Writing and Stuff by Anthony Chatfield

For most newbies to the freelancing game, the hard part comes in actually finding work. But, once you find the work and it remains steady, what comes next? How do you start churning out quality work at a rapid enough speed to actually make a solid living at this?

I’ll be honest – I type extremely fast. Usually not when I’m writing a book or working on a website’s home page, but when developing SEO articles I can hit a pretty mind boggling speed, but it wasn’t always like that. I started out writing just one 500 word article an hour, which for most of us will not pay the bills (especially after Elance or PayPal get their share), so I figured I’d sit down and share the five things I’ve done to kick my fingers into high gear.

Set Goals and Watch the Clock

I’m a competitive guy, way more competitive than anyone I know. So, when it comes to typing, the easiest thing I could do was compare myself to other people. But, it turns out, most people are annoyed if you ask how many words per minute they type. So, instead I start competing against myself by timing how long it took to write 500 words. Yes, a lot of it has to do with research and how much coffee you’ve had, but there is a surprisingly large amount of the process bound up in the physical act of typing. Start aiming for goals and you’ll be shocked how much faster you type.

Find the Right Keyboard

I’ve learned over the years that I need a few things to type faster. One, I need to be able to hear the keys, so the quiet touch keyboards on a laptop don’t work for me. Which in turn means I break them fairly easily by typing too hard. So, now I keep a $15 Logitech USB keyboard on hand whenever possible so I don’t hurt my laptop and so I can hear the satisfying tapa-tapa of fingers on keys. I also turn off the noise cancellation in my headphones. It’s fantastic on an airplane, but it messes me up when typing.

Learn Shortcuts for Popular Software

I’m probably going to write a longer post on this one in the near future, but for now I’ll just point it out. Keyboard shortcuts are extremely valuable when it comes to getting things done faster. Knowing that CTRL+W closes a tab in Firefox or that CTRL-SHIFT-> will make a selection bigger in Microsoft Word will carve all sorts of time off your typing speed. Memorize keyboard shortcuts – they will make your life easier.

Get a Faster Computer

Maybe not the most practical piece of advice I could offer, but it’s important nonetheless. I like to multi-task…a lot. I have between 5 and 15 windows open at a time when I’m writing, holding my notes, resources, links, and whatever additional research I need to do while typing. If it takes a minute or two to open a new window, that’s a minute you could have been typing. It may sound like nitpicking, but the speed difference adds up very quickly.

Copy and Paste Words You Have Trouble With

This is a fun trick if you use it right. I tend to avoid any copy/pasting when I’m writing longer content like eBooks, but when I’m doing keyword articles, a copy paste function is huge. For example, I used to write a lot of World of Warcraft content. Just take a look at some of the names those characters have – Agamaggan, Alexstrasza, Fizzcrank, Gorgonnash…the list goes on and on.

Not only do words like these slow me down when typing, they aren’t real words – so the word processor won’t spellcheck them unless you manually add them to your dictionary (another tip for later). So, copy and paste the word or phrase you’ll use most as you type. Oh, and make sure to use the keyboard shortcuts for copy and paste (CTRL-C and CTRL-V).

Before I end this post, I want to point out something very important – speed is not the end all of freelance writing. In fact, speed will get you in all sorts of trouble if you’re not careful. Quality needs to be number one on your list at all times. But, when speed is called for in SEO articles or for a side project of your own, these tips will help you really kick start your output.

Finally, I’d love to hear everyone else’s speed writing tips. What do you use when a deadline is looming or work is backing up to churn out a few extra words per minute?

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So, in the last year or so, I’ve realized the dream of every web freelancer and gotten to the point where I can make enough money each month without having to bid on projects at sites like Elance or Odesk. Now, they serve the purpose of escrow services and I can show off my fancy Level 10 Rating in the Writing category (number 3 ranking – woo!) But, I wasn’t always at this point. I did a lot of projects on Elance and that means I wrote a LOT of proposals to get those jobs.

When I started, it was a crapshoot. I would post my bid, hedging and hawing to impress and hope I got lucky. Then I realized that I needed to bid more, so I started sending out huge chunks of bids. Then I realized I just needed to spend more time working on each bid. Over the course of three years, I developed what I like to think is a good game plan for how to write an Elance proposal. So, I thought I’d share.

