want to get into the freelancing game? our roundtable has all the answers!

Photo Credit: Death to the Stock Photo
Photo Credit: Death to the Stock Photo

Can I tell you I’m privileged to have such good people in my life? If you would’ve known me 10, 15 years ago, you would’ve met a paled-down version of me–a woman who was anxious, defiant, focused on quantity over quality. But I guess that’s what happens with age, you come into your own so beautifully and acutely, that people have a tendency to cleave to that which is calm and good.

To that end, imagine my joy to discover that so many of my friends and peers were so generous with their knowledge and time in helping readers of this space get the answers they need should they want to pursue a freelance life. I’m humbled by their generosity, the fact that the time it took to read and respond to your great questions took them away from billable work. So I’m grateful for that, and I think part of being a successful freelancer is to know when you should give your time and to whom.

So thank you, dear readers, for your questions. As I was preparing to chime in with responses, I realized that my peers were so eloquent and so helpful, that I would only be parroting versions of their words. I hope you find value here, or at least inspiration to give of your time and pursue that which you hold dear and love. –FS

Question #1: This is going to be the newbie-est of newbie questions and rather embarrassing to ask, but…how does one start freelancing? In particular, how does one break into freelance copy editing, especially if one does not have many, many years of solid experience in the field? Honestly, I have no idea how to start! My background is mostly in academia, but I am in a situation in which I need to look for employment elsewhere, and I am thinking about freelancing as I navigate my way through the rough seas of job hunting and relocating. Well, thank you, Felicia and everyone else, for offering this great service! –RINE

Lindsey Tramuta: Great question! I would first start small and see if anyone in your immediate network could use copy editing services. If you can seek little projects on the side initially, you’ll build up your portfolio and get more comfortable applying for freelance gigs or connecting with potential employers once you have the experience under your belt. For me, I had an idea that I thought would fit in nicely with a magazine so I asked a friend who had previously written for the magazine if she would be kind enough to share her editor’s email (she was no longer writing for the outlet and didn’t cover the same beat) and she did. That doesn’t work every time but in this case, she opened the door for me, I reached out to the editor and I’ve been writing for them ever since. Also, if you’re looking to actively veer your career in a new direction, make sure you update your close friends and contacts with personalized emails (or phone calls!) so that they know to keep an eye and ear out for opportunities that would fit with your interests.

Amber Katz: My advice is to network beyond belief. Find some people doing what you’d like to do, in this case, freelance copy editing, and email them and ask them if you can take them to coffee for a 20-minute meeting. In the email, ask if a phone call would work if they’re not able to meet up and come to the meeting/call with three questions you’d like answered. Another thing I’d recommend is simply emailing your network and let them know you’re taking on freelance copy editing work if anyone has any leads. You may have to offer your services for a small fee (never for FREE, unless you really don’t have any related experience, in which case you may need to do a project or two gratis) so you can put together a portfolio. Good luck!

Leah Singer: I would suggest doing a few things. First, if you have experience doing copy editing (or any of the freelance skills you want to do) in your current job, make sure you highlight that on your resume and on your LinkedIn profile. Even if your job in academe is not a copyeditor, if you’re performing that work as part of your job, it’s relevant and should be promoted.

Second, start finding organizations that will use your talent in a volunteer capacity. For example, see if your church, synagogue or kid’s school or club needs a copyeditor for their newsletter, and volunteer to do the work. When you’re well established, I don’t always advocate giving away your time and service for free. However when you’re starting out, you need to get the clients and experiences to build your business. And remember, nobody knows the work you’re doing is volunteer or paid!

Third, harness the power of social media! Find a few friends or post something on Facebook that you’re starting this service and want to do some copyediting for people’s blogs, articles, etc. Then make sure to get testimonials for your LinkedIn profile and future website!

Matthew Sharpe: I’m a freelance editor and writing coach and I started freelancing somewhat by accident. I taught creative writing in the evening at a local university. Some of my students were grown-ups working on novels, and they got in touch after the course was over to see if I’d continue helping them with their novels. Same thing happened after I attended a few writers’ conference over the years. I confess I’m not great at advertising and marketing my own services, so most of my work has come to me via word of mouth.

As for copy editing: okay, so you don’t have many, many years of experience. Do you have any? That will certainly help. I’d get in touch with the copy departments of all the major book publishers and magazines and let them know you’re available, and what your experience is. If they have an opening, they’ll give you a test. If you do well on the test, they’ll start giving you some work. If you do well on the work, they’ll give you more. Etcetera.

