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Fifty Tips on Taking the Plunge
by Moira Allen

Return to Starting Your Writing Career · Print/Mobile-Friendly Version

When writing To Plunge or Not to Plunge?, I asked a number of writers to share their tips on how to "take the plunge" and go from a regular, paying "day job" to full-time freelancing. Nearly 50 writers responded. Here are their suggestions on how to quit your day-job and pursue the writing career of your dreams:

Moonlight -- and Line Up Those Clients in Advance

1. My advice for anyone ready to make the plunge is to line up as many gigs as you can before you give your day job notice. Write as much as you can for smaller markets, but write well for them. They will remember your work and seek you out again when other assignments come along. Keep your writing tight and crisp, because no matter what rights they offer to buy, the bottom line is that your name is on it and that is really all you have. Get your clips in order and don't be afraid to solicit new markets. The absolute worse thing they can say is "no," and what writer hasn't heard that before? They may attack your writing or your research abilities or even call you a horrible writer (my 10th grade English teacher said the latter but look at me now!), but taking your first born or your left hand is not an option. Remember, nothing ventured, nothing gained! (Felicia Hodges)

2. Establish yourself with some good clients over the course of at least a year before abandoning a steady paycheck. I was fortunate enough to work for an association that didn't run me ragged 24-7, so I had time to establish freelance writing gigs on the side. I'd been doing that for about a year and a half, with steadily increasing income, projects, and workload, when I went out on my own. (Last day as a wage slave, July 7, 2000.) At that point, I had one very large project that will represent probably a quarter of my income for the year, plus about four regular clients who paid between .50 and $1 a word rates. (Gina Shaw)

3. The tip I would like to offer readers is that, before you take this plunge, have several 'sure-things' lined up. I knew I would be receiving assignments from a Christian book publisher who pays outright for activity books. I also already had some things out that would be paying royalties beginning 1999, as well as some regular curriculum assignments lined up. So, I took the plunge, knowing I would most likely earn at least half my goal just by fulfilling obligations I already had committed to. This was my 'cushion' in case I had trouble selling articles and stories on a regular basis. (Mary Davis)

4. The move from full-time employment to full-time freelance wasn't exactly my choice -- I was "downsized" right out the corporate door two years ago. Fortunately for me, I'd been freelancing for ten years before that, just picking up the odd assignment and developing my portfolio. That's my tip -- for anyone thinking about taking the plunge, I'd strongly advise doing it slowly -- one toe at a time! While you're still employed, give up some free evening and weekend time in the pursuit of your freelance career. You need to build a reputation, you need to gain experience with editors or writing for technical or corporate clients before pulling the plug on your day job. It takes time. Don't rush in -- invest your time, learn the ropes, get some published clips behind you -- THEN GO FOR IT! (Holly Quan)

5. I recommend that you segue into freelancing from captive employment gradually. Moonlight for a while and don't make the cutover until you are making at least 50% of your captive salary from freelance sources. Everyone should read Gerry Weinberg's classic book The Secrets of Consulting, particularly the chapter on setting a price and not being held hostage to a single client. Do freelancing only if you like it. If you're uncomfortable being freelance (and many people are) don't do it. (John Hedtke)

6. If possible, build on something you've already started. I'd been freelancing part-time since 1994, building an individual and corporate client list for publicity purposes, "satisfied customer" blurbs, and future pitches. In my day job, I'd also established a reputation for clean, accurate writing and visually attractive, thoroughly edited presentations. Nearly all my current clients are referrals from past clients or my day-job colleagues. (Evelyn Hughes Maslac)

Learn to "Take Care of Business"

7. Learn to look after the financial side of your business, or find someone who will. Writers like to write, but auditors and RevCan [Revenue Canada] want to see numbers, and paper to back them up.

