Five reasons to freelance — and five not to

English: The Aviation and Missile Command can ...
English: The Aviation and Missile Command can now be found on two popular social media sites, Facebook and Twitter. (Photo credit: Wikipedia)

I lost my last staff job in 2006, at 3pm on a Wednesday afternoon, from the New York Daily News, the nation’s sixth-largest newspaper.

I decided to go back to freelancing, a way of life and generally unpredictable income stream that both terrifies and seduces many people. In the ongoing recession here in the United States, millions of people are “freelance” because they simply can’t get hired back into a full-time staff position.

I’ve been freelancing as a journalist, author, editor and writing coach since my second year in university.

I work with a wide variety of clients, writing for The New York Times, (since 1990), magazines like Marie Claire or Smithsonian, selecting and creating on-line slide-shows for HGTV. com.  to helping private individuals whose manuscripts need editing.

Luckily for me, I had role models — growing up in a family where no one counted on a paycheck or pension. My father was a film-maker, my mom a writer and broadcaster and my stepmother wrote for television shows, teaching me by example how to make the cube-free worklife enjoyable and profitable.

Slash your expenses to the bone

I think this is the single most essential element of deciding to quit a job or leave any reliable income stream. If you carry a $5,000 a month mortgage, a $400 a month car payment, private school tuitions and other enormous carrying costs for a lavish lifestyle, freelancing is likely not a choice you will enjoy or be able to sustain. You don’t have to eat ramen or wear burlap, but freelancers must fund every cost alone — including all health and dental fees, sick days, vacation days and retirement. (You will get to write off, up to 30 percent typically, many of your business expenses, whether subscriptions, dues, travel or professional fees.)

Be social media savvy

If you’re going to compete with people like me, who’ve been doing this for years, even decades, you’re entering a crowded field of experts. LinkedIn, Facebook and other social media links will keep you in the loop and let others know you’re ready for work. You must have a terrific website, (with a professional headshot), with a variety of work samples and update it frequently. A smart and helpful blog will keep driving traffic to your sites.

Be a little hungry — all the time

Freelancing is not a good fit for the lazy and undisciplined! The ability to manage your own schedule, a fantastic perk, means you have no boss, co-workers, annual review or external check on your productivity. You must work as many — or more — hours as you did in your loathed cube in an office. You must check in with past, present and future clients consistently. Go to meetings and conferences to meet influential people in your industry. Work will eventually come to you through referrals, but you’ll be chasing it a lot of the time. Remember the salesman’s ABC: Always Be Closing; i.e. you must constantly be closing deals in order to assure plenty of future income.

Think broadly and deeply

In my view, this is the most compelling reason to go freelance. The creative freedom to produce work you value, to work with people you admire and enjoy, to know your work is making a significant difference in the world is worth a great deal. It won’t pay the rent or electricity bill, but it will remind you why you’ve made this choice. With its freedom, you can travel whenever, wherever and however often you can afford — or find a client to fund it. You can attend conferences and meetings that intrigue you and may lead to totally new and different opportunities. You can visit a museum or gallery or movie in the middle of the afternoon to refresh your weary brain. You can (and should) commit to some regular volunteer activity. All of these are luxuries most employers don’t allow.

You’re 100 percent reliable

In 2007, I landed in a hospital bed with pneumonia because I just kept working as I became more ill. Never again! But I can count the number of deadlines I’ve missed in 30 years on one hand. More like two fingers. Your clients are offering their trust, time, energy, attention and limited budget. They are relying on you. If you or your dependents are in poor health, freelancing is an unwise choice, with no paid sick days and clients who expect results with no whining or excuses. Unless you’re in a coma, or a family member has died, meet your deadlines! (Your competitors are.)

Here are five reasons to keep your job or commit to another one:

You’re lousy with money

Some people just are. You have no idea what’s in your bank account. Your multiple credit card APRs are 20 percent or higher and your FICO score  — (you do know what that is?) — remains scarily low. You have a ton of student debt and/or credit card debt. You want that $3,000 vacation, dammit! Read the essential book, “Your Money or Your Life.” Then decide what matters most to you.

You’re disorganized/lazy

If your employer is putting up with it, you’re lucky. Freelancing offers no room to slack off, because no one will remind you to get back to work or work harder or more efficiently. It’s all up to you.

You have major and inflexible financial commitments

If you’re carrying enormous student debt, have a bunch of dependent kids or a non-working spouse/partner or a car/home likely to require costly repairs, freelance work — which can be feast or famine — might just add a lot more stress to your life. Having a low overhead and little or no debt, (plus three months’ savings, at least and a low-interest line of credit), makes this life choice workable. Sadly, that’s just not where many people are right now.

You’re selfish

Admit it. Some people have zero interest in sharing their skills or time with others. Freelancers who thrive long-term share their time and talent with others. You’ll suddenly need to pick up a gig — or are overwhelmed and need to sub-contract it to a reliable colleague. If you’re not someone who plays well with others, freelancing will be lonely and much tougher.

Your skills or work ethic could be stronger

The freelance life means competing with thousands of veterans offering a ferocious work ethic and fantastic skills. They invest regularly in new technology, attend conferences, take classes, network. The trade-off of working alone means you can’t fall back on tech support, your boss or staff or intern.

