Why work freelance?

By Caitlin Kelly

Here’s a powerful reminder that some jobs scar us for years, written by an HR expert I really admire and follow on Twitter, Katrina Kibben:

Trauma is the only way to describe what happens when managers go out of their way to demean and shrink their team’s confidence. Nothing is the same. The safety humans need to thrive, especially at work, is gone. Three years into owning my own company, those bad managers still influence how I lead my team every minute. I go to extremes to make sure I’m never like those bad bosses.

I will spend hours writing and rewriting a coaching email to ensure that people know I see them. Why? Those moments when someone you admire makes you feel small are seconds you never forget. When the shame happens on a daily cycle, it’s a whole new world of mind games. I can’t do that to people.

I know first-hand that the mind games don’t end because you quit your job either. After I walked away from my worst managers, I caught myself questioning the intentions of everyone with feedback. Let me tell you – that is not a good way to live your life. I still get coaching on feedback to make sure I deliver and receive it with empathy.

I’ve been doing Zoom sessions with American high school journalism students and really enjoying it — so far, with Florida, Michigan, Ohio, California and with Texas and Pennsylvania ahead.

One of the questions — why freelance?

What are its advantages?

My first reply?

Intellectual freedom!

I enjoyed aspects of my three staff newspaper jobs — at the Globe & Mail (Canada’s national newspaper), the Montreal Gazette and the New York Daily News.

But each job carried some truly heinous challenges as well: cut-throat internal gossip and competition, stupid or lazy or rote-minded management, sexism.

I loved breaking stories (i.e. getting them ahead of all my ferocious competitors).

I loved the crazy adrenaline rush of reporting and writing on deadline.

I loved learning so many new things and having tremendous experiences — from meeting Queen Elizabeth to visiting a rural Quebec commune to flying into an Arctic village of 500 people.

I loved knowing that my work was being read by so many people and could, occasionally, prove helpful to them.

The Daily News job, as Katrina writes, was the last straw for me. I won’t bore you with all the details but here’s one — I started in June and by late September my direct boss stopped speaking to me. He never again spoke to me until I was laid off about a year later.

As the unofficial company motto said — Sink or Swim!

So I’ve since stayed freelance, which is basically intellectual piecework. We joke that we eat only what we kill — i.e. no paycheck or pension or paid sick days or paid vacation.

Holidays? Hah! Only when we can afford the time and cost of using them.

But it also has freed me from working with and for bullies and brutes, a huge advantage for me.

I’ve also found a few communities of fellow independents on Twitter and participate in weekly Twitterchats, like #remotechat (Wednesdays, 1pm EDT) and #FreelanceChat (Thursdays, at noon EDT.)

The range of people on them is terrific — with people arriving from across the U.S., Canada and Europe. It makes us feel less lonely!

I also really enjoy the wild variety of my work.

In the past year, I’ve written on:

— STEM education (for an engineering magazine)

— pancreatic cancer research (for the Lustgarten Foundation)

— A Finnish energy executive (Neste)

— Why some long-resident foreigners in the U.S. choose not to become citizens (The Conversationalist)

All of these are on my website.

Working on your own — as so many are now doing because of the pandemic — is challenging, and next to impossible for women trying to manage multiple small children (800,000 have left the American workforce!)

It means being super-focused and self-disciplined, and not having an office with an appropriate chair, desk or lighting. (I write on a laptop on our dining table.)

It can also mean working to others’ needs and schedules — not, as some fantasize, sleeping til noon. My husband, a freelance photographer and photo editor, works freelance and his hours can start at 6:00 a.m. and sometimes go until 2:00 a.m.

But we enjoy it.

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.

BUSINESS OF FREELANCING

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?