Photo courtsey of Kathleen Cavalaro

I love carnival games. Ask me to toss a ring over a bottle to win a stuffed animal and I’ll peel off dollar bills until I win. When I saw an app for a skeeball game, I downloaded it and started working on getting a high score.

It took me a while to get the hang of flicking the ball into the virtual baskets by swiping my finger across the screen. Once I figured it out, I was hooked. I like the progressive game best. With each round, the computer sets a new points target. It’s harder to get the ball into the smaller baskets in the far corners of the screen – the baskets that are worth 100 points – so I focused my competitive energy on landing the ball in the safer baskets in the center of the screen, landing 40 or 50 points with almost every ball.

I played countless games before I realized that I’d stopped trying for the 100-point baskets. I stuck with the smaller targets that I was sure to hit to avoid the wah-wah noise that signaled I’d failed to meet the progressive goal and the game was over.

The skeeball game turned out to be an apt metaphor for my current approach to freelancing: I’ve been aiming for the sure things.

Let me be clear: Unlike skeeball, where each ball is guaranteed to land in a basket and earn a few points, not all queries – even the ones I think are sure things – turn into assignments.

In the midst of sending queries that I felt were almost sure things, I forgot to aim for the long shots, the ideas I felt passionate about but feared rejection; queries I wanted to send but pushed to the back burner in favor of more immediate ROI.

Guess what? I was hitting the target goal (in terms of monthly income) but not getting the ding-ding-ding thrill that comes from landing a 100-point shot or breaking into a magazine on my bucket list.

It’s the start of a new week and I’m aiming high, going for the 100-point shots. Who’s with me?

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Photo courtesy of D Services

I have a not-so-secret crush on Kenny Rogers. There are grainy Polaroid photos of me performing The Gambler in my grandparents’ basement when I was three; at 14, I had front row seats to see Kenny Rogers perform and felt dizzy with excitement when he reached down and touched my hand during his opening number.

You don’t have to like Kenny Rogers — but really, why wouldn’t you? — to appreciate his most iconic advice: “You gotta know when to hold ‘em, know when to fold ‘em, know when to walk away, know when to run.”

The chorus popped into my head last week after a phone conversation with an editor.

Several months ago, I signed on for a major project. It wasn’t going well. Thanks to logistical challenges and unexpected expenses, the assignment became a major source of stress. The editor had no idea about the problems when we scheduled a check-in call.

After we exchanged a little small talk, she said, “You’ve been given an impossible project. This is so much bigger and more complex than it needs to be given the timeline and I wanted to offer you the option to back out.”

Shocked doesn’t even begin to describe how I felt. Quitting never occurred to me. In fact, the thought of backing out of a project that I committed to made me feel a little sick.

While we were talking things over, she said, “As one woman to another, not editor to writer, I think you should seriously consider the option [of walking away].” I asked for a few days to think about it.

Kenny Rogers kept singing in my ear: “Now every gambler knows that the secret to survivin’ is knowin’ what to throw away and knowing what to keep…You gotta know when to hold ‘em, know when to fold ‘em, know when to walk away, know when to run.”

Sticking with a time-consuming, less-than-lucrative project that required a ton of travel — and, to be honest, didn’t excite me — kept me from pursuing projects I was passionate about. I backed out.

It’s the first project I’ve signed on for and not completed. But it’s not the first time I’ve turned down work.

Freelancing is perceived as a feast or famine business and writers are often tempted to take every assignment that comes their way. But one of the most important skills a freelancer can learn is — sing it with me — knowin’ when to walk away.

One of the writers on a freelance forum I belong to suggests asking three questions:

Am I going to have fun?

Am I going to learn anything or make good contacts?

Am I going to make bags of money?

She believes that if you can answer “yes” to at least two questions, go for it.

It’s a good starting point, I think. I’d argue that making a living as a freelancer requires limiting the number of gigs that meet the first two criteria but fall short when it comes to financial ROI.

Looking back, I can admit that the project I signed on for met just one of those criteria. I should have said no from the beginning. Lesson learned.