Here’s a recent helpful post about freelance life from Toronto writer (and friend) Patchen Barss.

Here’s one of my favorite websites, Freelance Folder.

And here’s a great blog, Dollars and Deadlines, by Chicago-based writer Kelly James-Enger.

If you’ve gone freelance, what are your thoughts?

15 thoughts on “Five reasons to freelance — and five not to

  1. passionwriting

    i love to freelance…i am passionate for writing but i end up working 12 hours even on sundays..!:( 🙂
    i really don’t know to be happy or sad for that..!

      1. passionwriting

        yep i totally agree…but i don’t know the hands just don’t stop:P
        definitely if i get a better breakthrough..i would love to spend SUNDAYS as SUNDAYS..!

  2. Thanks for sharing your excellent tips about being freelance. I just got accepted to the graduate diploma in journalism from the university of Canterbury (Christchurch, New Zealand). I’ll certainly have to start applying your tips as soon as possible 🙂

  3. yeah, you absolutely need to have a structured, organized way to your day-to-day life. You are a writer. So I am sure that there are topics, poems, anything that you would like to write about or on. With me, I am a prose poet, a label still in the making, though still a style of writing in more of an artistic realm that people dig reading. Kerouac, Antonin Artuad, Kenneth Patchen, and many more. I had a plan of making 100 submissions a month, would get on average 10 acceptances a month. But with 50 bucks an acceptance, that could pay my rent. Still a 90 percent failure rate, but I know that is a success. A writing professor I had in college a few years ago told me it took him 40 years to get published. I had every poem accepted the first time I ever submitted writing when I was 18. Pebble Lake Review out of Houston. Angel Exhaust out of the UK. I felt bad. I even feel kinda weird even writing this right here. the 2013 writers market is useful. awards, fellowships, grants are where its at, thats where your name is put out there. i have had a little over 300 poems published in zines and periodicals worldwide. even self published a book. think anyone gives two shits? its like, either get that degree, or win that award. I start art school in the spring. gotta play that game to beat it. and dont get me wrong, I am excited for school to start. Never forget about the DIY ethos. depending on where you live. I completed a graduates program and received a Professional Certificate in everything DIY. Publishing, advertising, PR, marketing, networking, zines, letterpress. Underground pro. one of 30. ever. Did you know that the second law of the Avant-Garde is the first law of Pop? and that a white, english catholic priest invented the style of rhyme underground hip hop rappers use? its called “sprung rhythm”.

    1. I would never in a million years try to make a living selling poetry, although some people try. The material I write is more commercial, for newspapers, websites and magazines, and rates have been drastically cut since the recession. You have to produce a lot to make a living, but if you’re not even selling, it’s hopeless.

      1. that you are correct. and wow, yeah, congrats on having such respectable clients. I will always write. I have um, what did they call it? the bloody eyed will to keep going on even when no one gives a damn..? but, come spring, I will be starting my BFA program in Sound Art and Video at the Pacific Northwest College of Art. Also living in Portland, where 10 million dollars was recently dropped into the Arts and Education, there are so many Arts Councils that provide artists with resources to have a project funded. Read winning grants 101 and you got it. I was awarded a grant to record a spoken word record which I would also score for aesthetic purpose, and release it on cassette only. I wont go into the reasons why it would work but if you wanna know I will gladly lay it out. Gotta love our artist pampering PNW. and there is now a 20 dollar walkman with a usb and recording software out now. so now you have a “secondary emerging market” in those plastic hissing fuckers. yet. much longer life time than any of the devices we switched to from them. Art of all mediums made portland the hip place to be anyways. I watched it happen. okay, sorry for rambling.

        Steven Jesse Bernstein – “Prison” (Sub Pop, 91)

        much much respect for your accomplishments and points. serious. The DIY punk ethos has taken me captive. I did a reading at Columbia University once. That was cool. Where Bill Murray and Dan Akroyd (spelling?) drank their flask.

      2. Boy, I envy you all that potential grant money! The Canada Council offers $20k/yr to writers with two books but the last time I spoke to a program officer she sniffed that the work had to be “art.” Well, that knocks most non-fiction right out of the ring….and the next time the NY state council for Fine Art offers grants for non-fiction is 2014, when I likely will apply for the first time.

        I certainly admire the punk DIY ethos, which, as you know, flourishes in places where rent isn’t necessarily $1,800 for a tiny studio and there is more support, culturally, for that choice — places like Montreal and Berlin also come to mind.

        OK, you’ve inspired me to go look for some more of that dough. 🙂

  4. Thanks for the shout-out! And I agree whole-heartedly with your thoughts on the realities of free-lancing. The issues aren’t unique to writing; a friend of mine is a photographer and has exactly these problems – including constant demands on his ability to innovate. The issue, I guess, boils down to the usual one of trying to run a small business (any business) where returns on effort are minimal and where the entire return devolves to your own actions. The arts, of any kind, are probably one of the riskier fields to try that in. Needs a good deal of grit if it’s the sole income. The real rewards are always going to be intangible.

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