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Business Basics

How Freelancers Can Protect Themselves From Not Getting Paid

Experts reveal how the self-employed can ensure they get their just dues

Freelancer getting paid
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By Janelle Harris
@thegirlcanwrite
Janelle Harris is a multimedia producer, director, and founder of Harris Two Productions with decades of experience in non-fiction storytelling for networks including Bravo, Discovery, and A&E. A Howard University graduate, she specializes in amplifying diverse voices across television, film, and digital media.
6 min read • Originally published March 5, 2013 / Updated March 19, 2026
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By Janelle Harris
@thegirlcanwrite
Janelle Harris is a multimedia producer, director, and founder of Harris Two Productions with decades of experience in non-fiction storytelling for networks including Bravo, Discovery, and A&E. A Howard University graduate, she specializes in amplifying diverse voices across television, film, and digital media.
6 min read • Originally published March 5, 2013 / Updated March 19, 2026

This morning, I didn’t have enough money to ride the train. My checking account is overdrawn, so my debit card had about as much value as the sheet of plastic it’s crafted out of, and the one credit card I keep on hand for these types of emergencies is pitifully over limit. I was stuck.

The irony of it all? I’m a freelance writer who’s owed, in total, about $13,000 for copywriting, editorial, even editing a novel. There seems to be a widespread misconception that the ‘free’ in ‘freelancer’ is meant to be taken literally, making the accumulation of overdue payments an unfortunate rite of passage for consultants and other media entrepreneurs.

“We know from surveys of our members [conducted in 2010] that over 77 percent have been stiffed at one point, and it’s happened to about 40 percent of them within the past year alone,” claims Sara Horowitz, founder and executive director of Freelancers Union, a collective that supports the contracting community. “We’ve heard and seen almost everything: horror stories about small claims court or people losing tens of thousands of dollars. About a dozen of our members were all stiffed by one company, which then required them to agree to do further work as part of an agreement to pay their back wages.”

To avoid being one in that dismal number, freelancers have to be strategic. We’ve got to put the following into regular practice, so we won’t find ourselves in the position of fighting for our own money. Grrr.

 

Join an organization or union

We know, we know: you work alone. But there’s still power in numbers when you belong to a professional group. More than 150,000 folks in media-related fields are currently members of the Freelancer’s Union. There are plenty of others, like the National Association of Hispanic Journalists, the American Society of Journalists and Authors, the National Association of Black Journalists, the National Association of Independent Writers and Editors, each with a hearty membership. Research, join up, and let a governing body with experience dealing with members’ needs be the wind beneath your wings in the face of a mounting non-payment.

The most ideal scenario is the one where we contractor types never find ourselves scrambling for payment in the first place. That means making the terms of our working conditions crystal, sparkling clear from the get-go — in writing.

Get project specs and payment terms in writing

“One of the biggest mistakes that freelancers make is they don’t have thorough communication with their clients regarding both parties’ expectations. In other words, a contract,” says Horowitz. “Last year, we surveyed over 3,000 independent workers from across the country, and only 33 percent always used a contract. What happens if the client doesn’t like the work? When is the client expected to make their first and final payments?”

Contracts are admittedly unsexy and sometimes awkward. But churning out freelance work without terms and conditions nailed down in print is like having unprotected sex: a no-no in this day and age.

Learn—and flex—your state’s contracting laws

2010 was a particularly rough one for freelancers in New York where, according to research gleaned from a study conducted by Rutgers University economist William Rodgers, 42 percent of independent contractors struggled to collect an estimated $4.7 billion in lost wages. The impact has been so great and far-reaching that Senator Daniel Squadron (D) sponsored Bill S8084, otherwise known as the Freelancer Payment Protection Act.

“The areas of Brooklyn and Manhattan I represent are some of the greatest neighborhoods in the world. They’re full of freelancers, but also very expensive. I’ve heard stories of folks who were at risk of being forced to move because an expected payment was never made,” says Sen. Squadron. “It’s difficult enough to work as a freelancer without having to spend extra time trying to collect your wages, or worry that the wage will never come.” The bill, he adds, will spare contractors who generally don’t have the legal protections they need from investing extra energy just to get paid for the work they’ve done.

Knowing the specific laws in the state your freelance business is based in can empower you to gently nudge editors for payment or, if need be, outright scare them. After all, they wouldn’t want to be in violation of the law, now would they?

Research the pub before you say ‘yes’

Freelance forums have a treasure trove of information, complete with names and incidents, about publications with bad reputations for failing to pay. Learning from others’ mistakes will keep you from making some of your own — at no cost.

“We’re very close to releasing a platform for freelancers to use called the Client Scorecard that will let them rate clients based on key factors like timely payment,” Horowitz explains. “That way, freelancers can protect each other and themselves, not to mention set expectations for good standards in the business world.”

Call, email, communicate. Call, email, communicate. Call, email …

About.com freelancer Allena Tapia is waging a battle of her own due to a sour business account. “Right now, I’m waiting on a magazine to pay me, a trade title that I’ve worked with for over two years. They’re having cash flow problems, and they’ve owed me a small amount since November: $300 plus a bonus plane ticket worth about $200.” Hardly a jaw-dropping figure, the Michigan-based writer admits. Anything less than $1,000, in her opinion, isn’t worth the time and expense of taking legal action. Still, it’s her money. She earned it, she should have it, and she’s making sure she gets it.

“I write and call every other day. They respond about once a week saying a vague, ‘We’re working on it.’ Today, I told them I need a solid date or I will go to both the Freelance Writers Union and Editorial Freelancers Association, and I’ll go to Whispers and Warnings,” a watchdog forum that puts an all-points bulletin out on non-payers and other freelance un-friendly losers. She pulled one more ace move out of her strategy book. “I told them I’ll publicly blog about it at freelancewrite.about.com, where I get about 100,000 hits.” Checkmate.

Horowitz admits it’s rarely worth the time and money to pursue a non-paying individual or company in court, but suggests freelancers continue to communicate with their debtors by phone and email, and should consider sending a formal letter if those tactics prove unfruitful. “We’ve seen some funny, unorthodox approaches to shaming clients who don’t pay, but most freelancers prefer to keep things quiet to protect their own reputation,” she explains. (Umm, the heck with that, by the way.)

It’s easy to get lost in repeat assignments (They like us! They really like us!), but when the unpaid invoices start stacking up, you have to pull the plug on a client until the check is officially cut. That makes staying on top of bookkeeping and accounting an essential part of the freelance life. It’s not fun, it’s not glamorous, and it doesn’t even give you that warm fuzzy feeling of a perfectly executed feature story. But it will keep a roof over your head and ensure that you can actually afford to heat your humble abode.

As for my 13 grand budget deficit, I was temporarily forced back into the 9-to-5 world of bosses and cubicles—oh, and regular paychecks—in order to keep the lights on. And, like Tapia, I also hold down a side gig as bill collector, with an active cycle of phone calls, emails, and shame-on-you messages for those clients in arrears.

Topics:

Business Basics
Journalism Advice

Pitches That Worked: How a Cold Query Landed in AARP The Magazine

A compelling pitch landed this writer her first big break at a top mag

aarp magazine pitch
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By Valerie Berrios
@valerieberrios
Valerie Berrios is a published author and senior content manager with nearly two decades of experience in digital publishing, including roles at Audible, Disney Streaming, Everyday Health, and Mediabistro. She specializes in content strategy, editorial operations, and international content launches.
8 min read • Originally published October 14, 2013 / Updated March 19, 2026
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By Valerie Berrios
@valerieberrios
Valerie Berrios is a published author and senior content manager with nearly two decades of experience in digital publishing, including roles at Audible, Disney Streaming, Everyday Health, and Mediabistro. She specializes in content strategy, editorial operations, and international content launches.
8 min read • Originally published October 14, 2013 / Updated March 19, 2026

Sometimes a great idea alone is enough to capture the attention of an editor — even if the angle of the original pitch wasn’t necessarily the hook. Joan Trossman Bien sent a cold query to AARP The Magazine on an idea she had to profile a 64-year-old filmmaker. The result was an FOB piece in the October/November 2013 issue of the magazine that focused on an element of her pitch — a program that pairs returning military veterans with older farmers who prepare the vets to be farmers themselves. The pitch was an especially big score for the writer because not only was AARP the largest publication she had successfully pitched, it’s also a magazine that accepts only about 1 percent of new-writer submissions.


