To freelance or not to freelance . . .

A friend of mine is thinking of quitting their day job. They’ve had a novel published, which is doing very well indeed thank you very much. Their publisher is solidly behind them and eager for more books. The friend has turned to me for advice. On account of how I’m already a freelancer.

However, their situation is very different from mine when I went freelance. I had come to the end of a fellowship so instead of seeking employment or another fellowship I opted to try my hand at writing full time. My friend would be leaving a job which has a clear path of promotion in a secure industry with great health insurance and all sorts of other perks. Also the friend likes the job, but they love writing. And the job is so full on that it’s very difficult to make the time to write novels.

My first impulse is to say, “Keep the job!” But the friend is a brilliant writer. Keeping the job means a book every three or four years. Tops. At the moment the money is about the same between the two options.

What to do?

Here’s my list of pros and cons of freelancing.

Cons Pros
very irregular pay
have to provide your own health insurance
your own super (savings for retirement—dunno what they call that in the US of A)
can be very isolating working long hours on your own
stationery no longer free
life ruled by deadlines
concentrate on writing
your time is your own
work uniform is pyjamas
no boss
can work wherever you want
can work whenever you want
travel is easy
its fun
no office politics
if you need to get out and go for a walk/swim/ice cream you can

I’m a bit stupid today so I’m sure I’ve forgotten heaps and some of them are a bit repetitive. Please chime in with your own pros and cons to the freelance life. What would you do in this situation? What’s your advice for my friend?


  1. The Bibliophile on #

    I would tell your friend to work part time to start. You know, enough hours to keep some of those great benefits and more of that steady income, while at the same time freeing up the calendar a bit more to write. Compromise!

  2. Justine on #

    Working part time is not an option. Totally not allowed in that particular industry.

  3. Kristine Smith on #

    Some background: I’ve been with the same company for 20 years. Good bennies. Health insurance. Retirement account is solid, but not quite where it needs to be. I’m 49 now, and barring a global economic collapse, should be able to bail at or before age 55. If I found myself in the situation your friend is in, I’d jump at it, but this is because I have financial/insurance padding in place in case the books don’t do as well as hoped and the advances I receive are all the money I get. I’d take a year’s unpaid leave, save enough from those advances to make up for what I’d lose from the day job, and give it a shot.

    It’s the solid publisher support that attracted my attention. Also, the fact that I’m a slow writer, too. It’s hard to find that quiet mental place in which to work. To finally be provided that opportunity…

    So I’d ask how old your friend is. I’d ask whether s/he has enough of a track record with the day job to take a year’s leave. Some companies will carry your insurance during that time, although they do charge you. Could they transition instead of quitting cold?

  4. Tim Walker on #

    1. I would also have said “go part time” if possible. If it’s not kosher in that industry, sometimes it’s still possible e.g. to set up a consulting arrangement, whereby you come in just for particular projects, at a set (high) rate of pay, but without benefits and so on. That could be a good transition.

    2. A friend of mine who freelances (actually I employ her to freelance) has made it work by *only* working from contracts. In other words, if she does any one-off articles, it’s outside and on top of her normal freelancing, because during business hours she’s delivering the goods for quarterly or 6-month or 12-months contracts. A variation on this is to line up, say, six months’ worth of living expenses in secure writing gigs before cutting the cord to the employer.

    3. In the u.s.a. it’s called a “401(k)” (employer-supported retirement) or an “IRA” (individual retirement account).

  5. Kelly on #

    a sub-header under the health insurance bit is this person’s health in general. if they are in good health, it should be easy (if expensive) to get insurance on their own. if they are like me with a chronic illness (or other form of continuing health problem), at least in the u.s., even qualifying for individual health insurance will be a major challenge.

    Oh, and retirement savings in u.s. through the workplace is usually called a retirement plan (and usually a 401K, but not always or entirely that).

  6. marrije on #

    Is your friend’s career one that will ‘keep’, i.e. can she go away and try the writing thing and then go back if she goes batty or broke? In that case I’d say go for it, absolutely.

    Or like tim walker says, the consulting thing.

    I think it mostly comes down to her tolerance of uncertainty. me, i’m a control freak and my well-being is intimately connected to the size of my bank account. i don’t need football-player income (or anywhere near it, thank heavens), but i get very very very cranky when I can’t pay the mortgage or have to skimp on food. not all people are made like this. but if you are, it’s probably a better idea to stay in the day job.

