16 Painful Truths About Freelancing

I'll_Cry_If_I_Want_ToToday is my six year freelance anniversary. For the past couple of years, I’ve paused to offer a reflection of sorts. Two years ago, I wrote about 20 things I learned the hard way. Last year I wrote about avoiding the trap of focusing on pay at the risk of quality, integrity, or personal goals.

Although this past year has been incredible in many ways, and I wouldn’t trade my job for the world, I’d be lying if I didn’t say that a lot of things about freelancing that just plain suck.

We all know about the great things: interviewing amazing people, writing posts that expose corruption or highlight the best of human nature, making an impact in the world, having a flexible schedule, and making good money doing work you love. But aside from minor quibbles, there’s a whole underbelly of hard stuff people don’t often talk about.

The only way around is through, but since it’s my party and I’ll cry (and swear) if I want to, I decided not to sugarcoat any of the hard but instead to sing it from the rooftops. So here’s a glimpse of some of the suck that you’ll want to be aware of before diving headfirst into freelancing, or ones you might relate to if you’ve been freelancing for a while.

Being a journalist won’t magically give you access.

For every person who will only talk to you (or a small handful of reporters), there’ll be a few who’ll dodge your calls or pretend they’re out of town or pull a no-show or turn off their porch lights just so you’ll think they are not home.

And then there are the people at conferences who will make a beeline towards you or anyone else with a media badge loudly proclaim that they don’t talk to the media, even if you didn’t try to talk to them at all. (Pro tip: taking cabs from your hotel/crash pad to the conference rather than getting on a shuttle or bus is expensive, but sometimes worth it for sanity’s sake.)

Sadly, the people you really want to talk to may not feel the same way, and the people who really want to talk to you are usually PR people who you don’t want to talk to at all, creating some sort of weird media love triangle. Or something.

Speaking of PR people…

You’ll get so inundated with PR pitches that you’ll want to scream. Screaming won’t help. Neither does responding, because most won’t take no for an answer, so now you have three pitches and six follow-ups to delete instead of just one pitch and six follow-ups. I try to deal with this by using SaneBox and setting up filters and having multiple email addresses and funneling pitches through Muck Rack, but you can still hear muffled screams coming from my general vicinity.

People will be dismissive and distrustful.

Most people (sources, editors, you name it) will ignore your calls and emails.You’ll get a great story but your source will back out at the last second before an interview and give it to another writer instead. You would’ve told it better, but the world will never know… Someone will listen to terrible advice on some podcast and decide to only do interviews over email…which will kill your interview. You’ll build trust but as soon as you can get one source there’ll be one you can’t get who you’ll want even more because human nature. The best solution is to find an editor with great contacts (good luck with that!) or to pick up Buddhism and renounce desire.

People will blame you for things outside of your control.

People will do interviews with you and break their own university’s conflict of interest policy (unbeknownst to you) and blame you when they get in trouble. That guy you know who gives workshops to journalists but seems to despise them probably didn’t find errors in the article you wrote so instead decided he’ll publicly share his opinions of a headline you didn’t write. Editors will introduce errors into your work, leaving you to choose between throwing them under the bus and protecting your professional reputation. More often than not, they’ll completely ignore your urgent emails about adding a correction…

Editors will kill or neuter your best stories.

You’ll have amazing editors that make your work shine, and you’ll fire all the sucky editors, but some of the amazing ones will sometimes do sucky things. You’ll write about NGOs working on human trafficking issues in Thailand and your editor will sit on the story for months and then kill it because she decided the person she asked you to interview, the person who gave up her life and moved across the world, “isn’t compelling enough.” And since you actually cared deeply about the piece, getting paid for unpublished work won’t be any consolation.

When a PR flack complains about an entirely accurate story, that editor who you thought had your back will lose his backboon and capitulate to insane demands quicker than you can say “conflict of interest.” There’ll be very little you can do. Freelancers are expendable, after all.

Editors will even ask you to send questions in advance when interviewing administration officials so that the state, with all of its resources, has all the time in the world to properly spin their answers. Up next: no blog post needed, just an Instagram photo of the government’s talking points… no wonder media folks are worried about robots taking their jobs.

You’ll fuck up.

Your editors will ask you to cover topics you don’t know on tight deadlines. You’ll fact check as much as you can and get things wrong sometimes anyway because you’ve got a blind spot and won’t double-check stuff you think you know. You’ll have to write corrections (or worse, send an editor corrections and be summarily ignored) and it’ll suck. They say fighters are only as good as their last fight. Writers are only as good as their most error-riddled post. I’ve seen entire industries turn on journalists with 15, 20+ years of experience because of a single error they immediately corrected. The sad part about fucking up is that it’s not always easy to learn from your mistake, because you can build resistance to these tactics and find new ways to fuck up that you haven’t accounted for in your new time-consuming strategy.

You’ll waste a lot of time because you’ll think you may have fucked up, when you hadn’t.

You’ll get vague criticism and go down the Google rabbit hole and then realize that there is debate within an industry on the way a term is used, but the way you picked is the more accepted one. +1 for wasting time realizing that you were pretty much right all along, I guess. If only you could bill for those hours.

Your worst posts will do the best.

The dumb post you dashed off on no sleep, fueled by sugar and caffeine, will get tons and tons of traffic because of a gimmicky headline and reference to porn or pop culture (that you may not have even written). The smart post about internet kill switches will go almost entirely unread.

You’ll want to blame this on site readers, but even in your own social networks, a cute new profile pic will be far more popular than that column you spent 15 hours on. You know some people are reading because they’re whining about something or other in all caps in the comments, but you’ll pretend they are bots because the possibility that they are representative of your readers is too depressing for words.

Everything will be unfair.

The writer who has no command of spelling or grammar and isn’t great at factual accuracy either will somehow start writing for glossy mags you can’t break into. Writers at the same sites you write for will scoop you (no wonder they wouldn’t share contacts when the editor asked). You’ll turn down countless trips and dinners and events and beers because of a stringent conflict of interest policy, and then your assigning editor will write about that same free trip you declined. Your favorite sources will think you’re batshit insane because you insist on buying your own drink, leading to so many awkward moments that you’ll want to switch to copywriting, where the perks flow freely.

But it’s not just COI that’s at stake. Your colleagues will get basic factual information wrong, casually dox people for page views, or find other creative ways to destroy people’s lives, and nobody will bat an eye. Your heroes will follow them (and not you) on social media and publicize their other work (and not yours).

Of course nobody will know own about all the (similar…not to mention lucrative) stories you turned down for ethical reasons. Nobody gives a shit about your ethics. Nobody will even notice your ethics. Nobody sees the stories you can’t publish because they might be inaccurate or because a source backs out or because publishing would be problematic for various reasons.

Oh yeah, and that person you’re ghostwriting for will get invited to speak about the post you wrote on a radio show with your favorite actor of all time who he’s never even heard of. It’s the freelance version of someone repeating your idea in a meeting, except you agreed to ghost, so you can only blame yourself.

You’ll get opportunities you can’t take.

Because who is going to cover your hotel and airfare to give that unpaid keynote or host that unpaid panel? Per diem? What were you thinking? You’re not even on staff.

Not to mention all the stories you lost because a site said yes and then changed their mind before a contract was signed, but after you could still pitch the time-sensitive idea to the other sites that originally expressed interest.

You will realize that freelancing is incredibly lonely.