What the Writer Did

Joan Trossman Bien: Well, [my pitch] started out as a different idea. A friend of mine introduced me to Dulanie Ellis, a documentary filmmaker. My pitch was about second stage of her life, a profile. When I pitched [Margaret Guroff, features editor, at] AARP she said it’s not really for [my department], but it might be just the thing for one of our editors [David Dudley]. And what he was most interested in was the farm-to-vet program featured in [Ellis’] latest film. I had initially pitched this to More magazine because I know it does stories about people reinventing themselves. I got an immediate answer — they passed — but it was better than waiting [on the feedback]. I had really gotten tired of getting assignments that paid next to nothing. I have written about 225 articles, so I really needed to get into a higher level — those that paid $1 to $2 a word.

The Pitch

Subject: Query: profile film, farms and vets [1]

Ms. Guroff:

I would like to write a profile for you about a woman who has truly found herself in the second act of her life and has made the many changes needed to accomplish her new passion.

Social Justice Through Storytelling on Film: Got Cause? [2]

There is a new trend developing among baby boomers [3] , brought about by a combination of circumstances and a belief that once you step aside, you lose your involvement in life. The majority do not intend to retire. Dulanie Ellis counts herself in that crowd.

Dulanie, who is 64, could be the poster girl for finding her passion later in life and devoting herself to making the world a better place. In this case, Dulanie has become a documentary filmmaker with her own production company. Over the years, she has worked on documentaries for HBO and the Southern Poverty Law Center. She was part of the team that created the Academy Award nominated Mighty Times — The Legacy of Rosa Parks.

Until her mid-forties, Dulanie had been a script supervisor for feature films. Although that skill is distantly related to documentaries, her job was technically demanding. At the age of 52, Dulanie took the leap and opened her own production company. As a filmmaker, Dulanie now has full creative control and is responsible for all aspects of a production.

Social justice has become Dulanie’s passion and family farming as an industry has become her cause. Her current film, Ground Operations: Battlefields to Farmlands is about a new program to save small farms. About half of the current farmers plan to retire in the next ten years. But their own families are not interested in continuing to run the farm.

Military vets have been coming home in great numbers but have not had many opportunities for really good jobs. They need the kind of work that can lead to a career, just like the rest of us. Many vets also still have a desire to help the country, a common reason for enlisting.

The program that is the basis for the documentary pairs older farmers with vets. [4] The farmer acts as a mentor and teaches the vet all about farming and that particular farm. When the farmer retires, the farm passes to the vet. That way, family farms remain active with new farmers who are both skilled and enthusiastic. Keeping the farms working can also help to revitalize rural America.

Dulanie has a compelling personal story. She was comfortable as a script supervisor for many years but, when she had her only child at age 43, she wanted to stay home. During that time, she moved to Ventura County where rolling hills of small farms formed a comforting landscape. Dulanie fell in love with the tamed rural open spaces that provided sustenance for so many people. Many of the farms are organic or raise specialty crops sold at the farmer’s markets. She had worried that these farms would disappear as she saw the county population grow and housing developments sprout up in what had once been tended fields.

Making a documentary about this farming program melded her two loves. Dulanie has taken control of her life and lives it fully. The satisfaction is what she reaps at a time in life when most people are preparing to retire.

Dulanie has weathered difficulties, such as losing 80% of her sight in one eye, yet has stayed focused on her life’s purpose.

Why should I be the writer on this story? [5] As a freelance journalist and general assignment reporter, I have more than 225 published articles in the past five years. My background is in television newswriting, having written for most of the television stations in Los Angeles over the years. I also earned a law degree in 2004.

Right now, I write long form features regularly for two alt weeklies, the Ventura County Reporter and Pasadena Weekly. Sprinkled in between assignments are other publications and websites for which I write occasional articles. So here are a few examples of my work [6] :

This was a relatively short profile of a local environmentalist/educator/political organizer who has led an unusually intrepid life. It was the cover for Ventana Monthly, an upscale publication.

http://www.ventanamonthly.com/article.php?id=316&IssueNum=29

This story was the cover for the VC Reporter. It was about the local politicians who were running for office, all of them being women.

http://www.vcreporter.com/cms/story/detail/?id=9865

This article for Pacific Standard (formerly Miller-McCune) is not a profile but demonstrates my research and reporting abilities. It is about safety systems for trains, the history of train crashes caused by human error and the attitude of the major rail lines towards public safety.

http://www.psmag.com/business-economics/rails-150-year-wait-for-safety-3433/

Dulanie is not actively preparing for retirement because she said she never wants to stop working. That attitude reflects the changing nature of growing old: Baby Boomers, by necessity or choice, intend to stick with their work for as long as possible. [7]

If a profile of Dulanie Ellis interests you, I do look forward to hearing from you.

Sincerely,

Joan Trossman Bien

Why the Editor Bit

David Dudley, features editor at AARP The Magazine: One of my colleagues forwarded [the pitch] to me because I edit the mag’s “Upfront” department. Obviously, good/great clips are very helpful, and for most stories pretty much mandatory. But the pieces in “Upfront” are so short — 250 words tops — that the idea itself is the biggest draw.

The bottom line here is that Joan’s idea had at least three or four big things going for it. It hit on an issue that we’d been wanting to write about (the fact that American farmers, as a population, are getting so old on average). It had a simple, easily understood premise that would make sense even in a short 200-word piece. It had a timely Veteran’s Day connection that allowed us to add a Web tease to AARP.org’s many resources for older veterans. And she named names and had what looked like a promising main character scoped out. It was just very easy to see how a piece on this nonprofit would slide perfectly into the October/November book.

What Happened Next

Joan Trossman Bien: I heard back on the pitch maybe a week later. I was surprised by the 200 words [and needing] two people to quote because I was used to long-form writing at much smaller publications. I was also not used to having that many people helping me with the fact checking, etc. It’s been a great experience. And my ego really needed it. AARP pays $2 a word, so I made more [on this piece] than on the assignments that were 2,500 words. I want to be with the big boys now. The advice I have is to write. Just write. If you don’t have an assignment, write anyway.

David Dudley: As I often do, I sent the first draft back for another round of reporting. Even though this was a short FOB piece [titled “Swords Into Plowshares”], it had two distinct characters and a good bit of explanation to get through, and we needed more details, livelier quotes, etc. We adjusted the original premise to better serve our audience, with more of a focus on the inter-generational angle and how the Farmer Veteran Coalition brings older farmers together with younger veterans. I think Joan was a little surprised by how much expense goes into even a modestly scaled AARP The Magazine piece; we sent a photographer out to shoot portraits of the main subject on his organic farm.

I’m certainly open to considering future pitches and working with Joan again; she definitely demonstrated the key skill of the freelancer — understanding exactly how your idea would fit the needs of the publication you’re pitching.

Key Components of the Pitch

[1] Never underestimate the importance of your email subject line. Joan’s, “Query: profile film, farms and vets,” is short and to the point yet intriguing. And the editor sees immediately that this is a query, which increases the likelihood that the message will be opened. Back to pitch

[2] In the second paragraph, Joan suggests a possible title for the story. Editors like writers who are one step ahead and offer ideas that can help round out the story. You are also giving the editor a better sense of what your story is really about. Back to pitch

[3] Joan is telling the editor right away why she should care about this pitch. It involves baby boomers, which is the core demographic of this publication. Back to pitch

[4] The description of the farm-to-vet program is approximately the point at which Joan sparked the interest of the editor she originally pitched. Had Joan not included such detail in her query (and only mentioned Dulanie Ellis in general terms), she may not have been given the FOB assignment. Back to pitch

[5] Near the end of the pitch, Joan details her writing experience, [6] complete with links to her work. She even briefly explains why she chose these particular examples. Back to pitch

[7] Joan concludes the pitch by circling back to why this story is appropriate for AARP‘s audience. Back to pitch

 

Topics:

Go Freelance, Journalism Advice, Pitches That Worked
Advice From the Pros

Olympic Skater Ashley Wagner on Her Possible Future in Journalism

The athlete discusses sports journalism and the double-edged sword that is social media.

