One thing I hear fairly often from people in leadership roles (whether it’s a founder, a CEO, a solopreneur, etc.) is that they struggle with writing about their personal experiences in a compelling, story-driven way.
They’ve had lots of interesting ups and downs, gained first-hand insight into complex situations (good and bad), and have a lot of fun stories to tell, but they never quite seem to get the words out of their brains and onto the page so they can be shared.
For some, it’s purely a time issue. (In these cases, I say: Record a voice note talking through the story and hand it off to a writer who can build out a polished narrative via a service like Content Remix!)
For others, it’s that they don’t feel confident in their writing abilities and don’t even know where to start as far as constructing the story arc in a compelling way. The blank page is just too intimidating.
And then for others, it’s a matter of: “I can write about this, but my draft needs a lot of work. I need help getting my writing to a place where I’d be comfortable sharing it in a public space!”
Today, I’m going to share a few tips and tricks in hopes of addressing these roadblocks that get in the way of smart folks sharing their insights in a written format.
Why? Because we NEED to hear these stories. Especially when they’re coming from founders/leaders within underrepresented groups.
Let’s get into it, shall we?
1. First: Structure.
Great storytelling typically follows a fairly basic structure.
If you’re just wanting to tell a story, you’d use a narrative arc.
This arc is made up of the events in your story—the sequence of occurrences in the plot—and the peaks and plateaus that set the pace. A good arc engages your readers from start to finish and delivers a satisfying conclusion.
There’s a relatively calm beginning, a middle where tension, character conflict, and narrative momentum builds to a peak, and an end where the conflict is resolved.
This structure works well for stories about lessons learned, obstacles/challenges overcome, etc.
Example theme: I wasted $10,000 on a marketing course. Here’s what I learned (and what I’m doing differently now.)
If you’re going for a more journalistic/content marketing style of writing, you’d use the inverted pyramid approach.
In this format, the most important information (or what might even be considered the conclusion) is presented first. The who, what, when, where, and why appear at the start of a story, followed by supporting details and background information.
This structure works well for stories about growth hacks, successes/wins, etc.
Example theme: Key takeaways from raising $2M in VC funding for X company
2. The outline
Once you’ve decided on the storytelling structure you want to use, next it’s time to start mapping out the elements of your story so they fall in the right places. This will make up your very rough outline as you get started.
Sometimes it’s helpful to think of this as a timeline.
Start writing down bullet points of how the story unfolds (in your mind) from start to finish. Include as many details as you want here; you can weed things out later on.
Just get it down on the page so you know what you’re working with.
3. Adding depth
When your outline is started and you see the basic flow of the story structure, from here, you’ll want to add some depth and color that will make your story interesting for readers.
A play-by-play that stays at surface level isn’t all that compelling for readers. They want to know:
How did you feel (internally) at different points in this story?
What were you stressed about, and what kept you up at night?
What were you excited about (and why?)
Note here: Try to go deeper than writing something like “I was excited!” or “I was so nervous!” as these basic types of sentences still feel fairly surface-level. Remember to show, not tell. What made you excited or nervous? What was driving those emotions? What was on the line?
This is an opportunity to build an emotional connection with the reader, so be fairly transparent about what was happening behind the scenes.
No one likes to root for the superhuman. We want to read stories from real, fellow human beings who worry and fail and are constantly learning (just like we are.)
Be a little bit vulnerable and open up for your readers so they can peek inside your brain.
4. The draft
If you’ve followed the steps to this point, you should have a pretty robust outline that can be turned into a draft fairly easily. It just needs to be built out. This is where you can add in your personalized writing voice so it sounds like you’re telling the story to each individual reader face-to-face.
Another good idea: Add in some images for context. If you snapped photos that relate to different parts of the story you’re telling and have images of the people/places involved, add them! This visual insight adds another layer to your story and makes your story even more authentic and real for the readers.
As far as word count goes, there are no hard and fast rules here. Trust your gut and deliver the core details of the story without getting too rambling or tangential. A good editor or a second set of eyes on your draft is always a good idea if you’re not sure how to gauge that.
5. Publish and repeat
The last step: Hit publish and share your story.
Maybe this is on a blog, a newsletter, a Twitter thread, an Instagram story…the format is up to you (and repackaging it into multiple formats is always a good idea for getting more eyeballs on what you’ve created.)
The bottom line here is: Don’t get hung up on your draft being perfect. Perfect is the enemy of done. You’ll learn and improve along the way as you continue to practice your storytelling skills.
Heck, even I look back at things I wrote five years ago and think, “Ugh, cringe!” But that’s part of the learning process. You can’t get better unless you keep at it. Also: You’re probably your own worst critic. No one is judging your story as harshly as you are.
All that’s left to do now is to start.
Got stories? Let’s hear ‘em. Get to writing, friends. This eBook I put together has even more writing lessons that'll help jumpstart your efforts.