I’m a huge extrovert, and though I have no trouble finding events to attend and making friends, there’s something about working with a group of people toward a common goal that I miss. Long gone are the days of work parties or happy hours. As a freelancer, I’m lucky if I can get more than a few sentences in an email from an editor. I have a handful of freelancer friends and we support each other and work through work drama, share leads, and take turns listening to each other vent. I go to cafes and co-working spaces and work parties. Even still, but most of the day is filled with dead silence. Add to that the fact that you typically have to email everyone multiple times to even get a response and even the most stable, well-adjusted freelancer might start to feel radioactive.

You’ll get limited feedback, and the feedback will probably make you feel shitty most of the time.

Since your editors don’t really give you feedback, you’ll instead be rewarded with…reading the comments, peaking at responses on Reddit or social media, and dealing with emails. The nicer feedback won’t tell you how to improve, and the other ones won’t be constructive either. Even if you go above and beyond and spend hours fact-checking the accuracy of claims until you’re proud as hell of a finished product, someone you actually like and respect at your favorite non-profit will tell you she wasn’t a fan because it didn’t include some favorite pet peeves & she didn’t like the order of suggestions given. You won’t make corrections since there’s nothing to correct, but this comment will probably cancel out all of the positive feedback you actually did get. But typically all you can hope for is that sigh of relief when nobody comments at all (or they just argue with each other).

No good deed will go unpunished.

Your future pay will hinge on that post you over-delivered on because you cared about the subject, but your sweat and tears won’t be reflected in the page views. You’ll stick up for other writers an editor is screwing over, and learn months later about how they retaliated—in a way that has negative career repercussions.

Continuing ed is a motherfucker.

As a freelancer, nobody is really invested in your long-term career except for you, so you have to be your own freelance hero. For me that means taking lots and lots of online classes or learning new things. I’ve set out to learn everything from programming languages to visual design to cryptography. Unfortunately, the courses are either easy/boring or pretty frickin’ hard and I don’t have the same level of support that someone working with other people at the same publication would have. (No afterhours study groups for me!) Nor is it obvious what will be useful a month or a year or five years from now. I have never believed in certainty anyway, but the support systems and group learning situations that non-freelance positions can bring have their own benefits.

You won’t even know what metrics editors are judging you by.

Sure, you can check WhoSharedMyLink.com, but you probably won’t have access to page view data or know how your work stacks up. And since nobody talks to you about it, you can’t offer feedback about all the reasons a post may have done well (or not). Because a lot of the time it’s the topic, or the image, or the SEO keywords used, or the headline. But metrics are a whole ‘nother ball game for obsessives, where no number will ever live up to your own expectations.

The good feelings don’t last.

Even if you write a dream post for a dream site, the buzz will only last a few hours to a few days. After the initial thrill, you’ll get depressed about how you’ll never be able to repeat the feat, or find some way to discount the experience. And if your goal is to make an impact on the world, there may not even be a good metric you can use to judge whether you’re doing that.

So what’s the verdict?

I’m not trying to talk people out of freelancing. I’m just pointing out that it’s not a bowl of cherries. Chances are that if you quit your job and start freelancing, you won’t be able to interview everyone you write, even if you work for Bigshot Magazine. That people will often be upset at you for reasons outside of your control. That editors won’t always improve your work and will sometimes destroy it (or worse, capitulate to brands or governments). You won’t always get things right. People maybe think you’re wrong even if you do get things right. The amount of energy you put into a post, or the gravity of the topic, is not what will get you traffic. Hard work won’t always pay off. Having high standards will make things harder for you, not easier. You won’t be getting a lot of feedback or even talking to editors for more than a few minutes. You’ll be lonely. You’ll probably cry a lot. And you won’t appreciate your own success as much as you should.

But this isn’t the end of the story.

I’ve been busy brainstorming ways to move past this, which may start with working fewer hours and coming up with new goals/metrics that are meaningful to me, and balancing heavy-hitting work with stuff that’s less exhausting, including a bit of brand work I’m doing. Here’s hoping next year I’ll have a more positive outlook to share.

Small Claims Court, Technical Questions, & Creepiness: Yael Writes’ Weekly Wrap


Where has the time gone? Week three of the Freelance Success/WordCount Blogathon is now coming to a close.

Blogathon Posts From This Past Week

I also wrote this for WIRED:


Coming Up This Week

I keep putting off the posts about online courses for writers, apps/tools of the trade, herbalism and science, and some security stuff for writers, so those are still in the running, along with more music to write by, perhaps, and maybe another page from the scrapbook diary…


How To Take A Client To Small Claims Court

14135683605_a5650500d5_zTurning in work and not getting paid for it is a pretty depressing part of freelancing. If you’re owed a substantial sum and have a bit of spare time, it’s often useful to pursue payment rather than just giving up. About three years ago, I wrote a long post about taking a client to small claims court and winning, but I wanted to put together a nuts and bolts how-to piece for those of you who don’t want to read about the details of my experience. Here it is.

(Disclaimer: each state small claims court system is different, and this is just based on my experience in Minnesota. However, there will likely be similarities.)

An Ounce of Prevention…

You can’t always avoid deadbeat clients, but getting contracts in writing can be really really helpful if things ever end up in court. (However, I did win my case with just a verbal contract, so it’s not impossible.) Even with a contract, you may consider asking for partial or full payment upfront if it makes sense for the type of work you do. Last but not least, don’t be afraid to walk away from a client if there are red flags. I personally will turn down work from a client if they spend too much time badmouthing the last writer they had. I’ll also literally get up and walk out of a meeting if the client is rude to their sysadmin or tech support person. The deadbeat client I beat in court was screaming about new bugs every few minutes in our five-hour planning meeting that should’ve taken an hour max. It probably shouldn’t have taken me that long to realize that if someone is super nice to me but a raging asshat to their tech guy, he’s probably not a nice person or one worth trying to work for.

The ‘Pay Or Die’ Letter

Often sending a certified letter to a deadbeat client letting them know that you’ll be taking further action if necessary will trigger payment. I like Kelly James-Enger’s template. The important part is to set a firm deadline of when you will take payment to collections and to follow through.


Some organizations, such as the National Writers Union and ASJA, will sometimes negotiate with a client on your behalf if you are a member. This is often ineffective, as all they do is send strongly worded letters and sometimes threaten to out clients publicly, but if you are already a member, it might be worth it. Paying for membership for this service, on the other hand, may not be.

Small Claims vs. Collections

If you have a contract and the client doesn’t dispute the fact that they owe you money, you can try to go to collections instead of small claims court. Or, you may need to send a client to collections at some point after a judgement is rendered. I like CashIn Usa, which is affordable even for small sums… but of course they do keep a percentage of payment received.

Going to Court

You should be able to find a local small claims court website in your area with instructions on what to do. Typically you just have to fill out a claim and pay a small fee, which may get added to the claim, and then the court takes it from there. Just make sure they amount you are seeking is below the maximum allowed amount you can go to small claims court for.

Settling out of Court

Once a court date is set, some clients will settle outside of court. It may be worth considering if you’re comfortable with the amount offered, depending on the circumstances. Of course, some debtors never make an offer.

Gathering Evidence

First you’ll want to gather evidence for each claim you intend to make. This could include contracts, copies of work completed, emails and texts about meetings, correspondence about the actual dispute, invoices, past due notices, and so forth. Often you need to make copies for the judge and for the deadbeat client as well as one for yourself.


Write your case out, summarize it on an index card, and practice it a few times in front of a friend. It helps. Judges also really value clear, logical thinking so try not to jump into tangents about peripherally related issues or getting too emotional. Just the facts, ma’am.

