Looks Like Work

Prioritizing Joy in the Entrepreneurial Journey (with Lee Rotenberg)

In this engaging conversation, Lee Rotenberg shares her entrepreneurial journey, emphasizing the importance of fun and authenticity in her work. She reflects on the challenges of defining success and happiness, the lessons learned from founding and selling companies, and the significance of being present and true to oneself. Lee discusses how her recent LinkedIn post about prioritizing fun in her next career chapter resonated with many, and explains why internal success matters more to her now than external validation. The conversation highlights the evolving nature of entrepreneurship, from the excitement of early-stage creation to the challenges of scaling and fundraising, offering valuable insights for anyone navigating their own path to fulfillment.
Key Topics:
Prioritizing fun and authenticity in your career decisions
Redefining success beyond external validation
Finding happiness through presence and mindfulness
Navigating the emotional roller coaster of entrepreneurship
The joy of early-stage business building versus the challenges of scaling
The drawbacks of fundraising for founders
Learning how to evolve and adapt throughout your journey
The importance of taking action on ideas rather than overthinking
Moving from ArtSetters to Ivy to Clay to Hulken
Notable Quotes:
"This next era of my work chapter will be one where I'm essentially focusing more on fun."
"I want to have delight in my day to day more than I want to have success."
"Being successful is being happy... being very present and not trying to think about what is next."
"When you're able to truly just be you and not worry about the external voices or external wants, that makes me invigorated."
"If you want something too badly, it rarely happens. When you're living your best self, you become a magnet for all different areas of your life."
"People's biggest mistake is they wait to launch or they're overthinking the steps. You need something very shitty in a sense, because that's the only way it's going to get better."
"Fear can still stay there and you can do it while you're scared."
Lee's Powerful Question: "What's the why behind what you're doing? Ask yourself the why and be really honest with yourself on that answer."
Resources Mentioned:
"Let Them" by Mel Robbins - described as "the most life-changing book" Lee has recently read
"How to Be a No Limit Person" by Dr. Wayne Dyer - recommended as motivational and energizing
"You Are a Badass" by Jen Sincero - endorsed as an excellent read
Lee's podcast with Alex called "Unfinished Business" - interviews with inspiring entrepreneurs
Follow Lee on LinkedIn for authentic insights on entrepreneurship
 

Work That's Worth It (with Georgi Enthoven)

 In this episode, Chedva talks with Georgi Enthoven, founder and author of "Work That's Worth It." They explore how to find meaningful work that balances personal fulfillment with positive impact. Georgi challenges the false dichotomy between doing good and earning well, and shares her journey from tech executive to purpose-driven thought leader. This conversation fits perfectly with the season's theme of questioning traditional priorities in our work lives.
Key Topics:
The meaning behind "Work That's Worth It" and why our career choices matter
Finding purpose within our 90,000-hour career journey
Challenging the divide between profitable careers and meaningful impact
The importance of being compensated fairly while doing good
How to discover work that energizes rather than depletes you
Embracing a beginner's mindset throughout your career
Notable Quotes:
"You can't convince ambitious people to give up income. It's about finding options where you can do good and well for yourself."
"I really want the kindest, most empathetic people to get to the top levels where they are pulling the levers of decision making."
"If you are doing good in the world and you burn out in two years, we lose you."
"Work that you're meant to do adds value to your life - it gives you incredible challenges that make you wake up eager to get out of bed."
"The powerful question is: what is worth your 90,000 hours?"
Georgi's Powerful Question: "What is worth your 90,000 hours?"
Resources & Links:
Purchase "Work That's Worth It": Available at major booksellers
Calculate your remaining career hours: https://georgienthoven.com/
Follow Georgi on Instagram: https://www.instagram.com/georgienthoven/
Subscribe to Chedva's newsletter: chedva.substack.com

Reclaiming Sacred Texts (with Chaya Gilboa)

 Chaya Gilboa, a Talmud scholar and activist who grew up in an ultra-Orthodox community in Jerusalem, shares her journey of reclaiming Jewish texts that women were traditionally forbidden to study. The conversation explores the intersection of spirituality, embodiment, and challenging patriarchal systems, as well as how ancient wisdom can provide comfort during times of crisis.
Key Topics:
Chaya's experience studying Talmud as a revolutionary act
The emotional and spiritual dimensions of reclaiming religious texts
Integrating body and mind in spiritual and intellectual practice
Creating new approaches to ancient texts during crisis and war
Balancing calling, career, and family life
Notable Quotes:
"I was pushed out of the door and I looked for the window to go back in."
"I couldn't breathe. I needed to take walks at Ben Gurion University because my body was not even excited, I was uplifted in ways that I didn't even know knowledge could uplift me."
"For many years, growing up, I didn't really know my body. We never talked about the body - the body was something that either you are ashamed of or you need to cover."
"I'm 41 and it's the first time in my life that I'm in sync with what I love to do, what I'm passionate about, what I'm good at, and what I think the world needs."
Chaya's Powerful Question: "What am I chasing after, and what am I running from?"
Resources Mentioned:
Chaya’s beautiful website
Follow Chaya on Instagram: @chayagilboa
 

Creating Safe Places (with Or Alterman-Barnea)