In the week since I made the decision not to continue with the project, new work has come my way and I’ve made significant progress on another long-term project I wanted to pursue. Once again, Kenny Rogers was right: “…somewhere in the darkness the gambler, he broke even.”

What factors do you consider when deciding whether to accept a project?

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Drinking tea during a morning walk in the woods

The past few weeks have been hectic: organizing tax documents and adding up reams of receipts for the accountant, prepping pitches for editors who are planning their 2014 editorial calendars, writing articles/meeting deadlines, planning an upcoming travel writing class and preparing a handful of raised garden beds to be filled with vegetable starts…I felt overwhelmed just looking at my to-do list. Even though it wasn’t the best time to leave the office, stepping away from the computer is exactly what I needed to do.

I rented a cabin in the mountains on a gorgeous 30-acre piece of land with trails through the woods. The dogs ran off-leash, dug up dead animals and rolled in foul smelling things and I followed behind, soaking up the silence. Being in unfamiliar surroundings, far from the ping of email alerts, ringing phones, stacks of mail and deadlines, I felt a creative spark.

Tossing a tennis ball in a clearing in the woods, I made a decision about a big project; a conversation in front of the fire gave me an idea for a men’s magazine; I started an essay over breakfast. There is something about stepping out of my routine that invites new ideas.

It’s so tempting to log 40 hours a week in front of the computer – after all, as freelancers, if we’re not working, we’re not getting paid – but it’s not the best thing for our businesses. We need to take a step back, to turn on an out-of-the-office alert and immerse ourselves in something other than work.

When I got home on Sunday afternoon, I had a mountain of laundry and a notebook full of ideas and I was excited to get back to work.

When was the last time you took a break?

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Image Courtesy of AliveFreeHappy

I got an email from a former student who works in marketing and wants to pursue opportunities as a speaker. She wanted to know whether I thought it was important to have a mentor.

Of course, I’m biased. I mentor writers who want to publish articles in national magazines so I think it’s important to have a knowledgeable guide who supports your professional goals.

But I was a big believer in mentoring long before I signed my first client.

I have a freelance career because I had a great mentor who helped me get started.

Before I started freelancing, I was a career counselor. When I moved to Portland in 2000, I volunteered for a small magazine, writing and editing articles while I looked for work. During a conversation with the editor-in-chief (who was a successful freelancer) I complained about the job search and she said, “You should freelance.”

I knew nothing about the business of writing but she promised to show me the ropes. Within weeks, I had a paying freelance assignment. Over the next few years, she continued to support me as I moved from writing for local publications to national magazines. Without a mentor who could review queries, make suggestions for potential markets and answer questions about contracts and editor relationships, I might be wearing pantyhose, working in a cubicle and working for the weekend.

Since then, I’ve taken writing classes, hired business coaches and booked one-on-one retreats to help me set goals, overcome roadblocks, see new possibilities and just plain get out of my own head.

If you’re thinking about seeking out a mentor, here are a few things to consider:

• Mentoring relationships can be formal or informal: Your mentor might be someone who meets you for lunch once a month to offer career advice and facilitate networking experience to help you meet your career goals. A more formal mentoring relationship might include in-depth hands-on experiences like those offered through VocationVacations. It can also take the form of coaching. In the latter examples, the timing and cost are pre-determined.

• Explore options within your network: If an informal arrangement sounds like a good fit, tap your network for potential mentors. You might connect with someone at work, school or church who will happily share their experiences and provide advice. Some companies even offer structured mentoring programs.

• Take advantage of free or low-cost consults: Prefer a more formal arrangement? Meet with several potential mentors before choosing “the one” to make sure it’s a good match. Most professional mentors/coaches offer introductory sessions for prospective clients. During the session, prepare to ask questions about their services and experience. You can learn a lot about someone over coffee or a call.

• Find the right fit: You want a mentor who specializes in the area you’re interested in pursuing. If I wanted to write a book, I’d look for a mentor/coach with publishing experience; for the former student who wants to pursue speaking opportunities, I suggested connecting with a professional speaker with a robust roster of speaking gigs. Finding someone who has a style you respond to is important. (Writers looking for a no nonsense coach who provides nuts and bolts advice to help them get published love me but writers who want a coach to gently lead them toward improving their craft know I’m not the right fit). Pay attention to your gut feelings about a potential mentor/coach. If it doesn’t feel like a good match, it’s probably not.