One specific warning based on experience: if you are asked to give an estimate for a project, meet with the client first. Get the clearest possible read on what it is they want, and when they want it. To me, the Client from Hell is the one who doesn't know what they want, and will keep you working away for weeks or month (for free, basically) while they figure out what they want. If you know it's going to be a long project, make sure you can do progress billing at least once a month. (Bill Armstrong)

8. [Part of the job] is "taking care of business" -- being my own office manager. I have to log work, send invoices, track payments, buy supplies, learn new software -- and all of that is non-billable time. My big tip is to use some sort of accounting program, like Peachtree or Quickbooks, especially for people like me who have no accounting or bookkeeping background. The programs are easy to learn and they won't let you make mistakes. They're a big timesaver. (Pat Valdata)

9. Understand your tax picture. A good accountant will advise you about filing quarterly estimated tax payments, what you can deduct, etc. The more of a headstart you have on this, the better. (Evelyn Hughes Maslac)

10. I looked at my business as a business. I invest the same time any owner would into creating plans for the next step, in forecasting the year ahead, doing my A/R and A/P tracking. In short, I take it seriously. (Shirley Kawa-Jump)

Diversify: Take on Anything, Send Work Anywhere

11. Broaden your scope. The trick to making a living as a writer/illustrator is to keep working. Try something different. If you write novels, experiment with poetry. If short stories are your thing, try writing a piece of non-fiction. If you write historical novels, take a shot at humor. Magazines, greeting card companies, ad agencies, businesses all need words and pictures. Expand your vision of what you're capable of writing and you may uncover some brand new markets. (Mike Artell)

12. I went beyond magazines. The bulk of my work is for trade journals on business issues. I didn't spend a ton of time striving for one assignment in Cosmo, instead I spend those same hours writing five or six articles for an editor who regularly assigns me work (and cuts me a check every two weeks).

I took my writing everywhere it could go. I write PR and marketing materials, provide copy for newsletters, ghostwrite for clients, anything that involves writing. (Shirley Kawa-Jump)

13. It's also important to note that I applied for virtually every writing job I saw that I believed I had a remote chance of getting. Looking for work this way creates lots of rejections but it increases your opportunities for acceptance. I was frequently surprised by how many gigs I didn't get when I was absolutely qualified and how many I DID get when my background was not the best fit. This phenomenon attests more to the inability of employers to match talents/background with jobs than it does to the people looking for work, so I learned not to take any of it (rejection or acceptance) personally! (Jill Terry)

14. My only tips would be this: Decide that you will do any writing related projects. Don't be afraid to give up all rights. You can rewrite the piece with a different slant (I've already done this). And, above all else . . . don't listen to anyone who says things like: "Oh, don't bother with Reader's Digest. They are the hardest market to crack." Research your markets and when you find one, tailor your query to their front cover. (I did that with Reader's Digest and ended up being one of their 'cover' stories.) (Joanne Keating)

15. My tips are really just common sense: be open to everything, and ask everyone about opportunities. At the beginning I didn't turn anything down, whether it was a tiny copyediting job or a daunting curriculum development morass. The tiny jobs pay off because they usually lead to others, and the big, daunting jobs pay off on one's resume. If I didn't have much experience doing something (copywriting, for example) I was honest, but open to the challenge. (Bethanne Kelly Patrick)

16. The scary part of going full-time is that you cannot always count on that editor or publishing house in which you feel you've made your 'home'. One of my biggest-paying markets went another direction with their products, and many of their regular writers were not called upon in 2000. That included me. What I should have done is continue to market myself so that I would be well-known by other publishers. Instead, I spent most of 2000 marketing myself, and will pick up some large assignments in late 2000 and in 2001. Thus, my earnings for 2000 will be considerably less than in 1999. (Mary Davis)

17. Overbook yourself. Although this isn't always the best advice, I believe it's better to go into your full-time freelance work with more, rather than less, work. At worst you'll find your first few weeks or months of freelancing incredibly busy, but that's never a bad thing. It's also important to cultivate contacts from a variety of companies, and industries. With employee turnover high in all industries, the chance your one contact at Company A will remain a contact for life is slim. (Pam Hansell)

18. Think global, act local! Were it not for the American and International outlets that I found work with, I would not have been able to survive. Canada simply does not have a big enough music magazine industry, so I approached people around the world. Surprisingly, they were thrilled to have a Canadian contact to file reports on local events. I have been the Canadian correspondent for outlets like allstarnews.com and Tower Pulse! magazine ever since. When I see an ad looking for writers in NY or LA, I write in asking if they want someone in Toronto, too.