1.    Know What You Want to Work On (but don’t be picky)

There is a fine line that all freelancers must walk. On one side you want to write about things that you like – topics that you have an innate interest in and some knowledge about. But, you also cannot be too picky. Picky writers are unemployed writers. On top of that, you’ll limit how much work you can get. There are hundreds of potential projects out there at any time – if you can only write about rice cookers and dog training, there are only so many you can bid on.

2.   Check the Buyer’s History

Bids are finite on sites like Elance. You pay for all of them, so spending 4 of them on a larger project when the buyer has never before awarded a project or has a history of poor sportsmanship with their providers is a bad idea. Always check a buyer’s history for three things:

• Their Award Ratio – Less than 10% means they’re just skimming for data and likely won’t award the project.
• Their Feedback – Look for people who had trouble getting paid, finalizing a project, or communicating with a client.
• Low Pay – Sometimes it is obvious from past projects whether someone is willing to pay enough to cover your rates. If they are used to paying $1 an article, don’t bid. The odds are stacked against you.

These are not always definite issues and if you are invited to bid on a project, feel free to toss in your two cents. Most invites are free to bid on and the buyer is likely to show at least some interest.

3.   Check Existing Bids

Look to see what the existing bids on a project are. If there are 47 bids on a project and both sponsored spots are full, the odds are that your bid may not even get read. Yes, a good half of those bids will be discounted from new providers or people overseas, but even then you’re up against 20+ bids from qualified writers. Unless you bid on a dozen projects a day, stick to the odds and find projects more likely to award to you.

4.   Check for Invitations and Other Disqualifiers

Many times a buyer will invite just one provider to a project but forget to make it private. These are easy to spot because there will be a single invite at the bottom of the project. Don’t bid on these unless that person has declined the invite or you feel you can truly knock the project out of the park. I’ve sniped a handful of these single-invite projects in the past when it was a topic I really knew well, but the odds are against it.

5.   Don’t Use Canned Bids

Every single bid you write should be original and catered to the project you’re bidding on. Don’t write a single bid for articles and a single bid for ebooks then copy and paste them. I have found very little advantage in sending PMB messages in lieu of bids – the award ratios are about even – but I have found that I get 2-3 times more awards if I personalize my bids, plus I get higher rates as a result.

6.   Polish Every Bid and Personalize It

Don’t just write original bids for each project, polish the bid and proof read it carefully. Imagine what someone thinks when they’re hiring a writer and they receive poorly written bids with typos and grammatical mistakes. Write the bid like you’d write their finished project.

Additionally, if you can find their name somewhere on their profile, in an attachment or on the proposal, use it to personalize your bid. This will have a profound impact on many buyers.

7.   Be Honest at All Times

Avoid the urge to “pad” your bid with experience you don’t have. If you really want to write about solar gardening but have never written about it before, be honest. Say “this is new, but I learn very fast and am extremely interested in it”. Many times, these buyers are experts themselves, so if you claim expertise and then fail to follow through, they’re going to notice. Be honest and you have no one to disappoint.

8.   Provide an Outline of Your Process

In your bid provide a complete outline of the process you use. For example, in my bids I tell the buyer the rates I charge, how I produce my outline, the deposit I require, and when I will deliver each milestone. This shows them that you are organized, have thought out how to approach their project, and have done this before. The more in-depth you can be with your proposal at this point, the better it will perform against vague, cookie-cutter bids from other bidders.

9.   Provide Everything they Ask For

Carefully review their proposal and make sure you answer every single question they ask. Some buyers have dozens of questions and the only way to prove you read it carefully is to respond to them all. Don’t take any shortcuts here – it will only harm your bid.

10.   Take on the Role of the Expert

Many people try to defer to the buyer to get a job. They say things like “I can do it this way, unless you like it done some other way.” Never do that. It belittles your intelligence and the natural abilities you have to write effective copy. Instead, tell them exactly how you will do it, exactly what you expect, and exactly what expertise you will bring to bear.

The only caveat you should add is a simple “I am very flexible in many regards – contact me if you have any questions or comments”. This covers pretty much any issues they may have. The confidence to tell someone how you will do their project is often enough to drive home your bid.

