On Quitting the Day Job…
May 12, 2008 by Deb
Filed under Freelance Writing
by Jessica Rosenberg
My hand is on the grey door that leads to my supervisor’s inner sanctum. I’m about to push it open and change my life forever. I’m giving notice to my boss. Leaving a job I’ve held for five plus years and taking the plunge into completely uncharted waters. I’m going to try my hand at freelance writing.
My husband and I have been talking in circles for months and months. What will we do for health insurance? How much money do I need to bring in to keep us afloat? Are the risks worth the rewards? How much more griping about my current job can he take?
Finally we’ve crunched the numbers and come up with something we can live with for a while. To be truthful it’s a short while, a very short while. We can afford to live without my income for six months. After that if I’m not bringing in some real money then we’ll need to reevaluate our situation.
Any freelancer who is actually making a living from the written word will tell you that six months isn’t enough. No one can drum up enough business or make enough lasting contacts to have a viable career at the end of six months, but I think we’ll be ok. If come January I’m not making enough to keep the family afloat I’m not averse to taking temp admin jobs to bring in some extra cash. Anything as long as it keeps me free enough to keep writing as often as possible.
In the meantime I intend to give it the old college try. I’m going to scour every job site I can find and apply to anything that seems even remotely up my alley. I’m going to keep blogging religiously and promoting my blog shamelessly just in case it attracts an editor, an agent, or even just someone who is looking for a blogger with just my style. I’m going to contact everyone I’ve ever met to let them know that I’m available for even their most insignificant writing needs. I’m going to interrogate every single writer I’ve ever met, online and off, for advice and tips. And I’m going to write, write, and write some more. And maybe, just maybe, all of that will be enough to keep this professional freelance writer in business. After all, a girl can dream, but hard work usually helps get those dreams off the ground.
“Excuse me? Hi. Sorry to disturb you, but do you have a minute?” I ask my boss as I finally push that door open. I take a deep breath and leap. “There’s something important I need to discuss.”
Help a newbie out. What good advice do you have to share? How did you start out on the road to freelancing?
Jessica (aka Rose) blogs every day at It’s my life… It’s all about her life. Go figure.
I’m just starting out myself, so I’m very interested to see the responses to this post. I wish you great luck! And just because six months isn’t a likely timeframe, doesn’t mean it can’t happen – miracles happen every day!
Good post, thanks. Something to consider for me for sure. I seriously don’t make enough now to replace my income, and at 20 to 30 cents a word, it won’t happen any time soon. But my FiL is full time freelance now, and he’s struggling. I’m glad I’m just here for the fun. For now.
I think six months is reasonable for getting some work at least. You might try a place like demand studios which offers $10 to $15 per article. They have a large pool of writer and large arsenal of articles needing writing. Use this to supplement your income until you get better and bigger clients. Using Write for Cash in that manner helped me.
Hi Jessica,
After having that same discussion with my husband (over and over again) I took that same walk into my boss’s office almost exactly a year ago. Achieving a year of full-time freelancer status is something that thrills and amazes me. I can’t wait for you to feel the same way next year.
My advice is to network like crazy, always carry your business cards, and don’t turn down any assignment (unless it’s unethical)—some of my smallest jobs have blossomed into my most profitable assignments. It’s also good to be around others in your same situation. In November, I answered an ad on Craigslist for a “writing partner” and, once a week or so, my new friend and I meet and talk about the highs and lows of being a freelance writer and I really value her perspective. Perhaps you can take out a similar ad in your area?
One last thing: Prepare yourself for times of famine. Last August, I literally had no work. I was worried. I was obsessing. I was terrified I’d be back in a stifling office in no time. Come September, the work trickled in and, by November, I was busier than I’d ever been . . . and the busy-ness hasn’t let up yet. Freelancing is feast or famine. Right now, I’m enjoying a rather excessive feast but I know this August could be a famine again. If it is, I’ve made myself a promise: I will troll for jobs every morning, and I will take pleasure in every August afternoon with spontaneous fun and adventure.
