Freelance Writing Rules (and Why You Should Break Them)

By Jennifer Mattern

Once upon a time, I was newly self-employed and living much too close to my mother. (In my defense, she moved near me, not the other way around – into my apartment building, I kid you not.) There was no avoiding her.

Every time she visited, without fail, she plopped a newspaper on my dining table – just the classifieds, sometimes with jobs circled. But these jobs were basic admin jobs – secretarial work, data entry, bookkeeping.

Not one of them was ever related to my actual industry (Public Relations), or interests for that matter.

She meant well. The start-up phase wasn’t easy. I’d also just split from my then-fiancé and was supporting myself solo for the first time since leaving school. The expenses covered by two people suddenly fell solely on me.

Mom was worried a fledgling business would never take off. She wanted me to have stability. Being an entrepreneur would never give me that in her mind.

You see, I wasn’t following “the rules.”

According to my mother, there were certain rules people were supposed to follow:

  • You find a stable full-time job and dabble in other interests on the side. Creative pursuits weren’t careers.
  • You keep your head down and never complain or speak out against anything that could make waves. Doing so might mean losing a job, being blackballed in your industry altogether, and / or never landing a husband.
  • You remain loyal to your employer so they’ll be loyal to you in return and you can spend your life with the same company.

Have you stopped laughing yet?

By my early 20s, this just wasn’t how the world worked anymore.

In college, they taught us to be prepared to change employers every 3-4 years and to be prepared to change careers once or twice during our lifetimes. Employers weren’t loyal to employees anymore, routinely laying off long-time employees to hire younger, cheaper talent. And as for keeping my mouth shut, you’d think she would have known me better by then. While I was generally a shy, quiet kid, nothing was going to shut me up when principles were involved – potential employers and husbands be damned.

So I broke my mom’s “rules.” Eventually she got used to the idea (when she, quite literally, saw the money I was making). And things turned out okay.

Sometimes you have to do that, especially in business. You have to break the rules. Would I have had stability in some low-to-moderately paying office job? Sure. Would I have been happy? Not a chance.

I see this in the freelance writing world all the time too. People constantly tell new writers what “rules” they have to follow if they want to succeed. Most are bullshit.

If you want to land freelance writing clients, you have to send queries regularly.”

I haven’t sent a query out of necessity in over a decade. I put myself in a position where clients come to me.

“You have to be willing to talk to clients on the phone or make cold calls.”

I’m great at landing deals on the phone. Almost never fails. But I enjoy taking client calls about as much as I enjoyed having a root canal. So I almost never do anymore. And guess what. When I stopped giving out my phone number years ago, it had no negative effect on my business, though it did stop middle-of-the-night calls from overseas clients.

“If you want to focus and be productive, you have to get dressed every morning as if you were going into someone else’s office.”

I’m sitting here in the most comfortable pair of flannel pajama pants in the world, and you’d have to pry them from my cold dead hands before I’d put on “real clothes.” This is my standard work uniform. My absolute best work tends to come in PJs, a warm robe, fuzzy slippers, and fingerless gloves before dawn on a freezing cold winter morning. I’d probably work naked all summer if I didn’t feel like the pets were giving me funny looks.

“You have to work on a regular schedule if you want to get anything done.”

My “regular” schedule means getting up at 4 a.m. and starting work by 5 a.m. Today, I woke up at 12:30 a.m. and started work at 1 a.m. I’ll be finished work by 8 a.m., and I’m kind of cool with that.

I go through phases where I’m good about sticking to my schedule. I go back to it when I feel off-course and need a reset of sorts. But beyond that, I’ll work overnight if I can’t sleep to get things finished early, will sleep in when I need to for my health or sanity’s sake, and will take personal days as I see fit as long as I don’t screw with a client’s deadline. I used to feel guilty about this. But over the years I’ve learned how to make it work for me to get more done when I need and want to.

That’s really the key. Success in business doesn’t involve following someone else’s rules. You can learn from what works for others, but ultimately you have to come up with a strategy and system that works for you.

Yet I frequently see freelancers looking for someone to hand them a playbook… to tell them what to do. But unless you happen across a fellow writer who’s exactly like you, with the same type of specialty, and the same type of clients, that simply won’t work.

Instead, try this:

  • Yes, read up on how other freelancers handle something – schedules, productivity tips, marketing, dealing with client relationships, or whatever you’re unsure of. But get more than one take.
  • Try different tools, tactics, and methods to see which suits you and which works in your market.
  • Put together a customized plan that works for you. And keep testing and tweaking things as you go until you’re reaching your goals and doing so in a way that makes you comfortable and happy.