Spread out! Initially, I aimed to have one new affiliation per month. No matter how much work I had on my plate, I forced myself to reach out and contact new editors so that I would have a wide network of people to work for. Magazines/web sites/etc. fold all the time and it was important that I didn't rely on one or two outlets, no matter how great they seemed at the time. (Liisa Ladouceur)


19. I made the transition over a year ago, and the first tip I'd give would be to tell everyone -- and I mean everyone -- what you're doing. Many of my first jobs that helped build that all-important portfolio/resume came from unexpected sources. They were leads from neighbors and friends, people I didn't think were in a position to offer such work or leads. So it never, ever hurts to announce your aspirations. (Amy Rea)

20. Develop a support network. Sites like Inkspot and lists like MAGWRITE are good places to network with other writers, as are writing conferences and groups. I've got some local writing buddies (I teach mag writing, and have met a lot of them through classes) as well as friends in Portland, Reno, LA, and Boston--all who I've met online or at conferences. It's a huge help to have people to bounce ideas off of, ask for advice or just complain to! (Kelly James-Enger)

21. Line up as many contacts and opportunities as you can before freelancing full-time. Network, network, network while you have a full-time job. Let everyone know you'll soon be freelancing full-time so they can have time to assign work to you. Also, the more people who know you're a freelancer the better -- you want those who may be able to send work your way to know you're available. (Pam Hansell)

22. Asking everyone about opportunities includes keeping up on the want ads in as many forms as possible. I've gotten jobs from Listservs, from Internet want ads, from professional contacts, and from personal friends. I've reached the point where my resume opens doors, and I try to at least enter and find out what's behind them. (Bethanne Kelly Patrick)

23. Tell everyone you know that you're now in business for yourself -- contacts can emerge from very unlikely sources. I compiled a mailing list of several hundred folks, most of whom received a brochure plus a personal letter explaining my change of status. Others received a different brochure targeted to children's book writers, the main target audience for my manuscript critique service. (Evelyn Hughes Maslac)

24. There's a tendency to guard your gigs from other freelancers but I believe in sharing information. I've been burned a few times by other writers, but for the most part I've enjoyed building relationships and have been given plenty of tips in return. I find out about new magazines starting up, special issues, etc. from my writer friends. And I always respect their affiliations and never try to move in on their territory! (Liisa Ladouceur)

25. I networked everywhere. I go to Chamber of Commerce events, attend writers' conferences, join writers' groups, etc. Not only does this bring more business to my door, it also gives me an opportunity to learn. (Shirley Kawa-Jump)

Build a Nest-Egg -- and Be Frugal

26. Save money before you quit your full-time job. Scale down your lifestyle; even daily gourmet coffee adds up when you're watching every dime. (Liz Russell)

27. I would suggest anyone preparing for the leap prepare also for living on a shoestring. The realization of one's dreams requires a certain amount of sacrifice... the local restaurants began calling to see if I was still alive! I tried to cut everything by at least a third, sometimes a half - heating bill, cleaning bill, food bill. I also learned the fine art of shopping at garage sales and consignment shops... I'm a pro! (Randall Platt)

28. Save up some dough before you plunge. I haven't had to tap into my savings yet, but it's nice to know it's there, since lean times are inevitable. (If you can swing it, having a spouse/life partner with a steady job is also a good thing.) (Evelyn Hughes Maslac)

29. Start out with at least four months of money, although six months is best. Very often checks from freelance jobs get delayed and you don't want to be in the position of waiting for money you have little control over when you'll receive. Start saving long before you begin freelancing full-time. If you already have money in the bank you'll be able to relax and spend more quality time on your writing rather than worrying about how you'll pay the rent. (Pam Hansell)