Cariwyl Herbert: No need to feel embarrassed at all! We all must start somewhere, and most endeavors begin with asking questions. If you are ready to take clients, put the word out to your network. Email your friends and family to let them know what you are offering. They’ll gladly hire you when they need copywriting, and they will tell their friends as well. You can also post your services on sites like elance.com and odesk.com; both are portals catering to freelancers.

Alexandra Ostrow: Good for you, Rine! Depending on your role in academia, you likely have more related experience than you’re giving yourself credit for. Take a look at the projects you’ve worked on, and make a list of the times when copyediting played a role. This list is the beginning of your portfolio. Also, let your network (colleagues, friends, family) know that you’re beginning to work as a freelance copyeditor and are looking to take on new clients. If you’re open to it, offer discounted services to new clients for a limited time period. This will help grow your portfolio. Bottom line, if you’re gravitating towards freelance copyediting, this is either a passion or an innate skill of yours. Believe in yourself and go for it. The hardest part is often just putting yourself out there.

Kim Brittingham: Years ago I worked as a legal assistant and I used to wonder the same thing. How do these freelancers get work to begin with, so they can eventually work only for themselves? And I’m still not sure I have the answer! I have friends who write full-time, and they get non-stop work just pitching ideas directly to publications. But I think that requires a lot of persistence, and you have to be good at coming up with a lot of different ideas all the time (enough that you can afford to have the majority of them shot down). I also suspect it takes time to establish relationships with editors who will look forward to your pitches and respond to you quickly, or even reach out to you and offer an assignment.

I also know of some writers who get work through eLance.com, Guru.com and oDesk.com, but I personally haven’t used those sites because I think most people who go there seeking writers and also looking for a bargain, so you wind up making really insulting money.

My path to becoming a full-time freelance writer was a little unconventional. It started in the ‘90s when I published a ‘zine called Café Eighties. I did a lot of interviews with entertainers, and after a while, people came to know me as a writer. Eventually, someone from a local publication reached out to me and said, hey, would you be interested in writing something for us? Then when the Internet came about, I was completely fascinated. I wanted to tinker and figure out what I could do with this thing. I had a really early website, I was on message boards, et cetera. I remember posting an ad on Craig’s List, offering to write what we call “web content” today, although I don’t think that term was being widely used back then. I got some responses. I wrote articles about personal safety in the context of dating for a telephone forwarding service; I wrote about novel ways to propose marriage for a diamond company. One thing led to another. Eventually I sold a book to Random House, in part because I had built a following with my personal blog and stuff I posted on social media. I was extremely lucky in that I didn’t have to work hard to get a literary agent to notice me; my agent approached me first.

Then I had some more skills in my pocket, like the social media, blogging, et cetera. I had even more to offer as a freelancer. Then one day I got a call from a guy I’d taken a class with at Media Bistro. He asked if I’d be willing to ghostwrite a book for him. I signed a contract that made it possible for me to quit my job as a legal assistant. Since then, I’ve taken some part-time jobs here or there to get by while doing the freelance writing thing, but I’m happy to say I haven’t had to do that in the last three years. Most of the work I get today is repeat business and referrals. People also find me on LinkedIn. For example, I occasionally publish a blog post to their content platform “Pulse”, and people have reached out to me with work after liking what they read. I think it also helps that I’ve carved out a niche for myself, working with executive coaches, management consultants and thought leaders. When you specialize in something, you have a better shot at winning business than if you try to be everything to everyone, in which case you disappear into a vast sea of other Jacks- and Jills-of-all-trades. I do still take outsourced work from marketing agencies, though, because I enjoy the variety. One day you’re writing blog posts for an insurance company that caters to teachers, the next you’re creating mildly crass Facebook memes aimed at 20-something heterosexual men who gamble. It’s fun!

Question #2: Thank you for offering us the chance to ask questions! I’ve been working as a freelance editor part-time along with my normal day job in academia. I’m currently looking to grow my business. I’ve been wondering about keeping regular clients happy, yet still being able to take a week or two off throughout the year. –EGEORGIAN

Amber Katz: There’s no reason you can’t enjoy a week or two off throughout the year. It’s all about sending your freelance clients an email 2 weeks before your vacation and letting them know you’ll be off the grid for a couple weeks and could they please submit any requests for work by X date so you have time to finish up before you leave. Then, use an Out Of Office notification to let people know you’re away and not checking email until X date and to contact you in case of an emergency using a special email subject line.

