Meet Josh Weiss Who is Killing it Freelance Writing

If you have ever wondered how to start a freelance writing career or have considered doing some freelance writing on the side then you will want to read today's, Success Story. Josh Weiss turned his love of sci-fi and pop culture into a full-time gig of freelance writing. In this interview Josh shares, some of his tips and best practices.

Freelance writer

About Josh Weiss

Weiss is a lover of all things pop culture and writes about movies, TV, comic books, and more for places like SYFY WIRE, The Hollywood Reporter, Forbes, and Marvel. Having gone to school for Public Relations at Drexel University in Philadelphia, he did a short stint in news production in New York City before he went into freelancing full time.

On that note, he still can’t believe he gets to geek out for a living. When not writing, Josh can be found curled up with a good piece of fiction or collecting vintage movie posters, vinyl records, and graphic t-shirts—don’t judge! He’s also working on a murder mystery novel set in the late ‘50s and promises he’ll eventually learn to play the ukulele currently sitting on the top shelf of his bedroom closet.

My questions are in bold, Josh's follow in plain text.

Josh Weiss on Freelance Writing 

What is a freelance writer, exactly?

 Sorry in advance for anyone who doesn’t watch Game of Thrones, but I’m like Daario Naharis and the Second Sons. In essence, I’m a mercenary-for-hire, but instead of killing people for money, I write stuff. My apologies if you were hoping that “freelance writer” was code for “globe-trotting assassin.”

However, my job title is kind of mercurial and fluid, able to take on several different definitions. That’s because the content of my pieces can span several formats: straight-up news coverage, opinion-based editorials, or elongated feature-style deep dive analysis/interviews.

To get more specific, the word “freelance” simply means that I’m not tied down to one company or brand and, therefore, I can write about a variety of subjects. To boil it down even further, I work for myself as a private contractor, taking on all kinds of writing jobs from several companies, outlets, brands, and, in some cases, individuals. If you need something written or edited, just hit me up at The rates are so low; I’m pretty much giving my services away!

Do you have any tips on how to become a freelance writer?

Before we get to the tips, I should preface my answer with the fact that freelance writing is a gig I sort of fell into from a mix of experience and sheer luck. Emphasis on the second part. I never planned on being a freelance writer and while putting words on a page is something I love most in this world, I didn’t think writers could make a livable wage. In time, I came to learn that that notion wasn’t necessarily true.

If you want to become a freelance writer, you need to show that you know how to write. Surprising, right? Seriously, though, you need clips, as many as you can get. Like I said earlier, you should strive to cover a range of topics to show that you’re versatile, but if you’re interested in something like entertainment, then you need to build up a base of entertainment-based clips. That goes for any area that grabs your fancy.

Ok, so you already have clips and just don’t know how to break into the business? Head on down to the next question for my answer.

How do you find freelance writing jobs?

 It depends. A lot of it has to do with luck and connections—at least it did in my case. The adage of “it’s not what you know, it’s who you know” is 100% true and don’t let anyone ever tell ya different, kid. Of course, you shouldn’t let that deter you from following your dreams. Knowing someone high up definitely helps, but it’s not the be-all-end-all of any professional setting.

When it comes to my journey of becoming a full-time writer, a college friend of mine (hola, Peter) put me in touch with the right person who not only decided to take a chance on me, but eventually passed my name to the editor of another outlet. That was pretty much the start of my freelancing career. Before that time arrived, however, I’d already been writing up weekly pieces for a company at which I’d once interned and fostered a positive relationship with my old boss.

But that’s just me. I worked hard up until that point and then it was just a matter of connecting the circuits for the right people to take notice.

As I said, you don’t need connections. You can always “cold call” your favorite outlets via email and inquire if they have any freelance opportunities available. I’ve done it before with highly favorable results. Just be sure to highlight your areas of expertise, what you can bring to the table. Look up editors on LinkedIn and ask there. If they respond (many times they won’t, but that shouldn't put you down—keep the hustle alive!), they may ask for clips. Pick your favorite pieces and send them over. If they like what they see, then your prospects at a freelance gig are looking very good.

Nowadays, it seems that the bulk of writing jobs are freelance, so there’s no shortage of actual freelancers to reach out to on social media if you have questions. And while we’re at it, you can, often, be a freelancer while still maintaining a full-time office job. Just make sure there’s no conflict of interest. You don’t have to give up those sweet, sweet benefits to become a writer. Some people treat it as a part-time hobby, and that’s totally and unabashedly ok!

Any tips for meeting your writing deadlines?