Following someone else’s game plan isn’t a recipe for success. Not for your business, which is different from theirs. The sooner you understand and accept that, the sooner you’ll figure out what works for you.

And when you do come across “rules” from a coach or colleague, remember to ask “why?”

Don’t do anything just because someone else tells you to. Ask why they’re giving that advice or why they’re touting some rule. Why is this better than something else? Why can’t you do X instead of Y? What are the risks and rewards… the pros and cons? Why should you do what they suggest?

I had a teacher who used to tease me about this frequently. I was the first female student he’d ever taught (it was an automotive course). He was used to telling the guys to do something and how to do it, and they’d simply do as instructed. I was different. I would always ask “why?” Thankfully he was good sport about it.

At one point I was working on an engine and a design choice seemed incredibly stupid to me from a repair perspective. So I asked why it would be designed like that. The teacher had no answer to any of my objections over why this little part was chosen (a type of nut that didn’t make much sense where it was located). His basic answer was, “that’s just the way it is; do the work.”

I did the work. But I still raised a bit of a stink over it. What can I say? I like things to make sense.

He finally asked if I had a better idea. I did. So he started letting me visit the machine shop every week to design and create a new piece just to see if I could. And I did. I came up with the design, learned how to program the CNC machine in the shop, and created a custom replacement piece. That project is what convinced me to study engineering for a couple of years.

And that’s my approach to most things. I physically build and rig up custom solutions to problems when I need to. And I’ve taken that attitude into business as well. I’ll listen to your arguments if you have a good one. I’ll follow your rules if they make sense and I can’t come up with something better. But if I find a flaw, I’m going to fix it. If I come up with another option I think will work better, I’m going to try it.

The next time you find yourself looking for someone else to hand you all the answers or rules to follow, try that. Hear them out. But then see if you can come up with something better. Don’t blindly follow someone’s advice or try to mimic their strategy thinking it’ll bring you identical success.

Break the rules. Or better yet, make your own.

I’ll be filling in again for Lori once or twice more this week. If you have questions you’d like me to answer or something specific you’d like to see here this week, let me know in the comments.


Jenn Mattern is a freelance business writer and blogger with 18 years’ experience. Visit Jenn’s All Freelance Writing, where she’s spent 10 years offering advice, job leads, free tools, and more to help new freelance writers build successful and sustainable businesses.

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  • Cathy Miller September 5, 2017 at 9:06 am

    This is why your blog so appealed to me when I first started freelancing, Jenn. I listened much too long to those “rules” until I finally began freelancing. In the short time I have done that; however, I’ve seen my attitude evolve to listen to my own rules and be happier for it. My only regret is I didn’t do it sooner.

    • Jennifer Mattern September 5, 2017 at 9:32 am

      I certainly won’t claim to be innocent here. I try to push things more in the sense of “hey… this had a huge affect on my business, and I really really really think you should give it a fair shot to see if it helps you too.” But I’ve drawn harder lines on things myself — like working for site with long histories of exploiting writers or the importance of specializing, even if it’s not as strict as some writers think that has to be. But like you say, things evolve. And my aim has always been to share how my own business evolves and let it be one example to learn from — though hopefully no one’s only. I’m glad freelancing’s made you happier Cathy. Any particular self-rules you can share to show how things have changed for you? Might help newer folks. 🙂

      • Cathy Miller September 5, 2017 at 11:40 am

        I could write you a guest post on that. How’s that for suspense? 😀

      • Jennifer Mattern September 5, 2017 at 1:16 pm

        So… that last comment was me. I was still logged into the site as Lori from posting earlier, so it posted the comment as her. Fixed the name, but apparently I’ll still have Lori’s face at least awhile until Gravatars update. lol

        • Cathy Miller September 5, 2017 at 3:54 pm

          LOL! A new kind of anonymous stalking. 🙂

  • Paula Hendrickson September 5, 2017 at 12:00 pm

    When I got to the but where you cited your mother’s rules and saw “…never complain or speak out…” I actually laughed.

    I’m much the same. I’m generally quiet, but not afraid to speak out as needed. I also ask a LOT of questions. I guess I’ve never been satisfied by the “because that’s how it’s always been done” explanation. More than once as a kid I’d respond to that with, “But it’s STUPID!”

    Maybe my main rule is that there are no real rules. Just guidelines—some which will work for you while others won’t. But you know there’s someone out there asking, “But why NOT?”

    In my family there’s a response for any “why” without an answer: Because B. I have no idea how or why it originated, or what it’s even supposed to mean. It’s just our way of saying there is no real answer.