    And can I just say that an industry that does not allow part time is stupid and will need to reconsider itself soon? it will get increasingly hard for them to keep attracting good people. stupid.

  7. Cheryl on #

    Something that probably won’t be an issue, but might be, is that it is way easier to get somewhere to live if you are employed. It isn’t the money, it is just that rental and mortgage companies will take your ability to pay as given if you have a job, but tend to require all sorts of evidence and payment in advance if you are self-employed.

  8. Edward Willett on #

    My advice to freelancers is to do what I did after struggling along for four years: marry an engineer.

  9. hope on #


    I am delurking to suggest that you warn your friend to examine very carefully the conditions that make it possible for him or her to write. she might find, disaster of all disasters, that when she quits and has all the free time in the world, that she can’t get any work done. If she is writing successfully now, it might be because the structure of her life encourages it. Sometimes, we get more done in 15 minutes, when we know that that is all the time we have, then we would if we had all day. your friend might not want to mess with a system which is producing good work, even if it is slower than we would like.

  10. Garth Nix on #

    If the “strong publisher support” means an actual contract for three books over the next three years, at a level that it is possible to live on, then I would say leaving the day job is an OK risk. But if it is not an actual contract, it is meaningless. All it would take is one editor or maybe even one marketer to leave and be replaced and all that ‘support’ is gone.

    I also agree with hope at (9). When I first became a full-time writer in 1998, I actually wrote less over the next year than I had when I’d been incredibly busy with my day job.

    I would also be inclined to see how the royalties for that first book pan out over 18 months or so before jumping ship. Sometimes books are very hot for a little while and then fade away, you can’t project the royalty earnings based on the first six or twelve months.

    But all those cautionary comments aside, as long as she can go back to the job or has very good prospects of employment, why not go for it? She can always give it 12 months and then get another job if she has to, or augment her earnings by working part-time in a bookshop or whatever. This is perfectly normal and shouldn’t be considered a failure or set-back, most writers through history have mixed and matched writing with other employment.

  11. Lauren on #

    I always err on the side of blind stupidity so I say dump the job. Decent health insurance is available for reasonable rates through and healthy new york.

  12. Diana on #

    Questions to ask:

    1) Age.
    2) General Health
    3) Children or other dependents?

    I quit my job to write full time because I’m young, have no dependents, and am in good health. Otherwise, I’d still have the 9-5.

  13. Darice Moore on #

    I freelance, though not as a writer (I’m a copyeditor/proofreader). I’d say some of the other difficulties are:

    1. Making oneself work on a regular, somewhat scheduled basis to meet deadlines without tearing hair out/breaking down/running away to join the circus. (I learned pretty quickly never to delay working!)

    2. Planning for financial weirdnesses. (Since I started freelancing, for example, the property taxes on our house have doubled and home insurance has tripled; this is making our financial life much harder than we planned).

    3. If he/she has children of a pre-school age, will he/she still send the kids to daycare or try to work with them at home? I work at home with my daughter. She goes to a short preschool program several days a week, and I work at night. This is not easy, but it works for me — it might not work for others.

    I will admit, I went back to do some freelance copywriting work in a local office as a favor to a friend, and I found that I really, really did NOT miss that. I love working from home.

  14. jenny davidson on #

    i’m way on the day-job side of things. including the “enabling conditions” point–personally i fear i would go stark raving mad on a full-time writing gig, much as writing is the need of my soul!

    (other missing pieces of info: if your friend is single and lives in the us, good health or no good health, it is crazy to give up a job with health benefits. if your friend can get benefits through a partner, it’s a totally different story. and frankly support-in-the-background-type stuff does rather come into play here–both financial and other kinds–if there’s strong family backing and/or money it makes the riskier option look more ok. and of course all these questions about dependents are very relevant also.)

    sensible options: an unpaid leave of six months or a year, to write the next book(s)? leave the job completely, but with a commitment for consulting work (but that leaves problem of benefits still standing, and there is also the way that assignments suck up time & such)? but esp. if you like the day job, seems a pity to give it up… so surely at least wait to make a very permanent career shift until the next book is sold? call me paranoid, but even if i had a couple hundred thousand in the bank earmarked for the next four years’ living expenses while full-time writing i would be desperately worrying every day about security…

  15. reality on #

    Heres my two cents

    1 Find a freelance writing job…part time. Some newspapers like to have published authors write columns for them.

    2 Unless the money on her first book was huge, that is to cover say 4 years of living expenses, then leave the job and concentrate on writing. Even if her next book doesnt sell, she can live off the proceeds from her previous book.
    Otherwise keep a job. There are no guarantees unless you are a Tom Clancy, Stephen King, etc.

