3 Steps to Prepare for Vacations, Holidays, and Time Away From Your Business

Episode 7

Niklas Zennstrom once said, “If you want to be an entrepreneur, it’s not a job, it’s a lifestyle.” Wow, there’s so much truth in that statement. It’s a really important concept to embrace because entrepreneurship impacts all areas of your life differently than if you had a traditional career.

There are many perks of the entrepreneur lifestyle. First of all, you are the captain of your own destiny. You get to set the vision, you get to create the plan, you get to decide how and when that plan will be executed. And you get to reap the rewards of all of it.

You are the Visionary, the CEO, and the Expert all at the same time.

There is however a reality that we can’t escape. In entrepreneurship every benefit comes with a drawback. If you’ve been at this for a while, you will already know this. If you’re just starting out, it won’t be long before you understand it at a fundamental level.

I could launch into a philosophical discussion about how life is really about deciding which combination of benefits and drawbacks you want but that’s not where this episode is headed.

Today we’re going to talk about how we as entrepreneurs can prepare ourselves and our business for those times when we want to take a vacation, celebrate the holidays or step away from our business for a short period. I’m going to share the 3 steps you can take to make sure your business runs smoothly while you’re away.

One of the drawbacks to being an entrepreneur is having to plan for your absence

Back when I worked for a corporate architecture firm, vacations meant total freedom from work responsibility. Whatever came up, someone else would handle. I could turn off my computer and never think about work until I returned.

For most small entrepreneurs, totally removing ourselves isn’t possible. The entrepreneur lifestyle means that the person responsible while we are away is us. This doesn’t mean we have to be glued to our phone or computer. It means we’ll have to put in a bit more effort before we close that laptop and walk away from our desk.

It all comes down to one important strategy: plan for your absence in advance.

The smaller your company is, the more important it is to prepare ahead of time for how your business will run with limited involvement from you during that time.

For the solopreneurs out there, this is even more important. In addition to being the Visionary, the CEO, and the Expert, you’re also the employee, tech support and customer service. Which means you’re on call 24/7.

That being said you may be wondering, if it even possible to step away from your business during holidays and while on vacation? Absolutely. Is it recommended? That my friend is a personal question only you can answer. It’s your business which means you get to make decisions that are right for you. There’s no right or wrong here, only what’s right for you.

Let’s talk about the 3 steps you can do that will make it easier for you to take time off from your business.

1 Create a list

No one knows better than you all the parts and pieces of your business. You have an in-depth understanding of the day-to-day operations and your role in each of them. You’ll want to take each specific component and make a plan for how they will be handled during your absence. If you haven’t taken the time to analyze all the part-and-pieces of your business, no worries. You can do that now so that you’ll be ready when it comes time to step away. Even if you don’ have any plans to take time off, you can still start this process now.

Here are a few things you can ask yourself to get started:

What needs to be arranged to make sure my current clients are taken care of while I’m away?

How do I want to handle prospective customers who reach out to me?

What is going to be their experience interacting with my business while I am away?

How can I make that the best experience possible?

Will I continue to grow my audience during this time, if so how?

Are there any other aspects of my business that require my time and attention?

If so, what are they?

How will my team be managed during this time?

These questions will help you to think about your role and responsibilities from a big picture perspective so that you can make a plan that is accurate and realistic.

I want to also encourage you to keep a time journal every day for a month. There are often small tasks that we do sporatically that may not pop into your mind when you’re planning for a vacation. Keep a list of these tasks so that you can account for them when you make your plan.

Personally, I love Google Docs and the Notes app on my phone to create the list.

2 Make a plan in advance

Once you understand what areas of your business are affected by your presence, the next step is to decide what will happen and how it will be implemented.

Planning involves taking that list of tasks responsibilities and deciding:

How will these be handled while I’m away?

What needs to be done to make that happen?

Who will be responsible for it?

If you don’t have a team, then it’s important to decide how you’re going to handle your regular tasks while you’re taking the time off.

I know that right now some of you are rolling your eyes and thinking “that sounds terrible.” You’re going to be tempted to either not do this at all or only do it half-heartedly. You may even be tempted with the excuse of how you’re too busy to do this now and you’ll get to it later.

