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The Freelancer Files: Sick Days and Freelancing Don't Mix – Or Do They?

by Dana Winslow


The unfortunate reality is that we all get sick and face unexpected events that keep us from working. As a freelancer, it's really tempting to let these interruptions become the source of stress, events that turn our schedules inside-out for weeks. Or, we "power through" sickness and end up prolonging the illness for weeks.

It doesn't have to be this way. In this article, I'm going to help you create a plan that allows for downtime and recovery time on those occasional days when you really need it.

Every Day Is a Good Day.... Right?


Let's face it. If you're a freelancer, you're a bit of a work-a-holic. Pffft.... A bit? No. If you're a freelancer, you are a severe work-a-holic with hopefully-minor OCD tendencies.

You live for the project. But one project isn't enough. So you work to gather multiple clients, shuffling together long-term projects with a few short-term ones. You have pay days circled on your calendar – or at least set to give you an alert from your iPhone (it's the same thing these days, right?).

Now, I know what you're thinking:

All work and no play makes freelancing a dull day.

Okay, okay. I admit, being known or even labeled as a work-a-holic isn't exactly a good thing. I mean, friends and family start alienating themselves from you; you forget to eat, drink, or even stretch. You can't go more than 30 minutes away from your computer without feeling that pull to go back "just for a second" to check your email. You're labeled as a neurotic who can't hold down real relationships because your true love is in your work.

Yes, I admit and I agree that being called a work-a-holic is not always a good thing. But if there were never any perks to being a work-a-holic, then no one would ever turn into one, right?

After all, being a work-a-holic myself, you can see the direct relationship between the quality of work you bring to your clients and the quality of payment those same clients bring to your bank account. Work-a-holics don't do anything half-as... uh, that is to say half-baked. And clients know this. As a freelancer, if you tell a potential client that you're a work-a-holic, will that client is not thinking "Awww... that poor freelancer probably doesn't have a very good social life..."?

Oh no.

That client is thinking "jackpot!" because she knows that no matter what you charge, the work you deliver will be top-notch. As a work-a-holic, you are going to turn in some extraordinary work. It's not going to be half finished, requiring multitudes of edits and revisions. In fact, if it does require any changes, it will probably be because the client changed her mind on something.

Oh yes, to a client, finding out that you're a work-a-holic is a jackpot. And it shows in how they pay you. You get paid more money more regularly. Your reputation grows much faster than your non-work-a-holic freelancer counterparts. And your income becomes much more stable. Therein lies just some of the perks of being a work-a-holic.

All Work...

Of course, being a work-a-holic as a freelancer is very, very different from being a work-a-holic climbing the corporate ladder. Work-a-holics who work as employees in the corporate world get a little bit stuck. Of course, most love it and I bet that not a one of them would admit to being a work-a-holic. But they are also a little stuck. They have to be at work by a certain time in the morning.... which means they have to battle it out with rush hour to get there.

The work-a-holic freelancer? She can start working whenever she wants. She can wake up early, fix breakfast for her kids, hop on the computer and work for two hours, then take a break to drive the kids to school.

And on her way back home to enjoy that second cup of coffee, she can watch rush hour just getting started on the other side of the median. Maybe she even waves to her non-freelancing work-a-holic counterparts. Well, maybe not the waving part...

A few hours later, our freelancing work-a-holic has decided to stop off at a local panini shop on her way back home from depositing her check at the bank. The corporate work-a-holic is shoveling down microwaved something-or-other (leftovers, maybe?) or is fighting lunch hour traffic to meet his corporation's V.I.P. client at a steak house to treat for lunch. Regardless of whether he's eating in the office or eating at a meeting, the corporate work-a-holic is still poring over books, papers, forms, envelopes, and work between bites.

And that's really one of the primary differences: a freelancing work-a-holic eats between projects, while a corporate work-a-holic works between bites. If you have made the transition from corporate work-a-holic to freelancing work-a-holic, then you know exactly what I'm talking about here.

