Brie Wolfson is Chief Marketing Officer of Positive Sum and Colossus. She previously worked at Stripe, where she helped launch Stripe Press, and at Figma, and has written about the culture at Cursor. — Dialectic conversation with Brie Wolfson (page and lessons).

Infographic for "Lessons from Brie Wolfson".

On Work and Career

  1. On Obsession: Wolfson: "so much of great writing and great anything is just about obsession. And when you're in your zone of obsession, everything looks interesting." — The Art of "Taste" with Brie Wolfson (video transcript).
  2. 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." — Culture Creator: Brie Wolfson - by Julia Levy - The Switchboard.
  3. 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. — Culture Creator: Brie Wolfson - by Julia Levy - The Switchboard.
  4. On Leadership: Wolfson says the great leaders she has worked for "have something to say and be opinionated", not just leaving the details to someone else. — Good Work: Brie Wolfson on company culture, creativity and her own path (video transcript).
  5. Clarity of vision: Great leaders have a clear vision and are obsessed with the details, which is exciting and empowering. — Brie Wolfson: Building Great Company Culture, Finding Your Creativity, and Carving Your Own Path - YouTube.
  6. Flounder Mode: "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. — Brie Wolfson: Learning to Love Flounder Mode from Kevin Kelly (Hyperlegible 013).
  7. 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." — Writing In Public, Inside Your Company - The Kool Aid Factory.
  8. Writing for clarity: "I very much think through my keyboard. I cannot think about anything clearly until it's written." — From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson - First Round Review.
  9. 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. — Writing In Public, Inside Your Company - The Kool Aid Factory.
  10. 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. — Writing In Public, Inside Your Company - The Kool Aid Factory.
  11. On leaving a company with a strong writing culture: "We all report feeling a bit lost and disconnected from their colleagues without it." — Writing In Public, Inside Your Company - The Kool Aid Factory.
  12. On Thinking Versus Doing: Wolfson: "you can get a weird relationship between thinking and doing." She adds that "sometimes actually just doing it is where your answers are." — The Art of "Taste" with Brie Wolfson (video transcript).
  13. On Code Settling Arguments: Wolfson recalls a Facebook value that "code settles arguments", where you can "just settle the argument or the principle's friction through just doing the thing and seeing." — The Art of "Taste" with Brie Wolfson (video transcript).
  14. On finding your niche: Wolfson realized through her "brag document" that analytical work didn't appear, which led her to a different career path. — Writing In Public, Inside Your Company - The Kool Aid Factory.
  15. 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." — Brie Wolfson: Building Great Company Culture, Finding Your Creativity, and Carving Your Own Path.
  16. On Building craft and taste: You cannot simply think your way to mastery; it requires spending time in the weeds doing the repetitive work until your hands develop an unconscious competence. — Dialectic with Jackson Dahl
  17. On Fork-shaped" leadership: The best leaders do not just delegate; they traverse between high-level vision and granular execution, willing to dive deep into details like copy edits without losing the big picture. — Dialectic with Jackson Dahl
  18. On Truthful marketing: Effective marketing cannot be faked; it requires a foundation of true craft and substance, making honesty the only approach that works at scale. — Dialectic with Jackson Dahl
  19. On Finding leverage in the overlooked: You can earn the freedom to take risks and explore by consistently delivering excellence in your core responsibilities, often finding value in neglected projects. — Dialectic with Jackson Dahl
  20. On Flounder Mode vs. aimlessness: To prevent curiosity-driven exploration from devolving into aimlessness, you must actively transform the things you consume into tangible output. — Not Boring
  21. On Execution and growth: "growth can hide poor execution." — Colossus: Inside Cursor

On Writing and Creativity

  1. 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." — Brie Wolfson: Building Great Company Culture, Finding Your Creativity, and Carving Your Own Path.
  2. Writing for a high-expectation stranger: Imagining you're writing for someone you admire pushes you to articulate your ideas more clearly. — Brie Wolfson: Building Great Company Culture, Finding Your Creativity, and Carving Your Own Path.
  3. On the Tuning Fork: Wolfson, on a metaphor she credits to Kevin Kwok: "Twitter is having a tuning fork and seeing what resonates." She says "I definitely processed things through talking them through with other people". — Good Work: Brie Wolfson on company culture, creativity and her own path (video transcript).
  4. On Becoming Yourself: Wolfson: "I'm becoming joyfully and defiantly myself". — Good Work: Brie Wolfson on company culture, creativity and her own path (video transcript).
  5. On Writing About Less: Wolfson: "the cardinal flaw, the cardinal mistake that Write of Passage students make is trying to write about too much." — The Art of "Taste" with Brie Wolfson (video transcript).
  6. On What the Audience Cares About: Wolfson on writing about a topic you are obsessed with: consider what the "audience is going to be interested in versus what you as someone who's obsessed with the whole world of it is obsessed with." — The Art of "Taste" with Brie Wolfson (video transcript).
  7. On Writing as Listening: Wolfson: "To me, writing is very much just a practice in listening to myself and trying to put the microphone close to things that I think should get more attention." — The Art of "Taste" with Brie Wolfson (video transcript).
  8. On What Writing Can't Capture: Wolfson: "there's certain emotions that I find it hard to capture in writing that are totally part of me." — The Art of "Taste" with Brie Wolfson (video transcript).
  9. On High-Low: Wolfson describes the magazine idea of high-low: it lets you "titillate our aspirational qualities", while being anchored by "maybe trashier stuff that actually is somewhat juicy and salacious too". — The Art of "Taste" with Brie Wolfson (video transcript).
  10. 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." — From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson - First Round Review.
  11. On Constructive editing: The best editors do more than reject work; they identify the specific changes needed to improve it, helping the creator reach the finish line. — Dialectic with Jackson Dahl
  12. On Easing into your craft: The ultimate goal of your work doesn't have to be fame; it can simply be developing a quiet confidence in your ability to produce excellent work without unnecessary stress. — Dialectic with Jackson Dahl

