Slipping Through the Side Door


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Want to go freelance, but don't know where to start? And you're not ready to give up your day job? Then why not start out freelancing part time. In this presentation, I discuss some strategies for launching your career part time.

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Slipping Through the Side Door

  1. 1. Freelancing. For different people, that word means a lot of things. For some, it's synonymous with freedom. For others, it's a euphemism for someone who's unemployed pretending they have a job. For me, freelancing offers a mix of freedom and flexibility. It lets me do the kind of work I enjoy and get paid for it. I'm sure that just about every full-time freelancer you meet will say the same thing. For all the people who say that they want to go out on their own, not many do. It's a big jump, one that they're not prepared to make. At least, that's what they think. It's possible to ease into the freelance world by starting off part time. You can use part-time freelancing as a springboard to a full- time career. That's what I'd like to discuss for the next 40 minutes or so. © 2010 Scott Nesbitt Slipping Through the Side Door - 1 Slipping Through the Side Door: Launching your freelance career, part time By: Scott Nesbitt
  2. 2. Why go part time? Instead of jumping in with both feet? Several reasons. Here are some of the most common: • Some people just aren't mentally or intestinally ready to take the plunge • They want to build a portfolio or a client list before going full time • They want to earn a little extra cash on the side, doing something that they enjoy There's also another reason: people want to build their reputations before becoming full-time freelancers. I'll be talking about this more in a while. How to do it? That's the question … I don't think there's one path to becoming a part-time freelancer. But some of the same dirt is spread on those paths. Over the years, I've heard people say that their goal is to make their avocation their vocation. That's a worthwhile goal. Freelancing part time is a perfect springboard for doing that. Embrace your inner geek That's what you need to do if you want to if you want to be successful at anything. That's especially true for freelancing. Some people get offended when I use the term embrace your inner geek. I guess because the word geek has so many negative connotations. We're all geeks, whether we know it or not. And by geek, and I mean that we're passionate about something. That doesn't have to be the stereotypical geek pursuits (although it can be). It can be anything – writing, photography, home repair, collecting teddy bears, whatever. It's that passion that will help drive you forward. It's that passion that will help you during the rough times. Let's face it: you probably can't make a full-time (or even part time) career in an area in which you have no experience or interest. I have a friend in Utah who's a full-time technical writer. He who also does some WordPress consulting on the side. He didn't plan to start out as a WordPress consultant. He just wanted to start a blog, which he later began to customize. To do that, he had to learn a lot about the internal workings of WordPress. People then started coming to him for advice, and he began helping others set up and customize their own WordPress blogs. It just developed from there. © 2010 Scott Nesbitt Slipping Through the Side Door - 2
  3. 3. Before you jump Some people have the idea that starting a freelance career, even part time, is easy. You hang out a shingle, start applying for gigs, and the assignments (and money) start to roll in. The reality is quite different. Before hanging out that shingle. you need to do more than just a little thinking, research, and analysis. The first thing you should do is ask yourself two questions: 1. Why do you want to do it? 2. What are your goals? Answer those questions honestly. Look at your answers and critique them. By doing that you'll be better prepared for what's to come. Next, look at the idea for your business. Is it viable? Will you be able to get enough business to justify the time and effort that you're putting into that business? If your goal is to go full time, will you be able to sustain that business and increase it over time? Next up, look at the area in which you want to freelance. Examine the market. Look at who else is doing work in that area. Get to know them. Get to know their mistakes and what they did right. Try talking to them, or emailing them. You might not always get a response. Many freelancers who blog often write about their mistakes and triumphs. Doing that research will give you a good idea of 1) how viable your ideas are, and 2) whether you have the right temperament and outlook to be a freelancer. What you'll need to get going Let's assume you've done everything that was discussed in the last few paragraphs, and it's only made you hungrier. Here's the bare minimum of what you'll need. I'm assuming that you know the area in which you want to freelance. It could be writing or blogging. It could be photography or Web design. It could be programming. Regardless, you've