Moving from staff to freelance? Ten crucial tips

By Caitlin Kelly

The New York Times newsroom
The New York Times newsroom

Are you (yet) a member of “The Precariat”?

It’s also known as The Gig Economy.

From the Alternet:

I caught up with Gerald Friedman, who teaches economics at the University of Massachusetts at Amherst and has written about the gig economy, to find out how this trend happened and what it means to workers and our increasingly unequal society.

Lynn Parramore: How did the shift away from full-time employment to the gig economy come about? What forces drove the change?

Gerald Friedman: Growing use of contingent workers (in “gigs”) came when capitalists sought to respond to gains by labor through the early 1970s, and in response to the victories capital won in the rise of the neoliberal era. Because contingent workers were usually not covered by union contracts or other legal safeguards, employers hired them to regain leverage over workers lost when unionized workers gained protection against unjust dismissal, and courts extended these protections to non-union workers under the “implicit contract” doctrine.

Similarly, the rising cost of benefits due to rising healthcare costs and government protection of retirement benefits (under the 1974 ERISA statute) raised the cost of full-time employment; employers sought to evade these costs by hiring more contingent workers…

GF: Talk of “microentrepreneurs” presents a favorable view of the rise of the gig economy, one consistent with liberal values of individualism and opportunity, even while ignoring the oppression and poverty-wages many find in the gig economy.

There are certainly some who enjoy the uncertainty of irregular employment. When unemployment rates fell to levels traditionally associated with full employment in the late-1990s, however, we saw how workers really feel about gig jobs: they rejected them and the contingent economy contracted.

Given a choice, workers choose careers and jobs, not freelance gigs.

By removing any social protection, the gig economy returns us to the most oppressive type of cut-throat and hierarchical capitalism, a social order where the power to hire and fire has been restored to employers, giving them once again unfettered control over the workplace.

I recently participated in an hour-long discussion of this, with Friedman as the opening expert, on WNPR; I speak in the final seven minutes and this is a link to that broadcast.

Rue Cler, Paris, where I spent 2 weeks. Vacation, for a freelance, is whenever and wherever you like
We stayed a block from the Rue Cler, Paris,  in December 2014. Vacation, for a freelance, is whenever and wherever you can afford to go. Some people choose to live overseas and work from there.

The American workforce is now one in which an estimated 40 percent of us work with zero safety net, beyond that which we create: (six months’ basic expenses saved, a separate emergency fund, a low-interest line of credit, disability and life insurance.)

Knowing how to survive thrive without a steady paycheck is a crucial new skill.

My husband recently left a secure, well-paid job at The New York Times.

Madness? Perhaps.

But, after 31 years there as a photographer and photo editor, having done almost everything one can do in a career,  (including helping them win a team Pulitzer Prize for their 9/11 coverage), and offered a healthy buyout package — which gave us the requisite six months’ of expenses cushion of savings –– he decided to leave a month or so ago.

While he seeks another full-time staff job — which he may not find — he’s discovering how pleasant life can be without a 2-hour train commute, (costing $300 a month), fighting his way crosstown through aggressive crowds and having to book vacation in the first week of January due to seniority issues.

It can be a huge adjustment, no matter how desired, to move from the relative security of a salary that arrives on schedule and is predictable in size and due date to the roller coaster life of the self-employed.

Jose has seen me work freelance since 2005 and knows I know those ropes.

Now he’s learning them as well.

I liked this piece about moving to freelance work from The Guardian — and her realization that giving away your time without financial compensation, even barter, however friendly and helpful — is something no full-time freelancer can afford.

Here’s a comprehensive and helpful guide from the Freelancer’s Union.

And five tips from Time magazine about readying yourself for that leap.

You can catch a midweek matinee!
You can catch a midweek matinee!

A few of the lessons I’m teaching him:

Don’t rush to say yes to every offer

Just because the client is prestigious and/or your bank balance is running low this month, don’t just leap at any offer you get. Is the client a good fit for your skills, experience, temperament? Have you done your due diligence on that client’s track record of payment and ethical behavior?

Don’t say no to what looks like a lousy offer; consider its every possible benefit

The hourly or day rate might be lower than ideal. It might be a low-prestige gig that pays well, or quickly, or both. The gig might introduce you to a new market and possibly expand your skill set, in effect paying you (even if not very well) to learn on the job.