Ashley Wagner
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By Valerie Berrios
@valerieberrios
Valerie Berrios is a published author and senior content manager with nearly two decades of experience in digital publishing, including roles at Audible, Disney Streaming, Everyday Health, and Mediabistro. She specializes in content strategy, editorial operations, and international content launches.
4 min read • Originally published February 6, 2014 / Updated March 19, 2026
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By Valerie Berrios
@valerieberrios
Valerie Berrios is a published author and senior content manager with nearly two decades of experience in digital publishing, including roles at Audible, Disney Streaming, Everyday Health, and Mediabistro. She specializes in content strategy, editorial operations, and international content launches.
4 min read • Originally published February 6, 2014 / Updated March 19, 2026

After finishing fourth at the U.S. Figure Skating Championships last month (where she fell twice during her free skate), Ashley Wagner endured some harsh public criticism when she was named to one of only three figure-skating spots on the women’s 2014 Olympic team. No matter that she had consistently scored higher results over the past four years than the Nationals third-place finisher and fan favorite, Mirai Nagasu. The bullying got so bad that Wagner, who had been active on Twitter and maintained a video blog on YouTube, took a break from social media. She told NBC Sports, “Twitter is a blessing and a curse. It’s tough to filter out the good things that you hear and the awful things that people will write.” But now she’s ready to pick herself back up and take her place on Team USA.

Beyond her athletic career, Wagner aspires to be a sports journalist. Her hobbies include writing and reading the classics, and she’s been tapped as a blogger for SI.com. Mediabistro caught up with Wagner just before she set off for Russia to compete at the Sochi Olympics:


When did you know you wanted to be a professional figure skater?
Well, honestly, I was driving my mom crazy at home. She put me in a skating rink so that she could get some time away from me driving her crazy. That’s how I became a figure skater. [laughs] But, beyond that, when I watched Tara Lipinski win Olympic gold in ’98, that was really where my Olympic dreams took off, and that’s where I felt like I really wanted to become an Olympic athlete.

Tell me about blogging for SI.com. How did that happen—and what are you writing about?
Well, I used to have a video blog, and that was really fun for me. I would take the camera and show people around backstage, show what it was like, you know, walking back to the competitor’s lounge, or what it was like getting rehab done on an injury. So I tried to show the different aspects of skating, beyond those perfect couple of minutes that you see on the ice.

It just comes kind of naturally to me to take something and try and make it relatable and interesting to someone who doesn’t know everything about skating. So I think that [the editors] saw that and thought, ‘Hey, she’s not too shabby at this. Why doesn’t she try blogging for us?’ And it took off from there.

So for SI.com, I’m mostly just giving people a glimpse of what it’s like on this crazy journey to Sochi. I mean because there are so many different aspects of competing and preparing and designing even that go on in figure skating, I wanted to give people a little insight into that.

You’ve said you’re interested in sports journalism after your athletic career.
Yeah, I want to stay involved in sports in one way or another. And I would love to coach, but I also feel like I’ve been on this one side of figure skating, and I’m so ready to see what it’s like to be on the other side—and be able to get those stories out of athletes.

What platform would you prefer—print, Web or broadcast?
Right now it’s pretty equal. It’s so daunting, because I know that journalism right now, it’s going through a lot of changes, and it’s all becoming integrated with social media. It could be fun to participate in something that’s completely changing, but also, I would be totally okay with being on air and interviewing athletes in that way and commentating on figure skating. So it kind of depends on where this road takes me.

Are there other sports you’re interested in reporting on?
I love hockey. That’s actually one of my favorite sports. And this season I have no cable, and I’ve been too busy to watch. But I think if I were to choose another sport, it would be hockey.

I heard you quit social media because you received some backlash over being selected to the U.S. Olympic team. Is that true?
Yeah, I mean I didn’t go cold turkey. I’m coming back. But, honestly, just a bunch of really mean, hurtful things were being said to me. You know, I had people telling me to go jump off of a bridge and things like that, that I was already going through a lot of things on my own. I didn’t need to see all that negativity. I think the great thing about social media is it gives people access to you on a totally personal level that they didn’t have before, so it’s really important and it’s a great way to get people involved and excited about what you’re doing. I’m definitely not gone forever, but I’m taking a break until those trolls realize that I’m not reading what they’re saying nor do I care what they’re saying.

Follow Wagner and all the Olympic action on NBCOlympics.com and TeamUSA.org.

This interview has been edited for length and clarity.

Topics:

Advice From the Pros, Be Inspired, Interviews
Business Basics

Essential Tax Tips Every Freelance Writer Needs to Know

Fretting about tax time? Here's what you need to know about filing as a freelancer

Freelancers doing his taxes
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By Amanda Layman Low
@AmandaLaymanLow
Amanda Layman is a B2B tech content writer and strategist with over 15 years of experience creating content for startups and enterprise brands. She founded Tigris, a content agency serving leading tech companies, and authored The New Freelance: A Book for Writers.
6 min read • Originally published April 1, 2014 / Updated March 19, 2026
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By Amanda Layman Low
@AmandaLaymanLow
Amanda Layman is a B2B tech content writer and strategist with over 15 years of experience creating content for startups and enterprise brands. She founded Tigris, a content agency serving leading tech companies, and authored The New Freelance: A Book for Writers.
6 min read • Originally published April 1, 2014 / Updated March 19, 2026

In my early freelancing days, the only advice I’d retained regarding taxes was “file them” and something about keeping receipts in a shoebox. Granted, I earned less than $20,000 my first couple of years combined, and my husband’s tax return always covered what I owed. But this year, for the first time, after filing my taxes I owed money back and had to pay a penalty for not filing incrementally throughout 2013. This was enough to scare me into reality, make me buckle down and admit it’s time to get my act together. If you’re in the same boat, here’s a little advice to avoid the headache and potentially hefty penalties of putting off your taxes until the last minute.

Paying annually vs. quarterly

There are two ways to pay your dues to Uncle Sam: Annually or incrementally throughout the year. If you owe less than $1,000, there’s no penalty for filing once at the end of the year, says Brittany K. Hopp, CPA of Clayton, York and Hopp CPAs. “However, I do recommend my clients do quarterly estimates so they don’t get stuck with one big bill at the end of the year.” These are due in April, June, September and January, and can be paid online at eftps.gov

Because freelance income is so erratic, it can be difficult to calculate how much you’re going to owe. William Perez, tax practitioner and freelance writer, says that you can use Publication 505, available on the IRS website, to determine your taxes by hand. “However,” he says, “I prefer using tax software. After building a scenario for next year’s taxes in the software, I capture the data and tax calculations in a spreadsheet. Then I use the tax calculation to create a budget.”

If you’re married filing jointly and your spouse gets a regular paycheck, an alternative option is to take your tax estimation and have a certain amount of money withheld from your spouse’s checks.

This is what writer and communication strategist Meg Maker did earlier in her career, although now that she and her husband are both self-employed, she uses the traditional quarterly filing method.

Keep organized and track deductions

Even if you’re a budding freelancer with nary a paycheck to speak of, it pays to make a habit of getting organized now. Perez recommends familiarizing yourself with the forms 1040, Schedule C and Schedule SE. Print them off, read them and get acquainted with which items are deductible and align your spreadsheets or other bookkeeping tools with its categories.

For example, I have one spreadsheet dedicated solely to potential deductions. Some of the things on my list include my membership to my local networking group, my Mediabistro AvantGuild membership and my coworking group membership. The miles I drive each day to get to my coworking spot are also deductible. Some other common deductions for freelance writers include office equipment, home office expenses, health insurance and retirement plans.

Occasionally, entertainment costs are deductible—say you’re a food or travel writer whose articles depend on spending money on these things—but they’re highly scrutinized by the IRS, so save as much evidence as possible (printed clips, receipts, correspondence with editors) in the event of an audit.

Regarding bookkeeping tools, you should use what works best for you. Maker uses Quicken for analyzing her current financial state and Excel spreadsheets for tracking invoices. I use spreadsheets backed up to the cloud, and I try to keep them as simple as possible: One book for invoices, and one book for income and expenses. Quickbooks is another tool that’s popular with small businesses, although its scope may be too wide if you’re just getting started freelancing.

About the self-employment tax

So, why does the tax bill seem so much higher for freelancers than traditional employees? The answer is the self-employment tax, which is a combination of Social Security tax and Medicare and comes to 15.3 percent as of 2014. If you’re an employee and you get paid through a W2, half of that 15.3 percent is withheld from your paycheck and the other half is paid by your employer.

