How to take two whole weeks off for the holidays as a service provider

Lindsay Page
Josette Journal
Published in
7 min readNov 9, 2021

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And why I am planning it now, at the beginning of November.

Rest is a huge priority for me, my team and my clients at Josette Agency. I believe that to do our best work, think strategically and create quality deliverables; we need to be intentional about our time off.

Photo by Alisa Anton on Unsplash

For me, even a three-day weekend will energize me and get my mind thinking about new ideas. I always feel inspired and motivated after some time off. I bet if you were to measure my quality of work and productivity while rested against a time when I am approaching burnout, I can guarantee rested Lindsay wins every time. I have more output and better ideas thanks to a clear mind and a recharged battery.

As someone who is neurodivergent, this isn’t a huge surprise. Since our brains are in constant overdrive, it makes sense that we need to rest more often.

You get it, and rest is important, especially for service providers like my team at Josette Agency and me.

Social Conditioning and the 9–5 work schedule

Before we go ahead and dig into taking time off, let’s talk about the social conditioning surrounding traditional work schedules.

Let’s be honest, most of us self-employed people moved into the online service provider space to enjoy the “flexibility and freedom” that goes along with it. When I ask my virtual assistant students why they want to be a VA, that is 9/10 the response I hear.

However, what ends up happening is we feel like we should be available 9–5 Monday through Friday because those are the working hours that our clients expect us to be available. So, we make sure we are available.

Then, when we want to work non-traditional hours like evenings and weekends or holidays, we get the opposite judgement. “Why are you working on the weekend?”

A lot of us believe that in order to be considered “hard-working” we need to be working a full 40 hours a week, with our two weeks of holidays a year. Because that’s what our parents did. And their parents. And before that, their parents had to work 14 hour days. To work fewer hours would mean that we are lazy, unmotivated and not ambitious.

However, there is a new perspective I am seeing more and more. If you’re an online business owner and you still work 40+ hours a week, you are doing something wrong.

We have entered a twilight zone that your work ethic is not measured by the time you put into your work but the amount of time you take away from work to prioritize self-care.

It’s about working smarter not longer.

My favourite course creator, Nesha Woolery, piqued my interest 5 years ago (I was one of her first students) when she said she works 3 days a week and travels most of the year. Suddenly I was inspired to craft a schedule and business that serves me and my needs and wants.

That starts with intentional time off.

We have entered a twilight zone that your work ethic is not measured by the time you put into your work but the amount of time you take away from work to prioritize self-care.

My holiday schedule as an online service provider

This is tricky. If you are a service provider, your income is determined by the number of deliverables you deliver in a given month. All of our retainer clients at Josette Agency have a set amount of items and tasks in their packages. So, that means, even if we take time off, they still need to be delivered!

The holidays are sacred to me. I’m a single mom and my daughter gets two weeks off. I love spending that time baking, cooking, watching Christmas movies (The Holiday is my favourite and I already watched it before Halloween, oops) and hanging with my daughter, playing in snow, painting, crafting and trying out some new skill — last year it was felt poking. (Is that what it’s called?) Of course, I want to take this time off completely so I can re-energize for the new year. I always feel so refreshed for weeks after this time off!

Even if I decided to grind through the holidays, my client probably aren’t and they definitely don’t want me pinging them on Asana asking for approvals. It would be considered poor service for me not to consider their holiday.

I take off every major holiday and since there are so many holidays sprinkled in that timeframe, it doesn’t leave many workdays open.

Every year, for the past 5 years, I have taken these 2 weeks off!

7 Steps for taking two weeks off for holidays.

Step 1 — Let your clients know at least a month in advance.

It’s still early in November, and I am letting my clients know I will be away and unavailable. I want them to be thinking ahead too so they can plan for themselves and not be bothered or stressed during their break.

My rule of thumb is 30 days' notice — more is better.

Step 2— Start pre-selling for the new year!

You can keep selling your services for a January start whenever you like. I’ve decided to offer $100 off VIP days in January if booked before the holiday break as an incentive to take action. That way, I can front-load my schedule (and income) and not think about it in December.

Step 3— Share your game plan.

If you need to get your deliverables done in half the time you would normally have, what’s your plan? Are you starting to work on that extra stuff now? Are you batching it at the start of the month? Maybe you have a full day blocked off in early December for each client to complete all the steps — like a VIP day?

Whatever you decide, let them know their options and what you need from them to make this happen! It might take a little bit of extra work for them, but they will appreciate it being done while they enjoy their holidays. This is part of the client experience, ensuring your clients (and you) are prepared!

Step 4— Execute the plan.

Be disciplined with your schedule. Lay it all out in your project management system so you aren’t stressed in those final weeks leading up to your break or worse — not being able to take time off because you didn’t complete your to-do list.

Overestimate your task list so you aren’t panicking as the date nears closer.

Step 5— Pre-book calls for when you get back!

If you want to get together with your client once you are back in action, book those calls before you go on break so you don’t get backlogged immediately upon your return.

Or better yet — send out a form questionnaire to collect all the info before you go on break so there is no need for a January check-in call and you can hit the ground running.

Step 6— Create boundaries over the break.

Communicate with your clients a couple of days before you head into your break and let them know that you are about to be officially “off-duty.” Remind them of what you are have done for them to be ready for the time off (is something scheduled to go out? do you have your deliverables in a Google folder?) Give them one last chance to make changes or requests.

When you have done your due diligence, let them know you are off the clock (and wish them a nice break!) Set your Slack to away, Asana to away, and your email to an auto-responder letting them know when they will hear from you after your break. Post on your social profiles that you are away (even if you still have scheduled posts going out).

Delete apps that you tend to revert to when you get bored so you don’t feel tempted to check in and respond.

Pro-tip (from experience) if you break the barrier of communication over your break, you are giving your clients permission to break all your boundaries.

Don’t be afraid to enforce your boundaries over your holidays. Nothing is an emergency, it really isn’t.

Step 7— Relax

Rest.
Recharge.
Enjoy.

Permit yourself not to be productive. Do whatever you enjoy and allow yourself to truly check out from your business for a couple of weeks because you know that the most productive thing you can do for your business is to rest.

The most productive thing you can do for your business is to rest.

Rupi Kaur Instagram

Are you taking time off this year? Have you started planning for it?
I hope you do! You deserve it.

Subscribe to my weekly entrepreneur self-care newsletter, café josette here.

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Lindsay Page
Josette Journal

I write your weekly newsletters to keep your list engaged | Minimalist Marketing | Content Repurposing | Kelowna, Canada