 I believe I said this earlier, but it bears repeating: Write everything down and organize it. You don’t need anything fancy to keep track of who wants what and when. I use the Notes app on my cellphone, which is synced with my laptop. Each outlet I write for gets its own heading, and below that, my assignments are organized chronologically.

If you prefer the ol’ pen & paper, there’s nothing wrong with getting a day planner and scribbling down your projects and their deadlines. Technology is fallible, so relying on the “old ways” of doing things is never a bad idea, especially when Skynet takes over and we’re all hurled back into the Stone Age.

What have you learned from freelance writing successfully?

It’s a bit of a cliché to say so at this point, but you just have to hustle your butt off every single day. You’ve gotta be like Jim Carrey in that movie from 2008 in which he just says “YES!” to everything, no matter how crazy the propositions may be. I may be a self-professed pop culture expert, but over the years, I’ve agreed to write pieces about things I had very little knowledge about beforehand like the stock market, missing person cases, criminal trials, reducing a business’s carbon footprint, and even pharmaceuticals.

True, it was hard at first, but you don’t want to limit yourself and make your talents so specialized, that job prospects suddenly become shorn down to a small pool of options. The more you say “YES!”, the more you learn and the more hard evidence you have to show how versatile you can be later on. Versatility has value. And in the words of Bigweld (he’s a meme now, don’t you know): “See a need, fill a need.”

Oh, also get yourself a good accountant and/or money manager. I’m incredibly lucky enough to have my mother who, in addition to raising me, is also a knowledgeable and wise CPA. She’s the one who takes care of my finances, squirreling away money for investments and retirement and what have you.

I may be a good writer, but numbers, equations, and all that stuff stops me dead in my tracks. If your parent isn’t an accountant, that’s ok. Just hire one you trust and, if you’re bad at math like me, don’t be afraid to let them hold your hand through it all. It’s either that or the feds arrest you for tax evasion. That’s what got Al Capone in the end—don’t be like Al Capone.

Is there a mistake you have made starting out that you wish you could change?

Yeah…I took on a lot more than I could handle. The old expression of biting off more than you can chew is very, very true, people. When I first decided to freelance full-time, I wasn’t totally prepared for the implications of working for myself. Sure, there was no manager breathing down my neck, but I still had deadlines to hit, and if I didn’t, people would get upset at me, and understandably so.

You can work in your pajamas and sip coffee from your favorite Stranger Things mug (guilty as charged), but it’s not like staying home from school when you’re sick. The traditional office structure isn’t there, so you have to make it up as you go along.

There’s also some give-and-take because I had to make the hard decision of giving up certain writing duties that brought in extra income. Look, we’re not superheroes; if you’re feeling overwhelmed, admit that you’re beat and throw in the towel with dignity. Don’t draw things out and make people increasingly more angry, tarnishing your own reputation for dependability in the process. In the long run, I’m glad about my decision to give up that other job because it freed up my mind to focus on other, more important projects.

To remedy an already overloaded workload, you just have to keep an organized list of what needs to be done. I don’t care how good your memory is, always ALWAYS (can’t stress that enough) write down what projects you have to finish and their due dates.

What advice would you give someone starting as a freelance writer?

Aside from being a “Yes Person,” you need to be proactive in seeking out the opportunities that interest you, even if you’re not sure how they’ll advance your career prospects. Let’s say you’re starting college, then I’m telling you now, you NEED to join some kind of extracurricular club, group, or organization. And don’t just throw some darts at a list of possible names; find one that appeals to you and your passions.

For me, that was the school newspaper. Throughout my college career, I wrote 100 movie reviews, which may not seem like a lot for an industry veteran, but you try writing that many articles while taking classes and working internships. It ain’t easy. And you know what? I don’t regret it for one second; getting to write for the paper gave me some of my best college experiences: early movie screenings, meeting celebrities, and a conference call with Steven freakin’ Spielberg!

But if you’re not a writer, the newspaper may not be for you. If you’re an Accounting major, join the Accounting Club. If you fancy yourself a political type, join the student government. Are you picking up what I’m laying down?

If you’re out of college already and you weren’t part of some club, I won’t say you’re up sh**’s creek without a paddle, but it is harder, particularly if you want to go into writing or something similar. You need to have clips and examples of past experience. Think of it as a corollary to your resume or CV.

Professionally what are you most proud of?

It’s kind of obscure, but I recently did an entire oral history piece on a little animated movie from 1993 called We’re Back! A Dinosaur’s Story. While overshadowed by Jurassic Park, which came out the same year, We’re Back! was also produced by Spielberg. It’s one of my favorite movies ever, so it was just really fun and satisfying getting to talk to some of the folks who were responsible for making it.