Finally, the freelancing work-a-holic take a final break right around supper time. Perhaps she is eating supper with her kids, or maybe watching her children's soccer games, dance recitals and concert competitions. She checks into work using her touchpad, smartphone or laptop while cheering the kids' efforts. Later, as the kids go to bed, the freelancing work-a-holic returns her undivided attention back to work. Writing the rest of those articles, finishing those codes, and debugging those new sites.

Meanwhile, back on the corporate ladder, the corporate work-a-holic stays at the office. Sure, he might place that client on hold so he can accept a call from his son and hear the exciting news that they've just won that big game. He has supper delivered – or maybe it's still leftovers? There are still reports to be done, paperwork to file, errands to run... then there's traffic-fighting to get home.

The freelancing work-a-holic might wrap everything up for the day sometime before midnight, 10 P.M. if she's really having a good day. The corporate work-a-holic wraps up at the office sometime between 7P.M. and 9 P.M. Maybe earlier if he's had a really good day.

All in all, the freelancing work-a-holic actually works more hours every week than the corporate work-a-holic, but her breaks allow for her to miss just a little less. The corporate work-a-holic works fewer hours every week, but those hours are demarcated by patience-trying travel and meeting with managers, CEOs, partners and anyone else higher up on the corporate ladder. Neither really receives an actual day off. But both love their jobs – and they're good at those jobs. Hence, they get paid the big bucks.

And No Play...

Now, like I said, both the freelancing work-a-holics and their corporate work-a-holic counterparts will miss a lot outside of their work. Neither one will get many days off, vacations, or alone time.

But the corporate work-a-holic won't seem to miss many of the things that he or she will miss. Of course, there's really no way to know for sure whether that corporate work-a-holic actually misses his family or friends. After all, none of us know what's going on inside his heart, right? Could be pangs of loneliness or could be ambition. You see, the corporate work-a-holic has learned how to turn one into the other. There are no physical signs of guilt because the corporate work-a-holic knows that he is doing the best he can – and the extra money and perks make up for it all. After all, work can't last forever. Retirement will eventually come and the corporate work-a-holic knows that his future is set and secure. It will all be worth it.

However the freelancing work-a-holic is quite often wracked with guilt over what he or she misses. And noticeably so. This is mainly because the freelancing work-a-holic quit the corporate ladder in order to stop missing so much of his or her life. But once the "illusion bubble" of a freelancer's life breaks, and the real number of hours kicks in, and they realize that they're still missing so much (even if it is a bit less), the guilt kicks in.

The corporate work-a-holic works right though his vacation; the freelancing work-a-holic doesn't even get a vacation.

The corporate work-a-holic ignores minor pains and bumps and decides to work instead of seeing a doctor; the freelancing work-a-holic doesn't have the medical insurance to be able to see a doctor.

The corporate work-a-holic stays to finish up those last reports because if he doesn't, no one else will be able to do them right. The freelancing work-a-holic stays up to finish those last tasks because if she doesn't, they won't get done.

I'm sure you can see the pattern that I'm going for here. Being a successful freelancer practically requires that you be a work-a-holic. So if you're not already one, then you'll probably start morphing into one soon.

...Makes Freelancing a Dull Day

Which brings me to today. Today, I miss sick days. Or sanity days, self days, me days... whatever you call them. Do you remember when you were younger, before the corporate world and deadlines seemed to rule your calendar? If you woke up and didn't quite feel well, you could make a simple phone call. Ah, that phone call that would allow you to stay in bed just a little longer before moving to the sofa with all your pillows, the television clicker, a blanket and maybe even a cat or two, and lounging for the rest of the day in complete relaxation.

While clinging to the rungs of the corporate ladder, even the strongest of the work-a-holics could call in sick (even if they didn't take advantage of this ability all that often) and still get paid. Contrary to what they might have you believe, their reputation wouldn't suffer, their projects would still get done and their clients would barely even miss them.