• Ask for references: Before hiring a mentor/coach, ask to speak with past clients.

• Pay it forward: There is always someone who is less experienced and eager to learn. Teach classes, volunteer for mentoring programs or take a new coworker for coffee. Sharing your knowledge and experience can make a difference.

Have you ever worked with a coach or mentor? What was the experience like?

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victor1558

I traveled to Bermuda on assignment last week. (Want to know how you can go to Bermuda or other exotic destinations for work? Join me for a travel writing workshop on May 3).

In the airport, I bought several magazines and spent the first leg of the flight flipping through them. And the second leg of the flight feeling a mix of envy and frustration because several of my peers had bylines in the current issues of national magazines and I had no “good” assignments at all.

I’m incredibly embarrassed to admit this but I had thoughts like, “It must be nice to have the time to write detailed pitches,” and “She must have an in with the editor.” (It’s not lost on me that I was bemoaning bylines while I was on the way to a tropical island for work — a fact that might have led others to think, “She must have an in with the editor…”)

Knowing these women – at least two are good friends – I know that the assignments came through hard work, talent and carving out the time to research and write great queries, not luck or connections.

My feelings had nothing to do with these writers and everything to do with ME. It distorted my thinking.

First off, it’s not true that I don’t have great assignments with national magazines. I work with editors I love, writing articles for magazines and websites where I’m proud to see my byline. I have gotten complacent, started to get comfortable with sending short pitches and outlines of ideas to editors I work with and setting aside goals to write for some new-to-me magazines. Unlike my friends, who made the time to query and landed the kinds of assignments I covet, my byline isn’t in the magazines I set a goal to write for in 2013 because I haven’t made the time to pitch.

Why am I admitting this?

I think we al have professional jealousy at some point in our careers. Coveting what someone else has isn’t about them, it’s about us. It highlights the things we’re not doing.

When I saw those bylines, it became clear that I was frustrated with myself for not doing the work to reach the goals I set. So, I took advantage of WiFi on the plane to research and write a query for one of the magazines I want to break into this year.

Do you have professional jealousy? How do you overcome it?

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Pixabay

For the past several months, it seems like everyone I’ve talked to from my sister and my BFF to sources and store clerks has suffered with a bout of the ick.

Upon hearing of another poor sod who succumbed to sickness, I was sympathetic but smug. I may have even uttered the phrase, “I haven’t been sick in ages!”

Note to self: Taunting the Universe is not a good idea.

I’m sick.

Over the last 10 years, I’ve discovered that getting sick is one of the hardest parts of being self-employed. Whether you’re laid up for 48 hours with a stomach bug or admitted to the hospital for a serious accident or illness, it can affect your deadlines and your bottom line.

Being curled up on the couch did spark me to think about a few ways to minimize the impact.

Be prepared: While I do some of my best work in the 24 hours before an article is due, I make an effort to get as much of the pre-writing work done as far ahead of the deadline as possible. If I happen to get sick, I have some wiggle room to recover without panicking about the interviews and background research that still needs to be done.

Be productive: You might not feel up to interviewing sources when you’re sick but there are other things you can to do minimize the impact of your illness on your to-do list. I caught up on bookkeeping, researched new markets, reviewed queries I want to re-send…anything I could do from the sofa.

Be honest: I had to cancel a class because I felt too awful to be “on” at the front of the room. If I can’t do my best, I’ll take a knee. Editors get sick, too, and most understand if you need a little extra time to recoup.

Rest: Even without sick days, it’s essential to take the time to recover. If you push yourself too hard – as every self-employed person I know tends to do – your work will suffer. It’s better to get some rest and return to work refreshed and ready to tackle your to-do list.

If you’re self-employed, how do you deal with sickness?

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Photo by RobLawton

Want to make a living as a freelance writer? Before you quit your day job, there are a few things you need to know to achieve freelance success:

It’s a numbers game: You know the old adage, “You have to kiss a lot of frogs before you find a prince?” The same holds true in freelancing. You have to send a lot of queries before you get assignments. Be patient. Have faith. And keep sending queries. I aim to have at least 6 queries out at a time to ensure assignments (and checks) keep rolling in.