Quantum Meruit

Look this up–it means that your client owes you the amount due for work performed, when he or she cancels the project before it is completed. See if there are any local laws referencing this that you can refer to during your case. It’s not absolutely necessary, but can sometimes help.

Subpoenaing Witnesses

Look up the fee for these, if relevant–it sometimes includes a witness fee, a fee per person, and travel expenses, as well as filling out an affidavit and signing it before a notary. Keep this in mind when calculating cost and time to determine whether you want to go to court. You don’t want to spend more than you are trying to gain.

Just Chill

I brought my now-husband with me to court, which helped me relax a bit. I also felt like trying to get the money owed to me was worthwhile in and of itself, even if I had lost. This helped, but the process was still nerve-wracking, especially because I felt like an imposter wearing my pearls and suit. Sometimes seeing the debtor will make you feel a bit frazzled, too. This is when your index card with the points you want to make will come in handy. Just be aware that you may not get the results that very day, and even if you win, there’s a small chance that your client may want to appeal to district court. For the most part, this is more trouble (and money) than it’s worth.


You don’t always get your money right away after winning in court. There is a process you most go through. Typically you need to get the judgement transcribed to the district court, which puts a lien on the client’s property. After that, you can try to obtain bank accounts or other information to help aid in collection. If you can’t access it, you can often file an Order for Disclosure, requiring the debtor to disclose his assets. There is a small fee associated with this (I paid $5 per mailing and had it sent to both a business and a home address). In Minnesota, if the form is not received back within a certain time period, you can fill out an Affidavit in Support of an Order to Show Cause. This would require the debtor to appear in court to fill out the form (or explain why he couldn’t fill it out). There is another fee for the County Sheriff to serve the order. If this doesn’t work, you can ask the judge to issue an order for a Writ of Attachment, a warrant for the debtor’s arrest for civil contempt of court. It costs another $55 and again, there is no guarantee that it will work if the debtor isn’t arrested or detained for another reason. In that case, they’ll have to fill out the form before being released.

If the form is filled out, or if you find the debtor’s assets (bank account, employment, etc.), you can often either put a levy on the bank account or garnish the debtor’s wages. In Minnesota, you need to pay $55 for a Writ of Execution for this. It is served by the Sheriff of the county where the debtor works or bank account is located. Having the papers served is an additional fee, and garnishing wages requires an additional form, a ten-day notice of intent to garnish. That needs to be served via certified mail (an additional fee). The good news is that any collection fees paid to the Court or Sheriff’s Office by the judgement creditor are added to the judgement and owed by the debtor–but again, there is no guarantee they will get paid.

Is It Worth It?

Although the process is time-consuming, it can also be–dare I say it?-kind of fun. In my situation, I was seeking $845 and $75 in court fees. The judge ruled that I would receive $500 and $75 in court fees. I also spent an additional $55 for the transcript of judgement, order of disclosure, and paperwork to file a partial satisfaction of judgement. At that point, I was going to drop the matter because it costs $55 to pursue wage garnishment in Minnesota, and spending $55 to try to get $55 didn’t make sense. However, I got the remaining $55 from the deadbeat client’s company from the new owners after he was ousted as CEO.

Small claims was worth it for me because I actually enjoyed the process and got $500 out of it, and because getting payment from a terrible client was personally satisfying. (I also ended up making a lot of friends with people who’d heard about the case and had their own bad experiences with the guy, so having cool people know  my name at events and get really excited about meeting me was an added bonus.) I can’t say whether it’d be worth it for you, but hopefully understanding the process a little better can help you make a good decision.



Leave ’em in the comments. (They’re moderated, but I’ll approve them as fast as I can.)

Lead image by Tori Rector

Here’s the Curriculum J-Schools Are Missing

Shimer_IS_5_fall_1994_Sappho_BibleI was this close to attending the University of Missouri at Columbia for an undergrad degree in journalism. Instead, I went to Shimer College, intrigued by the Socratic seminar-style classes and original source readings and hoping to feed my obsession with classic lit and philosophy. Through various twists of fate, I wound up as an independent journalist anyway. I’ve strung together my journalism education through professional groups, online courses, various forums, conferences, coaching, and trial by fire. I’ve been looking at grad programs recently to see what a more formal approach would look like.

Although each of the many programs I looked at teach the basics of writing, editing, and reporting, and cover media ethics and media law, I’ve noticed a lot of missing pieces. Many programs have worked to keep up with the times by adding in courses on computer-assisted reporting, and entrepreneurial journalism electives are also on the rise. Despite these additions, there are many missing pieces. Here are seven courses or electives I would somehow add to the excellent programs already out there–areas I think are painfully missing–based on my five years of freelancing experience.

1. Hostile Environment Training

Even journalists who hadn’t originally planned to put themselves in harm’s way for an assignment may find themselves in a high risk environment, whether they’re deliberately choosing to cover hostile regions or just hopping on a plane to a remote location for a travel story when a hot opportunity strikes. Freelance journalists are often the most vulnerable, both because we’re often still trying to make a name for ourselves and taking unnecessary risks, and because the outlets we write for don’t invest in us the way they would a full-time reporter.  Learning cultural awareness, threat identification, personal security, navigation, first aid, and even surviving captivity is frankly necessary in many regions of the world, and would-be journalists absolutely should receive this life-saving information in school. Many of these are five or six-day intensives taught to small groups, which could somehow be staggered throughout a semester.

2. Information Security

I’m not exaggerating by saying that even leaking metadata can get your sources imprisoned or killed and unfortunately, the actual mindset and practices that can increase your odds of keeping information (and people) safe isn’t something you can learn by reading a few articles, going to some conferences, or using some new apps or tools. This isn’t just for national security reporters or political journalists, either–at some point in time, most reporters will come across information they’d like to keep safe from an unwanted person or group’s prying eyes. Because it’s hard to predict scenarios in advance, this would be best as a hands-on course followed by a case-study heavy practicum, with scenarios based on real-world situations–sort of like Decisions on a Deadline, but with much higher stakes.

3. FOIA for Fun and Profit

I see all these people get great information from Freedom of Information requests, but usually I just get stonewalled. Reminding the agencies I’m querying that what they’re doing is illegal has been about as effective for me as trying to get organizations to enforce their sexual harassment policies–which is to say that it hasn’t been effective at all. Having experts available to give hands-on feedback on how to deal with various evasion strategies would be extremely helpful. I wouldn’t want to pass this course until I actually got documents–because that’s kind of how it works in the real world when you don’t have the data you need to report on a story.

4. Analyzing Large Data Sets

So your FOIA requests aren’t working, your sources aren’t talking, and you really don’t want to rehash someone else’s crappy blog post and don’t really trust their numbers anyway. This course would include hands-on projects where you actually have to scrape, clean, and analyze large data sets–real data, not a set someone created for the purpose of the course. It would then be analyzed with a fine-toothed comb by someone who’s really, really good. If your data is wrong or you can’t get any data, you fail the course. Again, that’s what happens in the “real” world of journalism. No data, no story. Bad data, you never write for the site again.

5. Dealing with Crazy

No matter how diligent of a reporter you are, there’ll always be some editor who will rewrite your post for link bait, ruin your relationship with your sources, and put you in this awkward no-win situation where you get to choose between throwing them under the bus (which looks unprofessional, ruins your relationship with your editor, and sometimes makes it look like you’re just making excuses for shoddy reporting), or taking credit for the editor’s error (which also looks unprofessional and can ruin your reputation and your relationship with your sources).