Cariwyl Herbert: Everyone is entitled to time off—even freelancers! It isn’t difficult to take a day off here and there; put an out-of-office alert on your email if you’re worried. For a longer vacation, simply give clients a couple weeks notice so they know what to expect.

Leah Singer: For me personally, it’s been hard to take chunks of time off and not do any work (although I know people who do it well). I usually always check email or have client work that needs to be done in some way. However, it can be done and it just requires a lot of planning and working in advance. If I know I need to take a few days off, I schedule time on my calendar to do work ahead of time. I also let my clients know I won’t be working on those days. Also, some seasons are slower than others. December always seems to be less chaotic, which is great since my daughter has the last two week of the month off of school. I also take advantage of holiday weekends since the rest of the world tends to slow down during these times.

Matthew Sharpe: I think just give them a lot of advance notice about your time off. If feasible, offer to do extra work in advance of your vacation so they won’t be stranded. Everyone needs time off. People generally accept this, in my experience.

Kim Brittingham: One thing that helps me is flat-out refusing to work with unreasonable and/or demanding people (FS note: Hallelujah!). I have a pretty good instinct about people, and usually after just one conversation, I can sense whether or not they’re going to be a giant pain in the rear. Life’s too short for that. Just say no. BACK AWAY FROM THE NUTJOB. That’s why I never have issues with clients calling me at odd hours or expecting me to be available 24/7 to discuss things that are in no way urgent. Also, I think it’s important to make sure everyone is on the same page from the start. Tell your client how many hours you have available to them, when you take calls and when you don’t, when and how often you will meet via Skype or conference call, et cetera. Put it in writing.

The work I take allows for a lot of flexibility. For example, I have clients to whom I provide the same amount of content every month. I know when my deadlines are, so if I want to go away for a week, I just work extra-hard to get everything done early. But I do make sure I’m available by e-mail while I’m gone. If that’s not possible, I let all of my clients know in advance when I will be out-of-reach. I also accept longer-term projects, like ghostwriting books, but when I accept those projects, I also accept that I won’t be doing any extensive traveling until the gig is over.

Alexandra Ostrow: It’s all about setting expectations. Just like you, your clients are likely looking to take a vacation (or three), and should understand you need some time away. It’s unlikely to be an issue as long as you let them know ahead of time about your plans, and then work out an arrangement where either a) you complete all deliverables prior to takeoff or b) you have a trusted colleague cover your role while you’re away. If it is still an issue, I would personally question whether that particular client is worth sacrificing work-life balance.

Photo Credit: Death to the Stock Photo
Photo Credit: Death to the Stock Photo

Question #3: First, thank you for this! I’ve started (sort of) freelancing as a layout artist/graphic designer and I'm trying to build a portfolio. I have some work ready to be shown off, but I don't know where to start! My Behance portfolio looks like a mess and so does my blog (ambermorrishao.blogspot.com). How do I make my portfolio look more professional? I really have no creative energy when it comes to that 😦 Should I make a brand for myself? —AMBER

Kim Brittingham: Granted, I’m not a graphic designer, but I definitely think it’s important to present a spiffy portfolio. After all, it represents you as a professional. Not only should you put your best work forward, but also it should be well presented. If I was in your shoes, I might study the portfolios of other designers. See what they’re doing. When you see a portfolio that really looks sharp, break down the elements of what makes it exceptional. Try to duplicate those elements with your own portfolio. Also, think about the kind of businesses you’d like to work for. Let’s say you want ad agencies to hire you. Maybe you can approach an advertising trade organization and ask if anyone in their membership might be willing to review your portfolio and provide feedback. It will be especially helpful if the feedback comes from someone who actively hires graphic designers, because he or she can tell you why one portfolio might stand out above others.