Never agree to a gig without a clear, written agreement as to the scope of work

One major non-profit recently advertised for a photo editor freelance job, with a long list of responsibilities — with no clue how many hours a day or days a week or weeks per month they were offering. They just kept asking “What’s your day rate?” Nope. Avoid low-balling yourself before you know what they expect in return.

We started one of our days dancing from 7 to 9:00 a.m. All the office folk headed out early. Not us!
We started one of our days dancing from 7 to 9:00 a.m. All the office folk headed out early. Not us!

Never agree to a gig without a clear, written, signed agreement/contract

Things go south: your editor quits or gets fired; the budget is suddenly cut; your client hires a new assistant who hates everything you produce. You need protection. Spell out all your responsibilities, all their needs and the dates when you will be paid. It must be signed by both parties.

Everything is negotiable — including your decision to turn down a gig or leave one mid-stream

No one, ever, wants to walk away from a (well) paying client. Sometimes, though, it can be a wise choice to politely recuse yourself from a quicksand scenario where one client is sucking up all your time, energy and patience. Life is too short. (See: emergency fund.)

Negotiate! When someone offers you X fee, always ask for more. It’s been statistically proven that men almost always do, and often get it, while women just say “Thanks!” and get taken cheaply.

Your best sources of work are referrals from people who know, like and respect you and your work

It’s completely counter-intuitive that the fellow professionals with whom you’re now competing for freelance work can be, in fact, your best sources of good opportunities. In an office setting, you can face politics, nepotism, favoritism, seniority, sexism. For every ally and work-wife/husband, you might face a Game of Thrones-ish power struggle with someone.

Freelance life can offer plenty of stress, but if you have a strong, sturdy network of skilled, smart and ethical people who you help as often as possible! — you’ll never starve.

On assignment in rural Nicaragua...Gin up some paid adventures!
On assignment in rural Nicaragua…Gin up some paid adventures!

A ferocious work ethic — even if you wake up at noon and work in sweatpants — matters more than ever now

No missed deadlines! No slacking off!

You are selling your time, skills and experience. Never underestimate their value

Every freelance dollar you earn must now 100 percent fund your healthcare, retirement, sick days and paid vacations. You’re also on the hook for paying the full 15 percent of your income to fund Social Security, (employers usually pay 50 percent.) Boost your rates accordingly.

Stop...enjoy life's beauty. Put a fresh flower on your desk
Stop…enjoy life’s beauty. Put a fresh flower on your desk

You must take breaks, both in  your workday and your year

Without exercise, friends, face to face meetings and pleasure, you’ll quickly burn out. It’s isolating and lonely to work alone every day all day. It’s also tempting to work far too many hours instead of shutting off all electronics and access to email at a set hour so you can enjoy a full life, not just a new form of wage slavery.

Follow my friend Wendy’s three rules whenever possible as you choose (or refuse) a job:

Is it fun? Will I learn something new? Is it well-paid?

It should hit two of three.

Have you moved from a staff job to freelance life?

How’s it going?

What else would you advise a newbie to this way of working?

12 tips for creative success

By Caitlin Kelly

Loved this, from Slate:

Most people agree that what distinguishes those who become famously creative is their resilience. While creativity at times is very rewarding, it is not about happiness. Staw says a successful creative person is someone “who can survive conformity pressures and be impervious to social pressure.”

To live creatively is a choice. You must make a commitment to your own mind and the possibility that you will not be accepted. You have to let go of satisfying people, often even yourself.

And this, from writer Myke Cole:

My sub­con­scious con­jured an image of a fab­u­lous party, filled with other writers and pub­lishing types. A place where I could walk in the door to a chorus of cheers, the “Norm” moment, where guard could be let down com­pletely, where there was only shared vocab­u­lary and a fluid ease that would make the jit­ters go away. There was a social circle that would be the payout for all the rejec­tion and worry and sweat equity I poured into my books. When I talked about it with my brother, I simply described it as “that.” I wanted to have “that.”