Up until his tragic death last fall, my friend Sam was the best sounding board I’ve ever had. One of the nicest things he did for me was help me transform profanity-laden epithets to problem clients or editors into respectful and sometimes even diplomatic prose in order to get the best possible outcome–even if I’d already decided to drop the client. Sam understood the need to intensely and determinedly focused on maintaining the integrity of one’s work and one’s professional relationships, even when you’re willing to burn the bridge for integrity’s sake. He would help me figure out what to say in order to at least try to do this in a way that showed respect the people around me, even when they didn’t give that back to me.

This is an ongoing skill that needs to be learned… and it’s not always about bad editors and link bait. It can be navigating tricky social or sexual politics at work, dealing with legitimately crazy sources, online PR crises, online harassment, or any number of tricky situations. It’s that press secretary who’s losing her shit because you didn’t know you were supposed to submit questions in advance, or that person or mob who keeps calling your editor to try to get you fired. Case studies and role playing and practice. Do it in school and you can fail in front of your friends and colleagues, instead of in front of the entire world.

6. Doing the Impossible

Whether you’re freelancing or working on staff somewhere, journalism is full of impossible tasks.

The worst is when you quickly have to get up-to-speed in something fairly technical with very little time, despite your pleas to your editor that you’re unqualified. It helps to have a lot of rock star friends who will answer really dumb questions in exchange for a beer or some cupcakes. But there’s really no way to predict the impossible objective thrust upon you.

Once I had to ghostwrite health posts for the front page of a major health site. This entailed compiling seven to 10 myths in about 90 minutes–meaning I was researching about 15 myths–and quickly read various med journal studies, attempt to fact-check, and writing them up so they’d be “surprising” but not misleading. (Somehow I only had a very minor error for one post and none–that I know of–for the rest. Eventually I hired a part-time fact-checker to help me with this. .)

One time I was sick as a dog and had to get up at 5AM anyway because that 7:00AM interview was not one I could miss. I’m surprised I even managed to drive to my destination without getting in an accident because I really was that cloudy. I am sure I looked like hell but luckily that doesn’t come across in print.

Then there’s the times when you have to build rapport with someone in 30 seconds or less before you ask them that question they may hang up on you for. Or trying to find an expert in international law with a four-hour deadline when three people no-show. Or having to stay up until 5 AM to finish a rewrite so the post can go live right when the embargo is lifted. Or trying to get a Google spokesperson to give you information you can actually use.

Some aspects of journalism are particularly challenging for introverts, but can confuse even the most outgoing extrovert as well. More and more of my clients these days have some sort of collaborative environment going, whether it’s shared visibility in the copyediting process, shared wikis, or even big gigantic interactive cc: all pitch sessions, where three editors will tell you three different things. Learning how to navigate these systems can be confusing, so throwing all these challenges into one big messy interactive class project or series of projects with different “roles” can help people learn to operate in the typical “impossible” environment that journalists have become accustomed to–just throw in a really crappy CMS or two, a few technically incompetent people and an overworked tech whiz trying to meet an impossible deadline of her own, and all sorts of budget cuts, and you’ll be set.

Whatever the impossible task, again, failing among friends and classmates can help inoculate you towards the stressors of everyday reporting. Plus, I think a course comprised of assigning impossible tasks to students would be a really fun one to teach.

7. Debt Collection

I’ve heard through the grapevine that most media law courses don’t teach you what you really need to learn how to do as a freelancer–find a way to pay people who try to screw you over. You really need to learn how to follow up on invoices, and understand the process of going to small claims court, turning a debt over to collections, etc.–even if you decide not to go through those steps. It just saves a lot of time and aggravation down the road…and maybe it’ll even help you circumvent some of the common rookie mistakes I’ve made, like signing terrible contracts or working with verbal agreements. Editors sometimes really pick their targets, and sometimes the same editor or client can treat two freelancers differently–so making sure you have a good contract is crucial.

There you have it–the seven courses I’d want in a dream J-school curriculum. Feel free to let me know what I’m missing.

My Most Popular 2014 Posts (For Other Sites)

I wrap up each year with the most popular posts I’ve written for any site without a paywall.

My Two Favorites

My favorite post of the year was actually a slideshow I put together for TakePart.com on seven healthcare innovations saving lives in the developing world. It was just such a treat to research and report on, especially a riveting 2AM Skype call with a source in Lahore, Pakistan. I was thrilled to draw attention to some of these technologies, and I got to work with Paul Tullis, who is a fantastic editor.

Another favorite post was a piece for Slate’s Future Tense blog called  FileVault 2: Mac Users’ Unsaved Files and Screenshots are Automatically Stored on iCloud. I came across the idea for this post after seeing technologists wondering on Twitter why there wasn’t more coverage on it. One of them, cryptographer Matthew Green, was the expert I interviewed. I never did get in touch with Apple, but it did speak with Business Insider’s Sam Colt.

There’s a third piece I really love, but it hasn’t been published yet, so mum’s the word…

The Best Video

This has nothing to do with content, but I just had to throw it in! My video of the year is one I took after some guy harassed me on the street on the way to my bachelorette party. His friend had a few things to say to him, and I managed to get it on video.

Writing About Content Marketing

I love linking to posts on Contently sites, because their editors I feel bring out the best in me and the topics I cover are interesting.  ‘Growth is Not a Hack’:  7 Strategies for Building a Loyal Audience (Content Strategist) was one of Buffer’s top picks and did really well. It’s actually a panel from a Contently Summit I attended. Other Contently posts that spring to mind include the 7 Deadly Sins of Content Marketing, a piece on ways newsrooms can catch up with digital-savvy competitors (based on a report called “The Goat Must Be Fed,” coming out of Duke Reporters’ Lab), and an interview with Brian Clark.

I got to write about BP’s op-ed in Politico , and explained why I thought Patch 2.0 will fail again (both for The Content Strategist). For Ad Week, I profiled Peggy Conlon, and wrote about how some filmmakers and producers are fighting back against Latino stereotypes through stories.

I penned some posts for Copyblogger, including one on why too much emotional appeal in your copy can harm your credibility, one on how demonstrating authority can be a disaster, an admonition against sacrificing trust for short-term sales, and strategies for simplifying complex content while maintaining sophistication and nuance.

I also wrote a piece for the Content Strategist called Serious About Brand Publishing? Don’t Send a Copywriter to do a Trained Journalist’s Job, which inspired all sorts of heated reaction, including a nuanced post by Joel Klettke and a more abrasive rant (which was a very defensive strawman argument written by someone who I don’t think actually understood the original piece).

Last but not least, I wrote The Distance, Basecamp’s online magazine, for the Content Strategist, in a post titled Why Basecamp Just Launched an Online Magazine that Shuns Technology.

Quizzes Galore

You’ll have to forgive me for summarizing my year in inane quizzes. I actually learned quite a bit about myself in quizzes this year. I learned that my plant personality is dandelion passionflower slippery elm, and that if I were a mythical creature, I’d be an elf. My dream career, according to quizzes, is a writer (imagine that), and the classic author that is my soulmate is Anton Chekhov. In a past life, I hear, I was Emma Goldman. If I were a Star Wars character, I’d be Yoda. In Harry Potter, I’d be Dumbledore. In Game of Thrones, I’d be Arya and would die in a sword fight. I should live in Portland, and if I were an alcoholic beverage, I’d be a fine glass of wine. My 90s one-hit wonder is One of Us. Were I elected president, I’d be going to Mt. Rushmore. Good to know, ey? Well, now that you know all there is to know about me, we’ll move on to more links.