I do wish there was a book deal mixed in here somewhere. I’ll talk more about that later, but it was always an ambition of mine to write a novel, and after more than 400 pages, I finally accomplished it. A lot of people always say they’re going to write a book and never do, so I’m proud that I was able to fall into the group that follows through on what they say.

Is there something you learned freelancing that you found surprising?

For sure. Since I’m a freelancer who works from home, many people don’t understand how I get assignments. Not that I blame them, because that process varies from outlet-to-outlet.

In some cases, I work a predetermined shift where I’m on call (much like a doctor—not that my work is nearly as important as an MD’s) to cover breaking stories sent to me by my editors. At the same time, I’m also on the lookout for interesting stories to cover and running them by my editors. In other cases, the onus is completely on me to pitch ideas to an editor who can either accept or veto it. If they accept the pitch, I write it up immediately or agree on a deadline with them. In other cases still, I can write pretty much whatever I want and publish it myself.

So there you go—that’s a short rundown of how I make my living as a freelance writer.

Also, if you plan on going into freelance writing, just be aware that you most likely won’t be taxed when a client pays you. That’s fine, but it brings us back to hiring a dependable money manager. Almost immediately, my mother began helping me make quarterly tax payments to the government, so I wouldn’t have to empty half of my bank account during tax season.

Can you recommend a book to help people be more successful?

I’m not a big fan of non-fiction or self-help books, but that’s just me. If you’re into that, godspeed and enjoy—you won’t hear a word against it from me. I read a lot of fiction or books about the making of fiction.

So, sadly, I’m not the best person to recommend books on success, but as a general rule, I always tell people to read and to read often. If you want to be a writer or just improve your writing, you need to crack open a book every once in a while, even if it’s a comic book. I consider myself a professional scribe, but I’m always learning new words and modes of writing. Never assume you know everything about your field; you can learn new things until your dying day.

Right now, I’m in the middle of Stephen King’s The Stand and reading my way through all of the Hellboy collections from Dark Horse as a primer for the new movie in April. Whatever Bill Maher might say, comic books and graphic novels are literature, so don’t be ashamed to admit your affinity for them!

 Social Media and Success

Has Social Media Factored into your success?

Oh, for sure. Twitter is where plenty of reps and publicists first get in touch with me about covering possible stories. Social media (mainly Twitter) has led to some very valuable professional connections in just the last year or so, even if I don’t get too many likes or retweets on what I post. That’s a shameless plug to go like and retweet my stuff, by the way: @JoshuaHWeiss.

I remember when my dad first told me about Twitter way back when and I  laughed it off. Now, it’s one of my main social media platforms, and between you and me, I spend too much time on it; just ask my girlfriend. It may be kinda shallow to say, but getting verified was one of the proudest moments of my life.

Anyway, social media is a way for the world to see what I’ve created and if I’m lucky, a celeb or two will share or quote my content.

As for a strategy or tips, I don’t have any. I post what I want, when I want, capiche?

In all seriousness, I have dabbled in social media optics and traffic over the years, but never truly got the hang of it. There are optimum times to post and all that, but I don’t bother myself with it. If you do plan to become some kind of entertainment writer or journalist, acquaint yourself with SEO.

Any mistakes you see people routinely make with social media?

I wouldn’t call it a mistake, and I would never dictate what people should post on social media (first Amendment, y’all!), but I cannot stand negativity, whether it’s over politics or pop culture.

I consider social media a fun place where we can come together and share fun stories and hilarious memes. I may sound like a utopian cult leader from the 1960s, but it gives us the chance to become connected like never before. I’m a man of simple tastes, what can I say? The vitriol sometimes espoused by others on places like Twitter and Facebook just seems counterproductive and depressing to me.

Of course, everyone is entitled to their opinions, and this is not me standing on a soapbox telling people how to live your lives, but I just don’t get the anger and insults hurled back and forth like we’re living in The Butter Battle Book.

Josh Weiss on Productivity and Time Management

Do have any apps, books or tips that you use to be more productive?

A lot of the stuff I’m telling you has been said before, but it’s proven to work, so why reinvent the wheel, right? You need to take a mandatory breather every once in a while. If you’re a freelancer like me, you’ll feel like you’re never off the clock and in a way, that’s true. Even so, you need to give your mind a respite, or it’ll start to produce the equivalent of a steaming pile of garbage. So, take a break, have a snack, browse Instagram, or watch an episode or two of your favorite Netflix show.