probably got most of what you need already. Things like a computer, a camera, the software you need to do your job – like a word processor or Photoshop. Hang out your shingle on the Web Set up a Web site if you don't have one already. The Web site is your sales brochure. It will contain information about you and your services, samples of your work, a way of getting in touch with you, and more. Your Web site is a central hub for your freelance business. How? Build it yourself. If you're a Web designer, that's a good showcase for your talents. If you don't know the first thing about building a Web site you can always hire someone to do the dirty work for you. If, on the other hand, you have some knowledge of the languages of the Web, grab a template from sites like Open Source Web Design or Open Web design and modify them. I did that with my © 2010 Scott Nesbitt Slipping Through the Side Door - 3
  4. 4. personal Web site and the Web site for my company and the results weren't too bad. Another route is to use WordPress or software like Joomla! or Drupal. A related note: get yourself a domain – something like It's looks a lot more professional. Another approach you can take is to use a site called Tischen. There you can set up your own page to showcase your services, skills, and samples. And do it very quickly. If you have your own domain, you can link it to your Tischen page. I can, for example, point (a domain that I own) to a page on Tischen. Instant Web presence. Just because you've built a Web site doesn't mean people will come to it. You have to promote it and your business. How? Use Twitter. Set up a blog. Use Facebook if you have to. If you post comments on blogs and/or forums, include a link to your Web site in a signature Handling your money How about money? Making money is one of the goals of freelancing. You should, at the very least, have a PayPal account to accept payments on the Web. Those payment could be from clients, from blog advertisers, or from goods you sell (like ebooks). A second bank account is also useful, even for a part time freelancer. It enforces a church and state relationship between your everyday finances and your side income. And, to be honest, the government will want a cut of that side income. In the past, a few people have asked me about registering a company and incorporation. For part-timers, registering a company can be a good idea. You can do it online, and it's fairly inexpensive – around $60 in Ontario. As for incorporation, that's a tricky one. I'm not a legal or financial advisor; talk to one for advice. Experience You've probably heard the old saw that you can't get a job without experience, but you can't get experience without a job. That might have been true once, but times have changed. Sure, there are still barriers but those barriers aren't as high as you think they are. Remember what I said about passion a little while ago? Chances are you do have some experience in your area. It might not be paid experience, but it is experience. There's no reason why you can't leverage that. If you're planning on freelancing as a writer, maybe you've written a few things for a community newspaper or a company newsletter. If you're a photographer, you probably have more than a few quality photos lying around on your hard drive. Or perhaps you've built Web sites for friends and family. You've got the beginnings of a portfolio right there. Even if you're not a writer, think about submitting articles or guest posts to online publications and blogs in your niche. For example, maybe you're planning to freelance as a Web designer. and are © 2010 Scott Nesbitt Slipping Through the Side Door - 4
  5. 5. two popular sites for people in that profession, and a guest post there will get you noticed. If you're not much of a writer, don't worry. Chances are you know someone who can write. Approach them, and offer to share the byline. And the fee for the post or article, of course ... Don't forget the experience you've gained pursuing your passion. Back in the late 1980s and early 1990s, I had a friend who loved playing with this family's video camera. Remember, this was before the advent of inexpensive consumer digital recording – it was all VHS. He got very good at not only recording but also editing. He started off recording parties and events held by friends, then used some of that footage in a demo tape. That got him some paying gigs recording weddings and bar mitzvahs. As his list of satisfied customers grew, my friend started getting assignments to record events for smaller companies. Using a community There are usually more than a couple of people out there who share your interests. Many of them are part of a community of enthusiasts. Online, there are thousands of boards and Web sites and communities where you can ask and answer questions. Chances are you're already a member of at least one of those communities. If you aren't, you should seriously consider becoming a member of those communities. Why do that? It not only offers you exposure, but also builds your credibility and expertise. If you answer questions on a topic in such a public arena, and do it regularly, you get remembered. People will respect your knowledge. They