Freelance Writing about Freelance Writing

So meta. A few that stood out for me include  8 Jedi Mind Tricks for Freelancers (and Star Wars Nerds), some tips for creating videos that don’t put people to sleep, an interview with Dan Levitin, author of The Organized Mind, and reviewed the book itself. And for freelancers who are often quitting jobs, I wrote a guest blog post about dramatic emotional exits and destroyed reputations for crisis management consultant Melissa Agnes’ blog. Finally, I wrote about Beacon and crowdfunded journalism for Ebyline. I taught freelancers how to find sources and break stories using LinkedIn, and how to protect their sources in the age of surveillance (both for The Freelancer).

Apps and Tools and Tech and..

I love covering emerging tech. My favorite posts this past year included a piece on tech trends that will change content creation (based on Amy Webb’s talk at the ONA conference), an interview with Robert Hernandez about wearable tech and augmented reality (he almost makes Google Glass sound cool), a roundup of time-saving apps (and more time-saving tools) for VerticalResponse,and a list of apps and gadgets for journalists on the go for the Content Strategist. I also listed apps for collaborative editing for Ebyline, looked at the Copyblogger editorial team’s favorite apps and tools, and wrote a roundup of health and fitness apps for Men’s Journal.

Ligher Fare

I got to write about matcha and put together a slide show about hot dog variations for Made Man. The site also ran my interview with Shane Snow. And if you’re looking to improve your golf swing, look no further than my article for Experience Life.

And that’s that!

2014 Awards Nominees…and Looking for Judges!

220px-The_sun1I thought it’d be fun to round up a purely subjective list of what I consider the best in journalism: reporters who do their job and won’t take a no even in a world of PR politeness,  fiercely political (or just plain funny) parody/satire/comedy, whistleblowers or citizen reporters putting systemic change in their own hands, or even just people calling media out when appropriate.

This is an incomplete list based on what caught my attention throughout the year, along with nominations from Facebook friends. I am looking for volunteers to make additional nominations, as well as for judges. Since new media comes out every day, judging will not take place until January.

Here are the preliminary nominees, along with a list of nominees that were disqualified, either because the story is from before 2014, or because the link didn’t fit neatly into any one category.

Best whistleblower/citizen reporter

 Most badass reporter

FU, Media

Best parody/satire/humor: political

Best parody/satire/humor: non-political

Disqualified (not in 2014)

Disqualified (didn’t quite fit in a category)

Reflecting on 5 Years of Freelancing

I’m reflecting on five years of freelancing today. A year ago, I wrote a reflection: Four Years of Freelancing: 20 Things I Learned the Hard Way.

I wrote about using good tools, taking time off, and making sure you get health insurance. I wrote about learning journalistic principles, looking at contracts, and negotiating higher pay. I wrote about finding anchor clients, diversification, and setting clear expectations and boundaries. I wrote about finding good conferences, helping other writers, and learning how to deal with rejection.

I even wrote about dealing with worst-case scenarios, and realizing that they usually aren’t career-ending.

This past year I’ve been reflecting quite a bit on worst-case scenarios. On articles that get sat on or killed. On sources that are misquoted because an unethical editor decides to tamper with them for linkbait. On editors that are simply incompetent, and add embarrassing headlines or misleading images, or sprinkle off-topic comments throughout a piece. On decision makers who won’t allow writers to review edited work before it goes live, or won’t make corrections even when they’re clearly called for.

There are scenarios that are worse than all those, though. The copywriter who wanted to work on screenplays but lost his way, distracted by the lure of riches. The would-be investigative reporter who gives up before anyone lets her write a meaty piece, instead succumbing to the endless offers of 600-800 word blog posts. And all the stories left uncovered because an ad manager somewhere wouldn’t approve a piece due to delicate negotiations (or in retaliation for stalled ones). No, this isn’t limited to brand journalism–it happens in old school newsrooms, too.

I could write paragraph after paragraph about how Basecamp changed my life (it did), or how all reporters should learn to use encryption and get a password manager (we should), or how ONA has the best conference of all time even though everyone’s glued on their computers and may not want to talk to you (YMMV, of course). But instead of yet another listicle, I think my biggest piece of advice for young freelancers is to set a goal that’s not purely monetary.

It’s not about the…

Anyone who says money doesn’t matter has never had to live without it. And my advice may be somewhat hypocritical, since I’m making twice as much annually as I did as a teacher (not including the hundreds of dollars I spent out-of-pocket on supplies), and am working far fewer hours. I have enjoyed a 14 to 30 percent raise each year I’ve worked,  and am projected to earn 232 percent of what I made the first year I started.

I don’t think making money as a freelancer is as difficult as people make it out to be.  Everyone needs content. Most people will pay double if they can put their name on your work. (I’ve been moving away from ghostwriting as of late, but the demand is definitely out there.) Money is easy. This is doubly true if you’re good. For every person who’s on a race to the bottom looking for Fiverr or Elance rates, there’s another who realizes he gets what he pays for, and is ready to invest in quality. The question is usually not “can I make money from my writing?” but “what kind of writing will I have to do this week in order to make money?” or, better yet–“will the work I accept this week solely for the money lead me off my path?”

Making money is the easy part, but making money doing work that you find personally meaningful, work that doesn’t force you to compromise your own integrity is difficult. Finding a good balance between work that’s interesting and fun and lighthearted and work that you feel truly passionate about is the hard part. (Most people need a bit of both.) Finding really awesome editors that will push you hard so you can continuously improve and learn from each project is difficult. Finding someone who will care about your professional development beyond the work that you do for them is nearly impossible.

I’ve been incredibly lucky in my short freelancing career. I’ve had some amazing editors, a handful of mentors, and the opportunity to cover some truly meaningful topics and even do a bit of investigative reporting. But somewhere along the line, I feel like I started seeing dollars and got a bit off track. This year, I’ve tried hard to correct course, giving up some lucrative projects in favor of ones I found more personally meaningful.

I got to write about BP’s op-ed in Politico,  and explained why I thought Patch 2.0 will fail again. I profiled Peggy Conlon, and wrote about how some filmmakers and producers are fighting back against Latino stereotypes through stories. I profiled Basecamp’s online magazine, and wrote a post for Slate’s Future Tense about Apple storing user’s unsaved files to the Cloud. In one of my favorite pieces for the year, I put together a slideshow for TakePart on health innovations changing the game in the developing world. I taught freelancers how to find sources and break stories using LinkedIn, and how to protect their sources in the age of surveillance.

When stories got killed or I couldn’t get assignments for them, or wanted more control over the final product, I took them to my own website. I have a super geeky roundup on encryption/anonymity tools on my own blog, put out a 20-page guide on staying safer online that is very accessible, and even started my own podcast when none of my editors would let me cover net neutrality.

The point of this isn’t to toot my own horn, but to say that if there’s one thing I’ve learned in year five of freelancing, it’s that even unpaid work that feels meaningful to me is better than high-paying work that is unfulfilling or at odds with my own sense of integrity. This isn’t to say that I only want to write hard-hitting long-form investigative articles for the most prestigious sites going forward, but I do think it’s easy to get sucked into focusing on pay at the risk of quality, integrity, or personal goals.