Rejection happens. Often: Sending a lot of queries means receiving a lot of rejections. Getting an assignment is about sending the right idea to the right editor at the right time. If all of the pieces don’t fall into place, an editor will reject an idea. Don’t take it personally. Every writer with a byline gets their fair share of rejections.

Homework is necessary: If you want to break into a magazine, you need to study it. Read the coverlines, study the tone of the articles. If the magazine is filled with “10 Ways…” “5 Things…” and “99 Tips…” articles, follow the format when you pitch an idea.

Bylines matter: Get to know who’s writing the articles in your favorite magazines. If all of the writers are on staff (check the names on the articles against the names on the masthead) there may not be a lot of opportunities for freelancers. The same goes if most of the articles are written by the same small group of writers (even if those writers are not on the masthead).

Editors need you: It’s easy to view editors as intimidating gatekeepers. In truth, editors don’t have jobs without writers. They depend on freelancers of varied backgrounds to send ideas. Freelancers write the majority of articles published in national magazines, which means you have a great shot at scoring an assignment.

It’s ok to start small: A lot of freelancers (including me) started out by writing for low paying regional magazines. Editors at smaller publications are more likely to give new writers a shot and the experience you’ll gain will help you break into top markets. Just remember, it’s impossible to make a decent living writing for $25 per article, so think of it as a starting point, not a long-term career plan.

Writing is a business: You can be the best writer in the world, but if you are a terrible businessperson, it’ll be next-to-impossible to have a successful career as a freelance writer. Sure, you can hire an accountant to handle your taxes and a lawyer to review your contracts – you can even hire a housekeeper to tidy your office – but the day-to-day responsibilities of bookkeeping, sending (and following up on) invoices, marketing and customer service all fall squarely in your lap.

Networking is necessary: It sounds great to work from home in your pajamas (and it is) but it’s essential to connect with other writers, either through online forums, conferences or writing groups. Your network will be a lifeline when you’re feeling low from rejection, want to celebrate successes or have questions.

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This morning, as I struggled with the best way to creatively tell a story, I asked myself, “What would I tell a coaching client to do?” It reminded me that I’d written a guest post for Rosie Molinary’s blog last year about tricks for becoming a better writer. I decided to take my own advice and I came up with the opening paragraph for the article.

If you’re struggling with a lede or looking to take your memoir to the next level, I hope this helps:

I am a writer.

Still, there are days when I don’t write a single word. Instead, I stare at a blank computer screen, my fingers poised over the keyboard, hoping the right words will find their way onto the page.

I check my email every 30 seconds, waste time on Facebook, start typing, decide the writing is crap and hit delete, give up and read trashy magazines hoping for inspiration. Rinse, repeat.

With deadlines looming, I have no choice but to sit down and make magic happen (or at least get words on the page). Since I make a living selling words, sentences, paragraphs, the articles I write need to shine.

Over the years, I’ve found that following three simple rules makes my writing much better.

Show, don’t tell: You’ve probably heard this before but it bears repeating. The best way to draw a reader into the story is through word art, painting a picture with your words.

In an essay about the thrill of completing your first marathon, you could tell the reader, “Running a marathon is hard” or you can show them what that means: “By mile 25, my legs wobbled, my breath came in jagged gasps and sweat dripped down my back. When I heard the distant cheers of the crowd waiting at the finish line, I felt buoyed by their energy and used it to help me finish the race.”

See how drawing the reader into the story by creating scenes instead of just stating facts leads to more compelling writing?

Do a sensory scan: One of the faculty advisors I worked with in the MFA program at Queens University suggested this exercise and I’ve found it very helpful: After you finish writing a piece, go back over it and mark the places where there are sensory descriptions. Note uses of all five senses: sight, smell, hearing, touch, taste.

I recently finished several chapters of a memoir about my dream to own a farm. During my sensory scan, I realized that none of the descriptions included scent. Farming is stinky! Writing the memoir without talking about the smells on a farm meant it was missing a key ingredient.