All I had to do was get a book deal. I would break out of the world I knew and set up in some secret corner of the social fabric, a back­stage pass to the world of writers that I just *knew* was out there, even though I had never seen it before…

There is no party. Not beyond the hour or two at a con or pub­lishing event where you get to show off for a shining moment, bask in the acco­lades for a few min­utes, fan boy gush face to face over someone whose work you admire but never hoped to meet.

And then it’s over, and you’re left with the work.

My husband Jose recently passed a major professional milestone: 30 years as a photographer and photo editor at The New York Times. On 9/11, the day he was to have moved into my apartment in suburban New York from his home in Brooklyn, he instead unpacked his scanner, printer and computer — and helped his colleagues transmit their horrific images from his apartment. His grace under fire helped the paper win that year’s team Pulitzer Prize for photo editing.

photo: Caitlin Kelly
photo: Caitlin Kelly

He grew up poor, the son of a Baptist preacher in Santa Fe, NM, far from the centers of media power and influence. He attended state school on scholarship. He’s slight, quiet, modest. Everyone else in his family became teachers.

One day, shooting for the Associated Press, the White House press corps — accompanying then First Lady Rosalynn Carter, landed in El Paso.

“Someday that’s going to be me,” said Jose, as he saw its four or five wire service photographers emerge from the plane.

Several colleagues snickered at his hubris.

And then he was, during his eight-year career in the White House Press Corps, photographing Presidents Bush, Reagan and Clinton.

Here’s his brand-new blog, Frame36a, (which refers to the extra frame we used to be able to squeeze from a 36-image roll of film), which will offer advice, insights and fantastic back-stories to some of his best photos.

We all won’t have a career like his.

But anyone with creative ambition — musical, artistic, photographic, literary, choreographic — will face obstacles, whether you’re 17, 27 or 57: lack of funds, no representation, a lost prize or fellowship or scholarship.

After a decade or so, they’ll probably morph into different challenges, but it’s rarely easy.

If you think it should be, this isn’t the world for you.

Start small

You don’t have to start out by winning a major prize or selling your work for a lot of money. You just have to get started. I began my career as a photographer, and one of my first sales was to my own high school, an image they bought for the school library. Was I scared to pitch our principal? Hell, yes! But it worked. I also had a show of my images in a Toronto library, again, because I dared to ask. The smaller the ask, the less scary it should be. Those initial triumphs are essential baby steps to your self-confidence as a creative person able to find, and sell into, the marketplace of ideas.

My high school award. Anything to boost your confidence helps!
My high school award. Anything to boost your confidence helps!

Start young/early

Don’t wait for permission to create! You don’t need a certificate or degree from anyone, anywhere, to create interesting, challenging and worthwhile work. Don’t be terrified if your competitor graduated from RISD or has a Phd from Harvard or was a star at the Iowa Writers’ Workshop. If you have the passion and drive to find the toughest teachers out there — and they might be someone you meet at a conference or class — you’ll be on your way. I sold my first photos, three magazine covers, when I was still in high school. Jose was selling his photos while a freshman in college to the Associated Press; by the time we both graduated, we had large and impressive portfolios of nationally-published work. We were far, far ahead of our 22-year-old peers competing for work and jobs.

She didn't win, because her goat behaved badly. But she learned how to compete.
She didn’t win, because her goat behaved badly. But she learned how to compete.

Don’t give up if you fail the first (second, third) time

I’m amazed how quickly some people give up. I interviewed three times at Newsweek and was never hired there. No harm, no foul. I’ve had an awesome life and career without them. I’ve applied two (three?) times for the Alicia Patterson Fellowship, and was one of 14 finalists (of 347 applicants) last time. I’ll probably apply a few more times until I get it. In the meantime, I just keep improving my skills and strategies.

If you’re really aiming high, you’re always competing against highly-educated, smart, talented and well-prepared competitors. Expect it and arm yourself accordingly. If you want it badly enough — whatever it is — you’ll keep coming back to get it. Or you’ll find something more interesting instead.

Both of my non-fiction books, both of which were published by major New York houses to excellent reviews, were each rejected by 25 publishers first. Fun!

It’s too easy to watch others win awards and prizes and fellowships and hate them. Bandage your ego and get back in the game.