On Personal Growth and Life

  1. On self-reflection: "It's a life's work to bridge the inside you and outside you." — Brie Wolfson.
  2. The six-month rule: "Everything will be different in six months." — Brie Wolfson.
  3. The value of stillness: "Sit still." — Brie Wolfson.
  4. The power of asking: "Everyone wants to help. Ask for what you need." — Brie Wolfson.
  5. On goals: "Write your goals down. Cross 'em out. Write new ones." — Brie Wolfson.
  6. Intergenerational friendships: "Have a real friend in the generation above and below you." — Brie Wolfson.
  7. 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." — Brie Wolfson.
  8. Earnestness over snark: Choose sincerity over cynicism. — Brie Wolfson.
  9. The value of small check-ins: "A light check-in now is better than a longer check-in never." — Brie Wolfson.
  10. Learning to cook: "Learn to cook a few things really, really well." — Brie Wolfson.
  11. Private memories: "Store memories somewhere private. Rifling through a shoebox of stuff beats scrolling through your Instagram any day." — Brie Wolfson.
  12. On being the generous one: "Everyone thinks they're the more generous one in the relationship." — Brie Wolfson.
  13. The joy of a small group: "A small group cranking is bliss." — Brie Wolfson.
  14. The cure of a drive: "A drive with the windows down and the music too loud can cure a whole lot." — Brie Wolfson.
  15. On feedback from friends: "Ask for feedback from friends like you would your colleagues." — Brie Wolfson.
  16. On Finding joy in usefulness: A fulfilling life often comes from engaging in the grounded, practical work of fixing things, solving problems, and contributing more than you consume. — Dialectic with Jackson Dahl
  17. On Navigating a less legible path: The real difficulty of taking a non-traditional career path is overcoming human competitiveness and finding satisfaction in exploration without external validation. — Not Boring

On Company Culture

  1. Culture is for everyone: At Stripe, the trope that "company culture was up to everyone to build" was put into practice. — Culture Creator: Brie Wolfson - by Julia Levy - The Switchboard.
  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. — Culture Creator: Brie Wolfson - by Julia Levy - The Switchboard.
  3. 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. — Culture Creator: Brie Wolfson - by Julia Levy - The Switchboard.
  4. The role of the internal communicator: A great internal communications professional is a "company poet/scribe," documenting lore and articulating the company's pulse. — Culture Creator: Brie Wolfson - by Julia Levy - The Switchboard.
  5. Marriott's "First 10 Minutes": An obsession with the guest's initial experience, from greeting to check-in, as a key cultural principle. — The Art of “Taste” — Brie Wolfson - YouTube.
  6. Transforming organizations: "I think we've got a shot at transforming organizations into the incredible sources of community and self-actualization they should be." — What I Miss About Working at Stripe - Every.
  7. The power of caring: What stood out at Stripe was that "people really cared about the work." — What I Miss About Working at Stripe - Every.
  8. Reciting company documents: At Stripe, "Employees could recite content from iconic company documents verbatim —sometimes years after they were originally published." — What I Miss About Working at Stripe - Every.
  9. A cohesive force: An open email policy where anyone can read communications from across the organization acts as a "really good cohesive force." — The Art of “Taste” — Brie Wolfson - YouTube.
  10. The Kool-Aid Factory: Wolfson's consultancy, aimed at helping organizations "approach company culture with the care and rigor they treat building products." — Brie Wolfson.
  11. On The ambition of great companies: The most exceptional companies share a defining trait: their commitment to quality extends beyond the product they build to the organization they are building. — Dialectic with Jackson Dahl
  12. On The power of enthusiasm: Top-down mandates can never beat genuine excitement; when people truly believe in and enjoy their work, they will go to extraordinary lengths to succeed. — Dialectic with Jackson Dahl
  13. On Individual contributors: "IC is genuinely the highest-status position at the company." — Colossus: Inside Cursor

Learn more:

  1. Brie Wolfson: Building Great Company Culture, Finding Your Creativity, and Carving Your Own Path - YouTube
  2. Culture Creator: Brie Wolfson - by Julia Levy - The Switchboard
  3. Advice to achieve greatness with your obsession | Brie Wolfson - YouTube
  4. Brie Wolfson: Learning to Love Flounder Mode from Kevin Kelly (Hyperlegible 013)
  5. Writing In Public, Inside Your Company - The Kool Aid Factory
  6. From kickoffs to retros and Slack channels — Stripe's documentation best practices with Brie Wolfson - First Round Review
  7. The Art of “Taste” — Brie Wolfson - YouTube
  8. Thinking vs Doing...which is better? | Brie Wolfson - YouTube
  9. Brie Wolfson: Building Great Company Culture, Finding Your Creativity, and Carving Your Own Path
  10. Brie Wolfson
  11. What I Miss About Working at Stripe - Every