Why Writers Need to Think Like Entrepreneurs

Old books on a wooden shelf.

Old books on a wooden shelf.

I sat next to a woman at a lunch recently who heads up the magazine publishing program at NYU, and she said the students are, understandably, feeling down about what they see as bleak prospects in magazine publishing—simply because those seats are becoming fewer and fewer.

It’s easy to interpret the shuttering of (many) print magazines and newspapers as ‘death’ to publishing, but I don’t see it that way. What we’re seeing is a shift in consumption habits, in expectations, and in business models. Content may be king, but we’ve also become accustomed to having it be, well free. What is and will continue to change is how we pay for it, and who is paying for it. Yes, that changes things.

Print magazines are, simply, a platform. No different from any other platform you use (newspapers, books, blogs, and so on). As beloved as they are to you, they were a platform, and platforms evolve or die off. We’ve gotten attached to them, of course—we’ve had them longer. Now social media and other content platforms come and go so fast that they seem disposable; we hardly have a chance for habits to form around them!

But one thing is for sure, and this I can say without question: There will always, always be a need for great writers and storytellers, people to create and curate. We need them to see, capture and interpret the world for us and always will.

How can we not? With all the content pouring at us from all platforms, streaming toward us through every device, we rely on editors to tell us what to pay attention to, and what not to. The era of the Big Magazine and Big Publisher may be shifting dramatically (and yet as you can see, they’re not totally gone), but what that means is that the role of the storyteller is even more important. You go to the salon for the stylist, not the other way around, right?

Enter: personal branding.

Writers are now responsible for their own brands. Many of them cry that the surplus of content has driven the fees (and quality) down. If you are a writer and your claim to fame is that you can string words together, you’re no different from a plumber; you both can combine separate objects so that something vital can flow through them. Fine. You can do a thing. Doesn’t mean I need to pay you for it.

Some writers feel they should be paid to do what they do because, well, they like doing it. Sorry! That’s not a reason for a job! Would you hire a plumber because he said, “But I really love plumbing! It’s my passion!” Nope. You hire a person based on how well they solve your problem, period. (See my TEDx talk for why passion isn’t enough.)

Enter: entrepreneurship.

The future doesn’t belong to just people who can do a skill; it belongs to those who can find ways to create value for someone. If you want to make a living as a writer, editor, OR plumber, you have to identify a need, ideally someone who will pay you for your solution. And you need to supply that solution in a way that suits your customer, suits your market.

This doesn’t depress me, and it shouldn’t depress you, either. We are living in a very exciting time for content! It used to be you had to pick magazines or books, and jobs for content were fairly limited (even if there were more seats at traditional publishers). Now, the degree to which you create something amazing determines how well you do. And that is in your hands.




The Cure for Boredom (You May Not Like It)

Screen Shot 2016-01-20 at 12.15.06 PMI’m not an incredibly patient person. I have a short fuse and I bore easy. It’s bad. I think it makes me good at a few things, like keeping people entertained and engaged, but makes me bad at other things, like coping with slow restaurant service.

Over the holiday break I turned away from the world a few degrees. I didn’t call anyone; no one called me. It was wonderful for a while. And then I thought: Why don’t I have anything going on? Why isn’t this person wondering what I’m doing or why does that one not seem to be interested in seeing me? There’s an underbelly to boredom that’s ugly indeed, because it reveals our neediness, our impatience, our hunger for attention.

But here’s what scares me most about boredom, and should scare you, too:

That I’m letting it dictate what I do. I get bored, restless, worried, anxious, and then I bail—not just on people, but on projects, situations. I lose interest and wherewithal and wander away. I make assumptions about it that aren’t true, all in the name of giving up because it fails to keep my interest. Right. If I subscribe to this theory, I’m saying that boredom shouldn’t happen, and that life only has meaning if I leap from peak to thrilling peak.

We give boredom perhaps a little too much power: We end up leaving instead of sticking around. Do something easy instead of something hard. Write off people who shouldn’t be written off.

Boredom has a role, no doubt. (Read what Bertrand Russell says about it in this piece on his book on Brainpickings). We need to get bored, to tolerate boredom, in order to appreciate real highs, real moments of deep, soul-filling satisfaction. But more than that, we need to wait out boredom for what’s on the other side.

On the other side of boredom is not just thrill and excitement. and it’s not busy. In fact, busy is not the opposite of boring, even though at first glance you think it is. And yet busy is what we do to combat it.

Sometimes to get past boring, you have to be the opposite of busy.

Our problem is not that we get bored (which our culture of distraction seeks to eliminate), but that we let it unseat us so easily. It’s that we aren’t willing to wait it out.

In Big Magic, a powerful and moving missive to creative souls, Liz Gilbert cites the wisdom of Buddhist nun Pema Chodron, who says that the biggest problem with people’s meditation practices is they quit too soon, or, “just when things are starting to get interesting.”

Gilbert writes, “they quit as soon as it gets painful, or boring, or agitating. They quit as soon as they see something in their minds that scares them or hurts them. So they miss the good part, the wild part, the transformative part–the part when you push past the difficulty and enter into some raw new unexplored universe within yourself.”

What’s happening is that we’re not hanging in there long enough, past the breakers of inhibition and self doubt. I’m guilty of this, and likely you are, too. The mistake is believing that interest, like an iPhone, starts to depreciate the moment you walk out of the store with it.

