Hey writers, you should be more vulnerable

It makes you more attractive than you realize

Earlier this year, I wrote this piece in the hopes that it would be published in a big fancy publication with a much larger audience than mine. Annnnddd yeah, that never happened. In my writing coaching practice, I’ve wanted to point people to the concepts in this essay many times, so I’m publishing it anyway. I even left the first bit in since technically you’re the biggest audience I’ve ever written for on my publication.

Enjoy!

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I don’t know if I can pull this off. This might be the biggest audience I’ve ever written for. Will my words resonate with you at all? Or will I just sound like a weirdo? And why are my palms so sweaty right now? It’s not like you’re sitting here watching me type into my laptop at my dining room table. Now that would be weird (and a little crowded).

Every week, for more than two years now, I’ve been sharing memoir-style stories that are extremely specific to my life—stories about my dad passing away, raising a daughter who has cerebral palsy, and questioning if I’m an artist. You’d think that consistently sharing the details of these types of experiences would give me some level of confidence to write with authority on the subject of vulnerability. But no, as almost anyone—who’s not a narcissist—who has put their ideas out into the world can attest, it doesn’t really work like that.

There’s still this lingering doubt—you might call it imposter syndrome—in the back of my mind. A voice that says, Who do you think you are? You’re not some expert on human psychology or whatever the hell this essay is supposed to be about. People are going to laugh at how incompetent you are. You should close your laptop and go watch Netflix instead.

Yet I keep writing. Because I know that if I share my story, especially the nitty-gritty details and emotions, you’ll see yourself in my words. In fact, you probably already have.

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It was September 2020 and I had just launched my newsletter. I was feeling that mix of trepidation and excitement that new creators are familiar with. Shortly after the launch, I picked up a copy of the memoir Love Warrior by Glennon Doyle. My wife recommended it because she had read some of my early drafts and my writing style reminded her of Doyle’s. Side note: I didn’t realize how much of a compliment that was until I began reading Doyle’s work and now it lives as a testimonial on my about page.

By page ten, I was hooked. Doyle’s prose wasn’t filled with flowery language or self-aggrandizement. Instead, it was arresting and brutally honest. But the thing is, she and I have little in common. Of course, there’s the obvious: she’s a woman and I’m a man. Beyond that, she wrote about her struggles with alcohol and drug abuse, getting pregnant and therefore needing to get sober, and dealing with a cheating spouse—none of which I have any experience with. And yet, the book resonated with me as a human being trying to figure out how to exist in this complex and often unfair world.

I didn’t judge her for the choices she made. Instead, I saw an imperfect person trying to make sense of her choices and work to improve herself. She made me feel the pain and loss she felt in her low moments. And then she would hit me with a quotable line or paragraph—one that could be impactful on its own merits but carried even more weight when it was shared within the context of her story.

“Grief is love's souvenir. It's our proof that we once loved. Grief is the receipt we wave in the air that says to the world: Look! Love was once mine. I love well. Here is my proof that I paid the price.”

The source of my grief was different—seeing my daughter born not breathing, her needing to be resuscitated and intubated to survive. And that was just the beginning. Doyle’s words rang universally true for me, despite our dissimilar circumstances. And she inspired me to continue sharing my story. 

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Morgan Housel is the bestselling author of The Psychology of Money. The book is filled with essays about how people relate to money in often surprising and counterintuitive ways, buttressed by his decades as an investor at Collab Fund.

But I’m going to talk about something else he wrote—something much more personal and vulnerable.

In “The Three Sides of Risk”, he tells the tragic story of when two of his best friends died in an avalanche while skiing at the way-too-young age of 17. Earlier in the day, Housel and his two friends had skied down the same out-of-bounds side of the mountain where the avalanche occurred. But he decided to sit out the second fateful run. It was a decision he didn’t put much thought into—he just didn’t feel like skiing again—but it had a profound impact on his life. Not just the fact that he’s, you know, still alive 20+ years later. He believes it had an effect on his investment strategy, as well, causing him to be more cautious and conservative, often opting for the more tried and true investment choices rather than the flashy, higher-risk/reward ones.