Elance is a big marketplace, but in reality, if you do a good job and build up your reputation with 5 star reviews and good earnings, you’ll immediately jump into the top 10% of all providers. From there, it’s a piece of cake to get new projects. You just need to be confident of your abilities. Trust me – the business owners and entrepreneurs on Elance are not as well versed in this business as you think they are. They’ll jump at someone who acts and talks like they know what they’re doing.

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I may not be the best person on the Internet to give you diet and exercise advice, but I can say this – it definitely helps. I have something of a forced incentive on this one. I have a gluten intolerance which means I cannot eat most junk food and have to cook most of my own meals. At first, this was a big chore. As time went on, I realized that I think much clearer when I am not eating McDonald’s and Doritos every day. Which of course lead to the big revelation (get ready for it)…. a healthy diet helps you think clearer.

Yeah, I know – I should have my own TV show, right? Seriously though, if you haven’t yet, give this a shot, because the effects are even more than I would have imagined. You know that fuzzy headed, cotton-ball feeling you get between your ears when you try to think of a word and it just wont’ come? It turns out that when you get all the vitamins and minerals you need every day and cut out all the processed junk, that feeling almost completely disappears.

So, what do I recommend? I’m not going to give you a diet plan to follow, because I’m not a nutritionist or a doctor. However, I can tell you what I’ve done. First, I eat breakfast bright and early every day. Not just a pop tart on my way out the door – it’s a bowl of fruit, a big glass of water, and some yogurt – occasionally with a bit of gluten free toast for substance. Next, I’m a vegetarian. It wasn’t some super-discovery on my part about how meat is raised (though since I became a vegetarian, I’ve read some horrible stories about farming practices and the hormones in meat and dairy). It was simply how much easier it is to not eat meat, and by proxy most dairy products. Finally, I don’t drink caffeine – at all. The only caffeine I’ve had in the last five years is when I take a red eye flight across the country and need to stay awake for another 12 hours.

The result is that I sleep better, wake up much better, and can think clearly throughout the day – not just when I’ve had my coffee. Now, when you top all that off with a round of exercise every day – at least 30 minutes of stretches and some form of aerobics – the impact on your mental clarity is ridiculous. Plus, it makes you feel good. Your body is pleased that it’s getting what it needs, so when you sit down to write, it hums with energy.

That’s my public service announcement for the day – exercise and proper diet are good for your mind. I know it sounds cliche, but it’s incredibly true. Don’t think of it as something to help you in the future; think of it as a way to boost your productivity right now and start living the dream of being a full time writer. That’s when things really start to kick into gear.

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For a freelance web writer, there are millions of projects available every year. There’s just one problem. They are generally about topics you have no interest in, no knowledge about, or very little desire to write about. It’s a pretty common problem, and unfortunately, there’s nothing you can do other than suck it up and write about less than glamorous topics, or eat a lot less and hope you get lucky. Eventually, you’ll grow beyond the necessity of doing “whatever comes your way”, but early on, few of us get that luxury.

So, what do you do when a fantastic job opportunity comes along in a niche you’ve never written about? How do you prep yourself to take on a topic with an authoritative voice when you’ve never written about it before?

First, Some Ethics

I should toss out a disclaimer here. If you really, honestly have no idea what you’re writing about and the project needs an expert in the field, don’t lie to get the work. It’s not only dishonest, it will rarely result in good feedback or more work. If a niche is new to you, tell the client up front. If they know that you’re starting from scratch, they can make the determination of whether they should look elsewhere. Of course, you’re permitted to speak highly of your research and learning capabilities, but never lie about knowledge you don’t have.

Learning the Niche

Okay, so you told the truth and the client is okay with it. They have seen your quality of writing, are impressed with your talents, and want you on the job anyways. What’s next? It’s time to start researching. Without research, you put yourself at risk in a number of ways. First, you will be tempted to cheat – either rewriting other content or making up bits and pieces. One is copyright infringement and the other is simply unprofessional.