However, when you’re self-employed, “you have to pay both sides of that, because you’re the employer and the employee,” Hopp says. “Self-employment tax is figured on your net income. So you receive your income, subtract your expenses, and then that amount, that 15.3 percent, is calculated.” From there, you take your net profit and determine your income tax from that. This is where you may see different benefits and drawbacks from filing jointly or separately from your spouse.

Sole proprietorship or LLC?

An important distinction that may impact your taxes is whether you choose to remain a sole proprietor or become an LLC. If you are the only person who owns your LLC, you’ll file a Schedule C (exactly as you would for a sole proprietorship). However, if your LLC is owned by two or more people, you’ll split the net income of the LLC between owners based on their percentage of ownership, says Perez.

Otherwise, becoming an LLC won’t have too much bearing on your taxes — but it could change some aspects of your business for the positive. Maker likes being an LLC for many reasons. Because an EIN (Employer Identification Number) replaces your social security number on legal forms, she states, “it’s nice not having to give out my social security number to everyone I work for.” In addition, it protects her family assets from any kind of business-related lawsuit.

She describes it like this: “If I’m just working as Meg Maker, they can file a lawsuit and go after our personal money. But if I have an LLC, all my client can go after is what I have in the bank for my LLC.” Of course, it’s best to talk to an attorney to see which entity makes more sense for you. If you’re still in startup mode, it may be difficult to justify the initial cost of setting up an LLC, which varies by state.

Tax advice and mistakes to avoid

Hopp recommends that if you’re going to hire a professional to help with your taxes and accounting, choose someone with whom you feel comfortable. “If you know you can’t handle it on your own, call around, get referrals, do interviews for CPAs or tax preparers. They shouldn’t be offended by that. You’re definitely going to be more willing to call someone throughout the year if you feel like you can trust that person.” She also recommends keeping a notebook handy to jot down potential deductions, like mileage, as you go. “I see so many people going back at the end of the year trying to recreate it. Get in the habit of doing it when you’re driving so you don’t miss things.”

The only regret Perez has about his early approach to money management as a freelancer is that he would have re-invested more of his income into business. “Today, I ask myself, where is this money needed, where can it be productive?” He cites the improvement of professional skills, technology upgrades and even ergonomic furniture as great ways to invest in your business—all of which qualify as tax deductions.

A few simple steps is all it takes

You don’t need to get a degree in accounting to be smart about your tax planning as a freelancer. Set small goals for yourself. Schedule a meeting with a CPA (many will do a free consultation), start a free online trial of a business accounting software program that looks good to you—or take a course like Mediabistro’s Develop a Successful Freelance Career, which includes a section on finances.

In the same way that you do a wealth of research before sending out a pitch to Glamour or Sports Illustrated, some advance planning and organization is all you need to pay your dues and get back to what you love: your writing.

Topics:

Business Basics, Go Freelance
Productivity

5 Actionable Steps to Build Your Media Career 5-Year Plan

Kickstart your long-term strategy with these nitty gritty details on how to get started

woman inspired to set 5 year plan
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By John Lombard
John Lombard is a content strategist and writer with over a decade of experience creating interactive and video content for brands like Apple, IBM, and Samsung. He previously worked at Mediabistro and now serves as a Client Strategist at Ceros.
4 min read • Originally published January 4, 2015 / Updated March 19, 2026
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By John Lombard
John Lombard is a content strategist and writer with over a decade of experience creating interactive and video content for brands like Apple, IBM, and Samsung. He previously worked at Mediabistro and now serves as a Client Strategist at Ceros.
4 min read • Originally published January 4, 2015 / Updated March 19, 2026

Whether you’re just starting out in your career, deep in the freelancing trenches or already at your media dream job, developing a 5-year plan is a bold, take-charge move. With a long-term goal in sight, and with actionable steps leading to that goal, you’re no longer simply floating by, you’re taking the reigns on your destiny. And that feels awesome.

Wondering where to start? Read on as we take a look at the 5-year plan, and how to really get it going.

1. Determine Your Overall Goal

Think of your overall goal as a finish line, the desired outcome of your 5-year plan: Maybe you’re looking to transition into a new career, or maybe you want to turn your idea for a startup into a reality. Whatever the goal, be sure that it’s realistic and concrete, as more defined goals make it easier to develop actionable steps towards your desired outcome.

Let’s say your overall goal (what you plan to achieve with your 5-year plan) is:

To create a blog with a strong online following that generates enough steady income from ad revenue to support myself by first quarter 2021.

Wondering what you’ll need to do to hit that goal? See below for more on how to make the dream a reality.

2. Determine Your Actionable steps

Now that you have your overall goal laid out, it’s time to figure out the actionable steps you’ll need to take in order to reach that goal. What are actionable steps? Put simply, they’re steps that require you to physically do something in order to get closer to your goal.

To just state your 5-year plan and attempt to achieve it would be incredibly overwhelming. Rather, set small attainable goals that lead to your ultimate goal. Using our blogging 5-year plan as an example, let’s take a look a couple of the actionable steps that get us closer to our end:

Build a following of readers.

For this step, you can break down all the smaller steps that lead to this being accomplished. You might list these steps as learn how to build a blog following via online classes, study other successful bloggers, write at least 10 new articles every month.

Use digital marketing techniques to raise my visibility online.

Here, you might list take a class in digital marketing .

3. Break Out the Calendar

Here’s where things get real: Take your actionable steps and substeps and give them real dates.

Determine which steps need to happen in which order, then begin filling out the calendar. Start with yearly goals, move on to monthly goals, then add your daily or weekly goals.

A good idea when filling out your calendar is to ask yourself with each entry, “Is this step directly contributing towards my 5-year goal?” Asking this will help weed out what are actually side-projects and what are essential steps needed in reaching your goal.

Here’s how this might look with our blogging example:

End of week 1
Set my 5-year plan in motion!
Began researching top bloggers in my field
Completed 3 of 10 blog posts to roll out next month

End of month 1
Finished researching online classes and signed up for at least one
Began following the top bloggers in my niche field
Created 10 quality pieces to roll out for the next month

End of year 1
Completed content and marketing classes
Reached out to popular bloggers for advice
Created quality content for my audience (at least 10 pieces a month)

To make your steps even more specific, and yourself more accountable, productivity strategist Mike Vardy suggests renaming “appointments” on a calendar with “agreements” helps make them more difficult to break. “Rescheduling an appointment is something that can be done,” Vardy says, “but rescheduling an agreement seems more daunting and less viable.”

4. Add and Adjust Steps as Needed

As you continue towards you goal, it is very important to revise steps along the way. Maybe you, our hypothetical blogger, thought a content marketing class would help, when you realized a creative writing class would also be beneficial. Or maybe you learned that you also need to add video and a podcast to your site in order to gain more followers.

The main lesson here: Don’t be afraid to make changes to your steps, as long as they are changes that will more effectively lead you to your 5-year goal.

5. Stick to Your List by Becoming Your Goal

It may sound weird, but this change of mindset can help you achieve your goals. Behavioral psychologist James Clear says that our current behaviors are a reflection of our identity. To change your behaviours and actions, Clear says, you must “start believing new things about yourself.”

How to do this? Clear recommends developing a new identity and backing it up with small wins (which in this case are your actionable steps). Let’s check out our blogger example one final time:

New Identity
A highly creative writer capable of pulling in large audiences from all walks of internet.

Prove It through Small Wins/Actionable Steps
Each month, get over 100 shares on at least 3 articles.

“You have to become the type of person you want to be,” Clear says, “And that starts with proving your new identity to yourself.” The more actionable steps you take towards your goal, the more you become your new identity.

Need that extra boost to jump-start your 5-year plan? Sign up for one of Mediabistro’s online courses such as Project Management Methodologies or Fundamentals of Digital Marketing. Developed and led by industry experts, these courses are designed to up your skills and get you closer to your goals.