    • Jennifer Mattern September 5, 2017 at 1:30 pm

      Same here. I pretty much trust no one simply on their say-so. If you state something as fact without any explanation or proof, my mind immediately pokes holes in whatever you’ve said or goes into “devil’s advocate” mode. If they can’t justify what they’re saying is absolutely necessary, I’m unlikely to take that person at their word.

      I find asking a lot of questions is something I do even more on the personal side now than when I was younger. I catch myself using it whenever people say, do, or believe something truly stupid (like making a racist or sexist remark). I ask questions to force them to think about it objectively — partially for their benefit, but partially because it helps me see if they’ve truly thought through the things they act on or if they’re just parroting bullshit they’ve been trained to say or believe. It tells me a lot about people. And that’s something I wish freelancers would do more on the professional front. Critical thinking skills are a lost art.

      “Because B?” That’s interesting! I don’t think we ever got more growing up than the good old “because I said so.”

      • Paula Hendrickson September 7, 2017 at 9:46 am

        My questioning authority was obvious when I was about 10. A friend invited me to a “swimming party” at her church. It was winter, so it was a novelty. I have no idea where the church was, but a group of kids were in a bus, after dark, singing hymns, some of which I didn’t know. When we arrived at the church, we were escorted into a side office, where we stood as the fire and brimstone preacher telling us we needed to be “saved.” Yeah, right, buddy. I was raised Lutheran, and they encourage questions. So I asked questions. I asked a LOT of questions. So many that he and a woman ushered me into an even smaller office and started pressuring me to shut up. I remember him asking me if I loved my siblings and parents – saying if I were saved I could “save” them, too. Otherwise we’d never get to Heaven. (He used far coarser language, when you consider he was addressing a child. He also didn’t know my my was dying.) I felt like a hostage. I prayed silently so God would know I was only playing along with these idiots so I could get away. Then he proudly trotted us out before a packed congregation (and it wasn’t even Sunday), showing them all the souls he “saved.” It backfired. As soon as I got home I burst into tears, told my mom everything. She called my friend’s mom. Their family left that church and joined ours. That experience proved to me why it’s so vital to ask questions so I can determine if that person can be believed.

        And re: “Because B” and “because I said so,” my dad had three brothers. They always said that between them they knew everything in the world. Uncle Wilbur died really young—none of us met ever got to meet him. So when we had a family event and I asked my dad something he couldn’t answer (or pretended he couldn’t), he sent me to Uncle Les, who sent me to Uncle Gale, who’d usually say, “Oh. Wilbur knew that one.”

        • Jennifer Mattern September 7, 2017 at 9:18 pm

          Oh wow Paula. What an awful thing to do to children. But I suppose sometimes it’s the bad behavior that tells us the most about people, and it’s good your friend’s family found out if they weren’t aware before.

          And that thing with your dad and his brothers is adorable. 🙂

  • Lori September 5, 2017 at 12:10 pm

    Hi guys,

    Thank you, Jenn for taking care of the blog as I deal with my dad’s health issues.

    I should be back to blogging by Monday. It’s wonderful to have great friends like Jenn who volunteer to help a writer in need. 🙂

    • Jennifer Mattern September 5, 2017 at 1:17 pm

      You’re quite welcome. One more from me, and we have one coming from Cathy too. You take whatever time you need, and if you help beyond this week, just say so. 🙂

  • Jake Poinier September 7, 2017 at 3:38 pm

    Funny, accurate, insightful…pure Jenn Mattern! My dad was a self-employed salesman for most of his life, so I witnessed a ton of rule breaking and bullheaded independence growing up. But I also saw a guy who busted his ass and prided himself on being positive, optimistic, gregarious, and focused on relationships. I can only hope I’m setting as good an example for my kids.

    • Jennifer Mattern September 7, 2017 at 9:10 pm

      Thanks Jake. Your dad sounds like a heck of a guy, and a great role model. 🙂

      It’s interesting that you brought up the family connection with self-employment. It makes me wonder if that’s a part of the pushback I got from my mother early on. Her father was an electrician who owned his own shop. I always saw his entrepreneurship as something that’s just kind of in the blood… I come from a long line of risk-takers, and he was just one of the more recent examples. I always respected that about him. But it can be a tough industry, especially in NYC. So I’m betting she saw a lot of ups and downs over the years. An uncle took over that business later, and I know he faced similar at times. Obviously it’s not the same as writing, but that could be a part of why she was so nervous about the stability of it all. Interesting food for thought!

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