Not true. Interest is the opposite of depreciation. You pay back a loan with interest. And what Gilbert is saying is that it can grow in your own life, if you hang with it long enough. We have it backwards, just as we have passion backwards (a point I make in my TEDx talk, “Stop Searching for Your Passion.”)

You can’t “busy” away boring; you can’t distract away boring. Boring dissolves in the unblinking eye of attention…it’s just that we usually aren’t willing to wait that long.

Do you know how many times I’ve started to write a book, and got all excited about it, and then got bored? My problem was I burned up all my energy in the prospect of it, instead of allowing it the slow, steady burn of attention to ignite.

But I’m starting to change that. I’m not looking at just the goal, the prize, the finish line. I’m looking at the road. The road is far more interesting. It really is.

I am not trying to “finish” a book. I’m simply writing one. Don’t ask what it’s about, because I don’t know yet. And I find the most interesting part isn’t talking about or imagining, but doing it. Writing it. And seeing what happens.

So consider making yourself that promise this year:

That rather than flee from boredom too quickly, see it for what it is: discomfort, internal conflict, fear. Decide instead to wait it out, to stick it out. To stoke the fire of your energy enough to keep you going. Take a cue from Pema Chodron and be willing to see what happens after.  Because that’s what’s most interesting of all.

How Stuff Gets Written: Insight Into the Creative Process

How does stuff get written? Depends on who’s writing it. I know some writers obsess about their “process” but the biggest challenge for me is sitting my ass down and doing it.

The one thing that makes a writer different from anyone else, including people who “think” they’re writers? Writers write. Period.

This piece is actually part of a blog tour, thanks to Paula Rizzo, founder of, who invited me. And someone invited her, and I have invited three people. It’s kind of like chain mail for blogs. Except, instead of hand-copying 15 letters like you did in the 80s (whoever made that up should be shot), you get to hear from a range of bloggers on how they get their shit done.

What am I working on?

You’ve caught me at the tail end of a few projects: I just finished my first story for, and I have a piece due out on yourtango soon on matchmaker Hellen Chen’s “marry first, date later” approach. Oh–and this just went up, the latest installment of “Full Disclosure,” a column I write for DailyWorth, about how I got into a relationship with a financial planner, and why it’s totally worth it.

Of course, there’s this blog, and if you have one, you know—starting one is like adopting a puppy. Lots of fun, lots to recommend it, but it’s always hungry. So that’s a box that never gets fully checked.

So, here are the questions that are part of the blog tour:

How does my work differ from others of its genre?

Anyone can write ‘about’ a thing. I make it a point to take a side, stake a claim, have an opinion—one that makes you question your own. And I try very hard not to say a thing that’s been said a zillion times. In my own writing, I’ve found it the most rewarding and valuable to swim upstream, to see a different slant, rather than pile on with the same old, same old.

My strength has always been a clear, unequivocal voice, and a fresh, sometimes counterintuitive take on a topic that makes you think twice about what you think you know. I write a lot about relationships, and as you well know there’s tons of it out there. But I find 80% of it is recycled or straight-up trash. I don’t see why I should bother to say anything if I don’t have anything new to bring to the table. So, that’s my goal. Always.

Why do I write what I do? 

To relieve an itch. Because that’s almost always what I’m doing when I write something. Whatever’s been building up under my skin, a rash of ideas and opinions, and when I write about it, it’s like a good hard scratch. The kind that feels amazing.

Now, as to why I write the kinds of things I do? Because I’m trying to peer under the hood of not just other people’s behavior, but my own as well. I write to understand. I had an excellent professor when I was in grad school at Emerson College who said, “We write to become smarter than ourselves.” If you write something you’re already bored with, the reader’s just as bored. A discovery must be made. And that’s always what I’m doing.

How does my writing process work?

How does anyone start with a blank page and end up with stuff on it?  There are endless ways to do it, though to work, yours must involve a solid chunk of focused time.

It’s like getting into a pool: It feels cold at first (“brr, screw this”) and so you hop out, then you step back in, wade around. But until you can get IN that pool, all the way, submerge yourself, you can’t start really swimming. And that’s where the magic happens.

And so I, like a lot of writers, spend most of my time trying to GET to that point. And it does involve: loads of laundry, catching up on other shit, general avoidance, and then…relief. Once I surrender myself to it. Of course, a deadline helps.

That’s the hardest part of writing for me: Getting in that pool. Because once I’m in, the momentum takes over—that’s where you find your inspiration: from doing it. If you wait for inspiration to get in the pool? Forget it. Not happening. Some people tell you to clean your house first, get the distractions out of the way, go for a run, create an outline. Ok, fine. But nothing beats just sitting down for at least an hour, uninterrupted, to do it. Because once you’re in it, it’s actually hard to get out again.

OK. So I’m passing the baton now to some bloggers I think you should check out:

Becky Karush, a colleague, friend, and one of the most thoughtful and sensitive writers around. I recommend a read for sure.

Sandra Keros is a breath of fresh air in the healthy food and lifestyle world. She healed herself from fibromyalgia through changes in food and attitude. I also know she’s been exploring her own writing lately and I’m sure she has a lot to say about it.

Diana Castaldini is a talented young writer and editor who I’m currently working with, who recently went through a very serious health ordeal that has left her world changed. Her blog is called Thinking Less After Brain Surgery and is worth checking out.