If you find yourself with some free time, try not to worry and enjoy yourself and time with your family. Believe that your talents will connect with the right people (well within six months!) and that you’ll be insanely busy in no time.
Good luck!
Kristyn
P.S. If you have any other questions, feel free to contact me at info at ecovixen dot com.
Great post! I just quit (well, it quit me via downsizing!) my full-time job and am giving the freelance world an all-out effort. I was MISERABLE at my job and wasn’t doing anything creative. I have been building up my client base for the past two years in a part-time capacity, but it hasn’t been easy. The first thing I did after I was downsized was to contact all of my clients and tell them I was now available 24/7 to them (I didn’t tell them why, just that I was now available!). Never stop believing in yourself and your talent and have faith in God to utilize the abilities He gave you and that you have worked to improve over the years.
I had it easier. I wasn’t working – when we had kids my husband and I vowed that they would not become latch key or daycare children. I’ve seen too many bad things happen with my friends’ kids in daycare and wasn’t willing to shell out that kind of money for a situation that might not be that fantastic. I had one friend take her two-year-old to the ER twice within three months because another kid had gotten hold of a board and swung it at him and the daycare owner had gone out shopping and left her daughter watching the ten kids. The daycare was shut down after the second incident, but it confirmed for me that my kids were going to have mom home no matter what.
Now that they are both in school full-time, I had days free to work. However, the jobs around this area pay $10 an hour tops for what I’m good at. I was a travel agent and that market’s weak at best and no one is hiring. I applied for a few jobs and was told that the company needed someone who had not taken ten years away from the work force to have kids–they needed someone who knew today’s computer programs and was using them on a daily basis.
I went online and started freelance writing and discovered I could make more than I would returning to work. Best of all, I’m not shelling out money for pantyhose, business attire and gas. (Nearest cities where jobs are common are 20 to 40 miles away, and public transportation is not an option in rural areas, so you have to drive to work.)
I’m inspired by your post because one day I would also like to take a similar leap. However, as the sole breadwinner in our family, the idea of leaving my FT job is hard to imagine. When my kids are a little older, and my wife returns to FT employment as a teacher, I may have the guts to try it myself. Until then, I’ll live vicariously through you as you share your story with readers. Blessings in your new endeavor!
I’m thinking of doing the same thing soon. Good luck! I think six months is enough time to make a good start!
Some unique human interest stories for your local newspaper might provide you with bits of cash here and there to start.
Interview the cat lady down the street or something that’s relevant to your town/city/neighborhood.
Adam,
Good tip, thanks.
My FiL keeps telling me to contact his friend at the local paper here (editor), using that kin of content in this small town is perfect for on-going stories. And we got lots! 
You can use places like Associated Content and Constant Content as ways to fill in the gaps when you have a dry spell – it’s better than nothing if there’s no work coming in.
LoL, kin pun not intended.
Enjoyable read, Jessica. It sounds like you are doing all the right things. Best of luck!
I wouldn’t quit my day job until I had at least a month or two of billable work built up beforehand. I freelanced for about a year on the side before doing so full time. I knew when I stepped into the office that I would have enough work coming in to keep me busy for two months, plus enough savings to last for six months.
I’d be sending out pitches like mad. I’d hold off on “interrogating every writer” unless you’re eager to alienate people. Most of those writers are likely to be your competition now, and may not be eager to give you advice on how to take money out of their pockets.
Good luck…
Congrats! I left my day job recently, too. My suggestion would be to retain resale rights whenever possible. Those little checks for $15, $20, or $50 for reprints in regional or other pubs really add up quickly, especially since you don’t have to spend the time to write a brand new piece. That’s my 2 cents for what it’s worth. Good luck!!
Re: Adam’s Tip
Make sure the newspaper will pay first. Many of the newspapers around me opened up their doors to free submissions for those looking to build bylines. So what was once a money-making market is now open to anyone who wants to see their name in print.
I’m going to disagree with some folks here and advise staying away from places like Associated Content and the $15 sites. The more time you waste with low paying jobs is time taken away from higher paying ones. I did some of those types of jobs early on and kick myself frequently for wasting my time.