My freelance writing advice? Don’t let other people define what success should look like for you. Decide what it looks like for yourself.

Then run after that with all you’ve got.

I definitely will be.

Protecting Your Sources In the Age of Surveillance: A Tool Roundup

If you’re a journalist, you’ve probably been privy to information that could put your sources at significant risk if it got in the wrong hands. I’ve written a post on The Freelancer with some basic tips on how to protect your in-person communications, but ran out of space to talk about the tools of the trade–patiently explained to me by Michael Carbone, Manager of Tech Policy and Programs at Access, Runa Sandvik, privacy and security researcher at Freedom of the Press, and a couple of other experts speaking on background.

You may want to start playing around with these tools now, as it’s best to get a handle on them before you actually need them. But before we delve into complex, high-tech tools, be aware that basic digital security measures should be in place. I’ll have a post within the next week or so on ways to make yourself safe(r) on line, whether you’re a journalist or not, but for now, here are some basics:

  • Make sure you use long, complex passwords, using a password manager such as 1Password or KeePass. (Memorizing your main password, not writing it down, and not using password hints is, of course, preferable… and think twice before )
  • Set up two-factor authentication, which can alert you to break-in attempts and make your data harder to compromise. You’ll have to use your password and type in a code texted to your cell phone when you log into programs with two-factor authentication set up.
  • Keep your software up-to-date, so that you’re not vulnerable to security issues that have been patched up in newer versions.
  • Try to stay on top of any concerning issues, such as Apple’s troubling default autosave settings (which I just wrote about for Slate’s Future Tense blog).
  • Be careful when clicking on links or opening attachments. You can view non-confidential attachments on Google Drive, or use Virus Total (now owned by Google) to scan links and attachments. Long URL expands shortened URLs for you so you’ll know what you’re clicking on.

Now that the basics are taken care of, let’s get to the fun stuff. Here are some tools you can pick and choose from to decrease the chances that your source’s identity will be compromised. 

Your invisibility cloak: Tor

What is it?

Tor is a robust anonymity network that protects your location and identity online by bouncing communications through multiple volunteer-staffed locations around the world. Originally developed for the U.S. Naval Research Academy to protect government communications, Tor was also famously used by whistleblower Ed Snowden to send information about PRISM to the Washington Post and the Guardian. Tor sometimes gets a bad rap because it’s been used as a tool to spam web forums or send anonymous hate mail, but it’s also been used by domestic violence survivors to avoid cyberstalking without needing to quit the internet cold turkey.

If you’re reporting from a country with internet restrictions, you can use Tor to access the websites that would otherwise be blocked. If you’re okay with giving away your identity but not your location, you can post on social media sites using the Tor browser.


The Tor Browser is incredibly easy to use, and doesn’t even require that you install any software. The operating system Tails, which can be used while traveling, lets you use the internet anonymously and routes traffic through Tor. It requires a bit more technical know-how.


Obviously, logging into Facebook, a bank account, or an email account associated with your name reveals your identity.

  • Opening documents, enabling or installing browser plugins, checking into email and Facebook accounts using your real name, and using Torrent are a few other ways that your identity can be compromised.
  • In addition, your internet service provider or local network administrator can see that you’re using a Tor relay unless you take special members to try to hide it.
  • Another potential drawback is that some websites either block traffic coming from Tor, or do not allow comments from Tor users.
  • Tor and Tails have posted warnings detailing other potential vulnerabilities.

Making user identity and location for both journalists and sources is highly useful, and the fact that it requires limited technical knowledge makes Tor a no-brainer.

Your Dead Drop


SecureDrop is used by prominent publications and websites, including the New Yorker, Forbes, ProPublica, Intercept, the Washington Post and the Guardian.

Difficulty: SecureDrop is challenging to set up without some computer know-how, and it’s recommended that an organization has an IT professional or system administrator to maintain it.


  • Secure Drop needs two servers and an old laptop, so the cost is between $1000 and $3000.
  • As mentioned, having a computer professional on staff is recommended. (Another option that may be better for freelancers is OnionShare.)
  • It’s not impossible for an entity to break or hack into the news organization to seize the document.

Your decoder rings

Encrypted email

What it is: PGP stands for “pretty good privacy,” while GPG, an open-source version, is “Gnu Privacy Guard.” Both tools allow you to send and receive encrypted messages to people online, using their public key code. These messages look like a jumble of text to anyone unless you sent it to them, and they open it with their own special private key code. Even if you don’t want to encrypt a message, you can digitally sign an email, so that the recipient knows it wasn’t tampered with in transit.

Difficulty: Let’s just say that I definitely wouldn’t recommend trying to learn how to encrypt email while on deadline. Although it’s not hard to download and there are numerous tutorials online (like this one by opsec expert Tom Lowenthal), it can be challenging to get all of the components to work together with your email client. (GPG also doesn’t work with Yosemite, if you’re on a Mac, and it looks like they will begin charging for the service once it’s ready.)

I was lucky enough to make fast friends with someone who gave a presentation on the topic. Even with assistance, I made multiple juvenile errors, including hitting reply to an encrypted message (thereby unencrypting it), sending something unencrypted when I thought it was encrypted, and setting an expiration date a year sooner than I’d intended.

The email client Thunderbird offers a robust encryption plugin called Enigmail that is a little finicky but can simplify the process, and a new program called Mailpile looks promising, though it isn’t finished.


  • As mentioned, email encryption can be hard to learn, and both the user and the sender need to use it to communicate.
  • If your computer is stolen, encrypted messages may be compromised, depending on the strength of your computer’s password, since a few mail servers unencrypt messages and store them in unencrypted form.
  • If a key is lost and you are storing messages in encrypted form, the data is gone forever.
  • Email service limitations and other issues sometimes make it difficult to send large files using encryption. (They can be shared through thumb drives, Onionshare, or other file sharing sites.)
  • Sending encrypted emails does not hide information about who is emailing who, when, how often, and with what subject line.
  • Senders need each other’s public keys, which adds another step to the process. Some journalists link to their public key on their websites, and I’ve loaded mine up to my Twitter bio and linked to it in my email signature.

Encrypted chat

What it is: Off-The-Record (OTR) Messaging is a chat extension you can use to encrypt chat conversations. It can be used through the Tor browser to protect user location as well. It is used with other software, such as Adium for Mac or Pidgin for Windows.

Difficulty: OTR is incredibly easy to set up. If you are routing another chat program through OTR, you can see the encrypted conversations happening in that chat window. However, learning how to verify the identity of the person you’re speaking with proves to be a bit more challenging.


  • Both users need to use OTR in order for it to work.
  • Separate steps must be taken if you wish to verify the identity of the person you’re speaking with.
  • OTR does not support group chat, file transfers, or audio and video communication.
  • National security researchers may want to stick with Jitsi because OTR does have a few security concerns that those with high-level technical experience may be able to exploit.
  • OTR with Adium appears to be saving some messages in plain text. This needs to be disabled manually.

Encrypted phone calls and texts

Open Whisper Systems offers two Android tools, Redphone and TextSecure, for calls and texts. Apple users can use Signal on their iPhone to make encrypted phone calls.

In addition, a company called Silent Circle offers encrypted calling and texting, with plans ranging from $12.95 to $24.95 a month to call non-user numbers. Otherwise, you can call users for $9.95 a month.