30. First, and most important, make sure that you have some money stashed to cover your expenses -- at least six months' worth. In the months before I quit my fulltime job, I paid off my car and my credit cards. I also saved enough to cover my basic living expenses for six months (about $4,600) when I left the law to freelance fulltime... and six months later, I was down to $111 in the bank when I got my first decent check. Magazines take a while to pay, and you may have to do revisions (or an editor may sit on a story for a month), which adds up to late checks. Plan accordingly! (Kelly James-Enger)

Accept Non-writing and Temp Jobs

31. [In addition to freelancing], I also accepted non-writing jobs which I could do here at home. This was simply the maintenance of data base lists for a local non-profit organization. Many times I had one project running on one computer while writing on another. (Randall Platt)

32. How did I support myself while my career was building? Temp work! For about eight months, I worked as a part-time office assistant in a law office where the pay was very good and the job demands were only moderately demanding. (I'm still grateful to my mother for making me take typing in college! Combined with my word processing skills, it's made me quite marketable for office work.) (Jill Terry)

33. I think the key is persistence and to find alternative ways of doing things. When I got to California, I knew I might have to do a few jobs out of my expertise just to make some money while I built clientele here. I went to a personnel office and had 2 opportunities that same day. The one I took ended up being an administrative assistant gig for a "work at home" type. The income bridged the gap until I had California clients on board. I think you just have to remember you're in control. You're at the wheel and have no restrictions. The Internet has been immensely helpful, I might add. I've gotten some very good clients from Internet postings. (Pat Whiteman)

Do Your Homework

34. I studied people I admired. I read the books by Robert Bly and others and realized if they could do it, so could I. (Shirley Kawa-Jump)

35. Read everything you can find about the business from other, more established writers. They can tell you about fees, contracts, etc. (Liz Russell)

36. [Read] Peter Bowerman's book, The Well Fed Writer. It is fantastic, and describes from beginning to end how to become a freelance writer specifically in commercial writing. It's a great way to make money writing for businesses, while pursuing the more elusive dream of supporting one's self writing fiction (my plan). (Ariana Adams)

37. First, I spent 2 months in the local library reading everything that wasn't glued down related to starting, running, and growing a solo consulting business. Second, I linked up with SCORE -- Service Corps of Retired Executives -- and was assigned to a mentor who had run his own PR/Marketing firm for 35 years. His help was free and freely given, and it saved me (and my sanity) on more than one occasion. (David Sakrison)

Schedule Your Time

38. Think about how you'll spend your days. Most of the successful freelancers I know keep some kind of regular hours or schedules (even if that means taking afternoons off here and there and then working on the weekends to meet a deadline). Committing to regular hours makes it feel more like "work" and hopefully will make you more productive as well. (Kelly James-Enger)

39. I worked, plain and simple. I didn't waste hours of my day avoiding my job. I sat down in my chair and went to work every day, at least 8 hours a day. I had to work those hours in around my kids (7 and 2) and my family and my house, and...a million other things, but I did it. (Shirley Kawa-Jump)

Make Clients "Steady Customers"

40. My secret? Make every client a steady client. Become indispensable. For every writing client where I take on a first job, I always come immediately back with ideas for a next assignment. Editors are sorely overworked, and if I can fill in by supplying them with regular story leads, always providing story art, and always including pull quotes, photo captions, headlines and other extras, then suddenly their job becomes that much easier. I've found I've been about to easily renegotiate my pay (up to doubling the initial offer within the first six months), ask to be added to the "staff" portion of a masthead or get "promotions" to titles such as "contributing editor" using these simply tips. Plus, I'm nearly guaranteed regular monthly paychecks. (Jennifer Dirks)

Work for Your Former Employer

41. Contract back to your former employer if you can. My full-time duties had included many different kinds of tasks, some of which didn't require an office presence. I'm still doing those, only now as a contractor. (Evelyn Hughes Maslac)

Mail that Manuscript

42. Stop nursing that manuscript. Some people spend years diddling with the same story. For heaven's sake finish the thing, mail it out and start a new project. The longer you hang on to a manuscript, the more emotion you invest in it. Starting something new renews your enthusiasm for writing. (Mike Artell)