But . . . everyone has their own goals and needs.
Have you done any freelancing work while working full time? If so, go to your editors and tell them about your change in status. I did that with an editor I worked for and she bumped up my work load from one or two articles a month to six or seven.
Patience is the most important virtue to being a freelancer. Don’t get too stressed if it takes longer than six months. Don’t panic if you don’t hear back from editors immediately. The key is to treat this as building a business, which it is.
Several ideas/thoughts:
1)Are you the majority (by a large margin) breadwinner for your family? If so, think long and hard before making the leap. I was in that situation 16 years ago with a wife who was five months pregnant. But my job moved, so my decision was made for me. I knew about some expenses of the self-employed (the “other half of FICA,”), as well as some of the benefits (own hours) and challenges (collections) thanks to my work as a business writer.
2. Do you have the discipline to work without an office/job structure?
3. Do you have savings to draw on if accounts go south?
4. Do you have a passion for the business. Passion is necessary to make up for the challenges of sales you don’t have in a job (unless it’s a sales job).
5. How is the market for what you have to offer? If you’re a sportswriter (I’m a reformed one), there are plenty of people who will do what you do for free just to get into games. Though you can make some money as a freelance sportswriter, being financially successful with that background is tougher than if you have a skill that’s in less supply.
No offense, but it doesn’t sound like you’re ready. Do you have any clients? Have you published anything? If the answer to both of these questions is no, I would completely advise against entering “completely uncharted waters.” You need work lined up, lots of it, before you quit. And remember, freelance gigs have a habit of falling through, so don’t rely on a gig or two to see you through. I like to have between 7 to 10 active clients at all times, and some days are still slow.
In all fairness, I only had one small client lined up when I quit my day job. If Jessica and her husband can afford it and have them means to try it out for six months, than I don’t see anything wrong with “taking the plunge.”
I do believe you can’t jump into it blind, and I don’t believe Jessica has. The loss of one income is a shock but we made adjustments and did fine. Now I’m earning more than I did at an office job.
As for where to start, everyone has different experience. I had a mixture of smaller $15 gigs mixed in with the bigger gigs. The smaller gigs really helped to pick up the slack and keep me fresh between the bigger gigs. It’s easy to rely on these places and get into a rut, so it’s best not to keep all one’s eggs in one’s basket.
Read, research and learn everything you can about freelancing. Then find the jobs and the pay working best for your situation.
Jessica, you’ll be very glad you did. Yes, you can drum up enough business in six months if you put in the leg work.
Don’t forget your local chamber of commerce — there are plenty of opportunities in there.
And maybe your old company will hire you to write as a freelancer for them!
I’m a big advocate of quitting the day job. In my own experience and watching other freelancers, it forces you to run out of excuses for why you’re not writing.
Congratulations, Jessica!
Funny this post went up today as I just handed in my notice as well. LOL, small world and great minds really do think alike.
Now that I’m done dispensing the cliches….
In all honesty, I’ve picked up a couple of clients from this board and then I had the good fortune to be working with a freelance company called The Brighter Writer. I’m pretty sure that I’ll be ok. Plus, I’m a screenwriter, so this frees up time for me to work on scripts as well. I don’t get paid to write them unless I’m contracted, but the sale of one script would be more than 10 years salary at my current job. Which would you chose? I’m not happy at the day job, plain and simple. For me, the choice was easy. I fully expect there to be times that I struggle, but the only thing I can do is give it my all. I’m confident that my skills and perseverance will get me through.
I think it’s a wonderful idea to talk to other writers! I have found writers to be some of the best people in the world – I’ve mentioned this before I know. But, it’s worth repeating because it’s the truth. Most writers are willing to share their knowledge. Occasionally you run into the old grouch who isn’t interested in helping anyone but themselves, but they probably aren’t very happy doing what they’re doing.
Anyway, great post! Best of luck to you and please keep us updated on how it goes!
Kristy
@ Ann G: Sadly, I can believe your local newspapers only take free content. It reminds me of CNN, who will do you the honor of posting your cellphone video of breaking news on the air if you send it to them…free of charge. No need to pay journalists anymore for content.