  • Both users need to have Open Whisper Systems tools installed on their phone. Silent Circle allows its users to call or text those not using the services, but this obviously makes the calls less secure. Otherwise, both users need to pay for the service.
  • Since your phone number is attached to the tools, anonymity is not protected, and your cell phone tracks your location through cell tower signals as well as GPS systems. (It is possible to use Signal with an iPod, however.)
  • It’s always possible to trace GPS information from cell phones (or location from towers), and phones can be turned into listening devices.

Encrypted video chat





Skype has a complicated security history both locally and internationally. In some cases, Google Hangouts can be used instead. Otherwise, Jitsi is a good alternative for secure video communication. It can be used for chat, as well, as an alternative to OTR. Jitsi is easy to set up and use, does not require any installation, and allow you to use current services you have set up, such as AIM, Google Talk, or Facebook chat.


  • Users need to be accessing Jitsi using the same chat program (i.e. AIM, Google Talk, or Facebook chat).
  • Account providers like Google or Facebook keep records of who is communicating and perhaps who they are communicating with. They can share this information with corporations and governments, even if the actual content is encrypted. (It’s possible to use programs like Ostel.co, but this takes a little more setup time.)
  • Jitsi requires you to install Java on your computer, but Java has many security problems of its own. If you don’t have Java installed already, and download it to use Jitsi, you may need to go through the added steps of disabling Java and its associated plugins from your computer.

Encrypting your hard drive

Say you’re covering border issues and your laptop is confiscated at the airport… or even that you misplace it at a conference. If anyone makes a copy of your hard drive, it’s best if the material on it is encrypted.

Using a full disk encryption service such as FileVault (for Mac), BitLocker(Windows) assures that the image of your hard drive will be scrambled. Most Linux providers allow you to encrypt the hard drive when you first install the service. If you are storing your data in the cloud, make sure to use a service, such as SpiderOak, that encrypts cloud backups.

Difficulty: Installing full disk encryption is incredibly easy, but encrypting cloud backups and especially sharing files through SpiderOak has a steep learning curve.


  • If you forget your password for any of these options, all of your files are lost.
  • SpiderOak is considerably more difficult to learn and use than its competitors (DropBox and Google Drive).
  • In addition, its features are less robust.

So there you have it—a wide selection of tools to choose from based on what your sources are able and willing to use, and what’s most appropriate for your specific situation. It may be worth picking just one to start messing around with before you really need to, so you’re not trying to install and master challenging tools on a deadline.

For more information, check out some of these links as well:

Privacy Tools: The Best Encrypted Messaging Programs (ProPublica)

The 7 Privacy Tools Essential to Make Snowden Documentary CitizenFour (EFF)

Surveillance Self-Defense (for journalists on the move) (EFF)

Also, check out EFF’s secure messaging scorecard.

The Writing Process Blog Tour

Writer's blockWhile everyone else is busy dumping buckets of ice on their head, I got tagged to participate in the Writing Process Blog Tour by Jenny Neill.  If you haven’t seen it, basically the game is to answer the four questions below, and then tag three more people to do the same. You can follow along on Twitter with the hashtag #mywritingprocess.

Question 1. What are you working on?

I always have to be a bit vague when describing specific assignments, since in many cases I’ve signed agreemerunts promising to keep the details under wraps until the posts are live. However, I can say that right now I’m in various stages of working on about 10 different assignments:

  • a list post based on a book/author Q+A for a men’s site
  • another author Q+A/book review for a writing site
  • a post describing the key differences between two different genres of writing
  • an opinion piece on curated news in the age of social media
  • a couple of SEO and content marketing posts
  • an app round-up piece
  • a post on the misconceptions in big data
  • two fighter profiles/interviews for MMA sites

In addition to my writing, I typically spend the first two or so weeks of the month working as a managing editor for a couple of brand blogs and an online fitness journal. I then switch to pitching in the last two weeks of the month when the editing dies down a bit. That’s true this month as well. I am always working on new pitches for Wired, since it’s been my long-standing goal to break into their FOB section. I’m also working on updating my resume because I want to apply for some online editing gigs.

Question 2. How does your work differ from others of its genre?

This is a tough question to answer because my work has never fit neatly into any one genre. I’ve done health and fitness writing, med devices/healthcare IT, business, tech,  etc. and since I train in BJJ, have always written a bit about combat sports on the side.

What makes my work stand out in these assorted genres?

First of all, most of my writing is pretty quote-heavy. I’m big on reporting and work hard to quote key players when possible, rather than just analysts. I prefer using multiple sources, and actively look for long-form writing opportunities.

Second, I try to back up everything I write with solid statistics or research from credible sources. This may be due to my undergraduate education at Shimer College, the Great Books school where I spent four years debating classic literature and philosophy around octagonal tables. The idea of finding references in the text to support our point of view was beaten into us.

This means that I don’t do well when asked to write posts that are overly simplistic, or when my writing gets edited in misleading ways. Also, I really enjoy it when I have great editors who ask skeptical questions and force me to dig deeper, even if it takes me a lot longer, because it improves the quality of my work and teaches me new skills. (Lately I’ve been thinking that I really want to be able to crunch my own numbers, so I’m actively looking for opportunities to learn data science so I can scrape and clean large data sets, beyond what one can get from simply taking a workshop.)

Last but not least, my writing is a bit on the edgy side. I tell the truth as I see it unapologetically, and go to great lengths  to maintain the integrity of my work. This isn’t to say all of my writing is hard-hitting investigative work. I’ve written plenty of fun, fluffy posts and enjoy gushing about products, books,  or organizations I love. It does mean that I don’t shy away from taking a stance, even if I know it may be unpopular, and that’s evident in a lot of my work. I named my podcast “The Elephant in the Room” for a reason.

Question 3. Why do you write what you do?

I think my underlying motivation in both writing and editing is to liberate information, especially if it’s inaccessible to the public or to readers in some way.  I think it is a radical act to create and share content that will positively impact people’s lives or that they’re really searching for, and to break it down for them in a way that is accurate and easy to digest. That’s why I seek out publications and brands that have a mission beyond simply selling a product, subscriptions, or ads.

I write because I want to dig beneath the surface. I want to figure out what really drives people or events. Writing is a great excuse to get answer. I’ve found that it also gives me a bit of cover to ask a lot of questions that would normally be offensive or be considered inappropriate to discuss. This is especially true if I’m reporting on a field or an industry that’s particularly male-dominated, as I often do.

Question 4. How does your writing process work?

First of all, I use Basecamp to keep track of all of my projects and their respective deadlines. Without that piece of software, I think I’d go insane.

After an article is assigned, I typically start with a lot of research and information-gathering beyond what I’d researched for the pitch. This involves a fair bit of internet stalking as I sleuth out relevant documents or reports, scout out background information, and work to get really great sources and then track them down.  Sometimes I have to do additional research after an interview because I don’t understand a key piece of information or something seems amiss.

After I’ve gathered everything I need, I usually transcribe any interviews and cut and paste relevant statistics into Draft. Once the prep work is completed and it’s time to start writing, I need to get really comfortable.

My husband used to joke that I had a “floffice” and a “coffice,” since I’d write from the floor or couch instead of my home office. On cold winter days in Minneapolis, sometimes I’d even work from my “boffice” since I wanted to stay curled up in bed all day.

I do like sitting at a table or desk as well, but it has to be  really comfortable. I just moved into a new place and sadly had to say goodbye to my last desk, so the hardest thing for me has been finding a place to sit where I feel comfortable while I save up for this $1100 desk set I have my eyes on.