Topics:

Be Inspired, Productivity
Journalism Advice

The Biggest Mistakes Now-Successful Freelancers Made Starting Out

Veteran freelancers reveal what they wish they'd known early on

freelancer making biggest mistakes
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By Paula Vasan
Paula Vasan is a four-time Emmy-winning investigative journalist and communications strategist whose reporting has influenced legislation and reached millions across broadcast and digital platforms. Her career spans Wall Street reporting at Yahoo Finance, senior investigative roles at TEGNA, and communications leadership at TEDx, with bylines in The Atlantic, CNBC, and The Boston Globe.
6 min read • Originally published January 20, 2015 / Updated March 19, 2026
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By Paula Vasan
Paula Vasan is a four-time Emmy-winning investigative journalist and communications strategist whose reporting has influenced legislation and reached millions across broadcast and digital platforms. Her career spans Wall Street reporting at Yahoo Finance, senior investigative roles at TEGNA, and communications leadership at TEDx, with bylines in The Atlantic, CNBC, and The Boston Globe.
6 min read • Originally published January 20, 2015 / Updated March 19, 2026

Any freelancer who’s built up a steady client base over the years can admit to having made their fair share of mistakes when he or she started out in the industry. Maybe it was underestimating the time it takes to get paid or taking editors’ feedback on their first, second or third drafts too personally. Here’s what a few veteran freelancers say were their biggest blunders — so you can avoid making them.

Noah Davis, who lives in Brooklyn, New York, calls himself a generalist, writing about everything from the future of women’s soccer in the U.S. to the rise of the font type Helvetica. He’s been a freelancer on and off since 2005 but has pursued freelancing full time for the last three years, writing on average 10 feature articles a month. His income in 2014 totaled about $125,000, and he earned roughly $95,000 the year before. He attributes his earnings last year — the highest he’s ever made — partly due to the fact that he has a specialty in soccer writing, and was pursued for many assignments related to the World Cup. He gives us our first two mistakes:

Mistake #1: Not understanding the difference between a topic and a story.

“When I first started out freelancing, I’d often pitch things I thought were cool or interesting, but it didn’t have a story behind it,” Davis said. “A trend isn’t enough. You need a face or story behind it.”

Davis soon learned he needed to do more than just pitch ideas. While the majority of those pitches went ignored, once in a while he’d hear back from someone who would offer advice on how to shape the story. “It depends on how much the editor wants to work with you,” Davis said. “Your job as a freelancer is to find something the editor doesn’t know about and turn it into a story with an arc.”

Mistake #2: Assuming you’ll bank payments right away.

A frequent misconception among new freelancers is that they will get paid immediately after their story is submitted. Ramping up a freelancing business, however, takes time.

There’s a huge difference between a) being a full-time freelancer and b) having another job — whether it’s full time or part time — while freelancing, according to Davis. “So it takes a long time for that cycle to start and for checks to start rolling in.”

Initially, Davis thought it would take three to four months for him to have checks coming in on a steady basis, but it took him closer to six or eight months to have that steady stream of income from freelancing and to feel like he was on his feet. “Luckily I had reserves to make it work, but it was surprising at the time,” he said.

To create a sustainable business, freelancers need to gain trust among editors. “If [editors] have a piece in mind, you want to be top of mind for them,” explained Davis.

So how do you make that happen?

Take the time to form a connection. “If I feel like I have a good relationship with an editor, I might send a note saying, ‘Hey, I’m full-time freelancer. Keep me in mind,'” Davis said. “Or I might ask to go out for a drink.” The goal, he added, is to not only develop relationships, but also to bounce ideas around and figure out exactly what editors are looking for at their respective publications.

Kevin Lincoln, who’s based in Los Angeles, has worked on staff at BuzzFeed and Fox Sports Live and freelanced on the side before leaving his salaried position to dive into freelancing full time.

He set himself up well for the transition. “It was easier to become full time by already having a few strong relationships with editors and a reliable number of assignments,” Lincoln said. He has our second set of mistakes to avoid:

Mistake #3: Failing to maintain relationships with publications you’ve already worked for.

“I think that at some point, to really make it work and be able to have a living wage as a full-time freelancer, you need to have steady assignments with particular outlets,” said Lincoln. Since April 2014, when he became a full-time freelancer, he’s been cultivating those established relationships and has already been developing new ones that he aims to rely on moving forward.He set himself up well for the transition. “It was easier to become full time by already having a few strong relationships with editors and a reliable number of assignments,” Lincoln said. He has our second set of mistakes to avoid:

Mistake #4: Forgetting to keep track of how much money you’re making.

“I now have a spreadsheet where I write down every dollar that I earn,” said Lincoln. Keeping track of his assignments and projects allows him to see his progress from month to month.

The rhythm of freelancing income is often hugely unpredictable, so freelancers must keep track of the flow of money to pay rent or your mortgage and other regular expenses. And it’s a good idea to have a good amount of savings before you become self-employed, Lincoln said.

Writer Taffy Brodesser-Akner, from West Orange, New Jersey, has been freelancing for five years, and in 2014, published a total of 79,200 words. Back then, her goal was to be a contributor for both GQ and The New York Times Magazine — and these days she is a contract writer for both outlets.

Her foray into full-time freelancing was spurred by staying at home with her son for a year after he was born. “When he turned a year I got some babysitting together, because I felt stay-at-home life didn’t play well to my skills. So I wrote personal essays about things going on in my life,” she said, slightly out of breath on the phone from her treadmill desk at home. “People said I should start a blog, but I felt I should be paid for my work.” Brodesser-Akner shares our last group of new-writer oversights:

Mistake #5: Letting the pitching process intimidate you.

“I wish I hadn’t been so nervous pitching,” Brodesser-Akner said. “I wish I realized early on that editors are just people, and they need proof that you’re just a person.”

She referenced a piece of advice from one of her editors, who said that in freelancing all you need is the following (and if you have two of the three you’re golden):

  1. Be good at your job
  2. Be on time
  3. Be nice

Mistake #6: Understanding that interviews and conversations are not always synonymous.

Early in her freelancing career, Brodesser-Akner said she would often spend too much time trying to relate to her interview subjects, rather than get those quotes she needed to write the piece. The result? Wading through hours of transcripts. “Why didn’t I just shut up?” she laughed.

Mistake #7: Taking revision requests too personally.

Keep in mind that editors want to make your work shine — and that’s not a bad thing. It will be your byline on the piece, after all. Don’t think you’re the only writer who’s gotten her story picked apart.

And if you don’t get feedback, that isn’t necessarily something to be concerned about. “I used to look for approbation from editors, but I finally realized that if an article was good enough to run and had a good editor… it was all I needed,” explained Brodesser-Akner. But always know you can send a quick message to your editor to make sure you were on target.

Mistake #8: Being afraid to ask for more money.

It’s a topic Brodesser-Akner feels strongly about. People often are so timid to ask for more money, she said. You may be surprised to find that many of your clients are willing to negotiate, especially if they’ve come to rely on you to meet deadlines and produce good work.

This interview has been edited for length and clarity.

Topics:

Go Freelance, Journalism Advice
Journalism Advice

Never Run Out of Ideas: How to Generate Story Pitches Editors Want

Learn how to cultivate a deep reserve of ideas

freelancer generating story ideas
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By Paula Vasan
Paula Vasan is a four-time Emmy-winning investigative journalist and communications strategist whose reporting has influenced legislation and reached millions across broadcast and digital platforms. Her career spans Wall Street reporting at Yahoo Finance, senior investigative roles at TEGNA, and communications leadership at TEDx, with bylines in The Atlantic, CNBC, and The Boston Globe.
4 min read • Originally published February 10, 2015 / Updated March 19, 2026
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By Paula Vasan
Paula Vasan is a four-time Emmy-winning investigative journalist and communications strategist whose reporting has influenced legislation and reached millions across broadcast and digital platforms. Her career spans Wall Street reporting at Yahoo Finance, senior investigative roles at TEGNA, and communications leadership at TEDx, with bylines in The Atlantic, CNBC, and The Boston Globe.
4 min read • Originally published February 10, 2015 / Updated March 19, 2026

Every writer — whether a novice or veteran journalist — has been there. You’ve got your laptop in front of you, a coffee by your side, maybe some snacks to munch on within reach. You put your fingers to the keyboard… and wait for a brilliant idea to strike — that eureka moment when you know exactly how to structure your story pitch to an editor, explaining why your idea is relevant to a particular publication and why you’re the person to write the story.

But when those ideas don’t come and you keep wrestling with vague concepts without any semblance of a story arc, it’s disheartening and all-around frustrating. Here, three seasoned writers share their tips on generating new ideas and spurring creativity when the idea well is running low.

Read industry sources. The mantra among successful freelancers: Read, read, read. By staying informed about everything going on about a particular beat and the news overall, your ideas will mature and multiply.

