Lessons from Brie Wolfson

Brie Wolfson, a prominent figure in the tech and creative industries known for her work at companies like Stripe and Figma, has shared a wealth of knowledge on company culture, writing, creativity, and personal growth. [1][2]

On Work and Career

On the nature of great work: "So much of great writing and great anything is just about Obsession. and when you're in your zone of obsession. everything. looks interesting." [3]
The importance of rollout: A key lesson from working with Stripe's former COO, Claire Hughes Johnson, was that "the rollout counts for just as much (sometimes more!) than the content of the work." [2]
Bringing people along: Always ask, "And how are we going to bring people along?" Accounting for stakeholder perspectives not only ensures work is well-received but also improves the work itself. [2]
On leadership: "All the great leaders that I've worked for they will like get in the shit and like have something to say and be opinionated." [1]
Clarity of vision: Great leaders have a clear vision and are obsessed with the details, which is exciting and empowering. [1]
"Flounder Mode": Coined from her time with Kevin Kelly, this is a way of building a career by following your curiosity, which may seem winding and weird but can be highly effective. [4]
The value of writing at work: "I've come to believe that Stripe's culture of writing is one of the organization's greatest superpowers." [5]
Writing for clarity: "I very much think through my keyboard. I cannot think about anything clearly until it's written." [6]
Internal documentation as a superpower: The vast library of content produced for internal eyes only is where the "real magic happens" in a company's writing culture. [5]
The scrapbook of pride: Keep a collection of things you're proud of—screenshots, emails, feedback. It's a joy to look back on and provides a real pulse on what you enjoy. [2][5]
On leaving a company with a strong writing culture: "We all report feeling a bit lost and disconnected from their colleagues without it." [5]
The downside of a writing-heavy culture: There can be a "weird relationship between thinking and doing," with a risk of getting over-rotated on thinking and pontificating. [7][8]
Code settles arguments: Sometimes it's better to "just settle the argument or like the principles friction through just doing the thing and seeing." [7][8]
On finding your niche: Wolfson realized through her "brag document" that analytical work didn't appear, which led her to a different career path. [5]
The importance of taste: "If you refine what you like and then you find a way to get it, you are just at harmony in the world." [1][9]

On Writing and Creativity

Writing to clarify your own thinking: "The kind of writing I've found that I do is mostly to clarify my own thinking on something." [9]
Writing for a high-expectation stranger: Imagining you're writing for someone you admire pushes you to articulate your ideas more clearly. [9]
The "Tuning Fork of Resonance": Discussing ideas with others acts like a "tuning fork" to see what resonates and helps refine your work. [9]
Embrace "Defiant Joy": Be "defiantly and joyfully" yourself in creative work, pushing back against norms with optimism. [9]
Writing less is more: "The cardinal mistake...is trying to write about too much...the narrower your scope the easier it is to write about that thing." [7]
The power of obsession in writing: When you're obsessed with a topic, everything about it seems interesting, but it's crucial to remember what the audience needs to know. [3]
Writing as listening to yourself: "To me writing is very much just like a practice in listening to myself. and like trying to put the microphone close to things that I think like should get more attention." [7]
The challenge of capturing your full personality in writing: "There's certain emotions that I find it hard to capture in writing yeah that are totally part of me." [7]
The "High-Low" of content: Great content often mixes highbrow, aspirational material with more accessible, sometimes "trashier," lowbrow stuff to keep it engaging. [7]
Distilling ideas takes time: "I would've written you a shorter letter, but I didn't have the time. It's really hard to distill ideas...and it's really worth it." [6]

On Personal Growth and Life

On self-reflection: "It's a life's work to bridge the inside you and outside you." [10]
The six-month rule: "Everything will be different in six months." [10]
The value of stillness: "Sit still." [10]
The power of asking: "Everyone wants to help. Ask for what you need." [10]
On goals: "Write your goals down. Cross 'em out. Write new ones." [10]
Intergenerational friendships: "Have a real friend in the generation above and below you." [10]
Expressing admiration: "Email the people you admire and tell them that. It'll make their day. And it'll make yours when they write back." [10]
Earnestness over snark: Choose sincerity over cynicism. [10]
The value of small check-ins: "A light check-in now is better than a longer check-in never." [10]
Learning to cook: "Learn to cook a few things really, really well." [10]
Private memories: "Store memories somewhere private. Rifling through a shoebox of stuff beats scrolling through your Instagram any day." [10]
On being the generous one: "Everyone thinks they're the more generous one in the relationship." [10]
The joy of a small group: "A small group cranking is bliss." [10]
The cure of a drive: "A drive with the windows down and the music too loud can cure a whole lot." [10]
On feedback from friends: "Ask for feedback from friends like you would your colleagues." [10]

On Company Culture

Culture is for everyone: At Stripe, the trope that "company culture was up to everyone to build" was put into practice. [2]
The magic of a strong culture: A "tingly feeling that something magical was happening" at Stripe led to diligent note-taking on how company cultures come to life. [2]
Onboarding as a cultural cornerstone: The employee onboarding process at Stripe was impressive for its focus on an employee's contribution to the company culture. [2]
The role of the internal communicator: A great internal communications professional is a "company poet/scribe," documenting lore and articulating the company's pulse. [2]
Marriott's "First 10 Minutes": An obsession with the guest's initial experience, from greeting to check-in, as a key cultural principle. [3][7]
Transforming organizations: "I think we've got a shot at transforming organizations into the incredible sources of community and self-actualization they should be." [11]
The power of caring: What stood out at Stripe was that "people really cared about the work." [11]
Reciting company documents: At Stripe, "Employees could recite content from iconic company documents verbatim —sometimes years after they were originally published." [11]
A cohesive force: An open email policy where anyone can read communications from across the organization acts as a "really good cohesive force." [7]
The Kool-Aid Factory: Wolfson's consultancy, aimed at helping organizations "approach company culture with the care and rigor they treat building products." [10]

Learn more:

Lessons from Brie Wolfson

On Work and Career

On Writing and Creativity

On Personal Growth and Life

On Company Culture

Written by Antoine Buteau

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