Question #4: In 2013, I left my full-time job in academia to ghostwrite the memoir of a prominent neurosurgeon. Now I want to build on the experience, and add to my small freelancing client base. I love what you have done with your site, and I want mine to reflect my personality in a similar way. But I also want to use it as a vehicle for attracting clients. What is the panel’s advice on how to balance the two goals? Is it better to use the blog as a home page or use a static page that potential clients can immediately see when they visit? What about leveraging connections? And btw, love that “Death to the Stock Photo” credit. Any tips on providing engaging graphics/photos would be welcome. —JEANNE

Leah Singer: I’ve been blogging personally since 2009 and started my freelance business in 2012. I do have a separate website for my business, but I don’t think it’s always necessary to do that. The first thing you absolutely need to do before worrying about a blog/website is to make sure your LinkedIn profile is ready for business. I advise a lot of clients that a well-written LI profile can actually serve as the website. What I’d recommend in the short-term is to add a page to your blog that says, “Work With Me” (or something to that affect) and write what you do and your services offered. Then include a link to your LI profile. You’re going to attract the right clients based on you and your personality. So don’t get too marred down in the details of static pages versus the blog, etc.

Amber Katz: I think you should create a website with your name (i.e., firstnamelastname.com, if the domain is available) and then create a blog as an offshoot (i.e., firstnamelastname.com/blog). Keep your portfolio of your work on the website and use the blog to reflect your personality. As far as leveraging connections, simply sending an email to your network or using a LinkedIn status update to let people know you’re taking on freelance work is invaluable. One of the big mistakes I made when I went freelance 5 years ago was not notifying all of my connections en masse. It took me about a year to build up a solid roster of work because it all happened via in-person networking at beauty events, but I would have secured more gigs initially had I just told people I was available.

Cariwyl Herbert: It all comes down to how the information is presented, as well as how relevant your blog will be to potential clients. I’ve seen many small businesses leverage blog posts/articles as the primary content on home pages, with consulting services being marketed alongside them. This serves as a way to showcase your expertise for potential clients. I’d start with this format and market your services in the sidebar and at the bottom of blog posts unless your blog topics are not relevant to your freelancing endeavors.

Matthew Sharpe: I have a fiction blog but not a blog for editing, and my site at this point is mainly about my work as a fiction writer. I’ve got a page specifically dedicated to my editing work at Blurb.com, and, honestly, I keep meaning to create my own web page specifically about my editing work, but I’ve been so busy with the actual writing and editing that I haven’t had time to set it up. A blog can certainly be good but I think there should be a home page stating what services you offer, what your credentials are, and who your clients have been—updated as often as is needed.

Kim Brittingham: Hm. Can you use the same website to express your personality AND attract clients? Yes. It’s entirely possible. But I think it depends. For example, if your personal blog is hilarious and maybe even a little sarcastic, AND you’re trying to sell yourself as a comedy writer, it would probably be a shrewd move to incorporate your blog into your professional website. After all, your blog demonstrates your skill. On the other hand, if your blog is jokey and snarky AND you’re trying to get work as a ghostwriter to spiritual leaders, that combo might not work. You get what I’m saying. Whenever you have a blog as part of your professional website, the important thing is to make sure the majority of your blog posts address the interests of the people you want to hire you. As to whether or not your blog should be part of your home page, I think it’s actually a good idea, as long as the content is appropriate. You’re demonstrating your writing ability right there on the front page. And hopefully your blog content is really engaging, so it will help pull the reader in.

When it comes to leveraging connections, it’s a great idea, as long as you remain respectful of others’ time and remember that your priorities are not necessarily theirs. I see nothing wrong with letting your network know that you’re available for freelance work. You’ll get a better response if you focus your communication more on how you can help them than on how you want them to help you. Also, be as specific as possible about the type of work you do and the types of clients you want to work for. Instead of saying, “Hey, if anybody knows somebody who needs a writer, give me a shout!”, you might say, “If you know any creative directors at ad agencies who hire copywriters or individuals in the medical profession who might need a ghostwriter, give me a shout”.

Question #5: What skills should young professionals build to ready themselves for freelance? Where/how to get started? –TORRIE JAY WIEBE (via Twitter)

Amber Katz: My advice is to take as many classes as you can afford if you don’t have formal education in the field in which you’d like to freelance. I graduated with a French Literature degree and wanted to write for magazines, so I took several Mediabistro, New School and NYU School of Continuing and Professional Studies courses on writing and journalism, where I met a bunch of people I’m still friends with today (this was 11 years ago) and some fantastic teachers with whom I’m still in touch. It’s an expense, but it’s worth it to provide a foundation for your freelance work. I’d also use your school alumni network and use social media to build relationships with people in your field, both potential clients and those who do what you want to do. Working in an office for a few years is also vital pre-freelancing. You need professional experience in-house before you go out on your own. Good luck!