Andrea Coombes, an award-winning writer in San Francisco with more than 14 years of experience writing about personal finance, said the best way to spur ideas is just to read more, and that includes relevant blogs. “I also receive email updates from a number of government agencies, including the Federal Trade Commission and Consumer Financial Protection Bureau and others,” she said. “Occasionally there’ll be a story idea in there, but it does mean dealing with a lot of emails.”

Sarah Laskow, who has been freelancing for five years since moving to New York City in 2010, admitted she is always reading studies and news on areas of interest to her. As a result, “I’ve done a lot of environmental reporting,” she said. “I came up with a story about deer farms that breed for antler size just by thinking about deer one day,” she explained.

For Coombes, the news — such as a new tax law — can prompt stories along the lines of “What does this mean for your bank account?” But she cautions that covering the news can be trickier as a freelancer, since the fast-turnaround stories are more likely to be handled in house.

Create a robust RSS feed. What better way to organize all the content you find online? Writer Alicia Lutes, who started freelancing after being laid off from Hollywood.com, her first full-time writing gig, said she has a thorough RSS feed that spans myriad topics in order to keep herself abreast not only of the news, but what issues, movements and social challenges are dominating daily conversations.

“When you immerse yourself in what’s going on in the world, you find not only new perspectives for yourself, but you see what and why things are resonating with society as a whole — all of which better informs you as a writer,” Lutes said. “You cannot write in a vacuum on the Internet.”

Use your surroundings as inspiration. In addition to being a voracious reader, Coombes said coming up with new ideas is mainly a matter of listening and asking questions. “And don’t forget that age-old idea generator: I wish I knew more about X, Y or Z,” she said.

A conversation with friends and relatives about their money problems or questions could be the beginning of a story for Coombes. Emails from readers might lead to a story. Talking with her sources about what they’re seeing, or asking them what problems their clients are facing are also great fodder for ideas.

And sometimes, said Coombes, it helps to work on another project — just as long as it’s outside of your usual beat.

“Whenever I’m out of ideas,” said Lutes, “I find leaving the house works best… a bit of reintegration with nature does the body good. Go for a walk, sit in a park, listen to the birds. Whatever gets you back to a place where you’re not stopped-up, ideas-wise.”

“If that doesn’t work, well, just keep writing,” added Lutes. “Write through the bullsh*t, as Ira Glass has said. Eventually, you’ll get there.”

Finally, don’t forget to record those ideas you generate on the fly. “I keep an ongoing file of things I find interesting,” said Laskow. “When I have time, I develop them into longer stories, and I have them on hand when editors email me and are looking for specific types of stories that fit into certain categories.”

This interview has been edited for length and clarity. 

Topics:

Go Freelance, Journalism Advice
Business Basics

Health Insurance Options Every Freelancer Should Know About

Find out which health plans are available when you're self-employed

health insurance form
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By Paula Vasan
Paula Vasan is a four-time Emmy-winning investigative journalist and communications strategist whose reporting has influenced legislation and reached millions across broadcast and digital platforms. Her career spans Wall Street reporting at Yahoo Finance, senior investigative roles at TEGNA, and communications leadership at TEDx, with bylines in The Atlantic, CNBC, and The Boston Globe.
5 min read • Originally published March 6, 2015 / Updated March 19, 2026
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By Paula Vasan
Paula Vasan is a four-time Emmy-winning investigative journalist and communications strategist whose reporting has influenced legislation and reached millions across broadcast and digital platforms. Her career spans Wall Street reporting at Yahoo Finance, senior investigative roles at TEGNA, and communications leadership at TEDx, with bylines in The Atlantic, CNBC, and The Boston Globe.
5 min read • Originally published March 6, 2015 / Updated March 19, 2026

The question as a freelancer is not whether health insurance is necessary (it’s mandated now by the Affordable Care Act), it’s what type of health insurance works best for the self-employed.

Without a doubt, shopping for health insurance can be a stressful and daunting task. You could shop around for an individual policy, you may be able to continue on your former employer’s plan or you could get COBRA if you’re between jobs. Whatever the case, it’s essential to research the process heavily. Perhaps there are options available to you that you didn’t even realize were on the table.

Be prepared. Shopping for the right plan will take a lot of time and likely many phone calls and emails. If you love your current health care providers, for example, reach out to all of them first, find out what they accept and see if there is a common denominator. Then you’ll have to decide if you’re able to go through a union, or if you’ll have to achieve the best type of health insurance through another means.

Here’s a breakdown of some of the options available to freelancers.

Sign up for an individual policy. On the federal website HealthCare.gov, you can compare single health insurance plans in your area. February 15 was the last day to enroll for 2015; however, you may qualify for the special enrollment period if you get married, have a baby or lose your previous health coverage.

“The process [of finding a health plan] can be overwhelming,” says Kerry Hannon, a personal finance expert and author. “I used an independent agent to help me sift through the choices, then selected one independently from that group.”

When doing your own research, ask doctors which carriers they accept to help winnow your choices of insurers and plans, adds Hannon.

Another source is the National Association of Health Underwriters, which can help you identify three to four insurance plans in your area.

Continue on your former employer’s plan. If you took early retirement, you can try to get on your former company’s health insurance plan. According to a recent Towers Watson survey, the cost for Medicare-eligible retirees getting health coverage from their former employers in 2014 averaged $4,986 for single plans and $11,689 for family plans.

Lean on your parents — if you can be claimed as a dependent. If you’re under 26 years old, you’re in luck. The Affordable Care Act requires plans and issuers that offer dependent coverage to make the coverage available until the adult child reaches the age of 26, according to the U.S. Department of Labor.

Freelancer John Surico, who is 23 and based in New York City, gets health insurance from a parent’s plan, thanks to Obamacare. “The ability to be on my parents’ insurance has lifted a frightening burden on my freelance career. But it also constantly reminds me how prepared I have to be when I turn 26,” says Surico, who started freelancing full time after graduating in 2013 and now writes for a host of publications, including The New York Times, VICE and Narratively.

“This option is definitely a good thing if you’re just getting started in your career,” says Hannon. So recent grads may be able to breathe a little sigh of relief until they are able to afford a plan of their own.

Get on a spouse’s company-sponsored health plan. With this option, your spouse would pay a higher premium for family coverage, but it would still cost less than if you obtained an individual policy, explains Hannon.”

In 2014, annual premiums for employer-sponsored family health coverage reached $16,834, up 3 percent from the previous year, with workers on average paying $4,823 toward the cost of their coverage, according to research by the Kaiser Family Foundation/Health Research & Educational Trust (HRET).

Just keep in mind that most plans won’t allow employees to add a family member after open enrollment season, typically at the beginning or end of the calendar year.

Consider COBRA coverage. According to Hannon, it’s a good option if you’re between jobs and need quality health insurance quickly, for a short period of time. “Freelancers should know that COBRA only lasts for 18 months, but it’s a good Band-Aid between full-time jobs for health insurance,” she says.

COBRA is not cheap, however. Freelancers should be prepared to shell out more than average for it, since you are paying for the cost of the coverage plus administrative fees.

Join a professional group. Full-time freelancer Noah Davis has paid $457 a month for health insurance for the last three years through Freelancers Union, an option for many New York State residents.

He explains: “In my mind, the issues are a) cost and b) the confusing details of all the different plans. Considering how much other people pay and what they have to go through to get health insurance, I feel good about my coverage and cost. Sometimes I think I should get a cheaper plan that just covers catastrophes, but then I reconsider and that feels like an unnecessary risk given my situation.”

Other professional groups to look into for group insurance rates include AARP, and alumni and church associations. If you’re running a small business, it would be wise to check with your local chamber of commerce or the Small Business Service Bureau. In addition, the National Association for the Self-Employed offers insurance plans.

Do your homework to see where you can get better prices within a group plan rather than going at it alone.

Open a health savings account. If you have a high-deductible health insurance plan, consider pairing it with a health savings account (HSA), offered through various banks and mutual funds. Contributions are tax free, and you’ll be able to make tax-free withdrawals for qualified medical expenses, such as deductibles and co-payments.

Unlike with some employer HSAs that have a “use it or lose it” policy, an individual HSA will carry over to the next year, and accumulated savings never expire.

Ultimately, it’s up to you to do your due diligence to get the best rates on whichever health plan you choose. Compare premiums, deductibles and out-of-pocket expenses — and comparison shop on sites like eHealth and NetQuote.com.

This interview has been edited for length and clarity. 