Use the Internet

43. Use the Internet. The Internet is the greatest research library on earth. You can find publishing contacts, technical info, names and addresses on that big glass rectangle you're staring at right now. Build yourself a simple (free!)web site. Swap referrals with other authors/illustrators. (Mike Artell)

Use Your Job Experience

44. I knew I would have to focus on my expertise from my previous job (where I supervised bank examiners for a federal regulatory agency) to give my writing any credibility. So, that's how I began. I also went to meetings of local Entrepreneur societies and the like, where I networked and let people know I was a writer. Some work came from that, too (though not much). In addition, I found a Web site that appeared to be volunteer in nature but professional in content and presentation -- it was a Web site that I enjoyed as a visitor and whose content I had more than a passing interest in, so I asked if they needed writers. They did. In a year and a half, I had three or four credits to my name, enough to give me some confidence to apply for gigs that I knew I wasn't completely qualified for but I knew I was smart enough to handle with research and common sense. (Jill Terry)

Don't Take Rejection Personally

45. One more thing for writers trying to do the full-time thing (or even new writers trying to get some clips): don't take rejection personally. I used to edit a regional parenting publication (before the marriage went bust) and I can tell you that often, I'd get excellent unsolicited manuscripts that I couldn't use simply because I'd run something similar a few months ago. The rejection wasn't for the quality of the writing, or even because it wasn't right for the market; it was simply a matter of timing. A good editor will share that with you. But sometimes, a busy one (who still may be good!) might not be able to... (Felicia Hodges)

Set Up a Website

46. One thing that's been very helpful: setting up my own Web site. I doubt that anyone will ever find it and hunt me down to write for them, but it's a terrific sales tool when I'm pitching editors who are seeking freelancers. It lets me put all my clips in one place. I recently found out about a terrific opportunity while checking my e-mail via remote on a trip to Greece. I would have had to spend quite awhile pulling my clip links together since I wasn't at my home computer, but because I had the Web site, I could just point the editor there... and she was very impressed. (Gina Shaw)

Educate Your Family

47. Of course, any freelancer -- male or female -- is only as 'free' as their family/friends allow them to be. I count a supportive spouse/kids as being my most valuable possession. I treat them well -- couldn't have done it without 'em! I practically had to offer a workshop for my family and friends on how to and how not to treat a full-time writer. Word sure gets out that so and so is home and can be the volunteer of all trades. Although I started my work day earlier so I could still get in 10 hours before my kids needed a driver, coach, cook, etc., I was careful to not short-change my own career. I learned to say no to friends and groups who thought I was just home writing my little stories and surely I could stuff 25,000 envelopes while waiting to hear back from Hollywood! (Randall Platt)

Make a Plan

48. Join organizations such as the ASTD, National Writer's Organizations, and any others you can find at your local library which may provide you clients, education, or support, including supporting you with benefits, market info., etc. Freelancing is lonely and you need somewhere to belong while you work independently.

Make a plan and adjust it as necessary. When things slow down, go back to the plan and consider it. Your plan should have detailed actions listed for you to complete. Remember no job is too small. Some of those small jobs I took when things were slow, lead to bigger ones! One manager asked why I was temping in his credit union (talk about out of work, I was temping as a secretary!) When I told him I was temporarily out of freelance work, he hired me on the spot, and we worked together for a few more months in my professional capacity.

Do a little research a lot of the time! When working in a specific field, always do some research up front to learn the lingo and the nature of the business as best you can. Use the library. Use professional journals. Get info from friends. Talk to family. You'll be amazed at the contacts you receive from them!

Be clear when discussing opportunities with potential clients as to what you can do for them. Tell them your understanding of the job at hand to be sure there is mutual understanding. Be clear about your charges and be sure you know who the true decision maker is before signing on any dotted lines. Meet that person whenever possible and reiterate all understandings with your client and that decision maker in a meeting as soon as possible before beginning your work. Be sure all deadlines are clearly stated.

