Celebrating Yourself Instead of Shaming Yourself - with Olivia Howell

Looks Like Work

#Careers #Entrepreneur #Business #Chedva Kleinhandler #Podcasting Education #Self-Improvement #Looks Like

51:57

On the Season 2 debut of Lost Cultures: Living Legacies , we travel to Bermuda, an Atlantic island whose history spans centuries and continents. Once uninhabited, Bermuda became a vital stop in transatlantic trade, a maritime stronghold, and a cultural crossroads shaped by African, European, Caribbean, and Native American influences. Guests Dr. Kristy Warren and Dr. Edward Harris trace its transformation from an uninhabited island to a strategic outpost shaped by shipwrecks, colonization, the transatlantic slave trade, and the rise and fall of empires. Plus, former Director of Tourism Gary Phillips shares the story of the Gombey tradition, a vibrant performance art rooted in resistance, migration, and cultural fusion. Together, they reveal how Bermuda’s layered past continues to shape its people, culture, and identity today. You can also find us online at ⁠travelandleisure.com/lostcultures Learn more about your ad choices. Visit podcastchoices.com/adchoices…

3 years ago 54:35

MP3•Episode home

How do you celebrate big changes in your life? Olivia Howell is the CEO and Co-Founder of Fresh Starts Registry and March Lion Media. At Fresh Starts she helps people create registries for all their life milestones, not just weddings or having children.

In this conversation, we explore–

The importance of making hard decisions & the support we need to make them
How Olivia’s launched two businesses with her sister
Olivia’s career journey and what work looks like for her now
Divorce stories and sharing our personal lives online
Embracing an anti-shame, anti-judgment perspective to change

If you enjoy our conversation, please subscribe, rate & review the podcast wherever you listen. And subscribe to the Looks Like Work newsletter for more updates!

Links:

Visit the Fresh Starts Registry website
Follow Fresh Starts on Instagram and Facebook
Olivia & Chedva's recent faves: Somebody Feed Phil, Only Murders in the Building, Summer Breakdown by Colleen Temple
For more information on the course Olivia is launching, follow her & Chedva on Instagram @thedigitalyenta & @chedvakl

51 episodes

Celebrating Yourself Instead of Shaming Yourself - with Olivia Howell

Looks Like Work

published 3 years ago

MP3•Episode home

In this conversation, we explore–

The importance of making hard decisions & the support we need to make them
How Olivia’s launched two businesses with her sister
Olivia’s career journey and what work looks like for her now
Divorce stories and sharing our personal lives online
Embracing an anti-shame, anti-judgment perspective to change

If you enjoy our conversation, please subscribe, rate & review the podcast wherever you listen. And subscribe to the Looks Like Work newsletter for more updates!

Links:

Visit the Fresh Starts Registry website
Follow Fresh Starts on Instagram and Facebook
Olivia & Chedva's recent faves: Somebody Feed Phil, Only Murders in the Building, Summer Breakdown by Colleen Temple
For more information on the course Olivia is launching, follow her & Chedva on Instagram @thedigitalyenta & @chedvakl

51 episodes

#Careers #Entrepreneur #Business #Chedva Kleinhandler #Podcasting Education #Self-Improvement #Looks Like

All episodes

Looks Like Work

1
Resilience Without Questions Can Turn on Your Values (with Chedva Ludmir) 25:21

18 hours ago25:21

25:21

In this deeply personal solo episode, Chedva takes us through her 17-year entrepreneurial journey - from translator to blogger to design journalist to marketing agency owner to tech startup founder and back to founder mode with her new venture, Consider. After recent trips to New York and Greece for conferences, she reflects on the seductive pull of "founder mode" and how easily we can lose ourselves in the pursuit of our dreams. Drawing inspiration from seeing Audra McDonald in the Broadway musical "Gypsy," Chedva explores the dangerous intersection of resilience and ambition when they're not balanced with introspection and question-asking. She shares her own experiences of getting sucked into work identity and offers a powerful warning about how positive traits like determination can turn against our values when left unchecked. Key Topics: The evolution of a 17-year entrepreneurial journey across multiple industries The seductive danger of "founder mode" and losing yourself in your work How resilience without introspection can make you turn on your own values The importance of maintaining identity and life outside of your business Learning to integrate work and personal life rather than compartmentalizing Growing up multicultural and the sense of belonging everywhere and nowhere The challenge of sustaining passion projects without burning out Using Broadway's "Gypsy" as a metaphor for entrepreneurial obsession The necessity of regular check-ins with yourself and your values Notable Quotes: "Resilience without questions or introspection can quickly make you turn on yourself, on your loved ones, and on your values." "When I don't regularly check in with myself and question my own automatic behavior... I can find myself alone, burnt out, and perhaps even worse, working towards something that is opposed to my values." "I actually love my life and I wanna be part of it." "I didn't really love my life back then... a lot of that time I didn't want to stay with my own questions." Chedva's Powerful Question: "When do these positive, celebrated behaviors or values like resilience and being hardworking turn on us or make us help turn on ourselves? And how can we ask ourselves better questions when it comes to it?" Resources Mentioned: Consider.club - Chedva's new venture focused on transformative question-asking CuriosityGPT - AI tool for asking better questions chedva.substack.com - Weekly newsletter with questions, musings, and thoughts and specifically this issue about integration Broadway shows: "Gypsy" starring Audra McDonald, "Death Becomes Her" Orca Global Network - Global network of Israeli business owners…

