I’m sharing my secret to finding pitch-worthy stories…

“Our love of stories is based on a less personal sort of eavesdropping: not only do we empathize with other people but we seek to refine our knowledge of the minds of others…taking a closer look at the ordinary can bring surprising insights.” 

— Oxford University Press

Most authors I know started by writing and pitching story ideas to newspaper, magazine or website editors. Many published authors, like me, still do. Writing shorter pieces, or starting your own blog or newsletter, is a nice break from writing a 170-page book.

Most publishers — not all, and it truly depends on what genre you’re in — want to see that aspiring authors have somewhat of a following. Getting bylines is a great way to get your name out there. (For a lucky few? Sometimes publishers and editors, especially if you’ve written a long-form magazine piece or have a themed blog, may read it and then ask you to expand on it for a book.)

My favourite Alice in Wonderland quote is “Why, sometimes I’ve believed as many as six impossible things before breakfast,” and like Alice, I really can come up with six story ideas before 10 a.m.

So, how do I come up with ideas and know if something is worth pitching? (Next week, I’ll tell you exactly how I pitch to editors and get them excited about a pitch!) 

Before I share my secret — a lifelong secret to a successful two-decade writing career, pitching hundreds if not thousands of ideas, seeing my byline in almost every major Canadian publication as well as the Los Angeles Times and the New York Times since I began writing for Post City magazines at 17 — I need to first talk about my insane love of eavesdropping. I consider it both a hobby and part of my job as a writer. And you should as well.

I think one of the most important traits — if not the most crucial — to having pitch-worthy story ideas is endless curiosity about everything and everyone. I really am endlessly curious about everyone. (This is why I know so much about my mail carrier. He’s obsessed with the Dave Matthews Band, has a son and is moving this month because his condo board complained about how loud he blasts music.)

I was recently talking on the phone to an author whom I’ve never met in person but who happens to be a member of the same golf club my boyfriend is. I told her to come say hi if the pool area ever opens up, that I’m the one with the earphones on. 

I also wear earbuds as a sign — isn’t this a universal signal by now? — for others to leave me be. I’m not being rude, I promise! It’s just that…I want to eavesdrop so, so badly.

(Cue me wondering if anyone will ever sit near me again!)

So I mostly wear earbuds to make it look like I’m listening to music or an audiobook. But I am not. I’m eavesdropping, because I’m so curious! The conversations I hear while pretending to listen to music are sometimes so funny, so entertaining and so unbelievable that I find myself biting my lip, praying, “Please, please keep talking. Not only am I still diagnosing you, but you’re giving me story ideas!”

The first time I remember eavesdropping was when I was a child. When I was supposed to be sleeping, I would put my ear to the vent on the floor to eavesdrop on my mother talking to her friends in the room below my bedroom. I felt this rush, like, “Oh, I never saw this side of my mom before!” It was…thrilling!

When I have date nights — or used to — and my boyfriend and I go out? Let’s just say I’m not always “present.” I just can’t help but eavesdrop on couples sitting near us. “They’re on a first date! I can tell because they’re asking each other getting-to-know-you questions,” I’ll say to him. Or, “That woman over there has sent back her wine glass three times!” Sometimes, I’ll just say, “Shhh! I’m trying to listen to the table behind me. They’re arguing. Oooh, this is getting good!”

Even during my second C-section, I swear, it felt like I was eavesdropping. As the doctor was cutting me open, he was telling other health-care workers in the room about a new restaurant. I wanted to scream, “Shouldn’t you be concentrating on my baby?!” equally as much as I did, “So, dude, what other restaurant recommendations do you have?”

As with the chicken and the egg, I’m not sure which came first: my love of eavesdropping or my intense curiosity, which really launched my writing career onto a whole other level.

When the National Post launched in 1998, I had been recruited and hired as a general reporter for the Toronto section. Within months, I was a columnist — generally considered a very prestigious, sought-after position. You get your name in bold with an illustration above your column (which, in my case, made me look like a horse).

Here’s how that happened. There was a full-on transit strike in Toronto. I decided to stand at a bus shelter for hours. I was so curious to find out how “nice” Torontonians were. A few stopped to tell me there was a strike, but the majority either laughed as they drove by or ignored me completely. I thought the fact that people were mostly rude was hilarious. Guess what? So did the second-highest editor, whom I hadn’t met, but he read my piece and thought it was hilarious, too! (Maybe because he was British?) 