Topics:

Business Basics, Go Freelance
Business Basics

First-Time Freelancer? Here’s How to Survive Tax Season

Get in control of your taxes by thinking ahead

piggy bank on tax season forms
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By Brittany Taylor
Brittany Taylor is an enterprise marketing manager and content strategist with over a decade of experience in B2B content marketing, brand building, and ghostwriting, with bylines in SELF, Teen Vogue, and Mediabistro. She currently leads content and branding across multiple brands at HireQuest Inc.
7 min read • Originally published March 16, 2015 / Updated March 19, 2026
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By Brittany Taylor
Brittany Taylor is an enterprise marketing manager and content strategist with over a decade of experience in B2B content marketing, brand building, and ghostwriting, with bylines in SELF, Teen Vogue, and Mediabistro. She currently leads content and branding across multiple brands at HireQuest Inc.
7 min read • Originally published March 16, 2015 / Updated March 19, 2026

Tax season is an easy enough concept when you’re a full-time staffer: You fill out a W-4 when you start, you get a W-2 in January, and then you pick a tax software, answer its questions and start dreaming of what you’re going to do with all the cash Uncle Sam’s been slipping out of your paycheck. But when you go solo, life gets dicey. There’s a whole new set of forms, a whole new set of taxes and a whole new set of rules. Yikes.

Before you give up on the IRS and pull the covers up over your head, hear us out. We interviewed a handful of fabulous accountants who specialize in filing taxes for creatives. Meet our tax guides: Howard Samuels, CPA MST, at Rosenfield and Co. in Florham Park, N.J.; Jonathan Medows, CPA, from New York City; Andrew Poulos, EA, ABA, ATP, from Atlanta, Ga; and Gail Rosen, CPA, PC, from Martinsville, N.J. Here, they answer frequently asked questions from inquiring, self-employed minds.

What is the 30 percent self-employment tax everyone talks about?

“When you work for a company, half of the social security tax comes out of your paycheck and the other half the employer has to match,” Samuels says. “When you’re self-employed, you have to pay it all. You are essentially the employer and the employee. All they did was change the terminology, calling it ‘self-employment tax’ instead of social security (or FICA) and Medicare.”

Self-employment tax comes out to roughly 15 percent. The rest of that 30 percent figure consists of federal and state income taxes, and while it’s a good ballpark, it can vary depending on your location. For example, a freelancer in New England will likely pay a larger percentage of state income tax than a freelancer in Florida.

Where you work and/or live will decide how much and how many different taxes you need to pay. Medows, who himself is a Big Apple freelancer, says after the typical federal and state, he also is on the hook for city, regional and unincorporated business tax.

What about other items that would normally be taken out of my paycheck pre-tax, like health care and retirement savings?

Ah, benefits — those are all up to you. “You can take [health insurance] as a deduction when you’re self-employed,” Medows says. That includes premiums for medical, dental and vision. “Same thing for IRA contributions, which have the potential to be tax deferred.” Both decrease your tax liability.

Since we’re talking about savings, also have plans in place for an emergency fund, just in case.

Will I be responsible for sales tax, too?

Here’s where it can get tricky. Generally speaking, sales tax is charged only for tangible products — something you can hold in your hand. If you’re a graphic designer, for example, you typically would not have to charge sales tax for a digital file containing a business card design. However, if you were to print out 500 business cards featuring that design, then you would have to charge sales tax. Got it?

Say you are selling tangible goods to an end user. First, you’d go to your state and register your business. You’ll receive a unique sales tax ID number. Depending on your sales volume, you’ll remit the sales tax you’ve collected to the state on a weekly, a monthly, a quarterly or an annual basis.

“Every state has different laws when it comes to sales tax,” Samuels emphasizes, so it’s essential that you visit a CPA [aka a certified public accountant] to establish whether or not you’ll need to start charging it. And if you do, he added, “It is very important that if you collect it — even if you’re late — [that] you file it or you will go to jail. The state sees sales tax as their money — so if you don’t remit it, you’re stealing from the state government.”

Does this mean I need to hire an accountant?

“It depends,” Medows says. “An accountant will help you take the right deductions, make sure you don’t miss deductions or take things you shouldn’t take. If you have any phobia about it, it’s best to get professional help.”

One other thing to keep in mind, Medow adds: “Sometimes it helps a freelancer to have a CPA relationship because later on, when they try to buy a house or borrow money, banks will insist on letters from their CPAs regarding their business. That can be difficult if you don’t have a professional relationship.”

If you do decide to go with a pro, Poulos urges you to find an accountant or tax professional who has experience and is licensed — look for an Enrolled Agent (EA) or a CPA. Yep, those letters have real meaning. “Approximately 60 to 70 percent of the tax preparers around the country are unlicensed,” he tells us. “A high amount of tax fraud and sometimes identity theft occurs from unlicensed tax preparers.”

And look for one who’s around for the entire year, not just during tax season, he advises. You’ll want guidance if you happen to be audited or if you have questions about estimated taxes, sales tax or anything else that comes up throughout the year.

Expect to pay $200 to a couple thousand dollars, depending on the complexity of your tax return. Poulos tells us he charges a freelancer with 10 or fewer 1099s and fairly organized records between $325 and $375.

What makes the price go up? Samuels echoes the importance of organization. His firm supplies clients with a spreadsheet that has the various deductions and expenses set up in a template. You would fill this out before you go, ideally. Alternatively, you can bring your box of receipts and piles of invoices and let the accountant sort it out — but this method will be far more expensive because, well, time is money.

What specifically do I need to keep track of?

Medows is emphatic about his No. 1: the money you earn. “Make sure you’re collecting money from your clients. Sometimes freelancers just aren’t on top of their receivables.” In line with this is the amount you’ve paid throughout the year in estimated taxes.

Next on the list: “Expenses!” Medows says. “You have to save original receipts or scan images of them. That’s a big deal for freelancers — they get an audit, someone asks them to prove what they’ve put down and they don’t have receipts. Credit card and bank statements are insufficient proof for IRS purposes.”

For an expense to be deductible it has to be “ordinary” and “necessary,” Rosen says. Therefore, keep track of the money you spend on office supplies, business dues, business publications, accounting fees for your business, business cards, business entertainment (50 percent deductible), gifts (limited to $25 a person a year), postage, printing, continuing education computers, software, etc.

And don’t forget about the business miles you drive. Log every trip — starting point, ending point, the number of miles in between, and why you were driving there — and decide how you want to deduct it. There are two methods, Rosen says: standard and actual. With the standard method, you can deduct a certain amount of money per mile ($0.56 in 2014), plus tolls and parking. The actual method is more complicated. First add up all of your automobile expenses and then multiple it by the percentage the car was used for business. To figure out the percentage, divide business miles by total miles driven for the entire year.

Needless to say, “organization can be a big problem,” Samuels tells us. “I advise all of my freelance clients to buy an accordion file and label each section with a different type of expense — health care, marketing, office supplies and so on. Make sure you get a receipt for everything…and put it in the folder. Then you’re all set.”

And how long should you hold onto all this paperwork? “Three years, per the IRS website,” Medows says, “but if they ever accuse you of fraud, that can go back six years. I would err on the side of caution and say six years.”

What happens if I mess up?

Nothing scary — you’re not going to go to jail (well, unless you hoard sales tax…).

“If you underpay, you might owe a penalty up to 10 percent,” Medows explains. “If you overpay, they’ll give you the money back (or you can put it toward next year’s estimated taxes).

Concludes Medows: “The biggest problem I see when freelancers start out is they don’t save money, and when it comes time to pay taxes, they don’t have the money and they blow it off. The IRS will help you. They’ll set up a payment plan. But if you don’t have the money, don’t not file. That’ll just make a bad situation worse.”

This interview has been edited for length and clarity. 

Topics:

Business Basics, Go Freelance
Productivity

7 Proven Ways to Be a More Productive Freelance Writer

Learn how efficiency can lead to a more profitable freelance career

productive freelance writer tackling projects
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By Amanda Layman Low
@AmandaLaymanLow
Amanda Layman is a B2B tech content writer and strategist with over 15 years of experience creating content for startups and enterprise brands. She founded Tigris, a content agency serving leading tech companies, and authored The New Freelance: A Book for Writers.
9 min read • Originally published April 24, 2015 / Updated March 19, 2026
Admin icon
By Amanda Layman Low
@AmandaLaymanLow
Amanda Layman is a B2B tech content writer and strategist with over 15 years of experience creating content for startups and enterprise brands. She founded Tigris, a content agency serving leading tech companies, and authored The New Freelance: A Book for Writers.
9 min read • Originally published April 24, 2015 / Updated March 19, 2026

I recently performed a little efficiency test to make sense of my profit and losses — the latter of which had been feeling especially heavy lately. I assessed my workload in terms of both money and time, and the results were surprising. When I broke down each client by hourly pay, my main client, the one that pays my rent and most of my groceries, was paying me the lowest hourly amount.