Get a mentor if possible, or use a freelancing friend for help when you feel in doubt. Join a local entrepreneur's club if there is one. Go to chamber of commerce meetings. Get as many people as you can on your side.

Get a sample of the same work done in previous years from other companies or from your client. Find out what worked and what didn't. Samples of similar work are a great place to begin. Whenever a client shows you anything, there is a reason for it...so ask for a copy. Remember, samples are out there! When I wrote brochures for the credit union, I simply marched down Michigan Avenue in Chicago and picked up all brochures from all banks and had my samples in hand within a half hour.

Analyze first. Would an outline or a flowchart make things clearer? Share these tools with the client if the job is complex, or to answer any questions. Once you feel sure of their needs, get writing! This is the fun part. If you think of anything you feel would help the client, mention it. Your interest in their work will be remembered. (M.C.)

Nurture, Recycle, Resell...

49. Nurture the good clients. The best lesson I figured out for myself is to not be perpetually trolling for new and more prestigious clients, but to find the editors with whom I work most easily and successfully and take very, very good care of my relationships with them. I do cartwheels and somersaults for them -- simultaneously if that's what they need. I do troll for new clients, but that can be brutal at times. I keep my sanity -- and solvent -- by working well with two or three publications. Also, I know how to pitch these pubs, so queries to them are less time-consuming.

Recycle: When a query comes back or gets turned down, polish it up, reslant it, try it elsewhere. Chances are very good that somebody someday will want it. Just keep it out and about. I've also had great luck in the two instances when stories were killed for various reasons selling them to other publications, one with major reworking, one with almost no reworking at all. Boy, did that help soothe the bruised ego!

Resell: Keep your rights, find resale markets, use them. It's like pennies from heaven, and sometimes it's dollars from heaven. Sometimes substantial dollars from heaven.

Find at least one good corporate account. They pay well, they pay promptly, they are often have less hassles than editorial accounts. Sometimes the writing can be fun, too -- it's not all annual reports. (Well, IMO those are not fun. Others may feel differently.)

Take full advantage of the benefits of freelancing: On days when you're not busy, knock off early and take a walk in the park, go to the movies, have the "freelancer's lunch" -- my name for the Friday lunch hour that starts at noon and lasts until Monday. There will be plenty of days and weeks when you're working like a dog, fighting for your money, debasing yourself for assignments. It can be a tough life and it's only worthwhile if you take advantage of its best qualities. It's the best of times, it's the worst of times. (Anonymous)

Get a cat

50. The second best advice I can offer is "get a cat." Working from home all day would get pretty lonely without one (I have two). (A. J. Sobczak)

Find Out More...

Balancing Act: Ten Reasons to Keep Your Day Job, by Denene Brox

To Plunge or Not to Plunge? Becoming a Full-Time Freelancer, by Moira Allen

Making the Leap from a "Real Job" to Freelancing, by Kathy Sena

Ready to Quit Your Day Job? by Hasmita Chander

To Job or Not to Job: A Writer's Question, by Antonio Graceffo

Copyright © 2001 Moira Allen

This article may be reprinted provided that the author's byline, bio, and copyright notice are retained in their entirety. For complete details on reprinting articles by Moira Allen, please click HERE.

Moira Allen is the editor of Writing-World.com, and has written nearly 400 articles, serving as a columnist and regular contributor for such publications as The Writer, Entrepreneur, Writer's Digest, and Byline. An award-winning writer, Allen is the author of eight books, including Starting Your Career as a Freelance Writer, The Writer's Guide to Queries, Pitches and Proposals, and Writing to Win: The Colossal Guide to Writing Contests. In addition to Writing-World.com, Allen hosts VictorianVoices.net, a growing archive of articles from Victorian periodicals, and The Pet Loss Support Page, a resource for grieving pet owners. She lives in Maryland with her husband and the obligatory writer's cat. She can be contacted at editors "at" writing-world.com.


Copyright © 2018 by Moira Allen. All rights reserved.
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