Why the Week Before Your Holiday Feels Worse Than Any Client Deadline

It’s three days before you go away. Your suitcase is open on the bedroom floor, still empty, and you’re replying to a client email at 11pm because “it’ll only take five minutes.” 😩

If that sounds familiar, here’s the short answer.

The week before your holiday feels so frantic because your projects aren’t set up to pause. The stages aren’t clear, your clients don’t know what happens while you’re away, and everything lives in your head. That leaves only one option: trying to finish everything before you go.

That’s not a time management problem. It’s a planning one. And it’s completely fixable »»»

The week that cancels out half your holiday

You know the one.

There’s a saying in office jobs that taking a day off just means adding that day onto every evening of the week before you go, and the week after you get back. Freelancing can make it worse, because there’s no one to hand over to.

So the last week turns into a sprint. Late nights. Messages sent from the airport. That nagging feeling you’ve forgotten something big. 😬

Then the holiday itself isn’t really a holiday. You’re on the sun lounger, quickly checking your inbox “just in case”, running through every project in your head and wondering whether everything’s OK.

Then you come home and spend your first day back working out where every project had got to and trying to figure out where on earth to start.

One designer I’ve worked with summed up a busy stretch like this: “I’ve been working late every night and at weekends too, and often in a state of panic because I’d already committed to everything and couldn’t see a way out!”

That pre-holiday week is that feeling, squeezed into five days.

---

If this resonated, you're not on your own. This is the kind of behind-the-scenes relatable freelance moments I write about every week in the Freelance Edit newsletter.

If you'd like that landing in your inbox, you can sign up free here and I'll see you there!

---

Here’s the thing: it’s not just you

Nobody taught us how to plan a project around time off, so the break gets squeezed in around everything else.

So whether it’s a celebration, the summer holidays or a long weekend away, the break arrives and the business isn’t ready for it.

You haven’t done anything wrong. It's just that nothing about how things are set up was ever built with a break in mind.

Now imagine closing your laptop knowing everything you promised has been delivered. Your clients know exactly when you’re back. And on your first morning back, you know where to pick up without opening a single file to check.

That’s how my holidays work now, and I’ve been taking unplugged holidays (no laptop, no checking email) since 2019.

In this post I’ll talk you through the three reasons the week before a break gets so frantic, and what changes when your projects are planned with time off in mind. Let’s dig in…

2016 Christmas Eve at the laptop

I was living abroad at the time and had come home to see my family for Christmas. Christmas is a huge deal for us, and I was so excited to be back.

And on Christmas Eve...I was working. 😩

The client was being awkward, yes. But in hindsight, that wasn’t the whole story. I hadn’t managed expectations or timelines properly, and I’d never been firm about when I was cutting off. So when they pushed, I had nothing to push back with.

Compare that to now. It’s October as I write this, and my clients already know my cutoff. There are no projects scheduled in December. Everything is due to wrap up in November. Six weeks out, I’m already sending gentle nudges like “Just to make you aware, there are only x many days left on your project, so I need your feedback by x date please.”

I’m the same person working with the same kind of clients. The only thing that changed is how my projects are planned.

If you're always working down to the wire before a holiday, here's 3 things to look at in your process:

1️⃣ Your projects don’t have clear stages (that your client knows about too)

When a project is just “the project”, there’s no natural place to pause it. Everything feels mid-flight, so stepping away for a week feels like dropping it.

Clear stages change that. You know what’s happening at each point, and so does your client.

For example, my design projects aren't just a "design project". I have multiple stages as part of the project timeline, for example:

A. Trend research

B. Moodboard

C. Initial Designs

D. Revisions

E. Technical Drawings

F. Tech packs

Each mapped out into a timeline that I stay on top of and communicate.

That second part matters just as much as the first. When the stages have been shared upfront and you keep talking about them all the way through, you both know whether you’re on track. There’s no last-minute panic when you mention you’re off soon, because the finish line has been in plain sight all along.

2️⃣ Your clients don’t know what happens while you’re away

If clients don’t know when you’re off, or what that means for their project, you’ll automatically try to finish everything before you go. Every loose end. Every “while you’re at it”. Just in case.

Tell them early (weeks, not days. Or even better, at the start of the project) and your time off becomes part of the plan instead of an interruption to it. Your cutoff date is just another date on the timeline.

And here’s the part I love. When your project has clear stages and dates, the ball sits in your client’s court too. Their deadline for feedback is part of the plan. If they’re faffing around and miss it, the delay is on them, not you, and it doesn’t turn into your Christmas Eve problem.

That’s not being difficult. It’s being clear.

3️⃣ Everything lives in your head

This is the sneaky one.

If your brain is the only place your project status lives, going on holiday means a massive brain dump beforehand and a massive brain reload when you get back. No wonder the first day back feels like wading through treacle.

When it’s all organised in a simple system, you can check at a glance that you’ve done everything you said you would before you go. And you know exactly where you’re picking back up when you return. You don’t spend your first morning back figuring out where the heck every project is.

You might be wondering: won’t my clients be annoyed?

In my experience, no.

In all the years since 2019, I’ve never had a client be awkward about me being away. They’ve always understood.

Most of your clients take holidays too. What makes them nervous isn’t you being away, it’s not knowing what happens while you are. Clear dates, early reminders and a project that’s on track take that worry away completely.

You deserve a proper break

So if the week before your holiday feels worse than any client deadline, it usually comes down to three things: projects without clear stages, clients who don’t know the plan, and everything living in your head.

Sort those, and the whole week changes.

Because you deserve a holiday. A proper one. Not one where you work your socks off the week before, work your socks off the week after, and spend the bit in the middle stressing about everything you’ve got to do and wondering whether it’s all OK. ✨

Freelancing was supposed to give you more free time and, ultimately, more fun. With a bit of planning behind the scenes, it can.

Want more on how to make freelancing work for you?

Every week in The Freelance Edit, I share the behind-the-scenes of how I run my design business around my life, not the other way round. That includes how I’m setting up the run-up to my own Christmas break as it happens.

It’s a free read, straight to your inbox.

Vicki Wallis

Founder, Freelancing Simplified

🔥 Est: 2021

👗 Freelance designer since 2016

🌎 Travel obsessed

🐾 Dog Mum to Max

💜 On a mission to help overwhelmed freelancers find freedom

• Free weekly email •

The Freelance Edit

Build steady income without burning out