Some Advice To Middle-Aged Writers Who Wish To Make A Living Off Of Writing

Yesterday, Robert Jackson Bennett posted some pretty wise words for aspiring professional writers – advice that boiled down to “Get a full-time job, manage your career, and write part-time.”  Because writing full-time a) takes years to pay off, b) is uneven with the cash flows even when it does succeed, and c) lacks health insurance.
However, he was then asked: “That’s for kids in their early twenties.  What if I’m an old fogey?”
I am an old fogey, so let me speak.
I published my first novel last year at the age of 45 – I am now legally obligated to tell you that novel is called Flex, and Mr. Bennett was kind enough to read it and give it a nice blurb so I could sell it to people. I got serious about writing at the age of 38.
And yes, things are slightly different for you.
If you have reached late middle age without getting published in the ways you want, that’s likely due to one of two reasons:
1)  You suck at writing.
2)  You weren’t serious about writing.
The good news is, both can be fixed.
The “serious about writing” is a large issue – I wrote on and off for twenty years, leaving my stories in desk drawers because it was a lot easier hearing my friends tell me how awesome I was than actually, you know, getting rejected.  After decades of writing just often enough that I could tell my coffee dates that I was a writer, I realized that it was time to shit or get off the pot – I could die in the nursing home with my relatives fondly lamenting how much potential I had, or I could see whether I was actually any good at this.
And if you’re middle-aged and just starting writing because it seems like A Nice Thing To Do, here’s my best advice for you:
Decide whether you want to write because it’s A Nice Thing To Do, or whether you want to hurl yourself bodily into the meatgrinder that is publishing.
Writing because it’s A Nice Thing To Do is awesome!  The kids these days churn out tons of fanfic, and they have a lot of fun goofing around in someone else’s universe.  It’s the equivalent of playing hoops in your buddy’s back yard during the summer – maybe you get a little competitive, maybe you’re way better than the average ball-tossin’ schmuck, but the main goal is to have fun.
Writing professionally is not always fun.
If you want to go professional, well, you’re likely gonna get rejected a lot, and hear some mean shit said about you from people who are right to say mean shit about you because your story wasn’t good enough yet, and you have to suck it down and agree with these very-rude-yet-very-accurate snarlbacks in order to make your writing better, richer, smarter.
It’s a lot easier to toss off Avengers fanfic to people with low expectations and happy thoughts.
(Which is not to say that all fanfic is low-quality – it certainly is not, and Seanan McGuire would beat me senseless if I said that – but a lot of fanfic is basically people enjoying themselves and not trying to sell their fiction for enough money to pay the rent.  Which is a methodology I fully support.)
Older folks often forget that “writing for fun” is an acceptable option.  This doesn’t have to be Career Part 2.  You can get your poems published in magazines that pay nothing and have a hell of a time. Dork around and self-publish your first draft. Pay money for a nice cover.  Who cares if there’s cash or success in it?
You care?
Okay.  Time to get serious, then:
You probably suck.
This isn’t a fatal flaw; I sucked for decades.  But if you’re older, and you’ve been working on your fiction for years and still that breakthrough eludes you, you’ve almost certainly got a couple of lazy habits clogging up your throat.  You may not even be aware that they exist.  But they’re stopping you from going further.
(And if me telling you that “you probably suck” gets your hackles up, holy God, let me tell you that this is perhaps the nicest thing you’ll have said to you when you’re starting out.  Consider the Nice Thing To Do route if that seriously ruffles your wings.)
If you wanna start writing, don’t quit your job.  Instead, learn to work in the time you have and figure out why you suck.  (For me, it was stiff plotting and bad prose.)  You need to find people who can be honest about your fiction in realistic ways, not the puff-pastry of your buddies who are just impressed you finished a story, and have them kick your ass like fighters at a dojo.
What worked for me was a Writing Workshop.  I did two; Clarion, which was six weeks long, and Viable Paradise, which was a week long.  John Joseph Adams, a bigwig sci-fi publisher, discusses the various workshops available in this post here.
These workshops are expensive. Hopefully, your middle age has been accompanied by middle class, and your sole advantage among these young whelps is that you have a paycheck to go into hock for this shiz.  But they do help.
People will tell you that writing workshops are the only way to get good at writing, and those people are so full of shit their T-shirts are one big brown skidmark.  But Tobias Buckell, another writer of some note, once told me that the Clarion Workshop was like a time machine – it can accelerate your career four years forward in a couple of weeks.  Being critiqued heavily by professionals, and insightful students, will highlight all the issues in your text.
If you’re running out of time already, workshops help.
They are not panaceas, though.  The dirty secret of every writing workshop is that the people who succeed are usually the most tenacious, not the most talented.  I certainly wasn’t the best writer in either of my classes, but I got a novel published because I wrote every day and refused to stop.
But that’s the other beauty of a workshop; you get to spend a couple of weeks seeing what it’s like to be a Professional Writer.  And some people look at all the work that needs to get done, and the rejection, and the heartache, and the crapshoot terror, and they say Fuuuuuuuck this.  I’ve got better things to do with my life.
Which is great!  Man, seriously, if you can pay a couple of thousand bucks to discover that you don’t have to waste the next decade chasing a dream that doesn’t suit you, do it.  Sometimes, a workshop is a success because it’s shown someone that they could be a writer, but they would be miserable doing it.
Yet again, workshops aren’t necessary.  (RJB did no workshop, and he’s doing all right.)  They are merely convenient, assuming you can get into one.  And if you can’t, well, let’s go back to the “You probably suck” phase – you’ll need to find some local writers’ groups or good online forums that will rip your fiction apart constructively…
And you have to listen.  You’re not good yet.  You have to be this bizarre blend of egotistic and humble – humble enough to accept the bodyblow of “Whoah, that was awful” when it’s true, egotistic enough to shrug off the complaints that would steal the uniqueness from your work.  And that’s hard to know, man.  It’s hard.
Which isn’t to say this is the only way.  Writing is bizarre like that; some people pick up the pen at fifty, and they’re geniuses out the gate.  Others find these alternative paths I’ve never considered, and they’re successes.  When I say “Here is how to do it,” realize that it’s like climbing a mountain – this is the bunny trail I’m pointing out, but there may be a shortcut that gets you there faster, and if you’re super-dedicated you can probably scale the cliffs bare-handed.  Don’t let anyone tell you this is the sole path to publication.
But yeah.  You’re older.  You can still do this.  But you gotta put in the work.  And you’ve got less time.
I’d start now, if I were you.