If your sensory scan reveals that you have only described the way things look, think about ways to incorporate descriptions of the other senses.

You won’t engage all of the senses in every piece but it’s helpful to use descriptions of at least two or three.

Go on a media diet: The worst thing I can do when I’m working on an article or writing a book is read what others have written on the topic. The reason? When I read someone else’s work, their words echo in my thoughts and I lose my own voice.

When deadlines loom, I try to steer clear of the Internet, magazines and books so that I can focus on how I want to tell the story. Sometimes I crawl into bed and write longhand in a notebook.

My creative juices really flow when I’m not staring at the squiggly green line in MS Word that tells me I have a grammatical error on the page!

Whether you’re blogging, working on a novel or writing the company newsletter, try these techniques and see what happens.

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1. “Dear Editor”

It’ll be hard for an editor to have faith in your ability to track down top-notch experts and find the latest research if you can’t even look up the editor’s name on the magazine’s masthead. If you looked at the masthead and you’re still unclear about who to pitch, pick up the phone, call the magazine and ask. Most editors will send queries addressed “To Whom It May Concern” straight to their trash folder.

2.     “Assign this article or else.”

Yes, this happens. No, it’s not a good idea. Some new writers think that the best way to get an editor is to respond is to offer a threat. I’m not talking about a statement like, “respond to me or kittens will die!” But there are writers who threaten to send their idea to a magazine’s competitor if the editor doesn’t respond by a certain date. Other lines I’ve seen in queries, “If you don’t assign this article, you’ll be sorry” and “You’ll regret not giving me this assignment.” Nobody wants to work with a bully.

3.     “Please, please, please give me this assignment.”

Editors are more inclined to assign stories to pros who pitch great ideas, not writers who beg for work. Including lines like, “I really need the work so if this idea isn’t a fit, I’ll take any assignments you might have,” or “I’ll work for half the regular rate just to get some work on the books,” is equivalent to walking up to a stranger in a bar and asking, “Do you come here often?” In other words, it’s a total turnoff.

4.     “I have no experience but…”

A query is an opportunity to show an editor that you have a brilliant idea and the chops to pull it off. Statements like, “I’ve never been published before but…” or “I don’t know much about the topic but I’m interested in learning” do not belong in a query. Instead, highlight your connection to a topic. When I started freelancing, I pitched articles on making the most of a career fair or acing an interview and let the editor know that I was a former career counselor. Remember, a well written pitch — even for a new writer without clips — is often enough to land the assignment.

You might be thinking, “Seriously, Jodi, no one does this.” I promise you, editors get queries like these All. The. Time. Avoid making the same mistakes and you’ll increase your chances of getting an assignment.

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A few weeks ago, I went rock climbing at Chimney Rock for an assignment. It was my first time. And it was hard.

I made it up the first two routes without too much trouble but the third route, called Vista Crack, kicked my butt.

About halfway up the rock, I got stuck. I couldn’t figure out where to put my hands and feet to propel myself toward the top. Every time I tried, I slipped. And every time I lost my footing, I got more frustrated.

Lindsay, my guide from Fox Mountain Guides, encouraged me from the top, using her knowledge and vantage point to identify possible routes and remind me to reposition my body for better leverage.

I really, really wanted to give up.

If Lindsay had said, “Do you want to rappel to the bottom?” I would have let go. She never offered, so I stayed on the rock and looked for the most promising hand and foot positions I could find and tried again. And again.

I made it to the top. And the minute I got there, I looked at Lindsay and said, “Thanks for not letting me give up.”

If I’d given up, I never would have known the thrill of overcoming the challenge, pushing myself, testing my limits and making it to the top (or the holy-crap-I-got-to-the-top-of-that-rock feeling that hit me when I rappelled to the bottom and looked up at how far I climbed).

It was a good reminder of what I can accomplish when I ask for help, when I let someone more knowledgeable guide me instead of stomping my feet and insisting I can figure it out.

If you’re tired of trying to figure out how to break into national magazines and earn a good living as a writer, let me guide you to the top. The view is pretty grand.

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