A New Chapter in the Writing Life

We begin with a brief glimpse into the world of a freelance writer ……

Two years ago I was a busy, busy boy. I was writing for three different websites and knocking out about 80 articles a month between them. My days and nights were filled with the steady clack-clack-clack of the keyboard as I tried to stay ahead of the workload. Sometimes it felt like a nagging, 500-pound demon on my back, all these assignments crowding my inbox. But I didn’t dare turn down a single one. I was making more money than I ever had in my life – and stowing it away for a rainy day, because I knew, I knew…..

I knew the gravy train would come to a screeching halt one day. It always does when you’re a freelance writer. You can set your clock by it.

Cut to today, right now.

I’ll be lucky to get 10 assignments this month. I’m not sure I’ll get more than 10 a month for the rest of my mortal days.

This will ring familiar to anyone who has taken a stab at freelance writing for a living. The work giveth, and the work taketh away.

My own experience as a full-time freelancer began in 2016, after I was downsized from a newspaper job and decided to just wing it on my own. The early years were lean, which wasn’t great for the bank account, but allowed me to do a lot of fiction writing,

During those early freelance years I had enough time to crank out a collection of short stories (buy it here!) and a novel (buy it here!). I also wrote dozens of other short stories, and a novella. Some of the stories were published in anthologies (read about them here).

I wasn’t making much money writing fiction, but it was fulfilling both personally and creatively — sometimes fun, sometimes exasperating, rarely boring.

Luckily, the paying gigs picked up just when I needed them most. I hooked on with a few websites that specialize in personal finance content. Over the next several years these web content assignments allowed me to make a decent living. They poured in, then they dried out, then they poured in, then they dried out.

And man oh man, are things ever dry right now.

Two of the websites I wrote for stopped sending assignments altogether – one because it specializes in evergreen content that the staff editors can now update every month without my help; the other because its freelance budget was slashed to nothing.

The third website – one I’ve been writing for around eight to nine years – recently shifted its freelance focus. Not long ago they still sent me about 40 assignments a month. Now that’s been cut by about 75 percent.

So, the gravy train is stuck on the tracks as I write this.

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I’ve been through it before – plenty. In the past I might have chalked it up to the nature of the business, knowing that the work would soon pick back up again.

But this time it feels different.

Freelancers who write web content now face something they didn’t face even a decade ago – the all-encompassing presence of AI. Not only does AI-generated web content threaten the livelihood of writers. It also threatens the very need for websites at all.

To succeed, websites depend on internet traffic. They need visitors, clicks, engagement. They need to prove to advertisers that they have plenty of eyeballs looking at their content.

But if internet users can simply hop on ChatGPT, Grok, Gemini or some other AI platform, then you’re going to see a lot fewer websites specializing in online content.

I have serious doubts that the internet freelance model will ever return. I even revised my budget to account for a steep and permanent drop in income.

Personally, this is not as big a problem now as it might have been a few years ago. I’ve reached an age when I qualify for Social Security benefits every month (the U.S. version of pensions). So, I get regular income whether I’m working or not.

But I still want to keep working. I can’t imagine a life without working, without writing. Why do you think I crank this blog out every week or so? Because writers have to write.

And since I won’t have as much work from outside sources, I need to create work for myself.

I’m in the process of doing that right now, by outlining another book project.

It won’t be fiction, though. Let me explain.

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One thing I learned about writing fiction is that for most people, it doesn’t pay well. In fact, it pays shit. I bet there are fewer than 50 fiction writers in the world who can get by on book sales alone.

I asked AI (that again) how many 21^st century writers have netted more than $1 million in book sales since 2000 – or enough to get by just writing books.

It came up with exactly 22 names. These names range from the obvious literary heavyweights (J.K. Rowling, Stephen King, James Patterson) to self-publishing whizzes (Amanda Hocking, Bella Andre) and one-hit wonders (Alice Sebold, Paula Hawkings).

To earn a decent living as a fiction writer, you need at least one of the following:

• An established agent
• An established publisher
• A genius for social media/promotion

I have none of those things – and I’ve done my best to corral all of them, believe me. I was no more successful at it than 99.73 percent of all the fiction writers in the world.

Which leaves non-fiction books. That sounds a little more realistic than fiction, at least for me, at this moment in time. I even have experience at it. I’ve spent decades writing non-fiction as a journalist. It’s something I’m comfortable with. (And yeah, I can hear your snickers about journalism being “non-fiction.”).

What’s more, tons of people write non-fiction books about tons of different stuff, from finance and self-help to history, health, sports, culture, politics, whatever. A lot of it is crap. But crap can still pay money — as long as you have a market.

So what is my market? What expertise can I share that might be of interest to readers?

This is a bit of a problem. It’s a pretty short list. I know a good bit about many things – baseball, tennis, personal finance, the 1970s, classic rock, 20^th century jazz – but I don’t have especially deep expertise about any one thing.

Every time I think I do know a lot about something, a thousand other people come along with much more knowledge than I have. I know this because I’ve hopped on tennis forums, or jazz forums, or baseball forums, and found out how many nerds are out there that can put my knowledge to shame.

But there is one thing I have more expertise in than anyone else:

Me.

I know me better than the rest of the world knows me (I think). I am an expert in all things Vance Cariaga (I hope).

Now, that’s not enough of a basis for a book – or even a social media post. The world is not dying to read about the life of Vance Cariaga. In fact, outside of maybe 23 people, the world does not give much of a crap about Vance Cariaga.

However…..

The world does like to hear unique stories that can provide a road map to important life decisions. And I feel like I have some unique stories to tell, and some important road maps to share.

At the age of 40, I left my job, home and life behind on the off-chance that I might fulfill dreams I had long held dear but never really came close to attaining. The whirlwind sequence of events that followed made those dreams a reality, against all odds, fairly late in life, which I touched on in this blog.

A few people have encouraged me to write about my experiences. I have always been skeptical that there was an actual market for it. I’m still skeptical. But what the hell. I have more time on my hands, so what’s the downside?

I consulted AI (that again) to find out whether my story might make for interesting reading. In no time at all I found myself plunging down the rabbit hole and ended up with 50-plus pages of AI advice on everything from how to structure, market and write the book to which literary agents and publisher might be interested.

Here’s what it said about such a book’s potential:

“That is a remarkable trajectory. Your story isn’t just a memoir; it’s a direct challenge to the ‘it’s too late’ narrative that many people begin to feel as early as their 30s. From a publishing and commercial standpoint, your story taps into several high-growth markets.”

Well, that’s certainly good to hear! Whether it’s true or not, who knows? But I guess I’ll give it a shot.

Stay tuned…..

Image: AI-generated (that again), with instructions to make the writer look like yours truly. It’s a scary good representation, though my chin and neck are increasingly more ski slopey as I age (damn it all). Also: I do own a fedora. But I don’t usually wear it when writing.