Five reasons to freelance — and five reasons not to!

By Caitlin Kelly

I went freelance, for the third time, in 2006 after losing a staff job at the New York Daily News — but I also freelanced, by choice, full-time for four years right out of college, so it wasn’t a terrible shock to lose an office, colleagues and a paycheck.

I grew up in a family of freelance creatives, people who wrote for print and television and my father was a film director. No one had a steady paycheck or pension to look forward to and rely on. So it all felt normal to me.

You can attend a mid-week matinee!
You can attend a mid-week matinee!

Five reasons to go, or stay, freelance:

You’re very intrinsically motivated (i.e. you don’t need a whip over your head to get it done)

Autonomy ‘r us! Some people are just a whole lot happier not having a boss. And any organization, no matter how small, is going to impose policies and procedures, some of which are usually inane and some of which you might deeply disagree with.

All of which come with someone else’s paycheck.

You want more control of your work/life scheduling

Maybe you have children and/or pets and/or an ailing loved one who needs your attention as well. Maybe you prefer to work from 4pm to midnight or 2am to 8am…or whenever it suits you. Freelancing allows you tremendous freedom, within limits, to set your own hours and schedule.

I take a jazz dance class on Monday and/or Friday mornings, from 9:30 to 10:30 or 11:00 a.m — and no staff job I know of would allow for that. It’s fun and social and gives me tremendous pleasure and keeps me healthy. And I like knowing this is a bonus no job would offer.

I also take as much vacation, whenever possible; my husband, even after 30 years at the Times, must request his vacation time in early January and defer to those (!) with more seniority than he.

This was a workday for us in rural Nicaragua. Sweet!
This was a workday for us in rural Nicaragua. Sweet!

You can choose a wide variety of clients and projects

Staff jobs, de facto, have set roles and responsibilities they have hired you to perform. Freelancers can freely pick and choose our clients and types of work, from quick 300-word stories to 3,500 word features to 100,000 word books. We can fly to another country to do some reporting or spend a week at a conference meeting cool people who can help our careers.

If you’re getting bored or have a difficult client, switch it up!

Intellectual challenge is up to you

If your personal life is crazy and all you have energy for is lighter projects, that’s your call. That’s a huge benefit when our personal lives go haywire and we need to lighten our loads for a while. When you work for someone else, it’s all up to them. Plus, your professional opportunities for advancement and growth (and pay) are largely within their budget, schedule and control.


Your income is your choice

Key! If you want to double or triple your income — or even just boost it by 22.3% — that’s also within your control, not something at the pleasure of your boss or company CEO.

Freelancers see a very direct and satisfying correlation between our energy, stamina, skill and experience, and the zeros on our tax returns — with no office politics and no bullshit excuses why you still, somehow, don’t deserve — or just won’t get — a raise, commission or bonus.

Five reasons to stay on someone’s payroll

You’ve got huge overhead you can’t quickly and easily reduce

If you’ve got multiple children expecting you to pay for their educations, freelancing is going to be tough. If you’re crushed by student debt yourself already and/or credit card debt (especially with a high APR), freelancing — i.e. not having a reliable income each month — can be really stressful, certainly as you are just getting started and cannot command the highest fees.

And many clients pay late (45 to 60 days after invoice) while some try to screw us out of our fees.

I know some people earning $100,000 to 130,000 a year freelancing, but they are not, certainly as writers in journalism today, in the majority.

You need someone telling you what to do, and when to do it, and how to do it right

If you’re the sort of person who craves routine and a structure and people making sure you have done the work correctly, freelancing may feel too loosey-goosey. Every single day’s productivity is completely your own responsibility, so if you’re someone who likes to watch daytime TV or Candy Crush, good luck with that.

Your ability to make enough income to gas the car, feed your family and take your dog to the vet are often the primary or exclusive measure of your success. Your primary goal is to find, nurture and keep ongoing and profitable relationships — not please your superiors and colleagues.

A lovely gift from my former assistant. Someone cared!
A lovely gift from my former assistant. Someone cared!

You really need the company (and input) of other people

Working alone at home is lonely and isolating. If you treasure your office pals and going out for margaritas with them, freelancing all day by yourself may drive you nuts. Yes, you can rent a co-working space, but you’re still there to work and paying for additional space, and not necessarily surrounded by like-minded folk.

Hustling scares you (to death)

Freelancers eat only what we kill. No, not literally! But we start many weeks, or years, with no clear, definite idea what our income is actually going to be. Sure, we set income goals — but clients die, turn into insatiable monsters we have to fire, publications suddenly close or trim their budgets and mayhem just happens sometimes.

Yet those monthly bills keep coming! If the idea of constantly seeking out, and nurturing, new client relationships fills you with dread, keep the day job.

You crave the validation of “I work at…”

A phrase that drives me crazy is “Who’re you with?” I’m with myself, actually.

The constant status-check of ascribing your value and prestige to your Big Name Employer seems, to me, sadly antiquated now that 30 percent of Americans work for themselves, or as temps or contract workers only.

But if you really like saying “I work for BNE”, then get and keep a job there.

