It's a great time to be a writer. Kind of.

During last year’s NBA Finals, I wrote an article reminiscing about the times I guarded Golden State Warriors’ All-Star Draymond Green back in our high school basketball days. It was going to be super timely, especially as I watched Draymond knock down five threes in the first half of Game 7. He was playing like the best player on the court, well on pace to become the NBA Finals MVP.

The Cavs came back, Draymond didn’t win MVP, but I still published my post. I also reached out to the sports editor back at my hometown newspaper, sent the article to him in hopes they would run it. Maybe a big Sunday spread in the sports section!

I never heard anything back.

Fast forward almost a year later, and I saw the following post on LinkedIn from the same sports editor: Hi friends, I just want to let you know that my position of sports editor has been eliminated.

Not fired, eliminated. The role of sports editor at that paper no longer exists. And before I get into that, I’ve got one more related story.

In June, I am self-publishing a novel that I’ve been working on since the fall of 2008. I’ve wrestled with the self-publish vs. try to publish traditionally question for over three years (I’ll have many posts to come on this very subject). One of the reasons I decided to pull the trigger on the self-publishing route was the thought, “Hey, I won’t be able to get into Barnes & Noble, or airport bookstores, but maybe I could channel my door-to-door salesman side and get into local bookstores. And, since my novel takes place in my hometown, maybe my favorite hometown bookstore (Sleepy Hollow) would carry it.”

I Googled “Sleepy Hollow, ” and the top article was an article from July of 2016, “The final chapter. Sleepy Hollow Bookshop plans to close.” The next result was Sleepy Hollow’s listing on Yelp marked, “Sleepy Hollow Bookshop – CLOSED.”

So what do either of these stories have to do with my title? “A great time to be a writer?” How so? In what way?

Well, allow me to start out with a slight modification. It is a terrible time to start a writing career IF you are looking for a set, defined road for your career to follow.

Twenty years ago, hell, maybe even just five years ago, an 18-year-old could’ve said, “I want to be a sports writer, so I’m gonna go to a great journalism school, get into a great graduate school, get an internship at a great newspaper, work my way up. At first I’ll be writing stories about grade school basketball, then middle school, high school, all the way up to the NBA. After 20, 30 years, I’ll be one of those people on ESPN’s Around the Horn. And THEN, once I have a big name for myself, I’ll write a book and it’ll be in every bookstore around the country, including my hometown store, where I’ll set up a table and sign autographs. I’ll tell a kid wearing a Chicago Bulls hat, ‘Now, make sure to study hard in school young lad, one day you can be right here.”

Where does that story fit into the 2017 landscape? Every step of that defined process is now in question. Newspapers struggling, bookstores struggling, many shutting down altogether. I mean even the value of a college journalism degree or graduate degree is in question. The only solid part of that story was ESPN’s Around the Horn because Tony Reali could host that show til he’s 95 and not look a day older than 28.

So yeah, I think it’s a terrible time to be a writer IF you’re using yesterday’s blueprint. It can lead to a devastating place where you’re left saying, “This isn’t fair. I played the game. I followed the rules. And this is what I have to show for it?”

Okay, when is this blog post going to turn around? Or did you just want to start my day off on a depressing note?

Alright, here’s the good part. Twenty years ago, my Draymond Green story would have ended with the lack of response from the local newspaper. And, since a bigger paper wouldn’t have taken it either, that’s it. Game over. Maybe print out a couple of copies, hand it out to friends and family.

But thank God it is not twenty years ago! I posted it right here on ChicagoNow. Available for the whole world to read.

And it didn’t go viral. Didn’t even go mini-viral, but it still was out there. Still was read. Same thing with my novel in a couple of months; twenty years ago that story ends the same way. Getting no response from a publisher or literary agent. The only option would be to print out copies at the nearest FedEx Kinkos. But, fast forward to 2017, it’ll be on Amazon, one click away.

Not having a blueprint or a defined path is scary, but take a look at those prior scenarios again. When was it ever good for the writer?

Granted, I’m old school, so I do love the Sunday newspaper, and I hate to see bookstores go under. If you’re in that same boat, I’m asking you to push the consumer side away for a second and think solely from the writer perspective. A quick game of “Would you rather?”

Would you rather…

Slave away for 10-20 years going to games that no one else wants to cover, slowly working your way up to one day cover the NBA, MLB, NHL, NFL


Start writing about your favorite sport tomorrow. Tonight. Pour all of that knowledge into posts that will be available to the entire world.

Note: And the views can be just as high, sometimes higher. I see the numbers reports for ChicagoNow. I’m not sure any newspaper writer, Bleacher Report writer, etc., is getting the type of traffic that “Cubs Den” gets every single week.

Would you rather…

Write a book, send it off to 5+ literary agents, wait, wait some more. Get rejected, send out another 5+, wait again, more rejections, then maybe, maybe, one finally takes a chance on you. They now try and sell your work to a publisher, the literary agent’s going to get 10-15 percent of the sales, the publisher needs to make money too, but that’s ok, because a year, two years, five years later they got you into a bookstore, you see the physical copy of your book on the shelf only to see out of the corner of your eye a sign reading, “80 percent off, going out of business sale.”