So, you should spend some time getting familiar with your topic. Buy at least three or four top books in the niche and start reading. Additionally, read some related content online, to get an idea of the common phrasing used and watch videos to absorb audio/visual cues (it’s always easier to write about what you’ve actually seen). I also like to visit blogs and forums where industry insiders will chat about topics in the niche. Familiarize yourself with the wording and the way the content is structured. This will help you create a more detailed persona in which to write your articles.

Writing the Content

When it comes time to write your content, only start when you feel comfortable in your knowledge. Also, put your research materials on hold. You shouldn’t be reading a book while you write about the same thing. The risk of offhanded plagiarism is too high – you may not even realize you’re doing it. Instead, take notes from all of the resources you have been gathering and use them to build your content.

Finally, when you’re done writing, run your content by someone who knows their stuff. You can ask someone on the forums or send it back to your client for review. The goal is pretty simple – you want it to pass as a comprehensive, generally informative piece of content. If you cannot do that, this isn’t a niche in which you should be writing.

Be Truthful

One last note. If you get to the end of a piece and realize that you just cannot write in the niche – maybe it’s too general, maybe it’s just plain awkward – let your client know. Most clients will be happy that you’re not only honest with them, but that you say something quickly instead of dragging out the project and wasting their time and money. Trust me, it’s better for your career to focus on things you know you can write well and not to send in subpar work to clients than to aim for profits and profits alone.

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A lot of newcomers to freelance writing have asked me whether the article spinning projects are a good idea. They are easy to get and they generally represent ongoing work – or at least that’s the argument.

And to be honest, I completely understand the attraction. When you’ve been writing for a few weeks and cannot get enough work to feed your family, let alone pay the bills, anything starts to look attractive. But, before you honestly consider taking on “rewrites” or “spinning” projects, consider a few things.

1. Your Time Investment – The argument most clients use here is that rewriting takes less time than original content. This is sometimes true, especially if it’s a research heavy topic. But, a good rewrite still takes a lot of effort. You cannot simply rewrite every line and call it new. It won’t flow, nor will it provide anything useful to the reader.
2. Who Owns that Article – Then there is the legal issue of who actually owns that article. If the article is not owned by your client, rewriting it is copyright infringement – a serious legal issue. Never rewrite content unless your client owns the original copy and you’re confident you can create an original piece of work.
3. Can You Really Live Off that Much? – This is the big one. Sure, it’s steady work, but can you live off $2 an article. Most people can’t. I don’t care if your cost of living is a quarter of someone who lives in the big city, you need to make at least minimum wage doing what you do, and $2 isn’t going to get the job done.

Of course, I know the realities of this business. When you first get started, it takes samples and practice to get anyone who will pay for original content interested in your work. I’ve talked about how Micropay can help, and I’ve also talked about how to start raising your rates when you get underway, but those first few weeks are brutal.

But, for your own sake and for the sake of the content quality on the Internet, avoid rewrites as much as possible. They are generally used for spamming or keyword stuffing, may present a copyright issue, and don’t pay very well. Plus, having them in your portfolio rarely looks good.

Do what you need to get started (within reason), but once you’re started, seek out work you can be proud of. It may make things tougher for a short while, but the pride you feel in what you write will counteract that nicely.

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Every now and then, someone asks me what kind of equipment I use. They see the iPhone and assume I’m a Mac guy or sometimes they just think “writer=Mac”. But, in truth I’ve been a PC guy for my entire career and don’t plan on changing any time soon. It would be too much of a chore – I’d need to overhaul how I do a lot of things, plus repurchase hundreds of dollars worth of software.

But, one thing I do change a lot is the kind of PC I’m using. As a freelance writer, being mobile is absolutely necessary. If I want to visit family, I need to have the option to login and check a project’s status. If I feel like working out of the house, I want to have as much power in the coffee shop as I do at home. So, I’ve experimented quite a bit with different machines and setups.

It works out pretty well as I tend to burn through a laptop in a year and a half or so. Apparently typing 150,000 words a month on a laptop puts a lot of strain on it. Who knew? But, lately, I’ve hit upon a nice balance between three very different devices…and yes, one of them is made by Apple.

