January 19, 2021 15+ min read
The number of stories published on the internet every day, on blogs and magazine websites, is pretty unfathomable. On WordPress alone, 70 million blog posts were published every month of 2020. We live in a time in which having an online “voice” is vital to positioning yourself as someone worth listening to. Whether you’re an expert, thought leader, entertainer or simply a business owner trying to set your brand apart from the pack — you need to put yourself out there to show you’re an authority with something to say, or to engage with a prospective audience. However, the reality is that most people creating content are not trained writers, journalists or storytellers, so they haven’t been taught how to develop a story angle that feels fresh, or to structure a compelling narrative, or to write headlines that pull people in. On top of that, there are rarely editors vetoing or improving their articles — a sounding board relationship that is necessary for even the best writers. At publications where there are editors, they’re often expected to publish so many stories a day that it’s hard for them to find time to make each story the best it can possibly be. Not to be too bleak, but all of this has resulted in a kind of vast, sprawling junkyard of content.
So how do you write something that shines, and catches the light in the junkyard? How can you come up with stories compelling enough that people will click on them, read them, and then come back for more?
You don’t need to be a professional writer to publish something useful or interesting. But in order to come up with ideas that capture readers, you need to push yourself outside of your mental box. Good ideas start with learning to be observant and looking at things from a slightly different angle. That’s why journalists are always talking about finding the best “angle” for a story. Merely having knowledge isn’t enough to make people want to engage with you; you need an intriguing “in” for sharing the knowledge.
I went back through some pieces that performed particularly well on Entrepreneur.com last year and spoke with the authors about why they thought those stories got so much engagement. Based on their responses and my own experience as a writer and editor, I’ve come up with some suggestions for how you can make 2021 the year that you write something that people actually want to read.
1. Write about your life
The Entrepreneur editors are always asking our writers to mine their own experiences for interesting takeaways. Humans are nosy creatures, and we love to hear stories from other people’s lives — especially when they turn out to have some kind of lesson we can apply to work, because that makes us feel productive.
Exploring the minutiae of your day-to-day life is also, surprisingly, a way to set your stories apart from the majority of blog drivel. The chief mistake non-writers make is in not being specific enough and not anchoring their points in colorful, real world examples.
If you’re an entrepreneur, you might wonder what anecdotes from your personal life have to do with business advice. Well, businesses exist in the real world to serve human needs. That’s why good business stories are always human stories.
Plus, as I have written before, writing about your personal life can actually make you a better entrepreneur. My main argument, to quote myself (do as I say and not as I do — quoting yourself is in very poor taste!), is that, “Writing about yourself for others is a skill that requires remaining true to yourself while creating something your readers will find value in — a balancing act inherent to entrepreneurship.”
In the business media ecosystem, there’s a lot of talk about providing “value” to readers, and this is often interpreted as tangible, concrete business advice. But I would argue many stories that offer advice without the anchor of the author’s personal experiences feel vague, platitudinous, and untethered to reality. Not to mention boring.
2. Keep a notebook, and jot down weird little things that happen to you
Yes, the Notes app on your phone counts as a notebook! This recommendation is a page out of your average writer’s process. When I say you should jot down “weird” things, I don’t mean that time you were stopped at a streetlight and a clown jumped into your front seat and asked you to take him to Walmart. I just mean things that happen that make you say, “huh,” or “hmmm.” When a moment catches you off guard — maybe someone makes an odd comment in passing, or you have a reaction to something that surprises you, or you get into an awkward exchange that leaves you wondering, why was that uncomfortable? — it’s often worth breaking that experience down and looking at it more closely. These are opportunities to learn something about yourself. Plus, this kind of exercise in observation will likely make you a better entrepreneur, because so much of innovation is about being awake enough to identify small problems, and then finding ways to fix them.
One assumption many new writers make is that they need to tell the biggest, most “important” stories from their lives, assuming the weighty nature of those stories makes them worth reading. But often, those “formative” narratives are a lot to bite off. Oddly, if not handled carefully, they can come across as cliche, because many of the great human dramas boil down to the same kinds of heartbreak and suffering. Specific, passing moments in time, however, are often more contained, manageable, relatable and, surprisingly, original. When you describe a comment a boss made to you in a meeting, or a judgment you noticed yourself forming about someone in the grocery store, you don’t have to explain generations of family dynamics or explore every facet of your personality. You can just focus on the aspects of yourself and your surroundings at play in that one, single moment. But remember to characterize yourself — what you’re thinking and feeling. Action is great, but what really pulls the reader into a story is when they can truly see the world through your eyes.
3. Dig into trending news stories for relevant lessons
For most of us, there’s a limit to how much we can draw inspiration from our own lives. Luckily, the 24-hour news cycle is serving up an all-you-can-eat buffet of juicy material every day. There’s always something happening — whether it’s the latest tech company not living up to its IPO expectations or a public figure apologizing — that can be broken down and interpreted, or seen as a metaphor with unexpected lessons for entrepreneurs. Let’s be honest: Most of us would rather be reading up on the latest news or gossip than working, so if there’s a way to combine professional improvement with a conversation on current events, that’s usually a winning combination for clicks.
