Who among you would prefer to be your own boss, really? Everyone, right? Okay, maybe not everyone — it is certainly risky after all — but how many of you, if you had your druthers, would elect to give up the commute and work from home in your underwear?

Or less?

Again, not all of you to be sure, but, for those reading this…

Here are ten strategies I’ve used myself over the years to stay above water, several I’ve utilized when transitioning to my passion for a full-time income, in no particular order.

Craigslist Writing Gigs

Don’t ever dismiss Craigslist as a legitimate source of writerly income. When I began haunting Craigslist ads about ten years ago, my first writing gig paid $1000. The second, a screenplay, paid $35,000.

Of course, that latter figure is an exception. The first is as well. But still …

Perusing Craigslist Writer’s Gigs ads, as with their Writer’s Jobs ads, with the intent of finding a treasure is similar to dating. You’ll need to kiss many frogs to find that elusive legitimate post. The thing is, those legitimate posts do indeed exist, and over the years I’ve earned well into the six-figures by responding to them.

Here’s the math: Let’s say 10% of all Writer’s Gigs ads are legitimate. That means, if you’re lucky, for every 10 queries or responses you send out, you’ll receive one response back from a poster who may want to speak to you further. They will receive dozens if not hundreds of responses typically, so your subject line has to stand out.

Mine was something like this: MULTI-PUBLISHED AND PRODUCED AWARD-WINNING WRITER.

That’s always gotten attention for me.

Back to the math: Up until maybe two years ago, though I still haunt those ads from time to time (old habits die hard), I accepted offers to write screenplays, books, book proposals and press releases. I wouldn’t touch a screenplay (and cannot now as a Writer’s Guild member) for less than $10,000, payable in installments. Books were based on the page count, generally $2500 per 100 pages. For book proposals I charged a flat $5000 for about 30–35 pages or they weren’t worth my time. One-page press releases were $1000.

Yes, I wrote the books cheaply. I was still experimenting with them then.

You may ask, “How could people who post on Craigslist afford those rates? My philosophy was this: Of those who called me back after responding, this was a way to weed out the b.s. from those who were real. In the span of a year, I exceeded my last full-time job income (from back in 2005) by taking on writing gigs from Craigslist. I sent an average of 20 responses daily (copied and pasted), received two responses on average and typically entertained one offer.

The successfully-attained assignments added up over the course of a year, as did the income.

Vocal.media

You get paid for articles on a per-click basis. I regularly share my Vocal.media posts on Facebook, Twitter, and Linkedin. I further share my stories with appropriate social media groups, and watch my numbers grow as I drink my morning coffee.

Money from a dreaded “content mill.” Who would have thought it?

Will you get rich there? No. I’m literally making pennies per ten clicks. But it adds up. Does it take me a lengthy amount of time to write my Vocal articles? No, maybe 30 minutes and they’re usually stream of consciousness. Do I need the money so badly that I need to do this? No. Is it a fun aside to collect extra income while I’m stretching my novel writing muscles, or screenwriting muscles for the day? Sure. Do I feel that I’m helping people with some of those posts? Absolutely. Well-meaning advice is always a positive as far as I’m concerned.

Am I somehow discounting my position as a working writer-producer in the television business, who owns a television development company (Council Tree Productions), by writing those articles? Why would I be?

The point is, you can earn a few hundred bucks a month by doing this BUT you need to share with your social media and hope at least some of the articles hit. I wrote the following for that forum, as an example: The 10 Greatest Comic Book Stories of All Time presently appears first on search engines with the input of “10 Best Comic Book Stories,” with nearly 10,000 hits to date.

Again, you’ll make about a penny every two or three hits. You’re not going to leave your job over it, but as a fun and passive income stream, it’s good to have.

HubPages.com

Another of the so-called “content mills,” this one pays less than Vocal, which owns several pages within different genres, but it’s still valid. Visit their site.

Infolist.com

Jeff Gund’s Infolist is a gift to writers in general, and those in the entertainment business. Sign up for his mailing list and you may well receive listings in your inbox for writing gigs that may not have appeared elsewhere. He also regularly shares information about parties, which are typically great networking events. See their website for further details.

Inktip.com

A wholly valid way to be discovered by Hollywood producers, regardless of where you live. Check out the Inktip website for more information.

ISA (networkisa.org)

The International Screenwriters’ Association. Sign up for their mailing list and you will regularly receive writer’s gigs in your inbox.

Medium.com

Among the most respected sites on the list, one that pays out on time every month based on clicks and responses to your articles. They have some rules you need to follow, and you will need to promote yourself well, but check them out. Medium is an excellent site to earn a side income.

Contently.com

Contently is simply an aggregator, where you can gather and post the entirety of your web content in one place. This is great for those sending out writing queries, as samples are always effective.

Refashion social media posts into 600-word articles.

And then share on some of the aforementioned content mills. You’re now making money from old postings. To be clear, your writing is a skill that is worth FAR MORE than you will be paid in these outlets. BUT, again, this article is about real strategies to replace a full-time income.

The more you write, the better you will become. The greater your output, the more seriously you will be taken, and the more money you will earn.

Network, Network, Network

Go where the elephants are. Get out of your comfort zone and meet people. Speak to everyone, as everyone you meet is a window to someone who may well be able to influence your career. Attend writer’s conferences. Join networking groups.

Get out of your home and get to work.

If you truly want to leave your full-time job and replace that income with your writing, you can. It won’t come easy, and you’ll need to work, but it can be done.

Many of my writer friends also enjoy outlets like Patreon.com, which is a very real way to attain sponsorship for your writing.

Two quick notes: 1) The above list is by no means meant to be inclusive, but a reflection on what I’ve used throughout the years in my transition from working nearly 100-day jobs to earning an income on my own terms. And 2) Regarding the “content mills” listed, including this one: Many writers tend to shy away from these sites, believing few would take them seriously as they pursue their more career-oriented writing efforts. I for one haven’t had that issue at all, and I will continue to write articles here for as long as I find them enjoyable. I discovered these “mills” earlier in the year. I had a knee replacement surgery and was laid up for a few weeks before and after. I found it difficult to focus on my usual writing (novels and screenplays) and decided to undertake an experiment to see what is legitimate out there for writers who simply wanted to write, and earn a passive income doing so. The above-listed entities have proven to be of worth, and so I’m sharing them with you.

Regardless of your path, never stop writing. If you want to ultimately transition from your job, be careful but if you follow some of the above guidelines, you have a shot. If you do it right, you may also have plenty of time leftover to write your novel or screenplay, and pursue the — I’ll use the word again — legitimate writing career for which you’ve long strived.