might even come to you for help because you've proved that you know what you're doing. Here's an example: last year, I was at a conference on Open Source software. One of the speakers was a developer and consultant who specializes in Drupal (a Web-based content management system). I've heard and read many people proclaiming that you can't make a living from Open Source. Well, he does. How did he get to that point? It wasn't overnight, that's for sure! He got involved in the Drupal community, first by posting messages to message boards, then answering questions on those boards. By doing that, his reputation and profile gradually increased. Then, he started writing modules for Drupal. People began using them, and some of those asked for customizations. At first, he did those customizations for free. But when companies started asking for custom version of the module, he began charging them. Now he does custom installations of Drupal, consulting, and even sells some of the modules he writes. If you use LinkedIn, you probably know about LinkedIn Answers – a forum for asking and answering questions. I know a couple of freelancers who regularly post there and they get some business because of it. Getting gigs You're all set up and ready to go. The only thing you don't © 2010 Scott Nesbitt Slipping Through the Side Door - 5
  6. 6. have is one or more paying gigs. That's where the fun begins. Back when I started freelancing, the Internet wasn't on computers. Well, not home computers. In fact, not many people had computers at home. I had to try to drum up business the old fashioned way – with letters, faxes, and cold calls. It was a lot of hustling and if I scored three gigs for every 10 approaches I made I was doing pretty well. Job boards and bidding sites Nowadays, it's a bit easier. Most people start with Internet job boards and job ads. You can find gigs in minutes and apply for them with a couple of clicks. A place everyone starts looking is Craigslist. There are a lot of gigs there, and some of them aren't too bad. Some of them ... Other places you might want to look are: • Freelance Folder Job Board • ProBlogger Job Board • Freelance Switch Job Board • Marketplace In addition to job boards, there are job bidding sites like, eLance, ODesk, or One thing that you need to be aware of is that most of the folks who post online are looking to get the job done as cheaply as possible. I mean really cheaply. It's not uncommon to see, for example, ads offering $5 for a 500 word article. Someone once offered me $150 to write a software manual for them. You can imagine what my response was ... That's not always the case, but for the most part you’re not going to get one big gig that will pull in a lot of money. It could happen, but it’s more likely that you’ll be working at and chasing multiple smaller gigs that don't pay much but which can add up. In the long run, though, job boards aren't the way to earn a good living. That comes through personal contact. Use your network Sometimes the people you know can help you get gigs. Chances are that you know at least one freelancer. And that person probably knows more than a couple of other freelancers. So why not leverage that network? Maybe you're a writer, and that Web designer you know needs some copy for a site she's building for a client. Maybe a management consultant of your acquaintance needs some of your graphics know how for a presentation. The opportunities are out there. Don't be afraid to ask. Then again, sometimes those opportunities fall into your lap. Remember when I was talking about LinkedIn earlier? A few months ago, a writer I know was approached by a client because she was a member of the group on LinkedIn. In fact, she passed some business from that client © 2010 Scott Nesbitt Slipping Through the Side Door - 6
  7. 7. my way because of my knowledge of But don't sit around waiting. Constantly put out feelers and make people aware that you're available, that you're skilled, and that you can do the job. The pitfalls There are a few, which freelancing part time can really bring to light. Have you ever heard the phrase the loneliness of the long- distance runner? As a freelancer you're often on your own. This is especially true of part timers. It's hard to build a support network around you if you're working full time and freelancing on the side. Posting to forums and chat groups is OK, but that really can't compare to sitting down with others over a coffee (or something stronger) and talking shop. We tend to wear masks when online, even if we don't realize it. in person, those masks crumble. Part time freelancing also takes time away from your friends and family, and from the things you want to do. To a client or editor, a deadline is a deadline. They don't care if you want to watch the latest episode of Boardwalk Empire or want to spend some time with that special someone. The client wants what they've contracted you to do. They want it on time, or sooner. Because you're doing the work on the side, you're going to need good time management skills. You'll have to learn how to fill those cracks in the day with your freelance work. When I was in journalism school, I read the The Freelance Writer's