How to prepare your business for a holiday

As I type this to you, I’m sipping on my coffee and sitting in my fave spot in the library, where I come to work with a girlfriend sometimes

But as you read this, I’m actually on a much-anticipated holiday with my hubby. (We’re currently in Positano and heading to Sardinia today to meet my family and celebrate my 31st birthday!)

I wrote this several days before we went on holiday, and scheduled it to send as a newsletter today, and to be posted on my blog and social media at the same time.

I did that because I’m on holiday, and I’m sure that right now my main concern is ‘Rosé or aperol spritz?’ or ‘Pizza or pasta?’ (The latter being a silly question because obviously in Italy, the answer is ‘Both!’)

I’ve done it this way because I’m on holiday and I’m giving myself a real break.

It’s not because I don’t love my business (I do!) or because I’m scared of what’ll happen if I don’t open my laptop for days in a row (I’m not!).

It’s because after running my own business since 2011, and working as a freelance makeup artist for years before that, I know what I need to do to prepare my biz for a holiday.

I know that while my biz is an extension of me (because I’ve created it to reflect my passions, interests, values and goals), it’s not actually me, and apart from holding my 1:1 kinesiology and business alignment coaching sessions, it can run itself beautifully whether I’m working in the library in Sydney, or reading my book on the beach in Positano.

It’s not about creating my business to suit ‘the laptop lifestyle’ although that is lovely.

It’s about creating systems that work, using software that supports your business, delegating what you can, doing some preparation and then giving yourself permission to let go, enjoy yourself and have a holiday, trusting your business can hold itself up as beautifully as if you were still at home.

Because – newsflash – it can!

Here are some tips to help you prepare your business for a holiday:

(Update: This post applies to anytime you’re taking a break from your biz. *She writes as she’s about to go on maternity leave.*)


Before your holiday

Make it easy (for everyone)

If/where possible, have some options for people to purchase digital resources and/or online courses and programs in an evergreen format (meaning they can sign up at any time).

This is a win-win for everyone; it allows you to easily receive passive income, while offering incredibly valuable resources and support to your clients.

By setting up your business in this way, it doesn’t matter whether you’re teaching the work or offering the content in a live format or as pre-recorded content; your business supports your clients, while it supports you, while it supports your clients. See that cycle? Excellent.

Building your online digital empire can take time, so be patient with yourself and give yourself the time you need to create what feels most aligned to you, your business and your greater vision.

Allow yourself to start exactly where you are; it’s the perfect (and only) place to begin.

For help creating content you love, check out my Love What You Create Workshop.


Plan ahead

Before you take leave, start getting your ducks in a row to take a break.

It’s important to let your clients know you’ll be going away beforehand, and invite them to book in for a session either before or after your trip to ensure they get the spots they want.

If you use an online booking software, check you’ve closed off your holiday dates and that it’s easy for clients to book in online while you’re away, to work with you when you’re back.

Let other important people related to your biz know you’ll be going away too.

Don’t take on new projects that you can’t easily complete either before your trip or within a good time-frame once you’re back. (You don’t want to push everything to after your trip, so you come home feeling like you have several thousands thing to start work on at once.)

You’re totally allowed to tell people that you’re going away and that this means your work schedule is slightly different because of your trip.

Check your systems and software to ensure everything is running beautifully.

Schedule some newsletters/blog posts/social media posts before you go, so they roll out while you’re away.

I usually schedule a couple of Facebook posts to be published each week for the duration of my holiday, plus a couple of newsletters/blog posts that I’ve written ahead of time. If I don’t stick to my usual weekly-ish newsletter/blog post schedule though, I don’t worry.

You can also schedule previously written blog posts to be sent as newsletters while you’re away. Just clearly say it’s an older post that you’re bringing back because it’s still so relevant (and P.S. You’re still on holiday!).

I don’t often schedule too much for Instagram, as I use it as more of a personal account while I’m away, posting snaps of my holiday and where relevant, linking back to my work. Otherwise it’s used for pure fun while I’m away!

On some level, didn’t you start your business to create more freedom in your life? Perfect; so here’s your chance to honour that now.


Delegate what you can

I have a wonderful VA (virtual assistant) who supports me in my business with admin tasks, email support and other jobs. Before my trip, I gave her a list of some projects/tasks I wanted her to work on while I was away to help lighten the load for me. And then… I trusted her! Part of delegating is the actual delegating, but what comes after that is trust.

While I’m away, Tash will also reply to anything urgent from my inbox, and she’ll manage the support inbox as she usually does.

Although I won’t be checking and replying to my main inbox while I’m on holiday, I’ll check for emails from Tash just in case she needs me to reply to anything urgent.