Laptop

First up, there’s the laptop. For a lot of years, I only had one of these – in fact, I’ve had three of them since I started working online (one of which was a few years old when I got started). Today, I run on a Toshiba Satellite A505 because it’s got a full sized keyboard and 7 hours of battery life – the perfect combo for travel and multi-tasking. Yes, it’s a bit heavy, but with a good backpack to lug it around in and regular stretches, I do pretty well with it.

Netbook

I never owned a netbook, but my wife did and when I upgraded my laptop in January, she got the older Gateway that I no longer would be using. So, we had a netbook lying around. I’ll be honest – I’m not a huge fan of netbooks. They’re too small for what I do. Yes, they’re great for email, but so too is my phone. And my hands are really big.

But, when I got my office space, I wanted to put something in place that minimize how often I had to lug my Toshiba to work but wasn’t too valuable to leave sitting around. So, I took the netbook, bought a keyboard, mouse and monitor and setup a makeshift workstation on my desk. I lock the netbook up at night and can go to and from work without any bags. It’s a great setup except when I need processing power for web design or video editing – in which case, I bring the laptop to work with me. Plus, if I need to go into the city for any reason, the netbook weighs less than a bottle of water and fits nicely in a hand-held pouch.

The Tablet

Admittedly, I didn’t need a tablet for work. I won’t be writing it off as an expense because it’s 85% entertainment, but the iPad I picked up in the spring has actually been fairly useful. It’s small and lightweight like the netbook, but far more versatile for travel. Basically the only thing I will not do on it is write articles because I type far too fast on a keyboard to be satisfied with the clunky setup of the touchscreen.

But, I can do email, login to check projects, and when I’m not checking work stuff, watch a movie or read a book. This device is awesome and it’s far more comfortable to hold than a laptop.

The Bottom Line

Yes, I have three computing devices, but they all serve their purposes nicely, fitting a specific niche of my life and making it as easy as possible to get between work and home and everywhere in between. Combined with Dropbox (the freelancer’s best friend), and Thunderbird, I can write an article in my office, send it from home, and check its status on the train – all using different devices. Ironically, I do not own a desktop and have not owned one in nearly four years. Maybe it’s just me, but without mobility, I don’t see the point in spending that much on a PC.

If you’re trying to figure out which device is best, I say start with a laptop – one with enough power to open 20 tabs in Google Chrome and run 15 or so windows in Microsoft Word. With the basics covered, everything else is icing on the cake.

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I think the title says it all…and the answer is nothing. This is an issue that goes way beyond freelancing, as millions are finding themselves in the dog house for saying the wrong thing about their boss, their family, or their friends on Twitter (or Facebook). Here’s the thing. Twitter is incredibly easy to follow, and if you’re lucky, your clients will gladly sign up for your feed as soon as they realize you have one.

So, what then would be the goal of putting your personal thoughts, or worse yet complaints, on Twitter where those very clients can see them? In this day and age of hyper-connectivity, it becomes your job to censor what you say and where you say it. Once upon a time, you could vent openly about how hard your day was to anyone, even online. People didn’t have access to your inner thoughts, usually stored in email or a personal site where very few people had access.

Unfortunately, people seem to lose that sense of privacy when they sign up for Facebook or Twitter. They feel like they’re simply sharing with a few friends – getting their ideas out there or shooting the breeze like they would at a bar after work. The problem with that is your mom, your clients, and your colleagues can all see what you’re writing.

It’s why I offer social media cleanup services, to help individuals coming out of college or trying to get a new job to clean out all the 20-something shenanigans that litter their accounts. Describing drunken debauchery or saying borderline offensive things on your page can cost you a job or your friends if you’re not careful. So, what do you think happens when you get online and start rambling on about how your latest client “really gets under your skin”?

There really isn’t much else to say. If you’re striving to be a freelancer and build a brand for yourself online, it’s time you start cutting out the cursing, the open commentary, and pretty much anything about your current clients. You can still personalize your feeds and Pages – clients love to see it – but at the same time, make sure you keep it as professional as possible. This is your livelihood we’re talking about.

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One of the biggest problems I see in my fellow freelancers is that they are unwilling to bump up their rates when they know they are worth the money. Well, not all of them. Some people will gladly bump their rates up too early and then inundate your inbox when you post a project on craigslist (ahem…). But, for the well-meaning majority, the issue of rates and getting paid what you are actually worth is a HUGE deal.