My home office is sadly filled with boxes at the  moment, but even when it’s all decked out, I sometimes get bored sitting at home all day. so I’m always in search of new cafes (or coworking spaces) with fast wifi to work out of.  I also play with different music options until I find one that matches my mood and helps me get in the groove. I use Spotify or Songza for tunes, or Coffitivity for background noise.

Once I’m comfortable enough to get started, I read through everything I have in Draft and a loose outline begins to form in my head. Then I just start writing. When I get stuck, I find that switching from Draft to Google Docs, MS Word, or even directly into WordPress can help. Often I have two files open and cut and paste clean copy from the sloppy post into the clean one. Changing the background color or font can also sometimes help, too.

After I’m done with a draft, I’m constantly reworking the lede and headline, which have been a struggle lately. I try to put posts and articles away and look at them later with fresh eyes. I’ll read through for style first, and make sure everything’s appropriately fact-checked and cited (if necessary) on the second go-around. If I’m lucky, I’ll be working with a great editor who can give me feedback and suggestions on improving each piece. One of my goals this year is to focus less on pay-per-hour and do things the long, hard way as long as I am enjoying the process and gleaning insights that will not only improve the specific piece I’m writing but my skills as a writer.

I just got a very nice package in the mail from a Twitter friend (!!) and it had these great college-ruled notebooks, sharpened pencils, and pretzel erasers! I have written almost exclusively with a pen when not on my MacBook, but am excited to give these a go. I’m always trying to think of ways to improve my skills, and perhaps some good old fashioned writing practice will help.

Next up: Sonia, Shane, Holden, and Gideon!

Yes, I was only supposed to pick three people rather than four to spread this meme forward…but I’ve never been good at following rules.

Sonia Simone is the co-founder and Chief Content Officer of Copyblogger Media, and one of my favorite writers and marketers of all time. (I added serial commas to this post just for her.) You can find Sonia on Google+ and on Twitter.

Shane Snow is a NYC-based technology journalist, CCO of Contently, and author of Smartcuts: How Hackers, Innovators, and Icons Accelerate Success (out September 9th).  He’s also one of the nicest people ever. Oh, and he has great hair.

Holden Page is up-and-coming tech writer based in St. Paul, Minnesota. He’s also a copy editor for Lawyerist. Holden covers entrepreneurs, startups, and devices. I made him co-teach a workshop on PR for Startups with me once. I miss him.

Gideon Walker is an entrepreneur dad living in Las Vegas. Formerly a copywriter at AppSumo, he now writes about parenting, marketing, business, and productivity, and is working on his first book, the Entrepreneur’s Guide to Copywriting.

What I Learned From My Failed Crowdfunding Attempt

avatar_aa368c6d5c31_128As you recall, I was working on getting 40 backers for a crowdfunding project on Beacon, to write about people overcoming odds to learn new skills. I unfortunately did not get all of the backers needed for the project to be a success. This really bummed me out because I love what they are doing and think the cofounder I interviewed is a genius… and because I really believed in the project–and still do. But as they say, every cloud has a silver lining, and I learned a few things in the process. Here are the lessons  got out of it.

1. Details are really important.

I hired one of the best editors I know to take a look at my project draft and help  me flesh out the concepts. And I think it was the best investment in the project. It helped me get incredibly clear on the stories I wanted to tell. Even though the project didn’t get enough backers on Beacon, I plan on pitching and writing articles in the same vein, and possibly working on a book proposal. Having great clarity on the approach for each segment will be my guiding light.

2. Did I mention that details are important?

Along the process in getting the project posted, I was asked some probing questions about my project description, which made me realize that the person asking wasn’t really clear about what I was trying to do. Some suggested changes would have given off a different impression than what I had intended. And a couple of times, updates with typos or errors were sent out, which I felt reflected poorly on the project and on myself. One of the biggest mental blocks I have right now is my often unrealistic expectation that people who manage projects I work on will have a greater understanding of them than I do. I’ve found that my desire for a de facto meritocracy is compounded even more when it’s a project I care very deeply about… the more passionate I am, the more I really need to work on my own patience.

3. Crowdfunding can feel like groveling.

I usually have no problem selling, but for some reason, asking people to pledge felt like begging. I was even more leery of asking multiple times. Although I got a lot of exposure about the project and thought it would sort of sell itself, I felt weird being very salesy and overly promotional when it didn’t. Even asking people to share the project with their friends felt a little icky to me. The truth is that you burn through a lot of social capital doing so, and I had a feeling the project wouldn’t be backed the entire time, so it felt like wasted effort.

4. Passion projects can make selling even harder.

Knowing that even 40 people at $5/month wouldn’t cover my expenses made it more difficult for me to work hard to reach the goal.

5. Timing is everything.

I was hesitant to launch this campaign so close to my wedding, when I already feel like a mere wedding invitation could come across as a request for gifts, and before a planned move cross-country. In retrospect, I wish I would have waited, even knowing that summer launches don’t work as well.

6. It is hard to mobilize people around a common idea rather than a theme.

I’m thinking a campaign based on just one central topic, such as weightlifting or programming, would have gotten more support within that specific niche than the way I went about the campaign.

7. Recurring subscriptions make people nervous.

They’re worried they’ll keep paying even when no updates are made. I think it’s a valid concern, since I subscribe to a Beacon writer who hasn’t updated in months. Having access to every other story in Beacon is pretty great, though.. In any case, a lot of people wanted a non-recurring model that was lower than the two we set (at $30 and $55), which would’ve been okay if I had reached critical mass. Otherwise, though, a$5 donation toward what is supposed to be an ongoing project doesn’t mean very much, which is why Beacon uses an ongoing subscription model I think people used to Kickstarter are more comfortable with a non-sub model and magazine/literary journal people are more comfortable with subscriptions. Both rely on a critical mass or a certain amount of cash in order to work and help fund a project. In any case, it seems that we are still learning what works and doesn’t work in the crowdfunding space.

8. Sometimes it may be easier to go through a gatekeeper.

I have never had luck building an enormous email list and selling people on my list info products. However, I’m really great at getting publishers and brands to pay me to write. Most people have the opposite experience. I don’t know that one is  necessarily easier than the other, but perhaps different people are geared towards different models. In any case, there’s no way I am giving up on this idea, though perhaps Beacon isn’t the answer.

9. There is no real sense of closure when a project isn’t backed.

Once my project didn’t get funded, I didn’t have a nice debrief call or anything. It just sort of fizzled and died.I don’t even have email addresses for everyone who pledged, though  plan to try to find them so I can keep people informed on the status of the project. I still don’t feel like the idea is any less valid and the amount of support I did get feels like a partial win for me, but I still feel like the whole thing isn’t really resolved yet.

10. Some projects are really sticky. Others aren’t.

In the middle of my crowdfunding attempt, I was asking friends on Facebook if they knew of a magazine that read like a cross between Wired and Made Man, or Men’s Journal, but was geared towards women. Women who like gear and tech, and want to decorate but only if it’s done in 20 minutes and costs $30 or less. Women who want to know the best beer bars or burger joints rather than the best grapefruit and yogurt. Women who don’t wear heels and like to go camping and are addicted to apps. A lifestyle site that’s less political than Bitch or Jezebel, and with less fashion and celeb news than PureWow or Refinery29. That post got hundreds of comments, with writers and readers alike very interested in getting involved. For some reason, some types of projects just get people excited more than others. I’m aware that this could be entirely different than how they’d react once it comes time to actually pay for it, but it’s interesting to me what people react to strongly, and what they don’t.