How to take time off when you’re self-employed (and why you should)


Getting here, however, hasn’t been easy. Well, let me clarify: physically getting here has been easy: or, at least, I hope it has – I’m actually writing this post three weeks before I leave, so while it should technically be as easy as hopping on a plane, and getting off at the other end, I have no idea what will actually happen. (And I’m scared of flying, so let’s just say my fingers are crossed really tightly right now…)

how to take time off when you're self-employed

And therein lies the problem. I had to write this post three weeks before my vacation, because I’m self employed: and when you’re self-employed, there’s no such thing as a “last minute break” – purely because when you’re not at work, there’s no one there to cover for you. That can ALSO be the case in some traditional jobs too, of course: but in most of my previous jobs, arranging a holiday was fairly straightforward – I’d just fill in a request for time off, and then brief my colleagues on what I’d need them to do while I was gone. Sure, they’d grumble a little, but when it was their turn to take some time off, I’d be there to cover for them, and so it went on.

Self-employment isn’t like that, though, and that’s actually something I think a lot of people aren’t prepared for. I know I wasn’t. I mean, I obviously knew I’d be a one-woman band, which meant no one to do my work when I wasn’t there, but I don’t think it really occurred to me just how difficult that would be. In fact, when I started my business, I had all kinds of naive ideas about how the increased flexibility would allow me to just drop everything at a moment’s notice, and head off into the sunset, taking advantage of all of those last-minute travel deals I’d previously been unable to book because I either didn’t have any holiday time left at work, or had to give them plenty of notice. Well, what’s the point of being your own boss, after all, if you can’t do things like that?

Well, as it happens, there are lots of reasons to be your own boss, but unfortunately increased (or easier) vacation time isn’t one of them: sorry. Taking time off is important for your well-being, though, and that can be particularly true when you’re self-employed, or trying to get a new business off the ground. In those circumstances, it’s really easy to convince yourself that you HAVE to work round the clock: not only is work never far from your mind (especially when you work from home, and it’s literally staring you in the face all day), guilt is a powerful motivator, and can convince us that any time not spent working is time wasted.



As I said, I wrote this particular blog post around three weeks before you’re reading it, but I started writing and scheduling other posts long before that: long before I even knew for sure that I’d be going away, actually. Unfortunately, spontaneity just isn’t possible for the self-employed: sure, I can set my own schedule from day to day, but I can only do that as long as the work gets done somehow. What I CAN’T ever do is just drop everything to swan off on holiday, or whatever – if I did, I quite possibly wouldn’t have a business to come back to. If you know when you’ll be travelling then, start planning for the break as far in advance as possible – you can’t really start too soon! Speaking of which…


Even when I don’t have a vacation planned, I try to work in advance as far as possible – so, rather than writing each day’s blog post on the day it’s published, or even the day before, I try to get at least a week’s worth of content lined up – more if possible. This obviously won’t be possible in all industries (and sometimes it’s not even possible in mine, because things WILL come up that you can’t plan for!), but if you can essentially “stockpile” work in advance, it will not only allow you to be a little more spontaneous with time off, it also means you’ll be prepared for emergencies – the thing you want is to be forced to work while you’re sick, after all!


I’m pretty bad at this, because I’m quite shy about asking for help, but you can’t always do everything on your own, so don’t be afraid to ask for help. Again, the type of help you can ask for will depend on the type of work you do, but if you know other freelancers/self-employed people in the same industry, you might want to consider teaming up to trade ‘holiday help’ – so they cover for you when you’re not available, and you do the same for them in return. Asking for help doesn’t just have to be restricted to work, however: it can be tough to juggle your career with family/household commitments, and it’s even harder when there’s no one around to take up the slack when you’re gone, so ask for help around the house, or with childcare etc – every little helps.


For a lot of self-employed people, it can be tempting to try to keep your business running exactly the same way during a vacation as you do the rest of the year – the idea that your clients (or your readers, if you’re  a blogger) shouldn’t even notice that you’re gone. This is also a really easy way to run yourself into the ground, though, so instead, I recommend telling people you’ll be gone for a week or two, so you can attempt to manage their expectations during that time. Don’t be afraid to admit that you need time off: everyone needs a break, and people DO understand that. (Or they should, anyway: I HAVE had readers complain in the past that when I’ve dared to take some time off, but you can’t please everyone, can you?)

how to take time off when you're self-employed


It’s one thing to tell people you’ll be unavailable for a certain period of time, but it can be another thing altogether to make it clear to them that you won’t be taking calls or answering emails from your vacation. When you own your business, or work from home, there’s a certain assumption that you’ll be available 24/7 – even on vacation. I always set up an email autoresponder to let people know I’m out of the “office”, and letting them know when they can expect to hear from me, but during my last vacation I was quite surprised by the number of emails I got which started with the words, “I know you’re on holiday, but…” and then proceeded to ask me to deal with something totally non-urgent, which could easily have waited. It can feel quite rude to respond to those requests by saying, “Yes, I am on holiday, so I’ll get back to you when I’m home,” but unless it’s something that REALLY can’t wait, you HAVE to do it for the sake of your sanity – and also for the sake of any family members travelling with you, who’ll soon get sick of their plans constantly being put on hold while you answer emails.


That’s all very well, of course, but what about things that ARE urgent? Well, a lot of people will tell you that vacations should be technology-free, and that you shouldn’t even THINK about work until you’re back in the office. That’s a nice idea, of course, but if you’re self-employed, it just doesn’t work that way, and there will always be times when you DO have to answer an email, or even do some work. To make that as stress-free as possible, you have to plan your tech. I don’t book hotels that don’t have WI-FI, for instance, but I also take a WI-FI dongle with me, just in case. I also take my laptop, phone, and camera, so that I basically have a little mobile office with me at all times: yes, it’s a bit of a pain, but almost every time we’ve travelled, there’s been a website-related emergency (I’m sure it’s just co-incidence, but it feels like I only have to set foot in an airport, and all of my blogs immediately crash!), and on my last trip I was offered a collaboration I’d have been stupid to turn down, but which required me to do a couple of hours’ work while I was away. So, go on holiday with the intention of it being technology-free… but make sure you have plans in place, just in case that’s not possible!


This one will sound a little bit hypocritical considering that the tagline of this site is “how to be a shoeperwoman”, but one thing shoeperwomen understand is that they can’t be shoeperwomen ALL the time. As I said, everyone needs a break from time to time, and you shouldn’t feel guilty about that, or try to do everything to the same standard, and in the same way you usually would. In my case, I’ve had to accept that when I go on holiday, I won’t always be able to update my blogs as often as I usually do, or with exactly the same type of content, and that my traffic will take a hit because of that. The only real way to avoid it, though, would be by ever taking a vacation, and that’s not much of a solution either, is it? So cut yourself some slack: work will still be there when you come home!

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