Taking the Plunge: Becoming a Freelancer
Posted on 26 August 2008 by Sharon
This is a guest post from Deb Wunder.
It all started with a blog. Seriously. And not even my blog. That was part of the process.
Nor did it hurt that I knew I could write. I knew that because a bit over a decade ago I sold more than enough sf/fantasy short stories to qualify for SFWA, and one had even sold a second time as a reprint. I had also sold a couple of articles on journal-keeping, and even one on e-learning
However, knowing how to write and knowing how to get work writing are two entirely different skills. In fact, the largest reason I didn’t get to find out I could cut it as a writer until shortly after my 40th birthday was that I had no idea about how to sell my work. I didn’t find out how to do that until I became friendly, through a now-defunct chat room, with some sf/fantasy writers, and they mentored me through my first few sales.
I learned a lot from them that still works for me as a writer, by the way. Gordon Dixon’s dictum about short story writing holds just as true for articles and blog posts:
Fan to Dixon: “What makes a short story work?”
Dixon to fan: “The time bomb you have set to go off on the last page.”
The Best Writing Advice
And there are no better rules for writing anywhere than Robert Heinlein’s:
1. You must write.
2. You must finish what you write.
3. You must never rewrite, except to the editor’s/publisher’s specs.
4. You must submit what you write a market.
5. You must keep submitting it until it sells.
Still, sf/fantasy is not where my heart was, so I knew that there was no way I would be able to make a living at it. I shelved that dream and turned back to what I had always done: being a super-capable administrative assistant. (This is not bragging…I really was good at pulling rabbits out of hats and making things happen with little or no warning.)
Based on promises of promotion into the non-support side of the firm I was working for, I went back to college – online – which was a beneficial experience, though expensive and ultimately fruitless, as the unit I was working in was pretty much disbanded via a reorganization. After being out of work for just under a year, I took the only thing I could get: school aide in an inner city high school that has had a bad reputation since I was in high school.
Book Talk
Don’t get me wrong…I love the job. Not only can I go to work in tee-shirts and jeans, but I basically get paid to yell at teenagers all day. The kids soon discovered that I was a bit different from the other aides: I talked to them about books, and decision-making, and learning to choose their battles. And when they told me about a book, I went and read it and got back to them about it, even if it was something I would never have picked up on my own. In turn, I found that when I recommended a book to them, I would find copies sticking out of backpacks, purses, etc. Once or twice, the kids (and some of the teachers) were startled by the fact that I would read what they would consider to be a black people’s book, but I just calmly pointed out that, as far as I could see, there were good books and not so good books, and the ethnicity of the author or protagonist was not what I used as criteria. I also learned that I no longer even wanted to be a part of corporate America.
Now, some of the above may look like wandering off to you, but it’s not. it’s all part of what has kept me learning new things and using, as Mom would have put it, “the brain that God gave me.” It kept me in contact with what is going on in the world outside my own little circle, and gave me lots of practice in talking about things I believed in.
Next Steps
At this point, the next crucial step happened. A friend of mine decided to clean up his finances. He was in nothing like the mess I was in, but his decision, and his keeping a small circle of friends updated on his progress via LiveJournal got me moving. I started working on my financial mess, and to keep myself encouraged when the going got tough, I started reading personal finance blogs. And, again, I got lucky. The blogs I stumbled on are some of the top blogs in the niche. And reading them, I realized that there were some gaps, and that I could fill them with things I had learned. So in March I took the first plunge. I started my own blog.
That has been an amazing experience. Among other things, I got to find where my writi9ng heart lies. I met some amazing folks online and found some wonderful mentors (and yes, Sharon IS one of them). One of my mentors suggested, after reading some of my posts, that it was time I started looking for opportunities to do guest posts. She also suggested I submit some posts to blog carnivals. Again, luck popped up…one of my favorite writers was going on vacation and put a call for guest posts on his blog. I emailed him, offering, and was accepted (even though I had honestly pointed out that I was just baby blogger). He liked my post and published it, and seconded the opinion that I should be applying to blog carnivals. Another mentor suggested that I become familiar with some of the social bookmarking and networking tools that are fast becoming one conduit for the kind of networking I needed to do to get my name out in the blogosphere. I started to learn a whole new skill set.
Getting A Rep
So I was slowly beginning to grow a reputation. My blog didn’t always get scads of comments, but the ones I did get were about how my articles made people think, and were well-written. And the social thing began to pay off. I was talking with other freelancers, who were very willing to share how they got started, how they found work, how they organized themselves, balanced their writing with their families and day jobs, and just about any other question a beginner could come up with. When a co-worker asked me how I was spending my summer, I told her I would be concentrating on my blog and on getting some paying writing work.
And luck reared its head again. Someone on one of my social networks was venting about something that had happened, and I offered to help out, if needed. It wasn’t needed, thankfully, but when something did come up that was entry-level, I was given the opportunity to try it. So I took my biggest plunge to date.