The downside? If or when you’re laid off from a staff job, your identity — and your income, of course — may take a serious and unexpected whack.

How about you?

Which lifestyle suits you best?

32 thoughts on “Five reasons to freelance — and five reasons not to!

  1. Love what you had to say on both sides of the matter! I’m off to college, possibly studying entrepreneurship. Being highly independent, I think the freelance route would suit me more 😀

    1. Thanks! And welcome…

      I think being inherently entrepreneurial makes having “a job” more challenging as it’s usually fairly narrowly defined for you. I get bored too easily! Best of luck in college.

      1. Well keep it up. There are a lot of young people out there who don’t have a clue and would appreciate hearing your story.

      2. I wonder. Now that 1/3 (!) of the American workforce is temp, permalance, contract or self-employed, we need many frank and full discussions of how that works, or does not. Public policy is lagging wayyyyyyyy behind on this front as Big Business has $$$$$$ lobbyists protecting their interests and we do not.

      3. Yup, you have that right. That is why I wrote the song “Sold Out”. Because we have been sold out. Certainly time for some change.

  2. themodernidiot

    Great stuff. Damn useful. Question: when you are poking around for clients and job opportunities, one thing that keeps popping up is the request for a work history (portfolio). Do you know why that old has-been is still around? They are looking for submissions, not full-time employees. Why wouldn’t they just read your piece and choose that way?

    1. Sorting mechanism?

      I always send my resume out to any new or potential client so they can see I’m not some weird random freak who has never been able to hold a job (their worst fear.) It reassures them to see I’ve also worked on teams and in offices, so I get their pressures as well.

      1. themodernidiot

        I can see that reason, but just when asking for single submissions? Seems a bit overkill?

      2. I can see why that feels weird.

        But here’s the reason that makes sense to me — in this era of complete job insecurity; if an editor is about to assign to someone totally new to them (and whose work might totally suck) why would they not ask for whatever will seal the deal and make them feel more at ease?

      3. themodernidiot

        Oh yeah, on assignments, heck yes, definitely know what you’re paying for. But for open-submission stuff? Just read the piece, yeah? If it’s good, print it. If not, don’t. Why would you care what else they’ve written? You’re only looking at one, very specific piece, not a promise for more. If the article wows you and you wanna bring them on board, I totally agree, ask for a portfolio and/or background. But not for crappy little op-eds or filler. That just seems…well, kind of elitist, doesn’t it?

      4. themodernidiot

        I lost your blog somehow. WordPress updated then, Poof! The Kelly was gone. I thought you said, “Screw it,” shoved Jose in a kit bag, and packed off to Central America lol. I was gonna have to give you points for that.

  3. my spirit is more of a freelancer, and i worked two jobs for years when i needed more money, and now find myself in a good place in the middle. i work one job, full time as a teacher, but have a lot of time away from work to do as i please. i’m my only source of income so i have to have a certain amount to live, but really have adjusted to needing less and am happier for it.

  4. I love freelancing, I’m exponentially happier now than I ever was at the PD. But oh man, you hit the nail on the head about stress and student debt. Currently everything I make disappears down that black hole. It’s really rewarding to make payments every month…and it’s incredibly scary to have nothing left over to show for it. I know I’ve cautioned people thinking about freelancing but are in similar situation to transition slowly to be sure they can meet all their commitments, because they underestimate the stress involved or overestimate their ability to meet them just starting out.

    I do sometimes miss the externally provided structure that an office provided, and it’s a learning curve to figure out how to create some things that a more traditional job provides (organization, socializing, a degree of time management – since in an age of email I’m available all the time, I’ve had to learn to develop and stick to my own hours so I don’t over extend myself, etc.). But on the whole, I just feel really lucky to finally be able to do work that I enjoy and have a degree of autonomy that I craved for so many years.

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    1. Don’t!

      Freelancing is not for the faint of heart or thin of wallet. If you need to bring home $2,000 to $5,000 every single month, on time and without fail, with no late fees or penalties, the stress is relentless; if it’s only to earn some fun money, go for it. I know very few people in the U.S. in 2014 who can pay all their bills and save for retirement on much less than that.

      Without a line of credit, freelancing for a living is almost impossible — clients now pay later and later and later, yet credit cards and gas and groceries and rent/mortgage all need to be paid at time of use/billing. The endless hassle of chasing payment is extremely stressful for every freelancer I know.

  6. Ah, you know this post is speaking directly to my core, right? 🙂 As one who has just made the leap, I’m sure I’ll be referring back to it many times. I’m very, very new, but also more energized and focused than I’ve been in a long time. I fully realize that I’m basically diving into the deep end without knowing how to “swim” – but there’s an urgency to that that I actually like (need?). A high stakes kick in the pants. That said, I couldn’t do it without some savings. The risk is burning through it all before I’m able to do it on my own. I will hustle/work my butt off and time will tell.

    1. There is a rhythm to freelance (faster! faster! :-)) but once you’ve discovered you’re capable of it (or even enjoy it), jobs will look very very different. They will be a deliberate choice, not a desperate need.

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