How to Prepare for a Vacation as a Business Owner

How to Prepare for a Vacation as a Business Owner |

August 2018 was a milestone for my business because it’s the first time I took a month-long vacation (it’s the longest period I’ve been away so far). 

Now, just to give you a clearer picture, I wholeheartedly believe in setting boundaries and taking frequent rest periods so I’m the kind of business owner who doesn’t conform to the hustle 24/7 365 days a year mentality. I believe in working smart and working hard but also in the power of prioritization, systems, automating, and delegating. My business name is Productive and Free, after all.

This year, however, I wanted to see if I could take a longer break from my business. At first I planned to take a two-week vacation for my birthday but when I made a list of things I could do/visit/experience, it just kept getting longer and longer! I finally settled on taking a four-week vacation and treated it as an opportunity to challenge myself. 

I’d also like to note that my business focuses on providing coaching services and info-products so while I don’t have an actual store to run or physical inventory to manage, my income isn’t 100% passive. This means that taking a vacation isn’t as simple as setting up email funnels because I’d have to take a break from my coaching clients as well.

Fast forward to today, I’m now back from vacation and couldn’t be happier. I did everything in my list plus other things, and I find myself well-rested, refreshed, and energized to tackle the rest of 2018. 

To be honest, I was quite uneasy during the first few days looking at my empty to-do list (“What am I supposed to do now?!”). I even felt unproductive sometimes because I wasn’t “doing” anything (of course, that’s not really true because resting can be a productive activity) and it just felt different because previously I had only taken weekends or a few days off (not an entire month). Still, I highly recommend taking a long vacation even if (and especially if) you’re a business owner. The rewards far outweigh those temporary discomforts. 

As long as you have systems set in place and you’re intentional about resting—spending the time with people and doing activities that make you happy and contribute to your physical, mental, and emotional well-being—it is possible and you won’t regret it.

Here are my five tips for preparing for a long vacation as a business owner.


01. Plan ahead

If you haven’t taken a long vacation before, the best way to go about it is to plan well in advance and identify what needs to be set up in order to make the transition as seamless as possible.

In my case, I started preparing in Q1 of 2018 to give me enough time to go over everything. Even if I had business systems set up already, I became even more critical, noticing even the smallest tasks that could be eliminated, automated, outsourced, or consolidated (aka batched). I even began taking note of things that could go wrong and how it could potentially be solved. Basically, I broke down how my business would run if I removed myself from the equation.

This may seem like a tedious process but I knew that if I could set up a more detailed operations manual or standard operating procedures for my business, this would come in handy later on when I scale my business and hire more people. 

Obviously I also planned when to do it (August because it’s my birthday month) but if your business follows a certain industry-specific season (school year, wedding season, holidays, etc.) then I suggest you take it during the times business would be slow because it’ll presumably be less demanding.

While one of the main obstacles to taking a vacation is maintaining your revenue stream (especially for service-based businesses), fortunately there are a lot of ways to approach this nowadays such as setting up passive income streams, cutting unnecessary or extravagant businesses expenses, taking on extra clients during the months before or months after your vacation, etc. Consider which options are most viable for you and your team, map out a plan, and execute.


02. Put your CEO cap on

Whether you’re a brand new side hustler or seasoned business owner, it’s a given that you need to know how your business operates. Preparing for a vacation, however, is a perfect opportunity to check everything again to make sure things are running smoothly and nothing’s falling between the cracks.

Now for some, this can be extremely challenging since they refer to themselves as “perfectionists” (myself included) but at some point we have to let go of our employee or solopreneur mindset and replace it with a manager or CEO mindset. 

Instead of asking, “What do I need to do here?” explore the answers to “What needs to be done here?” 

It's only a slight difference but you’ll notice how all of a sudden, automating and delegating become the focus of the conversation. You immediately stop thinking of yourself as a hamster on a wheel and instead treat your business as a machine with parts and cogs that all work together to make it run smoothly.


03. Take a hard look at your processes

Again, going on vacation shouldn’t be the only time you do this but as you plan ahead, go over the different arms/departments of your business (ex. financial, marketing and social media, operations, customer service, etc.) and evaluate every process that you have in place. 