  16. Penni on #

    I didn’t so much go freelance as never get around to getting a proper job. I don’t just write though, I edit and have started doing a bit of teaching as well. Most ‘full time’ writers I know do something else (whether it’s school visits and workshops, apply for grants, which is practically a full time job and a very specific skill, teach, edit, write articles etc). My husband helped cushion my early career, now I’m (just) earning enough to let him study full time (with help from little johnny). Like hope and garth, I write better now that I have kids and other (delightful) burdens on my time than I did when I had all the time in the world. And writers block is very scary when you’re full time.
    My pov on this is she should only do it if she can cope with a certain amount of (probably relatively comfortable middle class) poverty. I’ve never had a grown up wage, so I’m not that fussed that we live on a fairly tight budget. We don’t like expensive things anyway (I tell myself) – we live very simple lives, without a lot of stuff. But some of my friends think we still live like students and I know they hate that idea.

  17. Dawn on #

    I think that if you can make do with just being a writer and you love it so much, then I would do that. I know writing isn’t ALWAYS fun and isn’t ALWAYS easy (of course not!) but if you love something and you can make a living off of it, I would tell someone to do that. I know what it’s like to despise my job, and having experienced that, I would rather do a job I loved if I could get by.

  18. Chris S. on #

    Hope at #9 and Garth #10 made a really good point: sometimes really busy people accomplish so much *because* they’re so busy. If your friend has a hectic schedule, s/he may find the adjustment very difficult.

    On the other hand, a hard-working person is a good bet for getting out there and finding the freelance work — and chasing down the money (both extremely important skills).

    Save for it; plan for it; make some contacts; then do it! Better to be too busy for the last six months of regular employment than not nearly busy enough for the first six months of freelance.

  19. Dawn on #

    Garth Nix?! Wow! Justine, your blog is famous. You’ve got so many writer friends that I’m green with envy.

  20. Diana on #

    Oh, and tell your friend that if she *does* quit, expect it to take a year or more to get into a professional schedule.

    it’s been that way for me and for a lot of writers gone freelance I know.

  21. Ariel Cooke on #

    I think this person should hold off and really assess his or her situation after novel 1 is published.

    Here are some concerns to add to the excellent list everyone else has provided:

    -Does this person have or plan to have a child? (It’s not as much fun to be a freelancer when you have to maintain a routine for someone else.)

    -Does the job carry a pension and possibilities for lifetime health insurance that would be compromised by taking a year off? What about seniority?

    -Possibly most important: does this person already have a decent prudent reserve? (At least 3-6 mos. of expenses tucked away in a fairly liquid form).

  22. Justine on #

    Dawn: Of course I know Garth Nix. He’s Australian. All Australians know each other.

  23. ariel cooke on #

    justine, it’s true that there are a lot of interesting people on your blog. i hope this doesn’t sound too groupie-like but i read every writer you recommend and/or who appears on this blog. well, some of them i read before your recommends, like garth nix. anyway, you have done me solid. i love almost all of them, especially holly black and kate conroy, whom i absolutely read on your recommendation. i think the three of you do that very rare thing, which is to find a new way to think about magic. did i mention that i didn’t want to sound too groupie-like? yes, well, anyway, thanks!!!

  24. pam on #

    What a great discussion. My experience is that the worse my “big mucky muck” day job goes, the better my writing goes. My fury over stupid policies, procedures, and general middle management angst all gets channeled to depositing my butt into the chair.

    I often wonder where I’d get the inner fuel if I made writing my day job.

  25. andrew on #

    I must say, I think the uniform would suit me down to the ground.

    And there must be perks involved, such as falling asleep on the job. Nothing like waking up with Y G H B imprinted on your forehead. Irregular pay’s not a problem, couldn’t get any less than what I’m getting now ~ nothing.

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