Start writing the book tomorrow. Tonight. Ask friends for editing help. Go on any of the hundreds of freelance sites to find some more editing help, grammar help, book cover design, formatting, etc., and then, when it’s all finished, throw it right up on Amazon. One click away.

P.S. Amazon is opening physical bookstores too… just saying.

It’s a great time to be a writer.

Thinking back to the opening story about the sports editor, here’s another line from his post:

On a personal note, thanks to all my faithful column readers. We had a great relationship, and I’ll always, always cherish that. God is in control. I’ll land on my feet.

Following the old blueprint, it’s all over. Maybe find another paper, but what’s the point? That job could be gone next year. Next month. There’s no solid ground to land on.

But go off-roading, and the answer is simple: just keep on writing. Bring the faithful column readers to a new blog. Bring them to a book, either a new one or take the best columns over the last couple decades and make a compilation. Because just like the editor spot has been eliminated, so has the book publishing gatekeeper. Nothing is preventing that blog or that book from being out on the market.

Devil’s Advocate – Where’s the “Kind of”

Where these sorts of “Rah rah! Go self-publishing!” articles make their mistake, and where I’m kind of veering off into, is this severe black and white scenario of old school/traditional equaling death and destruction, but self-publishing, oh babay, that’s the California gold rush. We’re all swimming in money over here!

Time to debunk a few things.

The person who got into a great journalism school, got a great starting job at the New York Times, they’re going to be just fine. So is the novelist who was traditionally published on Monday or the person who wrote a memoir that just landed a literary agent on Tuesday. The publishing world will continue to shift and move around, but those with really high-level skill and/or a large following will continue to make a ton of money.

For example, let’s say the New York Times shuts its doors tomorrow (cue Donald Trump dancing in his boxers). Columnist David Brooks could either go to another paper, or online publication, OR he could essentially Netflix himself by saying, “Hey, for $3 a month you’ll get 3-4 columns from me direct to your email.” If all 125,000 of his Twitter followers sign up, he’s making a cool $4.5 million a year. Throw in a couple of book deals + speaking gigs, that’s some good livin’. Mr. Brooks, you’re welcome for this free Medium Rare idea!

And, on the self-publishing side of things, yes, there’s the story of E.L. James self-publishing Fifty Shades of Grey. Or Hugh C. Howey with the Wool series. Or Andy Weir with The Martian. Or fill-in-the-blank with whatever another story about an author making six figures a year, $40,000 a month, you name it.

But here’s the caveat for each one. E.L. James was doing well with her self-publish sales but, when it got picked up by Vintage Books, it went to another level of success. Hugh C. Howey has sold a crazy number of books, but he’ll be the first to tell you (on an amazing episode of the James Altucher podcast) about all the work that went into this. He had written nine books before the momentum got going. Nine books! It’s the classic iceberg metaphor; there was a whole lot of work going on beneath the surface of success.

The stories of people making self-publishing a career have the important fine-print note about just how hard these writers worked gathering e-mail addresses, making themselves available to readers, building their direct marketing lists.

Because simply putting the book out there doesn’t equal “quit your day job.” I’ve done the “just put it out there” approach with no real marketing strategy, and it’s a sure fire way to make six double figures.

BUT, even then, it was a great time to be a writer. The book was finished and available. Figuring out marketing, pricing, advertising, that all can come later. Trial and error. And maybe it takes eight flops before financial success. Or maybe “financial success” will only mean paying my Netflix bill. I don’t know.

I mean, I hate to be the, “Even if it doesn’t make money, it’s still worth it” guy; I feel like that’s the ugly cousin of little league’s, “It doesn’t matter if you win or lose, it’s that you had fun!” but that’s really what it comes down to. So maybe these last few sentences are my Ziploc bag of orange slices after the little league game, but I hope they can still provide some value and encouragement.

If the goal is to become rich as a writer, I don’t know how to help out. I haven’t accomplished that feat so I can only point you to podcasts, blogs, articles from those who have. What I can say, though, is there seem to be three main themes in these interviews:

  1. Write everyday
  2. Build an audience
  3. Don’t chase the money, the money will naturally follow

The first one is in our control, the third one not so much. But why I think it’s a great time to be a writer is because of the second one; nothing is stopping you from building an audience. You can start doing that tomorrow. Tonight.

And that’s kind of an awesome thing.

Thank you for stopping by. If you’re looking for the heavyweight boxer of this arena, someone who has even better advice on writing/self-publishing AND has the book sales to back it up, please go check out James Altucher (although, side note, in actual physical weight, we probably combine to be maybe 350 lbs). He’s written a ton on self-publishing, he’s a big advocate for it, and any sort of wisdom I have, he’s the one who taught the original lesson.

My plan is to do several more posts on writing, publishing vs. self publishing, how to start a new idea, and how to finish an existing project over the next couple months. My hope is this will be helpful to anyone interested in writing, whether it’s for the fun of it or a new career. Or both. And if you want direct help/answers to questions, send me an email at There will also be posts that have nothing to do with that so this doesn’t become like March on the blog where it’s just a sea of college basketball posts. If you’d like to subscribe to the blog and have these sent direct to your inbox, just enter your email address in the box below. See you next week!

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