Are there processes or tasks that you can create systems for or streamline? Here are some steps I recommend following:

a. Delete

An important but often overlooked step in maintaining a lean business, now is a good time as any to cut out anything that isn’t serving your business as well as you’d like. To be smart about this, try going over your expenses, financial ratios, and conversion rates to make informed decisions.

b. Defer

Are there some projects that can be deferred to a future time such as when you return from vacation or when you will have hired the right person for the job? Just because you want do get it done doesn't mean it has to be done right this moment.

c. Automate

This step depends on your type of business of course but for online entrepreneurs, try looking into the following tools: Zapier, IFTTT, Asana, Dubsado, G Suite, social media schedulers, and email marketing software such as ConvertKit. Don’t forget that new and sophisticated tools and apps pop up almost every month now so it’s best to regularly keep up with changes in your industry.   

d. Delegate

Remove yourself from the equation and identify who you can put in charge. It could be someone already qualified or someone who shows potential to take on more responsibility. Communicate with that person and set clear expectations.

If you don’t have an assistant yet, try outsourcing one as early as now. Start with small tasks then work your way up. If you’ve ever heard of an “ideal customer avatar,” you can apply the same concept and create an “ideal assistant avatar”—someone with specific characteristics and abilities who you can confidently turn over some aspects of your business to.

e. Consolidate

After you’ve deleted, deferred, automated, and delegated, the tasks left on your plate should be the ones that you alone can do, and are the best use of your strengths and talents. If possible, batch those tasks ahead of time (ex. batch writing blog posts, going on meetings, recording podcasts episodes, etc.); otherwise, set aside some buffer time to thoroughly handle it all when you return (ex. When you get back, dedicate three days to catch up on all your accumulated emails and meet with your team to get up to speed).  


04. Communicate with everyone

This tip goes without saying but it’s best to clearly communicate with your team who’s in charge of what, by when, how they should go about their work, and how often they should communicate with each other.

If you have a large team, ideally you'd leave your #2 person in charge. Commonly referred to as your Chief Operations Officer, integrator, or project manager, this is the person who oversees everything and everyone else (including contractors, freelancers, or virtual assistants). He or she is usually in charge of executing your vision and should therefore be able to handle things while you're away.

Before you take off and in case you haven't done it before, make sure to clearly define what success looks like for each of your processes so there’s no confusion and there’ll be no need to get in touch with you for small issues.

Remember the operations manual I mentioned earlier? This is the perfect time to use it, share it with everyone involved, and even get their input if you want.

Also take this opportunity to express your appreciation for and confidence in your team (just in case you haven’t been doing it yet).

Here are other things to consider in terms of communication:

a. Set up different levels of “emergencies” or contingency plans. Identify how little or how much your team or assistant can handle on their own, and only under what circumstances they should get in touch with you.

b. Send separate emails to anyone who might be affected by your absence apart from your team—clients, customers, students, subscribers, vendors, affiliate partners, mastermind group members, membership site members, your bookkeeper, etc. 

c. Set up an FAQ section in your website (if you haven’t yet) to cut down on inquiries or emails you’ll receive.

d. Set up an email autoresponder for how long you’ll be gone, when they can expect to hear back from you, who they can get in touch with in the meantime, or how they can find answers to common inquiries. 


05. Set boundaries for yourself

Last but not the least, remember your whole purpose of going on vacation. All this preparation becomes useless if you spend much of your time still sneaking in some emails, micromanaging, or stepping in during every little emergency.

To avoid feeling uneasy "doing nothing" during this whole time, I suggest creating a list of restful but meaningful activities you'd actually be excited to cross out. Think of things that could improve your relationships, environment, and physical, mental, and emotional well-being.

Examples are traveling, volunteering, nature-related activities like hiking or mountain climbing, exercising, reading, meditating, journaling, taking up a new hobby, joining a class, go on a food or wine tasting, trying out a different sport, visiting museums, etc.



Taking a vacation from work, routines, and your day-to-day activities is possible and highly recommended. It can do you wonders even if (or especially if) you're a business owner as long as you plan ahead, shift your mindset to that of a CEO, evaluate your processes, set up systems, communicate clearly, and set boundaries for yourself. 


Share in the comments below: Have you taken a long vacation from your business before? If so, what did you do to prepare for it? If not, are you planning to take one soon?

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