It’s amazing what people will do to see their work on TV/in print.
Devon makes a good point. For the first couple of years, my only two clients were my two previous employers. One drawback is that I got too comfortable and didn’t develop better prospect development skills until several years later.
Sadly, I can believe your local newspapers only take free content.
The local paper here pays $50.00 flat per article. After reading this paper for over 3 years now I can honestly say there’s nothing in that paper I can’t do in less than a couple hours.
@Adam and Matt
Really, we have one major paper in this area and the quality has gone downhill quickly. I’ve always made it a game to go through with a red pen. It used to be rare to find any mistakes, but now I’m finding mistakes that are horrifying. In one, a local teacher wrote about her experiences and spelled kindergarten – kindergarden. I find that unacceptable.
The amount of trashing that is allowed is also not cool. One of my former neighbors is the Game Warden for the area. Last year a bull moose went rampant in a downtown Burlington neighborhood in the heat of mating season. Now this is Vermont’s largest city and a bull moose in the downtown area is bad news. Kids walk to and from school and it happened to be time for school to let out. They had two options, tranquilize the moose and hope it dropped sooner than later or two shoot to kill. He opted to shoot to kill. I know him well enough to know it wasn’t an easy decision. Article writers flooded the newspaper with articles on how he was going to go straight to hell and that maybe people should line up and shoot him. The fact that the paper printed this stuff really bothered me, but the fact people were willing to say it at all was worse.
While I didn’t like seeing that the moose was killed, I can only imagine the outcry if he’d opted to tranquilize it and it trampled some kids walking from school before it went down.
@ Ann G: Vote with your wallet. If you don’t like the writing, don’t buy their paper. Or, submit content that you think is more appropriate and change it.
I happily left my job two weeks ago in an impromptu, unplanned manner. But, after the euphoria of not having to return to the office wore off, I realized I had basically a month’s worth of savings to live off of. Forget about the old college try, I need something now!!
So, as I’ve been pursuing writing gigs posted online,I’ve also asked friends for recommendations, extended my linkedin network, offered my services out for free (I’ll begin volunteering with the Taproot Foundation, which will connect me with media professionals who might in the long run be able to offer me jobs), made myself a website http://wordsmith.vpweb.com , and applied to temp agencies for legal and financial proofreading jobs.
Apparently, legal and financial proofreading is pretty lucrative. All in all I wish you the best of luck…. Even if you are competition.
Wow! What an outpouring of comments!
Thank you to everyone for offering feedback, both good and bad!
I know that what I’m doing is risky, but I’m fortunate to be in a position where that risk is manageable. If I were the sole, or even main breadwinner for my family there’s no way this would have been the course of action I would have adopted.
Congratulations to everyone who is taking the leap alongside me! May we all find work that fulfills and sustains us!
Deb, thank you for letting me post on your amazing site!
Jessica,
I don’t have loads of advice to give you, but I’d say to set small goals and work toward them. I left teaching to try and make the move to working in educational publishing. The first year I freelanceed, I made next to nothing and seriously had to consider what I was going to do. Last year, I made 1/3 of my teaching income (before taxes.) This year, as of this moment in May, I’m about $1000 short of making what I did all of last year. It’s still not what I made teaching, but it’s baby steps of improvement. I can now comfortably pay my health insurance premiums without freaking out about how to come up with that money. Hopefully, I’ll make more progress in the coming years as well. Don’t let the enormity of the decision that you made overwhelm you. Set small goals that will ultimately lead you toward larger ones.
The first year I freelanceed, I made next to nothing and seriously had to consider what I was going to do.
That should read freelanced, not freelanceed.
Jessica, I read your post, and it sounded vaguely familiar – yes, it sounded EXACTLY like me!
I quit my full-time job about a month ago because my husband and I are planning a move overseas. I wasn’t going to do anything with my newly found free time, except relax. It’s just that I couldn’t relax – I needed to stay creative and busy. So I started freelancing.