Case in point: Cheryl Snapp Conner wrote a story for us in June that trended on the site for days, “Kylie Jenner’s Removal From Forbes’ Billionaire List Underscores the Basic Rules of PR.” Snapp Conner took a top news story and pulled a lesson from the perspective of her expertise: public relations. It doesn’t matter if you love or loathe the Kardashians; polarizing celebrities stay in the spotlight because people who fall on either side of the love/hate divide can’t resist reading about them.
When I asked Snapp Conner why she thought the story performed so well, she said, “True stories that are surprising — even shocking — always make for good reading, and this is especially true when the story speaks to a principle that applies to all of us. Kylie Jenner’s PR team managed to get her on the cover of Forbes as the youngest female self-made billionaire, but she was later removed from the list when her company was acquired and its financials revealed another story. It was interesting to consider her PR team’s mistake. When the team touted their optimistic numbers to Forbes, nobody thought through (or perhaps even knew) that there was an acquisition coming…. It brought home the point that you should never lie or exaggerate to the press, because you don’t know how it may come back to bite you.”
4. Generally, people are interested in celebrities
There’s a reason we often put familiar faces on the cover of Entrepreneur. Readers want to know more about famous, successful, hot people. Personally, I don’t think the majority of celebrities have more insightful things to say than non-famous people. But familiarity bias means we’re more likely to pick up a magazine or click on a headline featuring someone we recognize and have been told (however subliminally) we should care about. Love it or hate it, you can take advantage of this by gleaning lessons from celebrities’ successes — and their failures, as Snapp Conner did with Kylie Jenner.
Maybe you even have access to a public figure and get the opportunity to ask them some questions. Danielle Sabrina did a story for us in December called, “NFL Superstar Bobby Wagner On Creating a Vision Off the Field.” The story was a hit with readers, and Wagner was asked about it in a press conference after a game. Sabrina says there’s a good chance this happened because, “I shared the article on social and tagged the local media outlets that I knew would be at the Seahawks game. I also tagged other players from the Seahawks in the social media post that I knew had similar entrepreneurial interests in hopes they would share it as well.” More generally, Sabrina says, “The article was engaging because I believe people are curious about how the minds of professional athletes work in regards to when and how they decide to invest their money into business ventures.”
5. People want to hear about vulnerable moments
Apart from her celebrity, another likely reason the Kylie Jenner story did so well was that she was in the midst of a public humiliation. Whether you see it as schadenfreude, rubbernecking or genuine empathy, readers love hearing about people who are going through or have been in a tough spot. It doesn’t come from an entirely bad place; people are just more relatable when they’re down. “Using your own or a highly public’s figure’s most vulnerable moment as a lesson to entrepreneurs is both interesting and helpful reading,” Snapp Conner says. “Bragging about yours or someone else’s finest hours — not so much.”
In the world of entrepreneurship, there’s definitely a culture of obnoxious bragging (advocates call it “selling yourself”). There’s nothing wrong with touting your accomplishments, but editors and readers alike tend to tune out pitches or stories that keep hitting the same self-congratulatory note. Not only are stories of perpetual success boring; they’re also dubious. When a story lacks humility — which only comes from working through failure, or being open about current struggles — we’re less likely to trust the narrator. Readers often respond powerfully when authors share about mental health struggles, for example, or doubting themselves.
6. But people also love to hear about overcoming failure
You absolutely do not need to wait to tell stories of failure until they’re tied up in a pretty bow and delivered with a “moral to the story.” That said, stories of people who have gone through hell and come out the other side are pretty reliable crowd-pleasers. One thing I’ve observed about the best of these stories is that they are not usually just about working hard — they’re about working hard on yourself and shining a light on things you were wrong about.
This was certainly true for my top-performing story last year: “‘Max’ Brenner Was Pushed Out of His Own Company, Financially Destroyed, and Banned From Making Chocolate for Five Years. But He Learned: ‘Hell Has Benefits’.” I think this story got so much engagement because a) the tale itself was quite dramatic, and b) Brenner really put himself out there in our interview. He talked candidly about mistakes that cost him a multimillion dollar company and what it was like to lose absolutely everything. He talked about the humiliation of going from being a big shot to needing to call up friends to ask for help, and he spoke about the harrowing work of reconsidering his whole personality. Ultimately, his journey through that dark valley led him to his real passion. And the lessons he was willing to share earned him hundreds of thousands of readers.
Along similar lines, another story that did really well for us in November was “The One Thing Instacart’s Now-Billionaire CEO Changed After 20 Failed Startup Ideas,” by Nick Wolny. Although Instacart founder Apoorva Mehta’s losses might not have been as devastating as Brenner’s, his story is also about pushing through many failures to eventually find success in the form of his real passion. Wolny thinks the biggest takeaway from this story was the repeated failure. “Researching Mehta made me realize I’m not failing enough,” he told me. “It feels like we can’t fail as entrepreneurs, and that all we ever see is success stories happening at warp speed. But successful leaders fail all the time. Reading up on how Mehta failed 20 times in a two-year period inspired me to be more agile and try new things, and it seems like other readers felt the same way.”