Find people whose work inspire you

This is essential. People who have succeeded in your field have likely hit (and surmounted) many of the same obstacles along the way that you’re facing. Read, listen to and watch them: at conferences, in TED talks, their websites or blogs or books. Follow them on social media like Instagram and Twitter.

If you’re feeling bold, reply to them or re-tweet their words. A relationship with someone who’s already carved their path is helpful. Don’t expect them to mentor you, though. Successful creatives are really busy!

Understand your industry or field: who has power and why?

The best way to get ahead creatively is not to shut yourself away in your studio or a hut in the woods, no matter how romantic that sounds. If you don’t keep up with the movements, controversies and players in your field, you’re too isolated and have no real idea how to access the powers-that-be, the ones whose choices are going to affect your ability to succeed as well.

Make sure to attend at least one conference a year in your industry so you can hear the latest and network with your peers. Showing up in person helps to prove your commitment; people see that and respond accordingly.

Self-doubt and self-confidence will perpetually war within you

It’s the ultimate paradox: to create means taking a risk, putting your skills and ideas into public view for possible rejection or criticism, but it also requires and demands enough confidence in your work to put it out there in the first place.

No creative person I know, or know of, hasn’t suffered — sometimes mightily — from this internal war.

Writers, even the most visibly accomplished, the ones we envy and admire, (who now have a reputation they might squander), lose their nerve or voice. Performers vomit and tremble before setting foot on stage. Artists burn work they’ve spent months or years to produce.

We’re human. It happens.

Make peace with your fears. Name and number them — “Oh, yeah, self-doubt 34a, how the hell are you these days?”

Then keep moving.

You will have to hustle, self-promote and shout louder than you might ever prefer

If you are a modest, gentle soul — like my lovely Jose — you may find the creative path more difficult, surrounded by arrogant, shouty chest-beaters. If you truly crave Big Success, however you choose define it, you may have to toot your own horn loud and long, no matter how declasse your family or friends or native culture consider that.

Volunteer your time and skills within your creative community

I think this is overlooked as a key to long-term success.

You don’t have time? Make it. People most respect, value and reach out to help those they respect personally — not just someone whose work they read about or saw in a show or in concert. I was only 19, still in college, when I volunteered to interview lions of Canada’s journalism industry for a book. How else could I ever have met or spoken to them, let alone learned their wisdom? Then they also knew who I was. Win-win.

I’ve served for years on volunteer boards for writers’ groups. It helped to hone my people skills, (still a work in progress!), taught me about fund-raising and how to defend and explain my ideas to a skeptical group.

It also shows clients and colleagues my pride in, and commitment to, my larger creative community.

Find, or create, a group that meets weekly, or monthly. Create an on-line listserv or Facebook group. Mentoring others comes back in waves of generosity, for years.

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Make time to reflect, recharge and revive your spirit

No matter what you hope to create or produce, make time to recharge. Sit still in silence every day. Stare at the sky, no matter what the weather. Make notes whenever you get an idea. Keep them!

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Travel as far and as often as you can afford

There’s no better way to sharpen your senses than to step out of habitual behaviors and routines: taking the same subway line or bus route;  eating the same cereal at breakfast; seeing the same faces at work. Even a two-hour road trip to a nearby town or city or nature preserve can offer you new ideas and insights.

Have a clear vision of what you hope to accomplish, today and/or in a decade

You can’t get there, wherever there is, without a clear idea what it is. Only by naming it can you start to lay the necessary groundwork — whether admission to the best program of study, a fellowship, a job, access to a busy mentor, publication of your novel or a gallery show. It’s too daunting to stare only at the cloud-shrouded Everest of your final goal. Focus on the foothills!

I recently started a writers’ group and called it Story Sherpas — no one gets there alone, without the help and support of a team along the way.

Study the work of the very best in your field

Don’t assume the best are working today. They might have powerful lessons to offer from their endeavors — possibly centuries ago.

Bonus:

Save a lot of money!

Creative “success” can, and often does, evaporate overnight — and with it your ability to dick around and await your muse.

Read this cautionary tale, from a New York writer whose book advance was a stunning $200,000, way more than any writer I know has ever received. She blew it.

Don’t ever rest on your laurels. They can wither mighty fast.

What spurs you to creative success?