How to take a holiday as a Start-up

Author: T-Marie

“Your calm mind is the ultimate weapon against your challenges. So relax.”
— Bryant McGill;

During my first year in business, I found myself working what felt like 24/7, saying no to social events, constantly having the need to talk about my business any time someone would listen, I was obsessed, I was so passionate about making my business work!

The sleep deprivation mixed with the stress and pressure I had put on myself to make my business work even caused a twitch to take residency in my right eye.

I always say ‘if you haven’t cried on your lounge room floor at 2am’ have you really started a business?

It might not be at 2am, but you will have cried, you will have thought what the f#ck am I doing? Am I really capable of this? How will I make this work? And, the one question we all ask… how long will it take before it gets easier?

I also started to think about things I missed, like reading, journaling and eating my lunch without working simultaneously, I even missed listening to new music, I mean who has the time to put a playlists together and what even is Spotify?!

But, what I missed most, was time out.

I missed my weekends and I really missed annual leave. Who doesn’t love the feeling of turning on that vacation notice and walking out the door without worrying if a customer was to call, or what was going in the email campaign this week. .

For me, it wasn’t long until those 5am starts and late night finishes took their toll. I remember coming home from work on a Friday night and hearing my alarm go off at 6am on Saturday, whilst excited for the project I was about to start work on, I walked into my bathroom, brushing my teeth and starring at the mirror in uncontrollable sobbing.

I had toothpaste foaming out the sides, tears streaming down my face and this god-awful sobbing noise that I assume was my brains attempt at crying.

Anyhow, I wasn’t crying because of working on a Saturday, I was crying because I was tired. Literally tired, I wanted sleep and I wanted to wake up to a light filled room, not be up before the sun rose.

Don’t get me wrong, I absolutely loved what I was starting, I loved and still do love the people I get to meet every day. I love watching my ideas transform and I even love seeing myself grow. But, if you want to see that stuff you can check my Instagram. This post is about the hardships of a business and realising that sometimes, personal timeout is the best thing you can do for your business.

This is for the seekers, dreamers and doers. This is for the people that believe in their product or service so much that they are willing to work for it, day in and day out, but are worrying they are running themselves into the ground.

That’s where I come in. I am going to tell you, how to take a holiday.

My 5 steps to prep yourself for a holiday whilst running a business are:

  1. Firstly, write down three things you don’t have time for anymore as a small business owner.
  2. Prepare, prepare, prepare.
  3. Stop saying yes.
  4. Prepare some more.
  5. If you feel guilty, just work.


Step one. The three things you miss.

Mine were; reading, writing in my journal, swimming and travel. (Wise, I know). These three things are three things you are doing for yourself. If you miss painting your toenails and having time to fake tan, write it down, if you miss playing golf or going on date night with your partner, write it down. It doesn’t matter how big or how little, if you miss it, it’s important.

Now, we’re going to come back to these a little later.

Step two. Prepare.

Setting up a business that can run without you is hard, but it’s also crucial. I’m definitely still working on it myself. But we’re not stepping away from the business completely just yet, we’re simply taking a holiday. To do that, we need to prepare the business to not have you there for that duration.

You need to be realistic about your time off, can you go for 4 days or can you go for 3 weeks?

However long, how will things run if you’re not there? How will the business go financially?

The customer is priority, so how are they going to cope? Do they know you are leaving? Who is their point of contact whilst you’re away?

Are you going to close off all those client jobs before you leave? Are you going to make the store close whilst you’re away?

Prepare & prepare some more.

Step three. Stop saying yes.

If you have a service based business like mine, you need to stop saying yes. I found this one particularly hard.

For some reason the moment I decided to take a trip, I had new enquires pouring in, and I mean that’s amazing right?! But wow, where were they two months ago when I was stressed about how slow the month was going?! #MurphysLaw

I found it hard to say no, and I didn’t at first.

I actually signed a client a couple of weeks before I left and promised them a website 5 days before I was departing. I cannot tell you how stupid this was of me. The extra stress I put on myself was completely avoidable if I had of asked them to wait.

I even had a meeting with another potential client 2 days before I left, this client was a big deal and one I was super keen to work with. And I was shitting myself about telling them I was going away. Worrying that they wouldn’t want to work with me! But I managed to string this sentence together:

“I can help you, but I will be away from xx to xx and that means your project won’t begin until I’m back, is that ok?”

They looked at me and said “that’s amazing, you deserve a break, that’s completely fine, I can’t wait to work with you”.

Now, this lady is a little further ahead in business than I am, and before I knew her I used to look at her and think ‘wow, she is so well put together, she looks like a power woman’ and here she was, someone I looked up to, telling me I deserved a break!

The moral of this is… not only do you deserve a break but, you’re clients will understand.

Step four. Go back to step three and prepare some more.

Step five. If you feel guilty, just work.

Before I left for my trip, so many people told me to leave my laptop at home and to make sure I switch off 100%.

It sounded lovely in theory, but my business is my baby and leaving it completely unsupervised was not going to happen whether I liked it or not.

Day one and two I completely indulged in the sunshine, swam in the ocean, finished the days with cocktails and had unforgettable experiences. Work was not on my mind.

Day three, a simple work thought slipped into my mind… followed by a quick peak at my inbox and I saw a few things I could easily reply to, but I fought the temptation and reminded myself my auto response was on.

Five minutes later there was no turning this switch off… How were things going? Have I told everyone I was away? Are my staff ok? Are there any new enquiries? Am I missing any opportunities?

At that moment, I decided it was ok. I jumped out of bed, grabbed my laptop, headed to the breakfast bar and caught up on a few emails, worked on a few small projects, checked in with staff and started writing this blog post.

I felt good.

I then started with step one, and went over the things I missed since being in business. I made sure I did as much of the things I missed most as much as possible over the next 4 days.

As my week continued, if worked slipped into my mind, I assessed the thought and really asked myself if it could wait… if the thought was still in my mind the next day, I actioned it and I worked.

I created a simple holiday / work balance.

Yes, it would have been nice to not work at all and some of you may be fortunate to have setup shop to this ability already, some of you may be better preparers than me, and some of you may have just been able to switch off. Which is great. But for me, I was happy spending 10% of my time off working, if it meant my mind was at ease.

So, if you feel guilty on holiday, just work. Allocate a certain amount of time even if it’s just one day for one hour, do it, forget about it afterwards and then enjoy your much deserved time out.

I’ve been back from my holiday for a little over 3 weeks now and whilst it took a couple of days to get into the full work swing, my mind has never been more clear and focused on how I can positively grow 2aT and take it on to bigger and better things!


T-Marie x



Remember, nothing posted on this blog or website constitutes, or is meant to constitute, advice of any kind.  If you require advice in relation to any small business matters, we highly recommend that you consult an appropriate professional. 

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