I totally understand. Planning is like choosing to eat rice cakes for dessert. Nobody really wants to do it, including me. And I’m a goals and accountability coach. Planning is what I do! I don’t make plans because they’re fun, I create plans and take action because it makes my entrepreneur lifestyle better overall.

Here’s the thing, as I mentioned earlier, this is about deciding which combination of benefits and drawbacks you want. You can do the not-fun tasks now and then maximize your fun later, or you can put off these tasks and deal with it while you’re on vacation or when you return. There’s going to be an element of discomfort but you get to decide when it will take place.

That’s why I suggest you plan in advance for as much as possible. Honestly, the earlier you can make a plan, the better. It gives you time to account for the things you may forget. Nothing will torpedo vacation fun faster than chaos that could have been prevented with planning and preparation.

3 Do the work now so you can relax later

Once you have your plan, it’s time to complete as much as possible before you take time off. This is where putting in extra effort can really pay off. If you’re already juggling a busy calendar, the further out you can start preparing for time away, the better it will be for you. Instead of last minute rushing, you can slowly chip away at each item, a little bit everyday.

I’m going to take a quick detour to talk to those of you who are thinking, “That’s a great idea and I know I should do it but this doesn’t work for me. I always end up running around at the last minute, staying up all night, and coming back to chos in my business.”

First let me say, you’re not the only one. This is really common. Second, every time you think that, you’re reinforcing this belief that you are somehow not able to get more organized and prepare ahead of time. When coaches like me talk about mindset, this is what we’re talking about. This is an unintentional way we reinforce beliefs that don’t get us closer to the results we want to create. If we have this belief and we have this habit, it’s actually easier for us to embrace it than it is to change it. Our brain prefers to stick with the familiar even if it’s to our detriment. I talked about this in Episode 6, where I discussed tolerable discomfort.

If you do want to change and you want to be more organized in advance, you’ll have to be intentional about taking the actions that bring you one step closer.

If the idea of implementing all 3 of these steps at once sounds overwhelming, start with one of the steps. Or reduce it down even further to decide one small area of your business that you can plan and prepare for prior to your time off. This could be scheduling social media posts, or automated reply emails, or setting up a chatbot. Breaking it down into small easy to implement pieces will not only get you closer to developing a vacation or holiday system, it will also erode any beliefs you may have about your ability to do so.

If you’re wondering what this looks like for me, here’s a few things I do that work for me.

Let me start by saying that I love being an entrepreneur. My businesses are my passion so I never want to be completely away from them for any length of time. When I’m on vacation, I like to do the business tasks that light me up. I might brainstorm new ideas of how I can better help women entrepreneurs or I’ll develop some of the ideas that have been bouncing around in my brain. I also make sure that I do the tasks that are needed for my business to run smoothly while I’m away.

For example, I own two businesses but I’m still very hands on with customer service for both of them. During vacation, I schedule time to check in to see if there are any issues that require my involvement. I intentionally fit it into the moments of down time that are available throughout the day. I’m an early riser so I check in while I drink coffee. If we’re going to drive somewhere during vacation, I’ll check in during the car ride. I’ve found that for me, I can stay on top of things really easily if I dedicate 20 minutes a couple of times a day. The same is true if we are spending time with family during the holidays. I’ll step away for a few minutes to check in and see if there are any issues that need my attention, that can be delegated or can be delayed.

All of the preparation in advance pays off. My required involvement during my time away is minimal. Any additional time I spend working on my business is purely optional.

There it is….your 3 step process to prepare for vacations, holidays and time away from your business. Create a list, make a plan, do the work now.

It pays to get ahead by doing all 3 steps but don’t let yourself get overwhelmed. Remember, start where you are and build on the process over time. One small step forward will still get you to your goal.


Danielle's message is spot on with achieving goals. Not only does she practice what she preaches, but she's your guide to help YOU achieve the best version of yourself! A must listen!


Grow a biz & feel good! Danielle is really skilled at bringing both the actionable steps plus the mindset work so we can feel good as we grow our businesses while being present for our families. I look forward to listening every week!



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