“My risk tolerance plunged after Brendan and Bryan died. I broke my back skiing (no nerve damage) a few months later, which crushed it even more. I haven’t skied much since. Maybe ten times in the last 15 years. If I’m honest, it scares me.

I’ve been risk-averse in other areas of life ever since, too. I drive the speed limit. I obey the seatbelt sign on airplanes. I invest in index funds.”

The investing portion of the post isn’t all that long; it’s almost an afterthought. Housel’s investing maxims on risk are fine on their own and no doubt helpful for a particular set of readers. Yet his heartbreaking story makes them much more impactful than they would be on their own. 

I’ve shared Housel’s post with many writers at Foster. As a core team member, I’ve seen dozens of writers who start off wanting to share their insights on business, tech, and other topics that don’t necessarily feel emotional. But as they quickly find out, including examples from their lived experience is the key to taking their writing to another level. And doing so also has the nice side-effect of drawing in more followers, subscribers, and customers, because they’ll relate to the universal human emotions we all know and feel. The examples don’t need to be nearly as intense or dramatic as Housel’s, but the more specific and relevant they are, the more they’ll attract the right people.

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The founders of Every, Nathan Baschez and Dan Shipper, have openly shared how they routinely go to couples therapy together. No, not as a romantic couple, but as co-founders. 

In an article written about them, Shipper explained why they go to a therapist as opposed to an executive coach:

“If you feel like what you really need is the tactical business stuff, get a coach. But our experience is that 80 to 90% of the stuff is actually emotional and about interpersonal relationships and yourself.”

I remember hearing about it and thinking it was a novel way to address the issues that invariably come up when you work closely with another person, especially when you’re attempting to build something from nothing. As someone with many years at early-stage startups under my belt, including co-founding one, their story caused me to reflect on my own experiences. 

Importantly, I never once thought less of them. If anything, I wanted to root for them even more than if they had only shared things like their impressive subscriber growth, month-over-month revenue, etcetera. Instead, they bravely shared their struggles, and that made them more relatable as fellow humans.

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Sharing more vulnerably can be risky business, though. It’s not always possible to share all the intimate details of your experiences—sometimes there are bosses or spouses involved, or legal grey areas and the like. Even when you set aside those types of concerns, many people have a deep-seated fear of sharing their personal lives. That fear is wrapped up in all sorts of different emotions, including shame, embarrassment, guilt, imposter syndrome, or even worrying about being perceived as too braggadocious. And those are just about the stories themselves. There’s also the concern that sharing a personal story will fall flat and won’t resonate with the audience, leaving you to pick up the psychological wreckage.

This certainly isn’t an invitation to simply copy and paste your diary onto the internet. That’s not the point. The idea is to bring your audience—be they readers, viewers, or even customers—into your world and show them who you are, why your point of view matters, and, ultimately, why they should trust you. 

Most online content is ephemeral. Unlike the vapid tweet threads or TikTok videos that we scan and quickly forget, stories laced with deep emotions are the ones that stick with us and prompt us to share them with others. The goal should be to make something that nestles in and creates a permanent home in someone else’s brain.

There’s an art to sharing personal stories. It can be difficult, emotional work. And it takes time and reps to get better at it. One of my favorite things about Foster is how we support writers through this journey. We do so via our compassionate professional editors and our cohort-based seasons where we lead writers deep into their individual truths and writing practice. I’ve seen this vulnerable work transform people, sometimes even bringing them to tears. They emerge from this exploration having shared more of themselves. And they feel the catharsis of putting it out in the world and the love they receive back when it inevitably connects more profoundly with their readers. It’s powerful stuff.

From my experience as a writer, editor, and coach, I’ve learned that there’s a difference between the stories we tell others and the stories we tell ourselves. When those stories collide into one and we bravely tell the singular truth that others would keep to themselves, that’s when our most relatable stories are created, forming our deepest connections with others. Because they’ve felt the same way before.

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