But we freelancers know differently, don't we? If we call in sick, our reputation will suffer. Our projects really won't get done and our clients really will miss us. No one else can pick up the slack for us because no one else is there to pick up the slack. And depending on the day, the projects and the clients, our schedule of deadlines for the entire week – or longer – can be knocked irreparably out of whack.

Which is why, when I woke up this morning with a stuffy head, I dragged myself out of bed to find some tissues instead of rolling back over and sinking into my pillows. And when I glanced out the window to see the gray skies and gloomy, salt-covered snow all over everything, I closed the curtains and turned up the heater a little bit instead of throwing on a sweater and curling up on the sofa. And when I realized that it was Monday (ugh) and that I had a lot of different tasks and projects due for today (double ugh) along with three different meetings with clients scheduled for today (what was I thinking), I opened up my iTunes, set up my "working music" library, and started typing instead of rolling my eyes and whining all the way back to bed.

It's for this same reason that when my head feels like it's going to split open... when my temples are pounding relentlessly and my sinuses refuse to let any real air flow through... I do what you might call powering through it. I make myself a hot cup of tea, find my lozenges, and head straight for my calendar.

And, usually, after just a few hours of working, I do start to feel as though I can survive the rest of the day.

If you're a freelancer, you know what I mean. If you're a non-freelance corporate work-a-holic, this probably doesn't sound all that different from what you do... except that no one else is there when I walk over to my computer and sit down with a box of tissues. There are none of those dreadful, circulating "it's going around" feelings, because even though there's no one here to pick up my slack, there's also no one here to catch my cold and, more importantly, to give it back.

So, I suppose that I get sick a little less often than when I worked in radio (microphones have a wretched reputation for clinging to and spreading even the mildest of cold germs in a very short time). So for that, I'm lucky. Perhaps I should stop complaining, then?

So, What's Your Point?

Yes, right... The point.

My point is that you shouldn't have to power through a sick day. Work-a-holic or not, you're still a human being. And human beings are prone to getting sick every once in a while. Human beings get tired, worn out, burnt out, and wake up crabby sometimes. And if this is one of those days for you, then you shouldn't be forced to just power through it.

As a freelancer, you have every bit the same right to take a day off and be sick as anyone else. And all it should really take is for you to call your boss and let him or her know that you're not feeling well and that you need the next day or two off.

Well, since you are your boss, you should be reasonable enough to accept the fact that you're sick and you're probably not faking it. So with that step done, all that's left to do now is to make sure that your company doesn't suffer.

This is where the corporate ladder has the big advantage. You see, when someone calls in sick on the corporate ladder, people on higher rungs begin reprioritizing and redelegating all of the absentee's current projects. Anything of major importance is delegated out to someone else, either on a higher or lower rung, and anything that can wait usually does. Slack is held up, and the individual who just yesterday was feeling stuffy-headed and achy can return to work relatively smoothly.

But, in your company, you're the boss, which means if your one and only employee (you) calls in sick, you have to reprioritize and redelegate what you can. That's where my little rant here comes into play – because I'm going to help you handle those sick days.

First, Plan to Get Sick

It might sound stupid, but in this case it's totally appropriate.

Whether it's the common cold, the flu, or strep throat, nearly every illness has one thing in comon: they all strike suddenly. No one knows exactly when he or she is going to get sick. Sure, you might have a few clues that let you know "it's coming" (insert spooky Jaws theme music here... Da-dum... Da-dum...). Maybe toward the end of the day your head feels a little heavier than normal, or maybe you can feel some aching at the back of your throat – but even those aren't exactly calendar-friendly advance notices.

So the only thing you can really do is to prepare to be sick before you get sick. Start with protecting your reputation and deadlines.

Buffer Your Deadlines

We talked before about meeting deadlines, and one of the tactics that I use for meeting all of my deadlines includes adding a bit of a buffer. If I think I can finish something in a week, I quote a week and a half. If I think I can have a project finished in a tad over a month, I quote two months. And etc.