Cariwyl Herbert: In most cases, there will be a variety of classes to take and/or certifications to acquire to gain knowledge in your field and make yourself more marketable. If you are new to your chosen field, taking on a few pro-bono clients may be necessary to build your portfolio; you’ll likely also need a website to serve as a hub for your services.

Kim Brittingham: Freelancers are essentially entrepreneurs, so business-related skills are bound to be helpful. Also, think about what industries you most want to freelance for. If you want to do technical writing for software manuals, it wouldn’t hurt to learn how software is written. Having that insight will give you an edge. Not only will it make you more attractive to prospective clients, but your job is bound to be a lot easier.

As to how you get started, I’m pretty naïve on that point. The way it happened for me was a little unusual (see my response above if you’re really interested). However, it’s a good idea to start by building a portfolio of writing samples. Even if you’ve never written professionally before, you can write some sample pieces that reflect the type of work you’re going for. Some writers offer to write for free just to get some clips or something on their resume. But if you’re going to do that, I would urge you to do it for a very limited time. Personally, I make it a rule NEVER to work for free for any FOR-profit organization. There’s just no reason for it. Our work has value. Tremendous value, even. If somebody’s going to make money off of your writing, then you should, too. Even with zero experience, there are people who may be willing to give you a chance based solely on your samples. As a beginner, you may not command a huge fee, but something is always better than nothing. And like I said – you only need a limited time to prove yourself. After that, you need to get paid.

Lindsey Tramuta: It doesn’t come naturally to everyone but strong networking skills is the foundation of freelancing (and, if we’re being realistic, most business today). That and professionalism, patience, perseverance and email etiquette. Almost all of the jobs I’ve had or have had come my way have been through contacts or friends of former editors, etc.

Also, do your homework. Read up on starting your own business, the inherent challenges and the financial implications. Have an idea in advance of how much you would like to earn vs. how much you need to earn to pay bills, eat and live comfortably. Many people don’t factor in vacation or sick time when they set goals but it’s key to account for time off so you know how much work you’ll need to have to reach your objective. Having a strong grasp on those things will help you set a strategy and establish potential avenues of opportunity before you’re even ready to fully launch your own business.

Alexandra Ostrow: For me, the most valuable skill as a freelancer is the ability to sell him/herself. After all, you’re your own boss, and if you aren’t bringing in business, no one else is going to. This doesn’t mean that you need to pitch yourself incessantly (thank goodness). You do, however, need to recognize that at any time, anywhere, you are potentially meeting a new client or contact. As such, you can’t be afraid to share what you do with new people, and also share why you do it. Passion and enthusiasm are contagious. Similarly, demonstrate your interest in others. When you meet someone new, ask a lot of questions, offer helpful, tailored advice without expectation of anything in return. It’s the easiest way to demonstrate value that can turn into a job or referral (while making wonderful friends in the process). Other skills of high importance:
• Estimating skills (to accurately assess how long/what resources a project will take, so as to ensure it’s profitable for you)
• Negotiating skills (don’t sell yourself short, but also know your market)
• Professional and reliable communications via phone, email, and in-person (please proofread)
• The resilience to weather the storm (some months are fantastic, while others may not be)
• Efficient and effective time management
• Basic accounting and budgeting

Photo Credit: Death to the Stock Photo
Photo Credit: Death to the Stock Photo

11 thoughts on “want to get into the freelancing game? our roundtable has all the answers!

  1. I agree-elance is a great way to pick up experience and get some feedback. You won’t make a lot but it’s fun. Also, many bloggers are interested in having an copy editor. I have a friend who paid an editor a flat fee for 500 words a day of editing. He loved the service! And although he didn’t use it every day, it was a still a great deal for him.


  2. I apologize that it’s taken me so long to comment, but thank you, everyone, for answering my question so thoughtfully and thoroughly. I will be sure to take your advice into consideration as I move forward. Thanks again!


  3. I would like to know how one can be assured of payment once the work is completed and delivered. I’ve had my share of unscrupulous, dishonest individuals who never paid after I delivered the work. Seems like the whole system is based on sheer trust. Unfortunately, there are plenty of untrustworthy shysters out there. What’s the best approach? Charge preliminary up front fee (ie; retainer, deposit, down payment)? Pay as you go? Any practical, proven ideas welcome.


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