✨TL:DR or What to expect if you subscribe:
So glad you’re here. I write about creativity, transformation, and asking better questions — in business and in life. Expect deep reflection, some light side quests, lots of pop-culture references, and the occasional dad joke.
Hi, I’m Chedva (you can call me Vivi) — and this is Consider.
I’m a serial entrepreneur, question architect, and business strategist who believes that transformation doesn’t start with a roadmap — it starts with a really good question.
I grew up in the ultra-Orthodox communities of Brooklyn and Bnei Brak, left that world at 37, and started over from scratch: new life, new home, new business, new name. What remained constant? Curiosity. The kind that makes you rethink what success is, where you belong, and how you want to show up.
After years of building startups, running an agency, and parenting in a neurodivergent household (shoutout to my autistic teen and our anxious rescue dog, Giovanni), I finally got my own ADHD diagnosis — and a new understanding of how my brain actually works. It’s been a game-changer for how I lead, create, and communicate (and why I believe questions > conclusions).
I took a beat to write a book… and that book became my new business, and basically a way for me to bring people into my brain and heart. It’s called Consider, and this newsletter is where that work lives out loud.
What You'll Find Here
I publish in two main sections — you can subscribe to either or both:
🌀 Under Consideration
Essays, reflections, and strategic side quests about work, identity, creativity, and clarity. These are my public journal entries from the foggy middle — the space between “something’s not right” and “aha, that’s the way forward.” This section also includes snippets from my podcast, Looks Like Work 🎙️:
Honest conversations about the messy, meaningful middle of work and life. I talk with curious humans about what it actually looks like to build, heal, parent, pivot, lead, and create. We skip the highlight reels and get into what’s real — with occasional musical theatre references, ADHD side quests, and deep dives into how people keep going when the path gets foggy.
👉 You can listen on Spotify, Apple or wherever you get your podcasts:
🪞 Portal Pages
This is a not-a-book-club community for people who crave introspection without isolation. We use books as portals into our own stories — and then come together in intimate Zoom or face-to-face gatherings to share what we find. Portal Pages posts reflect these sessions, offering deep questions, themes, and reflections (not summaries), as well as follow up resources and food for thought for participants.
Right now, all posts are free, but some may become gated for paid subscribers. Invitations to the gatherings themselves will always stay free.

How to Subscribe
👉You can choose which sections you want to receive on your account page:
Just curious? Choose Under Consideration.
Want to go deeper? Add Portal Pages.
All in? Follow both for the full experience.
Want even more? Select New chat threads to stay extra up to date.
A Bit More About Me
I’ve had alopecia universalis since I was 7 (an autoimmune condition which means I’m bald - so don’t be alarmed if you sometimes see me sporting my head without a wig or a baseball cap). I’ve been a loud feminist since before I knew the word. I’ve survived startup heartbreak, rebranded myself after divorce and religious excommunication, and built a career — and a life — by asking the kinds of questions that don’t always have easy answers.
Today, I lead Consider Labs, where I help founders, leaders, and creators use curiosity as a strategic tool. From positioning and storytelling to clarity coaching and team alignment, the work is always about asking better questions.
One of my favorite tools? CuriosityGPT — my free AI thinking partner that doesn’t give you answers, but offers breakthrough questions instead. It’s like carrying a strategist in your pocket (minus the judgment and calendar invites).
✨ This newsletter is where the personal meets the strategic.
Where questions stretch their legs.
Where transformation gets less mysterious — and more human.
Thanks for being here. I know how precious your attention is, and I don’t take it lightly.
— Vivi
