For short, three to four-day long getaways, do not bother anyone until you return for work. 

Keep Tabs On Office Activities 

Just because you shouldn’t bug your employees does not mean that you can’t keep track of their activities. Thanks to development in technology, we now have security cameras that can actually provide you with footage on your phone and laptop – even if you are a thousand miles away. Keep a random eye on what each person is doing and how they manage their work in your absence. 

Assign Work Before Leaving 

One of the best ways to keep your employees busy and know where they stand performance-wise is by assigning them work before leaving. This not only gets them hooked for a while but also helps you understand their level of motivation and capability while you are away. Also, with work assigned and not there, your employees will manage anything they can to cover the maximum number of tasks.

Make Your Privacy a Major Concern 

Whether you are going to Stone Mountain or the Sydney Opera House, maintain high security and data privacy standards. Public Wi-Fi can be an open door for hackers to access your data. Other than this, anything related to work like contracts or opportunities should be kept confidential from employees. Lock that one specific computer or remove the fax machine from your office until you get back. No matter how loyal, your employees must not have any access to things associated with contracts and clients. Assign someone to pick calls for you or at least forward the messages stored on the VOIP service. 


Small business owners may feel stressed when leaving for a vacation. This is a major concern among most new entrepreneurs. However, it is really possible to take a vacation even if your business is new. Just make sure to keep track of everything, delay all the major events until after your vacation. Most importantly, assign your employees tasks to keep tabs on while you are away. Your privacy matters a lot while you are away, so avoid giving any employee access to more than what they need. We also recommend that you keep tabs on activity but not bother the people working for you every minute. 

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