Unless something needs to be posted right away (i.e., breaking news), let a minimum of 24 hours pass before you revisit a piece of writing. A good night’s rest allows you to look at a piece of prose with fresh eyes and pick out any mistakes. If you’re working in a company’s CMS and need to publish things minutes after writing it, quickly run your copy through Word first to catch errors. I learned that the hard way, but it’s an actual lifesaver.

How do you manage time?

I already said it earlier, but I’ll reiterate for those of you in the back: WRITE EVERYTHING DOWN!!! Even if you have eidetic memory like an old-fashioned bank vault in the Old West, I still want you to write every single thing on your agenda down. You don’t need a fancy Palm Pilot (remember those?) Or spiral bound after school planner (remember the free ones your teacher used to give you?).

Me? I just use the free Notes app on my phone, which is connected to my computer. Since I work for several outlets, I break things down into umbrella-like sections, which then have the assignments below. Following the name and description of each assignment, I put the due date in big bold lettering, so there’s no mistaking when anything needs to be finished and submitted.

Freelancing is a juggling act, and you never want to look up and realize a spinning chainsaw is about to fall on your head. Again (and say it with me now, folks): WRITE.IT.DOWN.

Fitness and Success

Has fitness factored into your success? 

I’m not a fan of exercise, which is not good at all. I shouldn’t even be admitting that. My younger brother is the health nut, and I’ve tried (and failed) on several occasions to hire him as my trainer a la Burgess Meredith’s Mickey in the Rocky movies.

Anyway, I guess you could say that exercise—at least in my case—comes with the territory. In my day, I’ve walked plenty of city blocks and avenues in New York City after stepping off a Bolt or Mega Bus. I’ve also had to navigate the labyrinthine layouts of convention centers and unfamiliar cities for Comic Cons and let me tell you, your feet have never felt so tired than a day after they’ve been walking the convention floor.

To get to the crux of your question, yes, fitness is extremely important to success in that you want to live long enough to see the fruits of your labor. It sucks if you make it and then drop dead of a coronary right after. That’s no fun. Take care of your body, especially if there’s a history of heart disease in your family!

Do you enjoy working out? If not, how do you get motivated?

It’s a tad embarrassing to admit, but I hate to exercise just like some people hate eating their greens. Let’s be clear, though: I’m not advocating laziness or unhealthy living habits. I’m the first to admit that I need to work out and I always push myself to put some time in on the ol’ treadmill, which is just five feet away from my usual workspace.

When I do go on the treadmill after work in the evenings, I feel like a million bucks afterward. The only problem is that it’s just so dang boring. As someone who is always checking how long they’ve been walking or running, I cover up the display screen with a cut-out piece of printer paper, so the time doesn’t crawl by at a snail’s pace.

While morbid as Hell, I just picture myself dropping dead of that aforementioned coronary at the age of 35 and I’m motivated to get off my butt and shed some calories.

What's Next

Any upcoming projects you are working on?

I’m currently trying to sell my first novel, which is an alternate history/hardboiled murder mystery set in 1950s Los Angeles at the height of the Cold War. Along the way, and without any premeditation on my part, it is also somehow into an allegory for the current political climate in America, so I think it has some nice relevant legs to stand on. I won’t give too much away in terms of plot, but it was a highly personal project and labor of love that’s been in the works since the fall of 2016.

If any publishers or literary agents reading this are interested, just hit me up. In the words of Monty Hall, “let’s make a deal.” … Please?

Do you have anything else you would like us to know about? 

Other than my book, I don’t have much to promote other than my writing services. If you need something written or edited, just let me know. I’m not too expensive yet, haha! I guess I’ll plug my entertainment blog,, where I sometimes muse about pop culture and stuff. It’s where most of my rejected ideas go, so I suggest starting your own blog to let off some creative steam every once in a while. I doubt many people read my blog, but it’s a place where I am—to quote Seinfeld—“master of my domain.”

Where can people connect with you online?

Twitter, Facebook, Instagram, LinkedIn, Email. Or, if you’re old fashioned, you can send a carrier pigeon or a candy gram.

 Motivation and Handling Rejection

What is the one thing you wish everyone knew?

Something even I have to keep reminding myself of is that rejection is normal in my field. Unfortunately, creativity is subjective, and if someone doesn’t pick up what you’re putting down (so-to-speak), it can be disheartening. If you like chocolate and someone else prefers vanilla, you’re already on an uneven playing field.

I love dissecting geek culture but creating and selling my own fiction is something I’ve always wanted to do, and so far, it hasn’t panned out. Every single one of my short stories has been rejected by pretty much every sci-fi, horror, and fantasy lit mag on the market. Sometimes, you want to give up, but then you remember that a lot of your favorite authors dealt with overwhelming rejection before they sold even a single piece of fiction.

