Break The (Idiot) Rules!

Why the Old Rules Often Fail Modern Freelancers

For most people starting out in writing, the first thing they hear is a litany of do‑or‑don’t statements. They come in the shape of checklists, rulebooks, or those endless “how to” blogs that say you must submit only one piece at a time, always use a stamped addressed envelope, and never call your editor because they’re busy. Those rules sit on a pedestal, made to look like hard truths, while the writers who succeed in the marketplace seem to ignore them entirely. The reason is simple: the rules were born in a very different era. Publishing used to happen through snail mail, through a small network of editors, and through the slow, linear rhythm of print. Today, the world of content is fluid, digital, and driven by speed. If you’re a writer who wants to make a living from your craft, you need to evaluate every rule you’re told and decide if it still applies.

Consider the most famous rule: “Always include a stamped addressed envelope with your query letter.” The image of a neatly folded envelope sitting next to a manuscript is familiar from countless student workshops. It’s meant to signal professionalism and respect for the editor’s time. However, the majority of freelance writers who have been in the game for more than a decade, and many who are just starting, have never sent an SAE. They’ve never been penalised for it. Editors, when they review a query, are usually evaluating the writing and the proposal itself, not the envelope that arrives in the post office. If a query is compelling, editors will respond, regardless of whether an envelope was used.

Another rule that still feels like a relic is “No simultaneous submissions.” Many writers are told that sending the same piece to several editors or magazines at once is unprofessional. The logic behind it is that the writer is forcing an editor into a corner, creating a conflict of interest. But when you’re a freelancer, you have no single contract that ties you down until a publisher accepts your piece. You are free to offer your work to any outlet that would be interested. In practice, the most successful writers often submit the same pitch to a handful of publications, then follow up with each one, because that’s the most efficient way to land multiple gigs. An editor who is genuinely interested will reach out quickly – within a day or two, or even hours if the piece is a perfect fit. The “no simultaneous submissions” rule may hold weight in traditional publishing contracts, but it does not dictate how you approach the market as an independent writer.

In the same vein, there are rules about contract terms, about limiting query length to one page, about never calling an editor because “they’re busy.” Each of these guidelines is a suggestion, not a mandate. They were designed to protect aspiring writers from being taken advantage of. But they also create a culture of fear and hesitation. The writers who thrive are not the ones who cling to every rule; they are the ones who test the rules, ask questions, and adapt their process to what makes sense for their goals.

The industry’s gatekeepers – editors, literary agents, and publishers – do not operate on a one‑size‑fits‑all rule set. They look for quality, relevance, and a fit with their audience. They will say “no” to a piece that is well‑written but doesn’t match their needs. If you can demonstrate that you understand their market and can deliver what they want, you can negotiate the terms of your engagement. That flexibility is what makes freelance writing a viable career for anyone willing to think beyond the box.

Those who refuse to question the status quo often end up following a path that was designed for a different market. By learning to spot which rules have become outdated, writers can free themselves to focus on what truly matters: producing great content, building relationships, and building a brand. This mindset shift is the first step toward breaking the so‑called “idiot rules.”

To help you stay ahead of the curve, the book Renegade Writers: A Totally Unconventional Guide to Freelance Writing Success by Linda Formichelli and Diana Burrell dives deep into the real tactics that writers use today. It’s not about following every rule on the rulebook; it’s about figuring out what works for you and ignoring the rest. If you’re interested in seeing how the book was made and getting more freelance tips, you can join the Renegade Writers mailing list, which shares a behind‑the‑scenes look at the process.

Spotting Idiot Rules and Turning Them into Opportunities

Every writer encounters a set of guidelines that seems logical at first glance. The trick is to test the validity of each rule in the context of your own work. Below are a few common rules, and a framework for deciding whether they’re worth keeping or discarding.

Rule: Never submit the same pitch to more than one editor. Think about your end goal. If your aim is to get published in a magazine that pays the highest rate, you might want to target only that outlet. But if you’re looking for exposure or to build a portfolio, sending the same pitch to several outlets can amplify your chances. In many cases, the best approach is to create a core set of outlets that align with your niche and then tailor your pitch for each one. The rule itself is less useful than the insight that you can be strategic about where you pitch.

Rule: A query letter must be exactly one page. While brevity is valuable, a one‑page limit is arbitrary. Editors appreciate concise proposals, but if you have a unique angle or a complex project, you might need more space to explain why it matters. The real rule here is: keep it focused and relevant. If you can fit your pitch in one page, great. If you need more than one page to capture the editor’s interest, write the additional pages, but make sure every line adds value.

Rule: Never use email to contact an editor; always call. Many editors prefer email because it allows them to review your pitch at their convenience. Calls can be intrusive and might come at a bad time. Instead, use email to establish a clear and professional dialogue, and follow up with a call only if the editor asks for one. By respecting the editor’s communication preference, you’re more likely to build a positive relationship.

When evaluating a rule, ask yourself three questions:

1. Does the rule solve a real problem I’m facing?
2. What is the risk if I ignore the rule?
3. What advantage do I gain by ignoring or adapting the rule?

   If the answer to the first question is “yes,” but the second is “minor,” and the third is “significant,” the rule is a candidate for adjustment. For example, the SAE rule solves the problem of an editor needing a physical proof of your intent. However, the risk of ignoring it is minimal in most cases, while the advantage - speed, cost savings, and the ability to keep a lean workflow - makes it worthwhile.

   Another way to spot an idiot rule is by looking at the source. Rules that come from outdated training programs, old print guides, or the collective memory of a pre‑digital era are less likely to hold. On the other hand, guidelines that come from current industry leaders, successful freelancers, or real‑world experience are more trustworthy. The authors of Renegade Writers spent years in the field and drew from their own successes and failures to write a manual that reflects today’s realities.

   To put these ideas into practice, start by compiling a list of the rules you’ve been taught. Mark each one with a thumbs‑up if it still makes sense, or a thumbs‑down if you see an opportunity to do better. Then experiment. Send a query letter without an SAE and track the response. Pitch the same piece to two outlets and see how each reacts. Over time, you’ll notice patterns. Some rules will stand the test of time; others will reveal themselves as hindrances rather than helpers.

   It’s also useful to stay connected with other writers and creatives. Online forums, local writing groups, or social media communities can be goldmines of real‑world advice. Hearing how others have successfully navigated the same rules can inspire you to test them yourself.

   Ultimately, the most valuable rule you can follow is this: treat every rule as a hypothesis. Gather evidence, analyze outcomes, and adjust your strategy accordingly. By doing so, you’ll keep your freelance practice agile, responsive, and ultimately more profitable. Remember that the goal of writing is to communicate, not to comply with a checklist. When the rules conflict with your creative process or business goals, it’s time to question them and choose a path that works for you. After all, you’re not an idiot for thinking that the market and the writer’s craft deserve a fresh, modern approach.