If you sift through the archives here on the site, you’ll see that I once worked for micropay sites like AssociatedContent and Helium, making between $3-$5 for 1,000 word articles. It was horribly low paying, but at the time I was exhilarated to get paid for anything and to see my name next to a block of text. I even used to sit and track page views to see how many people had read my articles.

That jubilation passes when you realize you do in fact need to make enough to pay your bills if you want to quit your job.

So, I migrated to Elance, quit my job and promptly struggled by for the next 15 months. No matter how fast you type – and I’m a fairly speedy typist – $5 an article makes it very hard to get ahead. So, I slowly started creeping my rates up.

I was terrified it wouldn’t work, that my regular clients would abandon me and I would go broke. A funny thing happened though.

1. I didn’t go broke
2. Many of my regulars did abandon me, but a lot stayed on and paid the higher rates.

This told me that I had not been charging enough all along. People were gladly willing to pay more than they already were rather than go out and find another cheap writer. Stop and think about that – it’s a really incredible feeling. It means you’re not replaceable and that you’re a valuable commodity.

Pricing the Commodity

Once I realized that I was not working with men and women I needed to be buddies with, things go much easier. We’re talking about marketers, business owners and entrepreneurs who all think in terms of $$$. I make them money so they see me as a valuable asset. They might be nice to me, and me to them, but at the end of the day, it’s all business and if it makes good business sense to pay me twice what my old rate was, they’re going to do it – not because they have no choice, but because my work is worth the extra fee.

So, stop thinking of yourself as a starving artist who needs to take whatever people are willing to pay you. If you are a good writer with years of experience and a solid portfolio of happy clients, you have earned the right to be paid more for your time.

But, here’s fair warning. You WILL lose clients. It’s going to happen. Some people don’t care about quality. They don’t need to. They’re uploading articles to dead end blogs or posting on article directories. They just need quantity and if they can pay someone from Romania $3 an article and get the same results, they’ll do it.

Your task is to STOP competing for that low paying work and start putting yourself  in line for the high paying, rewarding work that real business owners and marketers offer on a daily basis.

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When you’re just getting started as a freelancer, which I know a lot of you are doing, there don’t seem to be many options. You can either work for $0.50 an article on Elance or roll the dice on Craigslist and hope someone accepts your email out of hundreds they’ll get for that single post. It’s a tough road.

I, on the other hand, kind of stumbled into it by working on so-called “micropay” sites like Associated Content and Helium where I generated my own topics, wrote at my own pace and got paid only if the content I wrote was useful to the site. Of course, that was also in 2007 when Associated Content’s stringent guidelines were not quite so hard to get around and you could get the occasional $20 offer for an article.

And to round out the story of my flirt with Micropay, it only lasted the better part of 6 weeks. I got up to about 20 articles a week with Associated Content and promptly realized that Elance was a far better place to test my talents – quickly obtaining a far greater supply of work per month than I would have been physically capable of writing on the Micropays.

So, Does it Work?

I will say yes. It might not be the most exciting thing in the world, but over the course of the first few weeks as a freelancer, you need something to do. You might spend 2+ hours a day carving out a name for yourself on forums, on your blog, or at Elance with bid after bid, but if you don’t actually sit down and write an article or two, you’ll never gain the experience you need to succeed.

It’s hard to be good at this job. You must not only be a good writer, you must be a fast writer – capable of adapting to numerous styles and tones instantly while shifting between dozens of topics. Only practice will give you the skillset needed to succeed.

So, where does that leave us? If you need a jump start to your career and some practice writing content that will help you hone your skills, get on the micropay sites. Until you actually get a real paying job on Elance or Odesk, it’s your best bet for getting some experience, feedback and much needed pay.

Don’t Forget Blogging

Regardless of your decision on micropay, though, don’t forget the value of a good blog. If you haven’t done so yet, get a blog started on Blogger.com or WordPress.com. You may not get a single reader, but the chance to sit down and write something that is dear to you and send it to the world is as good a way to build confidence as any. Just take a look at how many posts on this blog are from 2007 when I first got started. Whether you’re getting paid or not, you have to be writing, so stop reading and start writing.