It’s been almost a month, and I’ve landed a few projects. I put my portfolio on Elance, Guru, iFreelance, GetAFreelancer, and WriterLance, plus I tapped into my network of former co-workers and business acquaintances. It’s not anywhere near what I was making full-time; but I reckon I can keep building up my clientele to where I’m making that much in six months.
I’m with you – we can at least give it the old college try. And that’s what counts!
Big step! But hey, sometimes you have to dive in. Years ago I was a voracious reader of Writer’s Digest and I learned one thing to which I credit all my success. It was designed for the days when magazines were flourishing, but I imagine it works for the web just as well.
It’s all about marketing yourself. (You can write, that’s not a problem, it’s the selling your work that is the issue right?)
So tomorrow, do your homework. Come up with 3 places you’d like to write for. Write 3 pitches then send the letters (emails) out. The next day, do it again and do it again. (Keep track of what you’re sending out). You’ll get no’s, no answers, and questions but eventually you’ll start getting yeses. Do the work, but don’t stop pitching. When the work load becomes too much, then set aside 1 day to mail out pitches, but keep doing it. It’s all about stuffing the pipeline.
If you’re a decent writer and you make good on your deadlines, within six months you’ll have more work than you can handle.
At the beginning, the dollars may not be that good, but once you’ve got the ball rolling you start trading up. Give up the 10 dollar job for 20 job, for the 100 job.
The big point here is don’t rely on answering job ads – for everyone there are way too many people responding. Make opportunities for yourself but pitching to the places you want to write for.
Good luck
I just took the leap too! Best wishes!
I handed my notice in last week as my employer was beginning to get funny about me writing in my own time!
As I am a nurse and I write about health and medicine he demanded to see any work I intended to have published (as in in the magazines I write for), as he wanted to scrutinize the content to ensure it did not reflect badly on the company….. what a cheek!
I take my writing seriously and pride myself on my work and to be subjected to insulting connotations by someone who is neither medically trained nor a writer was quite frankly the icing on the cake for me!
I have built up a great client base for my writing projects and felt that in actual fact my boss kinda did me a favor by giving me the shove I needed!
Lynsey,
Way to go! Sounds like he’s a little paranoid, probably not trusting of you as an employee either. Sometimes that lost or quit job is the best thing to happen. Your mind frees up because you don’t have to protect yourself and feel so guarded.
It’s not easy to make changes, so congrats and best wishes to all who have made the plunge.
Good luck! I never had a day job so I’m not sure how it would feel! I started freelancing right out of university. It did take some time to get steady gigs so hang in there!
A freelancing schedule is quite flexible … but you do work by yourself alot … which can be a potential downside. (well for me anyways!)
All the best!
I never had a day job too, since I also started freelancing right off of university, so I can’t claim to know how it feels to jump off the ship, so to speak. But I can’t imagine doing anything else, so congratulations Jessica!
It’ll be difficult at first (and at times later on), but it’ll be great working for your self. If there’s any advice I could give, it’s to never forget to unwind and have fun every once in a while. I went on for seven months without a single day off (I worked even on weekends) before, and my mind and body gave out.
I’m working on making that leap in the future, too.
And I don’t agree that other writers will view you as competition. I’ve met several writers who are happy to talk to me — provided I do my own research first.
Read Bob Bly’s and Peter Bowerman’s books on freelancing. They’ll be invaluable to you.
I started freelancing when I got pregnant, to supplement our income. I’m hoping to build up enough work and I think I’m almost there. Best of luck to you!
just wanted to say good luck and keep at it! i’ve read a lot of positive things on this blog about freelancing. in the last couple months i’ve gone from ‘hmmm…maybe i could do this’…to ‘of course i can! why not?!’
my day jobs have been, at their best, just ok, and at their worst, well, totally not worth the money they brought in. my last day at my temp job is next friday. i may get another to pay the bills, but i won’t be stressing about it “being my hellish future” as i’ve done for so long.
there is obviously a place for us newbies in the land of self-employed writers….i’m ready to board the train that leads there & and i’m glad you are too.