How Weekly Writing Helps Me Lead

This post originally appeared in my weekly newsletter, BL&T (Borrowed, Learned, & Thought). Subscribe

Borrowed & Learned

Last Monday, I was on an onboarding call with a freelancer who recently joined the team full-time. He lives across the pond, so our days only partially overlap. As we wrapped up, he mentioned tuning in for our Quarterly Town Hall, which I was hosting later that day. He’d seen my Friday Update email the week before and didn’t want to miss it, even though it would be late on his end. I was taken aback and pleasantly surprised.

Moments like this make me glad I started writing in the first place. What began as a way to work through ideas has grown into a habit that strengthens how I lead and stay connected with the team. It’s a practice that started with this newsletter over five years ago.

I’ve always enjoyed writing. As a kid, I used to type short stories on my parents’ word processor, won a poetry contest, and somewhere out there, there’s an old Compaq Presario with a half-written “chapter book” still saved on its hard drive. My mom has always written in some way throughout her career, whether for the local newspaper or in grant letters for local government, so maybe that rubbed off on me. Still, despite loving it, I rarely made time for it as I got older.

I found this incredible ad of the exact word processor I grew up writing on.

When I was active as an artist, singer/songwriter, or designer, I always had some “portfolio” that showcased my projects and perspective. As my career shifted into leadership, I moved further away from creating directly and deeper into supporting and guiding others. Writing became a bridge between the two—an intentional space to think, create, and express ideas.

For better or worse, I’m the type of person who has to be all-in when I choose to do something. Rather than “trying to write more,” I committed to a weekly newsletter with an openness to see where it might go, but a dedication to showing up each week.

What I didn’t anticipate was how valuable it would become as a weekly checkpoint. Each issue gives me a moment to pause, look back, and make sense of what’s happening. It’s rewarding to hear from people who find something meaningful in what I’ve shared, too.

Over time, the blog where I post these newsletters has evolved into a personal archive: a collection of thoughts, experiments, and lessons learned along the way. I love revisiting old posts, remembering where my head was in different seasons, and seeing how things have evolved. It’s also become a way to share ideas with others, both personally and professionally, whether it’s something I’m working through or a concept that comes up in conversation.

Applying to Leadership

It wasn’t until I read “Smart Brevity: The Power of Saying More with Less" by Jim VandeHei, Mike Allen, and Roy Schwartz that I saw how I could apply this same writing practice in my role as CEO. The book tells the story of Mike Allen, who co-founded Politico and later Axios. Before either existed, Mike had a morning ritual. Every day at dawn, he sent an email to his bosses with the subject line “How we can rock today.” It was short, sharp, and set the tone for the day ahead.

Those emails evolved into Politico Playbook, a daily newsletter that became required reading in Washington. Eventually, Playbook grew long and dense, which led to the founding of Axios. Mike and his co-founders set out to make the communication easier to digest, and the Smart Brevity approach was born.

I read the book to learn how to communicate more effectively. I got that, but what I didn’t expect was a new perspective on writing as a leadership habit, and how it can create alignment and trust across a team. Around that same time, I revisited a passage from "Becoming Trader Joe " by founder Joe Coulombe that had stayed with me for years. Reflecting on the early days of his company, he wrote:

“In a white paper you try to write down everything you plan to do, and the reason why you think you should do it. That way, when things don’t work out, you can’t play the role of a Soviet historian and airbrush history… The other important use of a white paper is to circulate it to the troops, to engage their support and solicit their ideas.”

Both stories reinforce a simple truth. Writing isn’t just about communication. It’s about clarity and connection, for the writer and the reader.

Those ideas led to my Friday update emails (titled EOW), a practice I knew I could maintain because I’d already been writing this newsletter for years.

In Friday Emails: Keeping the Team Aligned with Real-Time Updates, written a few months after I began, I explained the shift:

“During the pandemic, we began weekly financial updates to the team, sharing revenue booked each week, new wins, and so on. These updates were born out of an uncertain time, and they helped keep the team informed. While data like this is important, it doesn’t tell the full story.

In my Friday emails, I can paint a clearer picture of what’s beginning, happening, or on my mind—everything from upcoming initiatives to new business wins and why they matter. As of a couple of weeks ago, these emails will replace the financial update.”

This Friday will mark the 60th week of this ritual.

Keeping At It

If that earlier conversation about the Town Hall reminded me why I started writing, the days that followed reminded me why I keep at it. We made meaningful progress, but several situations didn’t go as planned, requiring some team members to work long hours and make quick pivots. I was in NYC and tried to stay connected with the team as it all unfolded. At one point, that looked like hastily walking down 6th Avenue on Google Meet.

By Friday, I was back home. As I wrapped up my day, I found myself staring at a blank Notion page, ready to write like I always do. But this time, I could feel both the energy of what we’d accomplished and the weight of what hadn’t gone as planned. I tried to imagine where the team’s heads might be, what people were thinking or feeling after a week like this. Because I know that even if I can see the silver lining, they may not.

In Smart Brevity, the authors write, “You need to connect with your staff at least once a week. Resist the urge to blow off the newsletter.” It’s not just about consistency. It’s about facing each week as it is. When you sit down to write, you can’t hide from what’s happening. Or as Coloumbe puts it, you can't "airbrush history." You either face it or you don’t.

I always try to be real with the team. What’s powerful is that it often requires me to get real about what “real” even means.

What’s most important?
What’s the impact or potential outcome?
What’s happening next?

Especially when there are early signs of change or potential opportunities emerging, writing turns what might be a fleeting thought or a difficult moment into something we can learn from together.

Naturally, I leaned in. I acknowledged both the progress and the strain. I was upfront about a recurring issue and how we’re navigating it. I shared what I observed and how we’d have space to discuss as a team next week.

Later that evening, someone messaged me saying they appreciated that I addressed it head-on. No one else replied, which I’ve come to expect. It used to bother me, but over time I’ve realized that’s not the point. People often bring up these emails later, sometimes weeks after, and that’s how I know they’re getting through.

Like this newsletter, these Friday updates are another weekly practice that takes real commitment to maintain. But it’s weeks like these where I’m glad I do. Silence leaves people to wonder, grow frustrated, and ultimately create their own narrative. I know because I've been there. Writing gives me a chance to offer clarity and keep everyone connected to the same story.