On top of that, I was spending $217 a week on full-time daycare for my daughter, and out of a need to get my money’s worth, I was keeping her in daycare from open until close and using more of that time for recreation than work. Although it was helpful for my physical and mental health to get that break, it made it more difficult to get back into the flow of work in the afternoon. After assessing everything, I found I was really only working five hours a day, and most of that time was devoted to my lowest-paying client. Not exactly a strong business model.

Out of a desire to improve my own productivity, I interviewed four freelancers who shared their efficiency tips with me. Here, I’ve boiled down their advice to seven tips.

1. Create your own efficiency test.

It’s impossible to know how you can boost efficiency without understanding your weaknesses. First, track your time. Freelance writer Rebecca Matter suggests you determine how much time you’re spending on each client, and then evaluate your hourly rate for each. “I think people resist this sometimes because they think they know where their money is coming from, but in my experience, every time you track your time you will be surprised,” she says.

Matter goes on to describe the 80/20 rule, which means the best clients will only require 20 percent of your time, while the worst ones are likely eating up 80 percent of your time. It may seem counterintuitive, but she recommends identifying which side clients are on, “and if they’re on the 80 percent side of your time, it’s probably good to get them out,” she says. Cutting out busywork may make your schedule feel frighteningly open at first, but that’s time you could be spending acquiring less needy or better-paying clients.

2. Plan out your workday in advance.

Regardless of when you do it, making a plan for how you’re going to spend your hours will help you anticipate your workload and stay on task. It doesn’t have to be detailed down to the minute, either. When freelance writer Maria Bellos Fisher was caring for her newborn at home, she had to organize the limited time she had. “The night before, I would think of two or three tasks that I wanted to get done the next day and I would put them on my calendar,” says Bellos Fisher. That way, during any moment of downtime, she could quickly refocus on one of her goals.

Freelance writer Valerie Bordeau faces challenges with her schedule due to fibromyalgia and strategizes by batching her tasks together. She says if she has a day in which she isn’t feeling well, she’ll spend it working on all her rough drafts. You can batch home-related tasks, as well, to save time and streamline your day. Bellos Fisher schedules all of her personal appointments back to back in one day, so she doesn’t have to break her work flow to accommodate doctor visits and other errands.

I like to make a list the night before of everything I hope to accomplish the next day. It feels good to check each one off as the day goes on, and whatever I don’t complete that day gets moved to tomorrow’s list.

3. Do the hardest thing first, every day.

I remember reading a quote attributed to Mark Twain that really stuck with me: “Eat a live frog first thing in the morning and nothing worse will happen to you the rest of the day.” In my experience, it’s the same with working from home as a writer. On my handy daily to-do list, I’ll rank my tasks in order of difficulty. Not only does this quash procrastination, but it allows me to use the hours in which I’m sharpest — between 8 a.m. and 10 a.m. — for the hardest work.

Matter agrees with this notion: “There’s always going to be this thing on your list that you resist. That’s the thing you tackle first — because it’s going to weigh you down the rest of the day. You’re going to be thinking about it. You’re going to be worrying about it. It’s going to distract you. If you just hit it head-on, you can get it off your list and be done with it.”

4. Treat your business like a business.

It’s the oldest rule in the book — and for good reason. If you treat your business like a business, you’ll create an environment in which you can grow, write what you want and be profitable. If you treat it like a hobby, you may have fun, but it’s not going to bring the income or advancement you want.

The first step to treating your work like a business is to schedule both work times and break times. Without regular working hours, you run into one of two problems: either you’re never fully shut off, meaning you’re constantly returning to your computer and never getting a chance to refresh, or you lose track of time and run the risk of wasting the precious working hours you do have.

The next step is to establish a space or signal that separates your work from your home life. Matter says, “I think it’s important to put your physical self in a working spot…just something that tells your body and brain, ‘I’m at work right now.'” So, what if you don’t have the means to create an actual home office? Simply stake out a corner of a room at home where you can put your desk. Regardless, Matter continues, “I think it’s important to find a way to signal that you’re working.”

For Amy Shey Jacobs, a freelance writer and entrepreneur, when she’s at home, her signal is a closed door. “If I get a cup of coffee and sit at my desk…I find it’s kind of my sanctuary,” she says. If you don’t have access to a separate space, consider renting a desk at a coworking facility or becoming a regular at a coffee shop that inspires you.

5. Know when to say yes or no.

For the new freelancer who’s prepared to work for peanuts (or a byline), it seems insane that you would ever say no to a project. However, all freelancers face the decision at some point about which projects to take and which to pass on. Jacobs says you “have to go with your gut and intuition, and where you are at your best.” Choosing projects that fit your expertise, experience level and passions will result in your best work. Jacobs adds, “When things are in your wheelhouse, it makes it easier to get more work done. You’re not starting from scratch. You’ve built up a repertoire of people you can call… I find it is amazing for efficiency.”

In addition to knowing your expertise, you should also know your limits. Bellos Fisher explains, “I would never take an assignment if I was way too busy because I never want to disappoint anybody.”

Bordeau offers three criteria to run a project through before you decide to take it. “No. 1 is does it match the income I need,” she says. If not, depending on your financial situation, it may be better not to take it. However, for lower-paying projects, it may still be OK to say yes if it builds a skill set you need, if it’s actually going to advance you or if it’s something that’s going to give you better work, says Bordeau.

6. Know what distracts you, and face it head-on.

It’s important to identify those things that tempt to pull you away from your office chair. Bordeau suggests you make a game plan, knowing that those distractions will always be there. She says you should ask yourself, “How will I attack this distraction before it attacks me?” Bordeau herself struggles with chatty family members and receiving personal phone calls, and has found that carving out her own writing space makes a difference. One of her friends actually locks herself in the bathroom to write. It’s an extreme example, but if it helps set boundaries and keep your family from distracting you, something like this may be necessary.

In my five years as a freelance writer, I’ve always struggled with my propensity for Web surfing. It’s so challenging to not go down that rabbit hole of mindless clicking when I’m constantly using the Internet for research and email, but recently I’ve made a concentrated effort to change. I try to only check my email when I’m not in the middle of writing. As for social media, if I find myself checking Facebook every two minutes, I take a moment to assess why I’m feeling the need to switch gears. Sometimes it’s my subconscious trying to tell me I need a legitimate break — a snack, a moment away from the computer or even human interaction.

Bellos Fisher made the same observation about social media: “Facebook was my huge vice. But you know, it was a vice and it was a lifeline. I am an extrovert and I was doing an introvert’s job.” She says stepping away for a bit made her feel less isolated. Acknowledge and listen to your distractions: They may be telling you something essential about your work or personal life. Then make the changes you need to make to accommodate your work-life balance.

7. Be a good boss, to yourself.

Your efficiency and productivity is entirely dependent on you. Being your own boss doesn’t mean being the cool boss who tells you to take the whole afternoon off when there’s a hard deadline at the end of the day — it means you should treat yourself and your business with respect and professionalism. “Don’t let your business run you,” warns Bordeau. “You run your business. That’s the balance every business owner has, whether you’re running a burger shop, a freelance business or a Fortune 500 company.”

And a good boss knows how to separate work from play, and take each seriously. Know when you need to unplug and what refreshes you. Says Jacobs, “I find that mindless television starting at 10 is a necessity for me, so pretty much I’m watching ‘Watch What Happens: Live’ on a nightly basis. That’s my power-down [time].”

For me, spending time with my daughter, making art, working on my home and — yes, mindless time on Netflix — is essential to my unwinding process. Anytime I try to replace these activities with work during off-hours I find myself getting easily frustrated and, over the long-term, burned out.

Your efficiency and productivity is within your control. Believing this, and being mindful of how you spend your hours and dollars, is the closest thing to the secret to success as a freelancer.

Topics:

Be Inspired, Journalism Advice, Productivity

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