Is there anything you can delegate or outsource in your business while you’re away? (And also, just in general to support you in the day-to-day running of your business?)


Get your auto-reply ready

Your email auto-reply can do many things when you’re at home; it can set expectations as to when you’ll reply to people, direct them to more information while they wait for a reply for you, and give them links to your products and services so they can learn more about working with you or book in before you’ve even replied.

When you’re on holiday, it can do all of the above, and more, because you’re very clearly saying ‘I’m on holiday, and while I’m so grateful for your email, I’ll reply to you on my time.’

This isn’t rude. This is what healthy business boundaries look like.

Here’s my auto-reply for while I’m away in Europe:


Hey there,

Thank you so much for getting in touch.

I’m currently on a long-awaited and much-anticipated holiday with my hubby and as such, I’m not checking my email all that often.

Instead, I’ll be drinking aperol spritz while eating pizza in Italy, and taking photos of sunsets while eating feta in Greece, interspersed with swimming and reading and relaxing.

My wonderful assistant Natasha will be looking after my inbox while I’m away and will reply to anything urgent. For everything else, I’ll get back to you in late July/early August once I’m back home.

Thank you for your pasta patience!


It then lists some of the ways people can work with me (once I’m home) if they want, with links directing them to learn more and book in to work with me/purchase an online program if they’re keen to get started.

Note that I don’t list my travel dates – I used to, but in truth, it doesn’t matter what dates I’m away as I’ll always get back to people as soon as I can anyway. I’d rather not list exact dates to give myself more space, time and freedom to reply as and when I can.


During your holiday

Enjoy yourself and let your biz work for you

Your business will not fail or fall or fold in on itself if you’re enjoying yourself on a break.

There’ve been times I’ve been away on a holiday and brought in hundreds, if not thousands, of dollars overnight doing absolutely nothing but enjoying myself.

The first time I experienced this was in 2013 when my hubby and I went away for two weeks. At the time, the only digital product I had a $25 eBook that had been up for sale for over a year by then. Sales would come in consistently but it was only a small revenue stream.

One morning while I holiday, I woke up to find that about $600 had come through in eBook sales overnight, and they continued to flow in while Nic and I sat and had a long breakfast, lay at the pool, swam at the beach, had lunch… you get the point.

I hadn’t done anything differently. I hadn’t promoted it that day, nor had anyone I knew tagged me in a post that would lead to new traffic, nor was I using Facebook ads then.

All I’d done was enjoy myself on my trip, let myself relax, and allowed my business to run itself.


Don’t worry about your inbox

The sky won’t fall if you don’t reply to an email for a few days, or even a few weeks.

If it’s truly urgent, of course you can reply, or direct your assistant to reply if you can, but if it’s not urgent, and you’ve written an auto-reply that has clearly explained you’re away and not checking your inbox daily, then you don’t need to reply yet.

Don’t worry about your inbox. You can get home, make a huge mug of tea, give yourself an hour and punch out short and sweet replies to get to inbox 0 then.

In any given year, you’ll probably be on holiday for a lot less time than you’re at home working… so enjoy your holiday, and don’t worry about your inbox.


If you do work, do it well

If you really want/need to do some work while you’re away, make sure you already feel relaxed before you set down to do it, set a time limit, and do only what’s important.

What I sometimes do on holiday is pick an hour where I feel really relaxed and I’m not missing out on anything holiday-related, and give myself a time limit to check through my inbox for anything urgent, clear out some junk mail, and email my assistant Tash with anything important.

Otherwise, when I’m on holiday, I only do work that I feel really called to do, like writing, or brainstorming new ideas (the ones that so often come to us when we’re relaxed on holiday!).

On that note, take a notebook along with you; all those holiday-chill vibes mean some of your best ideas might land in your lap (and head and heart) while you’re allowing yourself to do absolutely nothing at all.


After your holiday

Take your time getting back into your inbox

If you’ve only given a general hint at when you’ll be back from holidays, you don’t need to feel pressured to get back to every person who’s emailed you, so go slowly.

When I get home from a holiday, I like to unpack, do laundry, get groceries, exercise, get a coffee from my favourite cafe, see my family, and settle in back home first.

Only then do I get back into work.

Do what you need to do first, and then move purposefully into your work.


Your business can so easily hold itself up while you’re away

You’re not neglecting or abandoning it; you’re going on holiday.

You’re letting yourself recharge, you’re celebrating, you’re enjoying travel, freedom, space and adventure.

How wonderful is that?

Enjoy yourself, and trust that your business is absolutely, wonderfully, perfectly okay while you’re away.

Because it is.




I’m Cassie Mendoza-Jones

My work is for you if you’re ready to change your beliefs about what’s possible for you.

It’s time to clear away your blocks, align your energy, and call your power back to you.

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