Time Off? How to Manage the Holidays

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Do you like to take extra time off over the holiday season? Or are you one of those people who can’t wait until it’s over?

When you run your own business, working out how to handle time off is difficult at the best of times. Planning for the holiday season it can all feel like even more of a minefield.

This article provides you with some essential tips for handling your holiday dilemmas.

A Quick Reality Check

In some respects, the freedom of freelancing means you have way more flexibility in organising your time off. It’s not like you need a “boss” to authorise leave if you want an extended break for Christmas. Nor do you have to forego time with your family because it’s “not your turn” or because you didn’t ask quickly enough.

However, like so many things in life, it’s not really that simple. If you sell services to other businesses, you may end up having to organise your time off around how they want to handle the holiday season.

Some companies are happy to “shut down” over Christmas and New Year. Other firms may have “Bah Humbug!” owners who will expect you back at your desk long before you’ve consumed the turkey leftovers. Young startup founders who’ve yet to have families of their own can be particularly bad for this! Then, on top of that, you have cultural differences, which often mean clients in different countries have vastly different expectations of when people will be available over the holidays.

Like I said, it’s a minefield, so here’s now to get through it.

Decide what YOU Want

If you work for yourself, it’s entirely up to you how you handle the holidays. This is one of the big plusses of self employment, so it would be an awful shame not to take advantage of it.

Christmas Calendar

So, before the season gets underway, work out what YOU want.

If you have lots of family to spend time with, perhaps you want a long, extended break? If you don’t, maybe you’d prefer to escape and take a holiday? Or perhaps you’re one of those people who’d cancel Christmas if it were feasible, and are actually perfectly happy to take on as much work as you are offered?

Work all this stuff out before you do anything else, because everything else depends on it.

Speak to your Clients Early

If you have lots of clients, especially businesses, you’ll need to find out what their plans are for the holiday season, because theirs will impact yours.

When I did lots of IT consultancy, I had about ten primary clients whose office networks I was responsible for. I’d often find eight were happily shutting down for a week while an annoying two still required cover from me. This was annoying!

You may find that you are obliged to accommodate certain clients and be available for them. However, the earlier you tackle the issue head on, armed with knowledge of what YOU want, the more likely it is that you’ll be able to make compromises.

Plenty of freelance jobs don’t involve anything like having to be on call if a server stops working; If you’re a writer, for example, you may well be able to take a long spell of time off by getting ahead on regular articles first. I personally do that a lot!

The key thing is that you ask, with plenty of time to spare, what your clients will be expecting of you, and align it to your plans. This means understanding how your clients’ businesses work, as well as your own.

Get Ahead

It’s always good practice to “clear the decks” before taking any time off as a freelancer.

Clearing the decks

This can mean various things; We’ve touched on doing work ahead of time to get ahead, but you will probably also need to do some routine tasks that would otherwise need doing during the time you plan to be off.

For me, this means things like using my social media tools to pre-load Twitter and Pinterest with posts, getting invoices issued, cueing up newsletters to send out while I’m off, and various other things.

It’s all very well thinking “I can just do that on the day,” but it only takes the smallest of tasks to kill the relaxation vibe and flip you back into work mode. It’s well-documented the time to unwind is crucial.

I often have some of my best ideas and inspirations once I’ve allowed myself NOT to think about work for several days. Sometimes it’s a good thing to “turn your hustle off.”

Manage Expectations

Part of managing expectations is ensuring your clients know, in plenty of time, when you are working and when you will be “back to normal,” but it doesn’t end there.

It makes sense to share your plans as transparently as possible. For example, if you have a busy social media presence and usually reply quickly, post a pinned message to explain that that’s going to change for a week or so.

The same goes for email; You don’t want clients to think you’re ignoring them, so make sure that they will receive an auto-response telling them when to expect a reply from you. This is basic professionalism, but it’s surprising how many people don’t make the effort.

And while we’re talking about etiquette, it’s good to show some gratitude during the holiday season too. It’s a good time to thank clients for their business and staff for their hard work.

Prepare for the Financial Impact

It’s not true for absolutely every freelance business, but for many the holiday season means a drop in income. One trend I’ve also noticed over the years is that it often seems to take longer for things to pick up in January than one might expect or like. My theory around this is that many of the workaholic types finally slow down enough at Christmas to rediscover relaxation and family life and don’t want it to end!

Money jigsaw

It’s one of the inevitable ups and downs of freelancing that there are quiet periods like this. It’s easy to get “the fear,” but it’s far better to accept reality and enjoy the downtime. Things do pick up, and the likelihood is you’ll soon be wishing for a day off again!

This is a good time to do some of the tasks you’ve been putting off, to take a training course, or to work out your big plans for the year ahead. Depending on your business’ financial position, you may have to make use of your overdraft or cut your expenses back in January. Thankfully it always seems (to me at least) like a perfect time to do so after the excesses of the festive season.

Of course not every business has a quiet holiday season. Some firms are at their busiest at that time of year – and not just the obvious ones. One thing I heard recently that surprised me was that investment-related companies often up their written output over the holidays because lots of people read up on such things while they have time off – who knew?!

However your time off impacts your finances, just remember it’s only temporary, and don’t let it spoil what should be a special time.

So there you have it – the strategies I’ve developed to cope with seasonal time off after 15 years of freelancing. If you have any of your own to share, I’d be delighted to hear about them in the comments.

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About Author


Founder of HomeWorkingClub.com - Ben is a long-established freelancer with a passion for helping other people take control of their destiny and break away from "working for the man." Prone to outbursts of bluntness and realism.

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