While I am nowhere near the level it would take to support myself, I am starting to have small successes. More importantly, I’m having fun again. Even when a challenge is frustrating, it’s great to be able to have something to pit my abilities against.
So, back to the beginning. In two years, my job is going away. The school, which I love, is one of the schools being phased out by the City, and the only thing that will remain is the building and – maybe – a name. It will be replaced by a number of the smaller schools that the City seems to favor these days. (It’s a shame, too. The folks who have been there for the four years that I have (or longer) are some of the most dedicated folks I have ever met. They really turned the school around from someplace parents fought to keep their kids out of to a place where parents were starting to fight to get kids into.)
It is my goal that, when my job is gone, I will be in a position to take the biggest plunge of my life. There is – no question about it – still a lot I have to learn before that point, both about the work and the business side of things. But, at the age of 55, I have hope of achieving one of my lifelong dreams, even if it’s not necessarily the way I envisioned doing it. It’s the way that is right for the me that is now, not the me that was thirty years ago. It’s the light in my eyes when I get up in the morning and turn the computer on. It’s how good I feel when I pull off a challenging assignment. It’s feeling alive, even when I am dog-tired from pulling an all-nighter to meet a deadline. And it is, without doubt, one of the best feelings in the world, and I intend to keep reaching for it.
Otherdeb (Deb Wunder) is a 55-year-old writer who lives in Brooklyn, New York. In addition to her writing (she is a published short story writer, and has a blog called The Dangling Conversation), she makes beaded jewelry and knits (and takes commissions for both), reads anything she can get her hands on, and gets paid to keep a high school cafeteria under control ten months a year. She is between half and three quarters of the way to becoming debt-free.
Photo: bluekdesign
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Tags | freelance writing, writing career

















August 26th, 2008 at 9:06 am
Great post, Deb! And Sharon? Thanks for having her as a guest!
Now, a question. What is a ‘blog carnival’?
August 26th, 2008 at 9:48 am
@Becky: Hi, and thanks for taking the time to comment! A blog carnival is an aggregation of entries about a theme. If you would like to take a look at one, the most recent one I’ve been included in is “The Carnival of Personal Finance #165, College Football Edition”, hosted at No Debt Plan.
Blog carnivals are a wonderful way to get known in whatever your niche is, and are fairly easy to get into. You submit an article that fits the guidelines, and wait to see if it is accepted (only one article that I have submitted didn’t make it in). BlogCarnival,com has listings and submission forms for carnivals on pretty much any topic you can think of.
Hope that the above is helpful.
otherdeb (Deb Wunder)’s last blog post..If I Ran the Zoo…(Just how important are proper spelling and grammar, anyway?)
August 26th, 2008 at 10:26 am
Your story is very inspiring, as I am on the road to pursuing my own freelance writing career. I echo so many of your sentiments. Thanks!
Mary’s last blog post..Blog Postponed Due To Back-To-School Hell!
August 26th, 2008 at 10:43 am
Wow, Deb, what a beautiful story! Here’s wishing you the best with all your writing endeavors and a hugely successful freelance writing career!! Way to go!
*smiles*
Michele
P.S. Sharon, I’m so glad you published this guest post!
August 26th, 2008 at 11:09 am
The most important thing I did, was write a piece of fan fiction that was over 100 pages long.
People liked it.
The worst thing I did was stop writing after I did it.
That was a mistake, as I have never been able to get back to the mindset that produced it.
Heinlein was right.
shelleybear’s last blog post..Sorry About the Self-pity
August 26th, 2008 at 2:54 pm
Great Post, Enjoyed the information. I’ll check out your site.
BlogSavvy’s last blog post..The 10 Best Olympic Gold Blog Titles for Free
August 27th, 2008 at 10:43 am
First, thank all of you for your kind words (my mama taught me manners, yes she did…)
@Mary: Thank you. I’m kind of in the middle of it, so it’s hard to see outside and know what others think. Most of my friends seem supportive of the idea, but have reservations as to whether I will really be able to support myself that way (except for me sweetie, who believes I can do anything I set my mind to). I’m trying to not rush it though. There are so many things I will need to have in place to make that next step happen. And changing your life around to follow your dreams is always scary. What I’ve been doing is watching Randy Pausch’s “Last Lecture” a lot, and even blogging about it a bit when something particularly strikes me, like his dividing people into Tiggers or Eeyores.
@Michele: Heya, girl! Thank you so much. I still have so many questions it’s not funny. But you know that I’m not afraid of asking so I will get them answered sooner or later. And, yes, Sharon was so generous to give me the space to say this. She is a great online friend and colleague.