Sure, maybe my writing is crap and doesn’t deserve to be published. That’s always a possibility you need to consider; it’s called being “realistic” as the pessimists like to say. So yeah, just keep in mind that rejection is more common than success and that someday, someone somewhere will clap eyes on your work and totally understand what you’re trying to do. Keep trying, keep chugging along. Again, it’s cliché, but it’s accurate: Rome wasn’t built in a day.

What is the best advice you have received?

I wish I had a sage old Yoda-like mentor who spouted wisdom, but right now, I’m drawing a blank on some profound piece of advice I’ve received throughout my career. One thing I do try to live by is “don’t be a grade-A jerk face.”

No matter how successful you become, don’t let it go to your head. Always be kind and courteous to others not in your position because, not too long ago, you were in their shoes. I really, really dislike those who think it is ok to be mean and derisive just because they have more power and opportunities than other people. I like to believe that (in the words of the Free Radicals) you only get what you give. Call it karma or whatever, but if you’re nice to people, they almost always reciprocate that kindness. If you’re a grade-A jerk face, you immediately turn people off, and after a while, you get nothing, good day, sir (or madam)! Another adage: You catch more flies with honey than with vinegar.

Do you have any advice for people that may feel discouraged about reaching their goals?

There are times when things will seem hopeless, and you feel like giving up. I’m getting angry and upset just thinking about those dark, dark moments, but the only advice I can give is not to give up. There’s no magical formula for picking yourself and dusting yourself off when nothing seems like it’ll work out for you. For me, I wallow in self-pity for a few days (or weeks if it’s really bad) and then get back on the figurative horse.

It’s almost like resting a limb after it’s been broken; it hurts for a while, but it’ll get better with time. This grace period is also time for reflection, however subconscious. Whenever I hit mental blocks with my novel, I would stop writing for an extended period and, out of nowhere, a stroke of inspiration would come to me like a strike of lightning, and I could dive right back in. In those moments, you’ll feel like you can take on the world.

In other words, you just have to let things run their course, or if you prefer food metaphors, you need to let things stew and allow the flavors to marry. Sorry if that’s a cop-out.

Geeking Out with Josh

You cover a wide range of geeky topics, do you have a favorite to write about? 

I love, love, love (did I mention love?) writing about anything related to Harry Potter. I can literally regurgitate Potter trivia off the top of my head until the Blast-Ended Skrewts come home. While my Jewish background technically forbids worshipping false idols, I am an ardent disciple at the altar of J.K. Rowling. I’m not saying I’d sacrifice a goat for her glory, but…

Sorry to my Hebrew school rabbis for that one.

I’m sure there are bigger Potterheads out there than I, but that was definitely a series that defined my most formative years and inspired me as a writer. That being said, I also love nerdy topics like Star Wars, Watchmen, classic Nickelodeon cartoons from the 1990s and early 2000s, and any fight between a giant monster and a robot of equal or greater size.

Is there a topic you find writing about more challenging? 

Science, especially if there are a lot of numbers or percent’s involved. I’ve already said that math is not my strong suit. I can write about every single character and plot point in the Harry Potter universe and not break a sweat, but present me with a table of numbers, and my brain stalls like a poorly-maintained automobile. My older sister and younger brother are the ones who got the family gift for mental math.

Every so often, I’ll be tasked with writing a piece about some advancement in rocketry (shoutout SpaceX) or the passing of a famous scientist, and I’ll be like a deer caught in headlights…at first.

Everything is a learning experience, and the best way to learn something you don’t know is to be thrown into the proverbial pool headfirst. That’s not the case with brain surgery, but you get my point. Another eons-old platitude— “fake it till you make”—also has its nuggets of profound truth. That being said, don’t (and I cannot stress this enough) try and fake your way through brain surgery.

What I’m trying to say is that even if you’re not 100% confident in writing about a particular topic, you never want to turn it down. That’s tantamount to giving up, and when you’re a freelancer, you want to say “no” or “I can’t do it” as infrequently as possible. At least that’s my philosophy. Instead, you hunker down, educate yourself, and build up your base of knowledge about the world. That way, you’re more prepared the next time you are asked to tackle a similar topic.

Whenever I’m faced with a topic that requires a little self-didactics, there’s never a moment afterward where I’m not happy that I dared to face it head-on.

That's great advice!

Thank you, Josh, for taking the time to share with us your success story and freelance writing tips. – Michael