Pros and Cons of Freelancing: The Three-Year Stretch

I’ve been freelancing full-time for a little better than three years now, and there are things about it I love much more than I loved the 8-to-5 – but there are also things I hate much more than I hated the 8-to-5.  Here’s a look at my top pros and cons of freelancing.

1.  PRO: I work alone. CON: I work alone.

Most Google Image search results for “alone” are depressing as all get-out, so here’s Audrey Hepburn enjoying some jazz records.

I’m an introvert who has the world’s worst time with social interactions, so I love working alone with only the occasional cat for company.  I can hear myself think; there’s no office drama; etc. ad nauseaum.

On the other hand, working alone for three years straight has pretty much destroyed the modicum of social interaction skills I actually once possessed.  The Oatmeal’s “degradation of social skills” due to working from home?  Yeah, that’s pretty much me.

2.  PRO: I’m in control of my time.  CON: I suck at controlling my time.

“Get better time management skills or Kit Kat will EAT YOUR SOUL.”

One of the things I despised about the 8-to-5 was the 8-to-5-ness of it.  Rarely did my tasks for the day actually require the amount of time I was expected to be present in the office, yet I couldn’t buy myself some free time with improved productivity. Enter Parkinson’s Law.

“Yay!” I thought, when I first started freelancing.  “I am now in control of all my time!  I can bang out my work in the first three hours of the day and spend the rest of my time writing short stories and getting into arguments with strangers on the Internet!”

What I didn’t realize is that when one has totally unstructured time and a large, open-ended task that needs to be done in that time, one of two things happens:

a.  The urge to fill ALL THE TIME with work becomes overwhelming, resulting in anxiety attacks whenever one tries to eat dinner or watch a movie; or

b.  Parkinson’s Law takes over – suddenly, minute tasks take infinite time to complete.

It turns out I’m actually much more productive when some, but not all, of my time is scheduled.  If I have to be at a 2:00 appointment, for instance, all my day’s work can be completed between 8:00 and 11:00 a.m.* – but if there’s nowhere to go for the day, I’ll spend 12 hours doing that same three-hour task.  So much for all that Free Time I was supposed to gain in this biz.

3.  PRO: Business expenses.  CON: Taxes.

The folks at the IRS rejoice at the sight of my tax returns.

Writers can claim some of the weirdest things in the world as business expenses, as long as we produce some kind of writing-for-pay as a result.  I’ve met writers who have successfully business-expensed stiletto heels and shrimping expeditions.

This is huge, because business expenses are the only thing on which a self-employed person pays no taxes.  Because here’s the nasty monster in the closet of self-employment: your payroll taxes (those go toward Social Security and Medicare) double when you leave conventional employment.  Why?  Because for the conventionally employed, payroll taxes are shared between the employee and the employer – but when you’re self-employed, you are both the employee and the employer.  Which means you’re suddenly paying an effective tax rate higher than Mitt Romney’s on every cent you make over $300 – and that’s before you calculate income taxes.

There are lots of ways around income taxes, many of which can be your best friends whether you’re conventionally employed or not.  But the only way around payroll taxes (other than making less than $300 per year, which good luck with that if you actually live on your own income) are business expenses.

Freelancing: The Thing You Never Thought Would Teach You Tax Law.

4.  PRO: Work flow.  CON: Cash flow.

Bee flow.

One of the worst things about my early years of conventional employment was knowing that, if the economy lost speed and work dried up, I was out the door – and there was nothing I could do to control it.

Consequently, the fact that available work depends solely on me is one of my most favorite parts of freelancing.  It’s not for everybody; ensuring constant work is available means being willing to do constant marketing, from sending resumes in response to blind ads on Craigslist to cold-calling. If you really, really hate the job-search part of working, you’re not going to like this part of freelancing one bit.  But if you see the job search as an exciting adventure where something new and fun is around every corner (like I do), you’re going to love it.

But then there’s cash flow.

The down side to freelancing is that you don’t get a steady paycheck. You get paid when the work is finished.  If you’re a subcontractor (as I am for one client), you get paid when your client’s client pays them – which, if you’ve done a major project for them, you may be waiting months for a check that represents a substantial part of your personal budget.

This is the reality of cash flow as a freelancer: you get paid when your client processes your invoice and sends you a check.  Some clients are super-prompt about this; some are lazy about it; some are stuck paying according to their own clients’ billing; some will try to avoid paying you at all.  Meanwhile, you get to juggle your own bills, and that’s entirely on you.

5.  PRO: I get to tell people I’m a writer.  CON: It’s not as glamorous as it sounds.

This is one of the major hurdles of life as a writer.

Actually, it’s not glamorous at all; I sit at my desk for as many hours as it takes to get the job done, whether I can resist looking at photos of baby sloths cuddling stuffed giraffes or not.  Most of what I write to pay the bills is here-today-gone-tomorrow stuff; the things I write that have a chance in cold hell of surviving my own death (mostly fiction) are done on my own time, just like they were when I 8-to-5-ed.  Marge Piercy’s advice holds true whether you write for a living or write for yourself.


*I’m one of those despised “morning people,” so I really do still start work at 8:00 a.m.  Your sleep cycle may vary.


74 thoughts on “Pros and Cons of Freelancing: The Three-Year Stretch

  1. I am not sure if I happy you wrote this or sent me into depression. 🙂 Seriously, this is a good wake-up call to those that assume a freelance writer is traveling the rivers of the world with a laptop astride their thighs. I have been at this in a full time capacity for a year now, after a retailer decided my age (51) did not fit their youth perspective for employees. I find I am pro-ing and con-ing this career choice quite a bit, but can say i am glad to be here doing it.

  2. Hahaha. Pros: Dogs. Cons: Dogs.
    I just started freelancing as well and am loving it. I did spend a few years working up contracts that became my 5-7 PM job, but would definitely recommend that path to people interested in the field as I now feel a lot more comfortable hitting bills every month and the yucky selling part was stretched over a longer period of time.
    Oh my gosh, taxes and controlling my own time are definitely the suck. Will definitely need to learn your tricks for business expenses.

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