This actually serves a few different purposes:

  • If I have accidentally bitten off a little more than I can chew, I have time to rework whatever necessary to get everything done without disappointing my clients; and if I'm doing my job right, they never even know.
  • If unforeseen problems outside of my control arise (can you say "hard drive crash"?), I still have time to work through them and finish the project on time.
  • If a family emergency arises or if I get sick, I can get it taken care of without worrying that my project won't be finished in time to make the deadline.

Next, work to meet those deadlines no matter what. Even if you know that you've given yourself a few extra days to finish a project, don't use them all just because you can. If you think that you can finish a project in three days and you quote five, don't procrastinate all the way to that fifth day. You'll completely negate the whole point behind allowing yourself extra time for unforeseen emergencies, events, and sicknesses. Procrastination is not unforeseen – and it has no place in freelancing.

If you procrastinate through all your available time and then, the day before your deadline, you find yourself sick... then what? You won't have that extra time bubble anymore. So yes, give yourself a small bubble of extra time when setting your deadlines – but only use that bubble the way it's meant to be used.

Prepare Ahead for Easy Communication

Next, you want to make sure that if you ever wake up stuffy-headed and achy, you can still somehow easily communicate to your clients if they need you to. So, for that, take a few minutes to set up some email templates that you can use as auto-responders.

At a minimum, you probably want three or four different email templates set up. You'll want one or two that will serve as the "notice" of your illness, and at least two or three responders for those clients who will email you with questions regarding their projects. This way, you'll at least have some variety, so you don't send out the exact same email every time you're under the weather.

Now, these letters are going to do a couple of different things for you:

  1. The initial email template will be the one you send out to notify clients that you're feeling sick and won't be working that day. When you wake up and discover that you're too sick to work, one of the first things you'll want to do is get that email out to all your clients. This template should include:
    • How long you expect to be sick for
    • Whether or not this unexpected illness will interfere with their deadline. Of course, if you've done everything correctly and have not procrastinated, then this section should really just be reassurance that it will not interfere with your ability to meet their deadline.
    • Instructions regarding how and when communications will resume. Let them know that you will not be answering your emails (or your phone!) while you are sick, but that they should still send you any questions and expect a response tomorrow (or the next day, depending on exactly what you're suffering from and how long you expect to be sick for).
  2. The secondary templates will be set up as auto-responders for your email. You can easily set these up by following your email program's directions. Basically, these should repeat most of what your initial email says. Depending on your email program, you may even be able to set up different responders for different clients. For example, you could have one that reads more like a reminder for clients who received the initial "I'm sick" email, and then set up a more generic "thank you for writing me, I am out of the office today" to be sent to any other addresses.
  3. Even though people don't generally like auto-responders, it does still exhibit an open line of communications. Your clients will appreciate the fact that you've chosen to let them know what is happening, and that they can still email you with confidence during your unexpected illess.

Prepare To Avoid Financial Stress

Next, you want to make sure that your finances don't hurt too badly if you do have to take that day (or days) off. I know, especially today, it can be hard to keep together a decent savings account. But if you're a freelance professional, you really should be working to save up some money for everything that might come up, such as taxes and other unexpected bills. Of course, if you're sick for just a day or two, you probably won't need to dip into that savings. But if you find yourself sick for a little longer than a day or two – such as when that strep or bronchitis knocks you out for a week – you'll probably start feeling the stress pretty soon.

And if there's one thing that will prolong your illness, it's stress.

Having at least a small amount of money set aside in a savings account of some sort will help alleviate this stress. It won't make it go away completely, I know. But it will keep you from coughing up your lung right onto your keyboard simply because you "can't afford to get sick".

Let me tell you something – if you're a freelancer and you can't financially afford to get sick, then you're doing something wrong.

Prepare Your Network

Last but not least, make sure your network is up to date. If you don't already have a network of other freelance professionals, maybe it's time you started building one.

Having an alliance with other freelance professionals is a great way to help keep you sane during your freelance career. First and foremost, they can provide you with answers when you have a question and sympathetic ears when you need to rant. Second, if something absolutely has to get done yesterday but you are too sick to get it completed, your network can provide you with your very own slack-picker-uppers.