Or Alterman-Barnea, co-founder and CEO of Mekomot Shmurim (Safe Place), discusses how she transformed theatrical experiences for neurodivergent children. After her own son's autism diagnosis, Or created performances where the lights stay on, sounds remain gentle, and children can move freely without judgment—revolutionizing cultural accessibility across Israel.
Key Topics:
The concept of "relaxed performances" designed for neurodivergent audiences
Creating theater experiences without surprises or sensory overload
The power of community in addressing unmet needs
Or's journey from cultural journalist to inclusive theater pioneer
The philosophy of adapting systems to people instead of forcing people to adapt
Notable Quotes:
"When we started it and thought about 'safe place,' we didn't imagine what kind of meaning 'safe place' would have for us now."
"Every single spoiler that you can think of. There are no surprises."
"It's like we call it a 'shoosh-free zone.' Nobody will shoosh them."
"Many, many families came and said to us, 'This is our first time in the theater.' And we're talking about seven-year-old children, nine-year-old children."
"We're so used to telling this child, 'Listen, if you can't sit then go out'... But no, we will leave the door open. It's on your terms now."
Or's Powerful Question: "When was the last time you thought about who makes the decisions for you? Who decides how people are supposed to dress, to act, to spend their free time, to sit in the theater?"
Resources Mentioned:
The 2025 Safe Place Festival is happening this month - details and tickets are here
Big Umbrella Festival (inspiration for Safe Places): Lincoln Center
Mama-Zone Facebook community (Or's previous initiative): Join here

When Your Dream No Longer Fits (with Natalie Rozenboim)

In this conversation with former Resonai COO Natalie Rozenboim, Chedva explores what happens when we achieve the goals we've worked toward, only to discover they don't feel right anymore. They discuss the pandemic's role in prompting career reassessment, the guilt associated with questioning achievements we've worked hard for, and how to navigate changes in what we want from life.
Key Topics:
The pandemic as a catalyst for questioning career paths
The identity crisis of outgrowing professional achievements
Guilt and confusion when questioning the life we've built
Breaking free from the "sunk cost" mentality
Generational differences in approaching work-life integration
Notable Quotes:
"There's like this pressure to find your thing, which has to encompass so many things. It has to be not only how you make a living, but also something you're passionate about."
"You almost gaslight yourself. Like, why would I not want this? The problem is me."
"We tend to think we just need to decide what we want and just go for it, but I think it's more of a continuous quest."
"We mistake control for progress - holding tightly to answers gives an illusion of forward movement, even when we're standing still."
Natalie's Powerful Question: "Am I building the life I want to live, or do I feel trapped in this life? And what am I going to do about it?"
Resources & Links:
Connect with Natalie on IG https://www.instagram.com/natalie_roz/
Kelly Mindell's blog post "The Year I Built a Life I Don't Want"
Book recommendation: "The Neverending Story" by Michael Ende
Article: "The Great Resignation and Rethinking Priorities Post-Pandemic"

The Questions We Don't Dare to Ask (Solo Episode)

In this solo episode, Chedva Ludmir introduces the new season of Looks Like Work, focusing on three pivotal questions: What do you do when your dream no longer feels right? How do you reclaim a system built to suppress you? And how are you questioning traditional priorities? She explores the concept of "gateway questions" - those gentle inquiries that help us approach what we're afraid to confront - and shares why staying with questions might be more valuable than rushing to answers.
Key Topics:
Introduction to the three guiding questions for Season 3
The power of staying with questions even when we crave certainty
Using "gateway questions" to approach difficult life decisions
How world events have led to deeper questioning of our choices
Notable Quotes:
"When the world feels like it's on fire, there's this powerful urge to flock behind anyone speaking in exclamation points."
"We need gateway questions, those gentle indirect inquiries that help us approach what we're really afraid to confront."
"What I could ask myself at that point was: when will I be ready to ask myself that question?"
Resources Mentioned:
Chedva's newsletter at chedva.substack.com
Previous seasons of Looks Like Work podcast

Solo episode: On grief

Hey folks, I'm back for a solo episode and this one is especially lighthearted… no, of course I'm kidding. But I really wanted to take a minute to talk about grief and I'd love to hear your thoughts and feelings too. 
 
Links & resources
 
You Could Make This Place Beautiful by Maggie Smith
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Questions, inspiration and the idea of work with Stephie Knopel

I first met Stephie on a retreat back in 2016. I was wildly out of my comfort zone, discovering a lot about the entrepreneur I wanted to be and about leadership - and a new incredible friend. Since then, Stephie and I have found that our value systems as people and as entrepreneurs are aligned, and I'm so grateful to finally have this conversation with her. We cover the place of questions and curiosity in entrepreneurship, inspiration and productivity, burnout and being a constant outsider and in-betweener.
 
Links & resources
 
Unboxable 
Double You 
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Your expansive self- with Orit Gidali

Fair warning? This is one of those episodes. Ask me what’s it about, and I’ll respond by asking: what is it not about? I met up with Orit Gidali – like, actually packed my microphone and went to meet her – who’s one of my favorite poets and writers. Over a few glasses of red, we talked about… the human condition, I guess: Sorrow and joy, scarcity and expansiveness, attachment styles and meditation, divorce and heartbreak and exaggerated earrings and sex and passion and the brokenness of us all and violence and war and hurt and vulnerability and empathy and compassion. It’s one of my favorite episodes ever, even with the wine and acoustics messing up some of the sound - maybe even more thanks to that, actually. Enjoy.
Links & resources
 
Orit Gidali’s website (English | Hebrew)
Sadnaot Habait creative writing school (English | Hebrew)
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Building and learning early and fast- with Gil Eyal

Gil had a front row seat to startup life and to working with celebrities. That experience, as well as defining and differentiating himself as an Israeli lawyer in an American business school, has taught him the value of stories and messaging. We speak about startup life, marketing, influencers, career trajectories and important questions.
Links & resources
 
Stardust Ventures
Silverstein Properties
Gil’s podcast with Einat Ben Moshe (Hebrew) 
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Please subscribe, rate & review the podcast wherever you listen. And subscribe to the LLW newsletter for more updates from Chedva!