Jane’s World: Living in the Entrepreneurial Hinterland

I’m no stranger to people having no idea how I make a living. I’ve been a self-employed journalist for going on 40 years, so I figured out my elevator blurb years ago. At the time – around the turn of the century – it went something like this:

Me: I’m a freelance writer.
Them: Who do you write for?
Me: I write for a lot of different newspapers and magazines, both print and online.
Them: Would I have read anything you’ve written?
Me: Probably. I’ve written for the New York Times, Los Angeles Times, Family Circle, Woman’s Day, Ladies’ Home Journal … newspapers and magazines like that.
Them: Do you write for any local publications?
Me: I used to write for the Record-Eagle, Northern Express, Traverse City Business News, Traverse Magazine … but it was a challenge making ends meet, so I started writing for bigger publications that pay more.
Them: So you make a living at it?
Me: Yes.

It’s always tough for non-writers to understand how a person can make a living as a writer. Most people think it involves writing books. But I can tell you that only the upper echelon of book authors make enough money to pay their bills, and only the tiny few at the top make far beyond that amount. We’re talking the Stephen King, J.K. Rowling, George R.R. Martin level of authors.

Most of the book authors I know, while amazingly talented writers, barely break even and sometimes even lose money if they have to self-publish and market their own books. That’s the explanation I would like to give every time someone tells me I should write a book. Which is at least once a day. Instead I just nod and say, “Maybe some day when I have the time.” (In other words, if I suddenly come into a lot of money where I don’t need to worry about making it every day and can afford to lose it by writing a book. The book publishing business is brutal in every way.)

When it comes to making a living as a freelance newspaper and magazine writer, what most non-writers don’t realize is that writing is only about 10 percent of the business. The rest of the time is spent generating ideas, pitching stories to editors, and waiting sometimes months for an editor to get back to you with a yes or no.

If it’s a yes, then you set about researching the story, gathering sources, doing interviews, writing the story, submitting the story, waiting sometimes months for notes from the editor, possibly gathering more sources, rewriting the story, submitting it again, waiting for it to be published, and then there’s the obligatory month or two of chasing the invoice and actually getting paid for the story. You can see that you have to have a lot of stories in the pipeline at all times in order to make a living at it. Most writers I know, including myself, are spreadsheet people.

When I narrowed my niche to entertainment writing, around 2008, my elevator blurb got a little more complicated.

Me: I’m a freelance entertainment writer. I write about movies, TV and celebrities.
Them: Who do you write for?
Me: I write for a lot of different newspapers and magazines, both print and online. I’m also an editor at AOL’s TV Squad, and I write for their other sites, Moviefone and Popeater. I also write a syndicated movie column that’s published in hundreds of newspapers and magazines, mostly regional.
Them: Would I have read anything you’ve written?
Me: … [thinking] … Do you read People Magazine? Then you’ve probably read my stories.
Them: So you make a living at it?
Me: Yes.
Them: And you do it from your home here in northern Michigan?
Me: Yes. I do a lot of interviews over the phone.
Them: Have you interviewed anyone famous?
Me: Oh yeah, all the time.
Them: Like who?
Me: Tom Hanks. Julia Roberts, Kiefer Sutherland, Kristen Bell, John Grisham … basically anyone who has a movie, TV show or book coming out…
Them: Wow, that’s really cool.

Yeah, it was really cool, but around 2013, the allure of interviewing Hollywood stars was waning, so I started coming up with an exit plan. There was really only one option. Start my own newspaper covering the Old Mission Peninsula where I grew up on a cherry farm. It’s an idea that’s been brewing in my head ever since I was a kid reading about Jo March and her sisters in “Little Women” forming the Pickwick Club and creating their own newspaper. I knew one day I would create my own newspaper, too.

What I didn’t know is that now, more than any other time in my writing career, I’d be living in what I call the Entrepreneurial Hinterland. Meaning, I’m basically out here on my own in the uncharted, sparsely-populated Land of Small Town Newspaper Publishing.

During my early years as a freelance writer, at least there were other people doing what I was doing. I joined a few online writers’ groups, and we’d commiserate about finding good sources, working with difficult editors and venting about late payments.

But since launching Old Mission Gazette about four years ago, and despite my best efforts to find someone, anyone, in my vast network of writers who might have started their own newspaper (and who I could look to for support and commiseration), I am way out here in the far reaches of the Entrepreneurial Hinterland by myself.

I mean, who starts their own newspaper? Apparently, only me. Oh sure, I know lots of people who hold various jobs at small-town newspapers – editor, publisher, photographer, copywriter, advertising manager, and so on and so forth. But I haven’t found anyone who started a newspaper from scratch, who built and manages the website, gathers advertisers, writes the stories, takes photos, interviews people, attends community events, manages all the social media, gathers subscribers, built and manages an email newsletter, built an accompanying online store to help support the newspaper, designs and sells Old Mission Peninsula items, manages the social media and sales for said store, and so on and so forth. You get the picture.

It also explains why if you email, call or text me, it might take me a day or three to get back to you.

And when I write it all out, it’s easy to see why no one else is dumb enough to start their own newspaper. Wouldn’t it be easier to just get a job at Costco and work the remainder of my years there? Sure, but it wouldn’t be nearly as fun or fulfilling.

But here’s the thing. If I’m living in the Entrepreneurial Hinterland within my own network of well-connected writers, imagine what it’s like to live there in a community populated by retirees from General Motors, software companies, government jobs, state universities, venture capitalist firms and other corporations with 401Ks and pensions – all polar opposites of my livelihood.

I might as well be living Beyond the Wall in Game of Thrones’ Seven Kingdoms. I am at the Frozen Shore in the Far North fighting off White Walkers with nothing but a keyboard and a camera and a lot of faith that I won’t go bankrupt.

Yet even with the three thousand things involved in running Old Mission Gazette and OMPstore.com, the elevator blurb has actually gotten a little less complex: “I run a newspaper covering the Old Mission Peninsula and an online store selling OMP items.”

That statement is usually met with a mix of surprise, admiration and incredulity. As one of my writer friends said recently (when I was venting about being out here on my own), the idea of creating a sustainable job for yourself based on your specific skills and knowledge is pretty unimaginable for a lot of people. But I learned long ago that I’m not really a corporate kind of person. Before I turned writing into a career, I held a few office jobs, learned some good work management skills and met some wonderful people.

But even back then, I always felt like it would never be enough. When it all boils down to it, everyone needs money, and in order to get it, you trade your time for money. And a LOT of time, at that, over the course of your life. In an ideal world, you’d land a job you love and find it to be the most fulfilling use of your time ever. Or at the very least, you’d like it enough to spend vast amounts of hours, week after week, year after year, decade after decade until you get to that promised land – retirement.

But I never really liked working FOR someone else, and now, after decades of setting my own schedule and working hard to build my own business, the idea of ever working for someone else is probably off the table. Maybe it comes from growing up in a farm family, where self-sufficiency was the norm and if you just worked hard enough, good things would happen.

Still, whenever a friend announces their retirement from [insert corporation] or when I’m having a crazy deadline day or my inbox is out of control or my monthly revenue doesn’t quite meet my expenses, that corporate job doesn’t sound too bad.

Until I go farther down the road and envision myself at the end of my life wondering why I didn’t take that chance to keep pressing forward with a life of my own making.

Then my Entrepreneurial Hinterland seems amazingly quiet and peaceful.