Handbook. One of the authors of the book described how he fell into part-time freelancing. He'd been discharged from the army, went back to school to get a PhD., and started a family. His income – from the G.I. Bill and teaching at the university – was about $8,000 a year. This was in the 1970s, but even so it wasn't enough to pay the bills. So he approached the editor of a local paper and offered to write features and reviews at $15 a pop. To do that, he'd get up early in the morning and grab a bunch of assignments. Between classes and at lunch he'd do research and phone interviews. In the evening, he'd write up his articles and submit them. All of that on top of doing doctoral work. You might not have to do that much, but that's the kind of tight time management you'll need to learn. And fast. Time vs. money That’s definitely something you have to weigh when considering a side gig. Consider how much time you’re spending on a project, and how much you’re making. You might be offered $600 to write a quick start guide or to create a small help system. You might be writing 500 word articles for $10 a shot. Is that extra money worth the time that you’ll spend working on those projects? Well, if you can write five articles an hour or finish the documentation in 10 hours it might be. But chances are, those jobs will take you longer. Also, consider the time you’re going to spend searching for © 2010 Scott Nesbitt Slipping Through the Side Door - 7
  8. 8. and applying for gigs. That can be a lot of hustling, especially when you’re using your spare time to do the hustling. Burning out You'll also question why you're doing what you're doing. Yes, even part-timers can suffer burnout. Two years ago, I had a few writing gigs on the side. Yes, even freelancers take side projects. I was making decent money overall, but I didn’t have as much time as I wanted to do the various other things that I wanted to do. So, in an attempt to rewire my systems, I took a close look at some of those gigs. The amount of time that I spent working on them wasn’t worth the pay. So, I dropped them. Speaking of pay, low pay has always been the bane of people starting out. As you're beefing up your portfolio, you might have to work long hours for minimum wage (or less). That's frustrating and it might not seem that it's really worth your time and effort. Sometimes, you'll just need to step away. Remember the friend I mentioned earlier, the one who does WordPress consulting? About a year ago, he experienced a bit of a crisis. He was doing a lot of that consulting, but it wasn't as satisfying as it used to be. He was pretty much going through the motions, the money wasn't great, and he wasn't spending all that much time with his wife and daughters. He had to admit that he was human, and he took a break from doing that work. When he went back to WordPress consulting, he was refreshed and better able to serve his clients. Going full time That's the goal, isn't it? Say goodbye to the day job and work for yourself. The question is how do you know when it's time to make the jump? This can be hard to determine. You should seriously consider going full time if: 1. Your freelance work is taking up more than 30% of your time. 2. You're having to regularly turn away work 3. You're earning anywhere between 25% and 30% of the income of your day job with your freelancing Those are pretty subjective measures. But they give you an idea of how to gauge whether or not you're ready. Say you do decide to make the jump. You should have at least three months worth of savings as a backup. Probably more. You never know when your next gig will appear, or if a client will be late in paying. Also, you might want to think about private health care. You won't be getting benefits from freelancing. For a family of three, a basic health plan costs under $200 a month. Of course, if your spouse or significant other has a jobs with good benefits, you probably don't need to do that. For © 2010 Scott Nesbitt Slipping Through the Side Door - 8
  9. 9. example, at the moment my wife is in grad school. She gets a good health and dental plan from her university for under $600 a year. Do you need to go full time? That's up to you. Freelancing part time is like leading a double life. Leading that double life becomes a grind after a while. Not matter how mentally strong you are (or think you are), it can be very difficult to master and sustain that double life. Some people are content with part-time freelancing. For them, it's a little extra cash and freelancing part time allows them to something a little different from their day job. It's fulfilling, but they also have all the security (real or not) of a full-time position. Whether or not you do go full time is up to you. But freelancing part time is a great way to get your feet wet and your hands dirty. You might find that going full time is what you want to do. You might find that the constant hustling and scuffing for a buck isn't your cup of tea and decide to stay in the part-time ranks. Either way, you just might find that freelancing is an enjoyable career (or sideline). Contact Me Web site: Email: Blog: Twitter feed: © 2010 Scott Nesbitt Slipping Through the Side Door - 9