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When I got started in this business, one of the biggest perks I saw was being able to sit back and relax on the beach with a laptop, because I had the freedom to travel where I wanted and when I wanted.

It’s been a few years since then, and I’ve learned a few things about travel. Yes, it’s possible to go somewhere whenever you want, but even more so than when you have a job you need to plan EVERYTHING out perfectly if you actually want to enjoy your trip.

1. Lost Pay Adds Up

First up, you need to save up money for a trip. When you only go on vacation once every year or two, it’s not a big deal. You have a fund in a jar on top of the fridge and everyone knows you don’t go until it’s full. When you’re a freelancer with itchy feet, you want to get out there as much as possible, but you still need to pay for the trip.

To top things off, you don’t get vacation pay. It seems obvious enough, but too many people neglect his little detail. Sure, you can go away whenever you want, but if you do, you don’t get paid because you’re not working. And if you plan on working while you’re gone, trust me – it’s not going to happen.

2. Juggling Clients During Vacation

Another toughie is figuring out how to juggling existing, ongoing, or new clients while away. I’ve learned, over time, to tell my clients about my vacation at least 1 month before I go away…then I remind them weekly in subtle ways so they don’t forget.

The first trip I took, I spent three hours a day in the hotel room replying to emails and editing documents. The second trip, I forgot my laptop at home and came back to a dozen irate emails. By the third trip, I had a system in place where I worked my butt off for 10 days before I left to get EVERYTHING done early.

However you do it, make sure your clients A) know you’ll be gone and B) have a lot of time to unload whatever they need on you beforehand. If they don’t, it becomes their problem, which 99% of them will recognize.

3. Having Work to Come Back To

Here’s why I don’t try to get everything done before I leave, and actually build the trip into my schedules. It’s because, when you get back you don’t have anything to do. I’ve been in this trap twice before – once after a 2 week trip to New York City in 2008 and last year after I got married.

Both times, I took extended leaves of absence (two weeks and three weeks), having planned ahead to cover the lost time and get everything done early. Unfortunately, when I got back, I had nothing to do – no edits, no projects, no responses from those clients.

They hadn’t moved on – they’d just taken a break themselves and I lost another whole week finding work on Elance. The lesson here is to always bid out in advance of leaving and try to convince your regular clients to have stuff waiting for you when you get back.

Ideally, you’ll eventually have regular monthly projects that you can use to fill these gaps, but for now, a good bit of pre-bidding or even a day or two mid-vacation spent bidding, can help stave off the lost week.

4. Enjoying Your Trip Properly

Enjoying your trip is important. What good is all that travel if you’re miserably thinking of your email the whole time. If you’re traveling with family, it can be even worse as you drag down your spouse and kids with you.

So, instead of worrying constantly, be realistic and set aside at least 1 hour a day to check email, hash out work details and make sure everything is okay. The rest of the day, leave your phone at the hotel. A blinking BlackBerry can be the death of a good vacation and your clients should already know you’re away.

If it’s important, they’ll leave a message and you’ll have your hour at the end of the day to deal with whatever comes up.

5. The Best Time to Get Away

So, with no boundaries on when you travel (unless you have kids), when is the best time to get away? I don’t have any preferred times, but I have been very lucky in offseason traveling. For sure, consider taking a trip in December. It’s the slowest month of the year for most freelancers and offers tons of opportunities for cheap travel if you go in the first two weeks.

September-October and April-May are also great times because of the pre and post seasons discounts at resorts in areas that are still quite nice. Avoid mid-summer travel like the plague if you can get away with it, and keep a close eye on nice weekends in the later winter and early spring.

My wife and I had a fantastic weekend in the Redwoods two years ago in April. No one was there but the weather hit a balmy 75 degrees. Last year we did the same thing in Vancouver, Canada in February. If you can time it right, you can get the entire destination to yourself.

The key to successful travel as a freelancer is to cut out as much of your work life as possible. I made the mistake on this one more than once and it can be extremely frustrating. Do it right, though, and trust me – you’ll have a blast and your friends will be super jealous (which is always fun).

Freelance Lifestyle freelance writing, home business, make money online, traveling, working on the road