Cotton years, cashmere years — what full-time freelance is really like

By Caitlin Kelly

The New York Times newsroom

Many of you have — or want — a full-time job. One with paid vacation, benefits, a boss, colleagues. Maybe an office of your own.

But one-third of Americans are now working as I do, freelance, temp or on some sort of contract. At tax time, we look forward to a thick stack of 1099s, the forms sent to us (and the IRS!) by every client who we billed for more than $600 per job. We can also claim a raft of business expenses as deductions, from car repair to a new computer to travel to a distant conference.

I recently spent four weeks in Paris and London; while in England, I reported three stories. I plan to write off my airfare and some of my costs as well as I clearly produced paid work while there.

My last staff job was working as a reporter for the New York Daily News, the sixth-largest newspaper in the U.S. I had a big laminated press credential I wore around my neck on a metal chain. It showed everyone I was one of the cool kids, working press conferences and stake-outs and racing every day, sometimes physically down the street, to beat reporters from the New York Post and New York Times; (they always showed up wearing silk and linen — starting Times salary being a cool $90,000.)

I enjoyed having a paycheck, the job less so. I was let go in June 2006 and have been full-time freelance ever since, a sort of work I had done many times before then as well. I apply occasionally for a full-time job but my heart isn’t really in it; I’ve already worked for three big daily papers and had the most fun there one can have and get well-paid for it. (As many of you know, the newspaper industry these days is about as steady and viable as a whaling ship fleet.)

I wrote about my trip to Corsica for The Wall Street Journal

But freelancing is a way of life that some people just aren’t cut out for.

How about you?

You must hustle every single day. If you slack off, you have to hustle twice as hard (vacation, illness) to make up for lost time

Clients come and go: editors get fired, move to Thailand or Berlin, take maternity leave and don’t come back. Entire magazines shut down overnight. Relying on a steady set of clients means you better have a lot of them. I see them like a pack of sled-dogs — you need a bunch of them, all pulling hard, in case one goes down or gets injured.

You have to be self-reliant. Tech support? Supply closet? Training sessions? Hah

You’re the CEO, CIO, CTO, CFO, R & D, sales, marketing, distribution, payroll and the janitor. No one is standing by to help you so it’s up to you to find, create and nurture those relationships. You also need to set aside some of your income for this stuff.

Nope! Not til the workday’s done

Working alone at home requires self-discipline

No one cares if or when you clock in or out. No one cares if you sell a thing. It’s all up to you! But, on the other hand, no one is standing in your way if you decide to double or triple your income this year — a feat all but impossible in any staff job. Your earnings are up to you. But you have to put your bum in the chair and get on with it. I’ve only turned on the television in working hours during major news events, and now just check Twitter instead.

Your networks will save you, time and time and time again

Paradoxically, you’ll need other professionals in your life far more as an independent worker than you probably ever did in a staff position. Whether you need advice on contracts or rates or how to handle a PITA client, you’ll need to find, join and nurture a wide range of professional networks so you’ve got access to people you can trust when you need their help. You also have to give it! I belong to more than four separate writers’ groups — one with 2,300 women writers in it — and check in with them daily. I find new markets, ideas, insights and offer my advice when possible; what goes around comes around.

My desk, in the corner of our living room

Social media matter more than ever

You need to find sources, fast. You need advice, fast. You need to boost your brand’s visibility. Your new book needs thousands of eyeballs. Your networks will come through for you — if you’ve been a good egg for them as well.

Mentor whenever and wherever possible

The freelance world is filled with clueless, helpless newbies. They can suck you dry! Give them your help when you can; charge for your expertise the rest of the time. (I coach, $200/hour.)

Stay healthy!

Making time for regular exercise, social events, lots of sleep and healthy food choices will keep you ready to work hard. I work a standard six to eight hours a day, five days a week. I very rarely allow work to leak into my nights and weekends. Yes, that lowers my income. It also reduces my stress!

My story in July 2014 Cosmopolitan (U.S. edition)

Have little to no debt, low overhead and a cushion for slow payments

The hardest part of freelance? Not finding work or clients. If you have skills, charm and hustle, you’ll find them. But even the biggest — sometimes always the biggest! — can take months to pay you. In the meantime, you still need food, rent, gas, health insurance, haircuts. A life! I have a $16,000 line of credit through my bank and two low-interest credit cards. But I never work without a contract and insist on payment 30 days after receipt of invoice.

Forget the word freelance. You run a small business

Too many people fantasize wildly about the incredible freedom they’ll have once they work for themselves. Yes, you will. But the romance fades mighty fast when your payments are months late or your work dries up (see: cotton years) or you end up, as I did in March 2007 for three days, in the hospital with pneumonia — from overwork and exhaustion. You must decide on your income goals and do everything in your power to make them real. It’s not a cute hobby working from home. It’s a business.

Your business!

Does freelancing appeal to you?