No one likes to have to refer work over to someone else; but as any professional freelancer will tell you, sometimes there just won't be a choice in the matter. And sometimes, it's better for the client (and, in return, for your reputation) if you do refer another freelancer, at least temporarily, while you're sick. Make sure you have a standing agreement with at least one or two freelancing buddies regarding sick-day policies. If colleagues are willing to pick up a few tasks, or even an entire project, while your sick, you should certainly return the favor when they're sick. By setting up this sort of policy ahead of time, you will have already determined your guidelines and expectations, such as how much notice to give each other regarding referrals and illnesses, breaks in schedules, and the like.

These are all tasks that you want to take care of while you're well because, trust me, if you wait until you're sick to try to tackle them, you're going to have a much harder time getting them all done.

What To Do When the Big Day Coughs

If you've completed your preparatory tasks correctly, when you wake up on that day in the middle of the winter (or, even worse, in the middle of the summer) and your stuffy head serves as a painful sign that you are too sick to work, it shouldn't take long to execute your sick-day plan and crawl back into bed.

Your Step-by-Step Plan

First step, after wrapping yourself up in that extra blanket and grabbing the box of tissues, is to go over your to-do list. You'll need to reprioritize and redelegate everything scheduled for that day. For the most part, this means taking your to-do list and just setting yourself up to get them all done tomorrow or the next day. Although, I should say, don't reschedule everything for the same day. If possible, split them up so that the most important tasks are done the day you get back and some of the minor tasks wait a few days. This will help you avoid burning out right after returning to work... especially if you're the type of person who returns to work too soon simply because you feel guilty about not working.

Tasks that absolutely can't wait until tomorrow should be referred to someone else (which is where your network of freelancing friends comes into play). Email that client and explain the situation, and be sure to copy the freelancer that you are refering in accordance with the sick-day policy that you set up with him or her previously.

Second, once you have reprioritized and rescheduled your to-do list on your calendar, it's time to let the rest of your clients know. If you want, write each client personally. Usually, though, you'll want to streamline and use the templates you created earlier. With the template, you can either send the same one to everyone, or maybe make a change or two and send it out one at a time. Either way, it will save you a lot of time, and you should be finished before the water for your tea even starts to boil.

Once you've emailed all of your existing clients, it's time to set up those auto-responders. These will serve as reminders for some clients whom you've already contacted. Additionally, any potential clients who might be inquiring about retaining your services will know that you are temporarily out and plan get back to them, instead of thinking that you're slow to respond or are ignoring them.

Breath Deeply

And finally, it's time to take a deep breath and release that anxiety that you are inevitably feeling. Work-a-holics hate being forced to take time off – especially for being sick. And that leads to feelings of guilt and anxiety when they aren't working.

Now, I'm not saying that it's unnatural to feel a little guilty or anxious over the sick day. On the contrary, I think it would be a little weird if you weren't feeling guilty. Change is not always comfortable – even a little change such as taking your first sick day in two years. Here, I can even prove it to you.

Without looking down at your hands, clasp them together with your fingers interlocking.

Now, glance down and see which thumb is on top. That's your natural, comfortable grasp. Now, change so the opposite thumb is on top.

Keep them there for a little bit – don't separate your hands. Feels a little different, right? A little uncomfortable? That's because even the smallest change can be uncomfortable. And to us work-a-holics, taking a sick day is a major change. We just don't do it. And I know that.

Relax – Everything's Now Under Control

Even work-a-holics aren't invincible. So, when you've gotten to the point where you just can't work for a day or two, it's important to let yourself deal with the discomfort of such an odd change, and then let that feeling pass. It will feel uncomfortable, but it will pass. So, wrap up in that blanket, grab the box of tissues, the television clicker, some water and even some tea, set yourself up on the sofa and take a deep breath. Let that feeling of guilt finally pass, and really let it go. You've done all you can do related to work today; now it's time to take care of yourself.

And I bet your hands are starting to feel just a little more comfortable now, huh?

How do you handle sick days as a freelancer? Share in the comments below!

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