How to Vacation as a Freelancer

March Break is approaching, and for many people, that means vacation time!  After a long winter, what better time to take a break and get away? It’s one of the few times that the kids are off school, so you won’t need to worry about them missing any time. For many, it’s as easy as booking your vacation days and going. But if you’re a freelancer, “booking vacation days” is not a term that has any meaning in your world.

It’s a common misconception about people who work for themselves; the idea that being your own boss means you can take as much time off as you want. That working from home is the same as just being at home.  It sounds like a spam email: be your own boss and get paid to work from home! So it’s not a surprise that when someone hears that’s what you do, they assume it’s a pretty easy lifestyle. You shouldn’t even NEED a vacation, you’re on vacation all the time! Right?

When you’re a freelancer, hours of the day and days of the week do not have the same meaning as they do for someone who works full time. When you’re a freelancer, you need to be available to work when work is available, or else that work may well pass you by. When you’re a freelancer, you must be constantly aware that the money you are making now is not necessarily an indication of the money you might be making in the coming weeks, months, or years. You need to budget so carefully with the money you earn now, so it will cover the slower times. So how can you possibly afford (literally and figuratively) to take any downtime?

This is a struggle that has plagued all self-employed individuals, and not just when it comes to vacations. Separating life and work is a lot more difficult when your life depends on your work, and your work happens in the same physical space as your life.

So are you doomed to never experience a vacation? To work all hours of the day forever? To have a sick feeling in the pit of your stomach that you’re missing something if you do force yourself to go away?

No, there is a way. It just requires planning.  Planning in a lot of different departments.

Plan the Money:


It’s a double financial hit for Freelancers to go on vacation.  Not only are you saving up money FOR the trip, but you also won’t be making any money while you’re away ON the trip.  So on top of the money you’ve saved to pay for your trip, make sure you have also budgeted properly for bills that need to be paid while you’re away. You’ll also need to consider everything you will spend while you’re actually on vacation.  All-inclusive vacations are getting popular, but even then, it’s easy to spend on souvenirs, clothes, and off-resort tours etc. So be very honest with yourself about your spending habits. If you know you will want to buy some things, but tell yourself you just won’t, you’ll end up feeling very guilty about it when you ultimately do.  This is a vacation. Give yourself permission to enjoy yourself, just make sure you set aside the funds in advance to do so.


As we discussed, you don’t get paid vacation days. But in a full time job, vacation pay is just 4% of your pay set aside to cover vacation days. You can do that yourself, it just takes a little determination…or, failing that, try automation. With online banking, it’s easier than ever to set money aside, and with no-fee accounts, you won’t lose any of that hard-earned money.   A great way to painlessly set aside money is to open a free savings account and set up an automatic transfer of $10 or $20 a week, an amount that could easily be spent on takeout and will likely go unnoticed. Set it aside as your vacation pay, so when you’re away, you won’t have to focus too much on the fact that you are not bringing in any money that week.

Plan the Time:


Tell everyone, EVERYONE, you’re going to be gone, and keep telling them repeatedly in the weeks leading up to your vacation.  Give your clients and contacts lots of notice to ensure that you have time to address anything that may need doing before you go. You know the old expression, better to beg forgiveness than ask permission? That does not fly here. It may seem like your clients are so demanding that you would never be able to tell them you won’t be able to help them for a while, but even demanding clients can be quite understanding if they know the playing field.  If you don’t tell your clients that you will be away, they may not understand why you are not responding to them. They expect you to be available because you usually are. Simply manage their expectations in advance, give them time to come to terms with the idea that you will be temporarily unavailable, and there will be no hurt feelings or misunderstandings while you’re away.


As you’re letting your clients know you’ll be away, phrase it as a courtesy, ensuring all their needs are met before you leave.  It’s also a good idea to extend this courtesy to clients you haven’t heard from in a while. This often prompts clients to think about what needs to be done over the next while, even if it’s something that hasn’t been on their mind lately at all. From there you can work out a timeline as to which things need to be done right away before you leave, and which projects are larger and should be tackled on your return. This will not only make your clients feel like they are getting the star treatment, this will also allow you to come back to some solid money-making work.


Make sure you have an email autoresponder and a voicemail message set while you’re away, and make sure it tells people that you are totally unreachable, even if you may not be.  Clients will email you and call you, even knowing you are away.  Often they forget that this was the week you were gone, other times they just remembered something they want you to do, and don’t want to forget.  If they know you have internet access, they will expect some sort of acknowledgement. If you happen to be attempting to swim across the lake that day, they will not get a response, and they will get frustrated. You don’t want your clients to get frustrated with you, so set their expectations at the lowest mark. They won’t expect anything from you while you’re away, and you won’t need to stress that you might be letting them down.


If you have a lot of trouble detaching for even just a week, you may want to consider finding a backup. If you are the only person managing a website for a client, and that website goes down, it can be very stressful knowing there is nothing you can do about it while you’re away.  It’s not a bad idea to speak to friends you may have in the business to see if anyone might be available for emergency work while you’re away, or speak to a freelance agency about potentially booking someone on an as-needed basis at an agreed-upon hourly rate. That way, if you pick up an emergency voicemail from a client who needs desperate help, you can delegate that work to another professional without the risk of losing your client to a competitor.

With all of these steps in place, you can go away on vacation and even leave your laptop at home.  Truly unplug, breathe in, and enjoy yourself knowing that your freelance business is not going to dissolve into those gently lapping waves on the sand…


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