@Shelleybear: Hey Girl! I’m so glad you got to see this post! (Shelley is a real life friend of, oh, thirty years’ or so.) I was in a writers’ forum last night and one of the writers asked what to do when discouraged or otherwise in a slump. Someone suggested putting up a post it with the word “BICHOK” (”Butt in chair, hands on keyboard”) on it. Seriously, when you want to make writing a career that means you write, whether you are in the mindset to do it or not. Sharon, and probably a few of the other folks here, can tell you about the kind of mind-numbing stuff you put out to pay the bills while also finding time for the stuff that fills your heart and soul, especially at the beginning of trying to start a freelance career. I know you are doing a major retooling of your life right now, Maybe this would be a good time to get back to writing, even if it’s nothing more than a paper journal with your thoughts about the changes you are going through.
@BlogSavvy: Thank you. New readers are of course, always welcome; new readers via Sharon’s site, doubly so.
@the trackback comments (other than my own): Thank you for reading this and passing the word on!
August 28th, 2008 at 2:36 pm
I’m absolutely thrilled that I found this site! I have recently resigned my job in order to have My Adventure and will be travelling across the US for the next few months (goodbye 401K lol). I know I can write but haven’t tried to make money at it for years… needed that guaranteed paycheck! I’m operating out of the box now and am looking at alternative income sources while I travel about. Thank you, Thank you and Thank you for the site, and the post!
annie
August 28th, 2008 at 5:15 pm
So pleased you like it, Annie. I hope to see you back here soon.
August 29th, 2008 at 2:04 pm
Hello Deb!
Thank you for sharing your story! I’ve recently become unemployed, and I’m using this time to rediscover my talents and pursue my dreams of a freelance writing career. The tips and information you’ve provided is extremely helpful. I wish you the very best. Continued success!
September 15th, 2008 at 1:15 pm
I am just starting to look at free lance writing as a means to pay the bills. My job and I parted company last June and I’d rather not drive thirty miles each way to stand on my feet for six to eight hours behind a cash register. Needless to say writing looks tempting although I know BICHOK could be a problem. Thanks for a reality check.
September 19th, 2008 at 8:20 am
Thanks to Deb and Sharon for this great article. I’ve copied and pasted that “best writing advice” so I can memorize it.
Easton Ellsworth’s last blog post..My Struggle With Perfectionism and Procrastination
September 22nd, 2008 at 1:58 pm
Hi Deb,
love your post…I’m a veteran nurse trying to get my freelance writing biz off the ground…want to badly quit my day job, but at this point gotta eat!
please visit my blog at http://clara54.wordpress.com...
Sharon is a great motivator as well!
Clara
September 23rd, 2008 at 2:34 pm
@Annie: Wow! I’m impressed by your project of travelling across the US. Question: Do you have a good digital camera that you are bringing? I am told that selling stories about travel is so much easier when you have some great pics to go along with the articles. Also, you might want to keep an eye on some of the “call for content sites” because sometimes the content they are looking for will be along the lines of “great bars in $City” or “Neat things to do for under $10 in $City”.
@Cassandra: Thanks for your kind words. For me, the goal of going completely freelance is what is enabling me to juggle a semester where I am working 8 hours straight instead of six, working against the sleep cycle my body prefers, and dealing with a two-hour-each-way-by-public-transit-commute, and job conditions that are growing more stressful by the day. Whether I quit or retire when this job goes away, I am clear that working for someone else is no longer an option I want to pursue — at least not in the go to a gig, do scut work all day, then take home a miniscule pay check for my efforts.
@Neva: Boy does that ring a bell. The reason I ended up at the day job I have is that when I got downsized, I decided to live off the Unemployment and write. However, I did no planning, had no contacts or clues of where to look for writing jobs, and had already determined that sf/fantasy was not what I wanted to be writing. So while I cobbled together an existence for a year, it really ended up being more of a “what not to do” learning experience. I can;t say I have all the answers this time around, either; at least, however, I have a clue as to the questions I need to have answers for before jumping in all the way.
Re BICHOK: I actually found it a lot tougher to do that when I was writing fiction than I do now, even when writing about a subject I don’t know much about. I found that I enjoy the researching that goes into a project as much, if not more, than the actual writing, so for me, doing web content, articles, and blogging is a “best of both worlds” situation.
@Easton Ellsworth: Thank you for your kind words. I’m merely passing on what I have learned over the years. If it saves you any grief on your path, I am delighted.
@Clara Freeman: Yeah, I know about being stuck and raring to move ahead. Sadly, when I worked corporate, I managed to dig a fairly large (for me, anyway) financial hole. Before I make the jump, that hole has to be plugged. And, by that I mean the student loans need to be getting paid, all my credit cads and personal debt must be paid off, and I need to have a budget, so I know how much has to come in each month, as well as an emergency fund to make sure I can handle things if there is an emergency. This starting over at 56 thing is a bit more complicated than when I decided to start over at, oh, 18, because I know better what can happen if you don’t do the planning first. On the other hand, having a day job in this economy is not the worst thing in the universe. It means I can eat and pay bills while planning my escape.
Good luck to you in planning yours, by the way. What type of writing do you do/want to do? Is there stuff you could be writing where your professional credentials can give you a competitive edge?
Oh, and to everyone: I have found that two of the best ways to be a good write are 1. Be an omnivorous reader; and 2. Be curious about everything.