7. Be contrarian; reconsider assumptions and think against the grain
One unique article that killed it for Entrepreneur was written by Scott Greenberg. It was called, “OK, Maybe You Should Run Your Franchise Like a Circus.” The story was a follow-up to another article Greenberg had written in October called, “Stop Running Your Franchise Like a Circus.” After the original story ran, Greenberg was contacted by an actual circus ringmaster who took umbrage at the cliche characterization of a circus as a chaotic freakshow. In fact, the ringmaster argued, running a circus required immense coordination, attention and organization.
Greenberg was wise enough to take this correction in stride and make this interesting — and more fact-based — perspective work to his advantage. He interviewed the ringmaster, Carl Barltrop, and what emerged was both an interesting glimpse into a little-known profession and a genuinely instructive guide to running a business like a highly complex production with many moving pieces.
“In addition to the ideas within the piece, many people commented on it as an apology and mea culpa,” Greenberg said, when I asked why he thought the readers loved it so much. “They appreciated my restoring dignity to an industry (the circus) that is often ridiculed. I think ultimately readers prefer positive examples that celebrate people rather than cautionary tales that point out flaws. That speaks to our deep need for more than information; we also need motivation.”
If you ever discover you’ve gotten something wrong, don’t push it under the rug and pretend it didn’t happen. Grapple with the new information in order to shed more light on what you’re trying to understand or explain. What is true might not always line up neatly with your assumptions, but being open to thinking about things in a new way will always make your work — and its message — more compelling. And if you’re ever stumped for provocative headlines, think about a tired saying or worn-out piece of advice you’ve heard recently. Then try making an argument for why it’s wrong. Don’t argue for something you don’t believe in, but play around with interpretations.
8. Write headlines that offer “small tweaks for big results”
Humans are crafty, ingenious creatures, but we also kill for shortcuts. Readers pounce on the hope that there’s a super simple, easy, fast fix to all of their problems, and they hope to achieve these results with very little effort or financial risk. We are always optimistic there’s a magic formula out there — and every now and again, there just might be (but no, there will never be a single healthy or easy trick to lose 10 pounds in one week).
I am definitely NOT advising that you write misleading headlines that promise unrealistic results. These kinds of click-baity stories make up a lot of the trash in the content junkyard. But I do suggest that you think carefully about your story’s advice, or discovery, and come up with wording that makes the takeaway more accessible.
Nick Wolny describes this headline positioning as “small tweaks for big results,” and he thinks it’s another reason his story (“The One Things Instacart’s Now-Billionaire CEO Changed After 20 Failed Startup Ideas”) did so well. The “one thing” Mehta did differently when founding Instacart was to “create a business that solves a problem you’re passionate about,” Wolny says, “Not exactly earth-shattering advice.” But the phrasing makes the concept sound simpler, and more doable. “Many of us want to improve, but a list of 100 steps sounds intimidating,” Wolny says. “I notice having just a few action steps or even just one action step feels more surmountable, and therefore gets more clicks and engagement. I also think this headline did well because readers know what they’re getting themselves into when they click.”
Similarly, last July Neil Gordon wrote a story for us called “How to Craft an Elevator Pitch that Gives People Chills in Under 20 Seconds.” Our readers loved it, and the story trended for days. What Gordon is advising in the article does involve effort, but he thinks the draw for readers was, largely, the big promise in the headline.
“Perhaps the most critical element in writing something that people want to read is your content’s headline,” Gordon says. “You could write the most compelling, empowering piece of writing that’s ever been written, but if you give that piece a terrible title then no one will ever even look at it — let alone share it with others. I think that ‘How to Craft an Elevator Pitch that Gives People Chills in Under 20 Seconds’ works because it offers a powerful promise (an elevator pitch that gives chills) within an unlikely context (it can happen in only 20 seconds). This tension between what’s being promised and what actually seems possible aroused enough curiosity to make people click.”
9. Find an editor, or at least a trustworthy reader, for your work
There is no such thing as a perfect first draft. The most talented writers write, and then rewrite, and then rewrite again, honing and clarifying their sentences until the reader glides effortlessly toward the intended message. One of the best ways to edit your own work is to read it out loud.
But writers also need editors and readers — to point out confusing phrases that muddle meanings or the chronology of a scene, to show them the gaps in their logic, or to let them know if a punchline is landing or a headline is falling flat. If you really want to improve your ideas and writing ability, hire an editor to work with you. If you can’t do that, at least seek out a small group of readers you trust. If they’re members of your intended audience, even better. Having readers that you can test-drive or workshop stories with is an integral part of the writing process.
Related: Easy Reading Is Damn Hard Writing