I was not given a column because I had strong views on things; it was because my curiosity led me to do silly things. During the Toronto Film Festival one year, I called a few top restaurants pretending to be a publicist of an A-List actor. I was so curious to know what happens in a fully booked restaurant when a celebrity wants to dine there. It turns out that every single restaurant can and will make room for you…if you’re an A-list celebrity. That was fun to write about!

And if I’m not eavesdropping, my curiosity leads me to ask people questions. I know how much money the crossing guards near my house make a day because I asked. On a beach in Mexico, I met a flight attendant and asked what she does if there is an emergency mid-flight. I will not share this. I want you to fly with peace of mind, which I will never again be able to do, all because I was curious and asked and she was friendly and shared.

You’ll be surprised at how much people share if you ask a question and sit back and listen, which, if you want to find good, original ideas to pitch, you should want to do.

I learned from a plastic surgeon, whom I met while tipsy in a restaurant washroom after I complimented her boobs, about her 7-out-of-10 rule: if you think your boobs are at least a 7 out of 10, then you should not get a boob job. I rate my natural boobs a 7! (Never say never! I may have a boob job savings account.) I pitched and wrote a story on this 7-out-of-10 rule, all because I struck up a conversation, with a stranger, in a public washroom.

So what’s my secret to finding good stories to pitch? I have my own rule. 

I call it my 20-minute rule.

If I find myself in a conversation with someone, or a group of people, for at least 20 minutes, and I want it to continue? There’s a story there. If I’m eavesdropping on a conversation for at least 20 minutes without getting bored? There’s a story in there.

Why? 

First, I recognize I am no different, really, from anybody else. We all share many of the same universal struggles when it comes to relationships, lifestyle goals, parenting, what makes us happy and what makes us miserable. The only difference is that I’m a writer.

I always believe that if a conversation interests me for at least 20 minutes, it would interest others and it would be a topic that others would have an opinion on. I’m simply taking what I’ve heard — via eavesdropping or after asking a question and then having a conversation — then putting it down in a story pitch. And editors really, really like pieces that start conversations. 

I get most of my story ideas this way, by finding insights in what others see as just the ordinary. What other, non-curious people would think is mundane? I usually find it super interesting, based on my 20-minute rule.

When I lived alone, I once pitched and wrote an entire column about the rotisserie chickens sold at Loblaws for the National Post. I would see so many other single women also buying rotisserie chickens on Sunday evenings, like I was. I swear, to this day, that column remains one of the newspaper’s most read and one of the editor’s favourite lifestyle columns of all time. (You can ask her!) 

After eavesdropping on a conversation at a party, I pitched and wrote a story about this underground group of men who collected and traded high-end watches every weekend, with the headline “Watch Widows.”

A few months ago, I posted on Facebook a black-and-white photo of myself with my head down, writing how I was upset after having to end a friendship. Based on the number of people commenting on how they too had ended lifelong friendships and how hard it was, it was pretty clear that this was a story worth digging into and writing about — for a publication off Facebook.

I find social media a great way to find story ideas. It’s like eavesdropping with eyes. I pop into many Facebook groups to see what “non-writers” are asking each other, or discussing, or concerned about. When I see a thread with many varying comments and opinions, I know there’s a story in there, especially if I find myself, again, reading the thread for at least 20 minutes. 

Many wouldn’t think writing about whether fresh-made bagels should be toasted or not would be a pitch-worthy story. But I pitched and wrote about this after seeing a photo of President Joe Biden walking out of a bagel shop. See? Something as mundane as people’s preferences on fresh bagels turned into a very entertaining piece and started a deeply divided conversation…over bagels. 

Never underestimate what you may think is, on the surface, a nothing topic. Be curious! Ask questions! Strike up conversations! Sit back and listen! If you find yourself interested for at least 20 minutes? I can guarantee you there’s a story in there. 

The very latest story I pitched was to the editor at the Canadian Jewish News, who accepted my pitch about how often I’ve reached out to a rabbi instead of a therapist during this pandemic. 

Because I don’t believe I’m much different from anyone else, I thought, surely I couldn’t be the only one doing this. I wasn’t wrong.

If I’m doing it, saying it or thinking it, then others most likely are, too. It’s true that “taking a closer look at the ordinary can bring surprising insights.” Again, the only difference is that I’m a writer.

Now that you know about my 20-minute rule and the way I use it to find original story ideas, next week I’ll share exactly how I pitch to grab an editor’s attention. 

(P.S. I also have another 20-minute rule that I live by, in life, that has nothing to do with writing. If anyone is more than 20 minutes late after we set a time to meet? I’m gone!)

Until next time, flip your hair and flip the page (and start eavesdropping!).