Looks Like Work

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More Values, Less Effort (with Meirav Rosenberg) 50:53

22 days ago50:53

50:53

In this deeply personal conversation, Meirav Rosenberg, CEO and founder of Paz Interactive and author-to-be, joins Chedva to explore the complexities of balancing multiple roles as a mother, entrepreneur, and partner. Together, they dive into themes of vulnerability, taking up space in the world, and the crucial importance of prioritizing yourself to better serve others. Meirav shares her journey of self-discovery, the lessons learned from writing "60 Dates to Love," and how fine-tuning your values leads to effortless alignment. The conversation touches on managing internal voices, the challenges of motherhood, and the power of asking difficult questions to live authentically. Key Topics: The courage and challenge of taking up space, especially as parents Managing the internal dialogue and voices in our heads Prioritizing self-care as the foundation for good parenting Values-based prioritization in life and work The relationship between authenticity and success in business and dating The importance of letting go and surrendering control Finding purpose and calling while maintaining balance The intersection of personal growth and professional success Burnout, functional medicine, and listening to your body's wisdom Notable Quotes: "I want to take up space... I have a certain purpose and a certain duty to speak for people who don't have a voice." "One of the things that I prioritize is, how can I be a great mom? It's focusing on me first, which is the first priority." "Filling up my cup so that I can help and I can be there for them in my best way." "I feel like our body tells us exactly everything." "The bigger the why, the easier the how." "I'm not scared of dying, I'm just scared of not living exactly the way that I want to." "The more honest I got with myself... the less effort [I needed]." "Sometimes I have to ask myself those hard questions, but I do love asking questions." Meirav's Powerful Question: "What do you want?" - A simple yet profound question she asks women to help them express their desires and live more authentically. Resources Mentioned: Meirav’s free resource "Dating Like a CEO" Paz Interactive - Meirav's digital marketing agency Chedva's Curiosity GPT Chedva’s newsletter on Substack…

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Prioritizing Joy in the Entrepreneurial Journey (with Lee Rotenberg) 29:03

6 weeks ago29:03

29:03

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…

Looks Like Work

1
Work That's Worth It (with Georgi Enthoven) 49:01

7 weeks ago49:01

49:01

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…

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Reclaiming Sacred Texts (with Chaya Gilboa) 54:40

8 weeks ago54:40

54:40

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…

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Creating Safe Places (with Or Alterman-Barnea) 51:45

9 weeks ago51:45

51:45

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…

Looks Like Work

1
When Your Dream No Longer Fits (with Natalie Rozenboim) 45:28

9 weeks ago45:28

45:28

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"…

Looks Like Work

1
The Questions We Don't Dare to Ask (Solo Episode) 10:24

10 weeks ago10:24

10:24

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…

Looks Like Work

1
Solo episode: On grief 20:20

43 weeks ago20:20

20:20

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 Subscribe to the LLW newsletter Please subscribe, rate & review the podcast wherever you listen. And subscribe to the LLW newsletter for more updates from Chedva!…

Looks Like Work

1
Questions, inspiration and the idea of work with Stephie Knopel 1:00:17

48 weeks ago1:00:17

1:00:17

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 Subscribe to the LLW newsletter Please subscribe, rate & review the podcast wherever you listen. And subscribe to the LLW newsletter for more updates from Chedva!…

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1
Your expansive self- with Orit Gidali 48:09

50 weeks ago48:09

48:09

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 ) Subscribe to the LLW newsletter Please subscribe, rate & review the podcast wherever you listen. And subscribe to the LLW newsletter for more updates from Chedva!…

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1
Building and learning early and fast- with Gil Eyal 55:54

51 weeks ago55:54

55:54

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) Subscribe to the LLW newsletter Please subscribe, rate & review the podcast wherever you listen. And subscribe to the LLW newsletter for more updates from Chedva!…

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1
Seeing yourself as the core of your life - with Hila Segal 59:41

52 weeks ago59:41

59:41

Many of us can be pretty jaded or cynical when it comes to spirituality - I know I can - but knowing Hila has completely changed my perception of spiritual guides. Hila is as funny, pragmatic, sharp and smart as she is spiritual and heart-led. In this conversation, we dive into notions of abundance and scarcity, ego, effort and how they reflect in life and work. Links & resources Hila on Instagram (Hebrew) Hila and Danielle’s podcast - My Happy Place (Hebrew) Subscribe to the LLW newsletter Please subscribe, rate & review the podcast wherever you listen. And subscribe to the LLW newsletter for more updates from Chedva!…

Looks Like Work

1
Curiosity, attention and liminal spaces - with Natalie Shell 45:28

1 year ago45:28

45:28

Hop into the time machine and join me and my friend Natalie Shell, Co-founder of Message Lab as we explore curiosity, creativity, the concept of rest and how we can grow in times of turbulence and be kinder to ourselves and to each other. Links & resources Natalie on Linkedin Message Lab TTT - the poem Natalie mentions Subscribe to the LLW newsletter Please subscribe, rate & review the podcast wherever you listen. And subscribe to the LLW newsletter for more updates from Chedva!…

Looks Like Work

1
Solo episode: Questions, narratives and self reflection 44:56

1 year ago44:56