Character with Anne Benveniste – Details, episodes & analysis

Most people don’t struggle because they lack discipline. They struggle because they aren’t tuning into what lights them up. They struggle because they’re trying to grow without fully releasing what no longer serves them. They struggle because they think life needs to look a certain way in order to be successful.

In this special Character season finale, I’m sharing a workshop I taught called “Be Your Own Guru.” Over the past 18 months, I’ve become deeply obsessed with tarot—not as a way to predict the future, but as a tool for strengthening intuition and recalibrating when you’re out of alignment. Transitions are uncomfortable and the tendency can be to look for a map or set of instructions. But the truth is: the map is inside of you. You just need a way to hear it.

I teach three core Tarot archetypes that help you close out 2025 and start 2026 from a soul-aligned place: The Empress (follow your sparkle), Death (release what you’ve outgrown), and The Magician (be the artist of your life). You’ll get a guided meditation designed to surface what felt sparkly this year, what wants to be released, and what your soul most wants for the year ahead. This is followed by a group Tarot pull to help you clarify what’s blocking and what’s supporting your deepest goal for 2026.

If you’re navigating change, craving clarity, or searching for a way to create more fun and playfulness in your life, this workshop is your reset to kick off 2026 in a fun and powerful way.

What You’ll Discover in This Episode:

-How to use tarot as a tool for self-trust (not fortune-telling)

- How to follow your “sparkle” when life feels heavy

- How to release old identities without needing the full plan

- How to become the artist of your life instead of following a success formula

Listen to the Full Episode

YouTube: https://www.youtube.com/@characterpod  

Apple Podcasts: https://podcasts.apple.com/us/podcast/character-with-anne-benveniste/id1645863102 

Spotify: https://open.spotify.com/show/63UcUnBWGGxAjTiX9Q2RnN 

Follow Along: 

Substack: https://annebenven.substack.com 

Website: https://www.annebenveniste.com  

LinkedIn: linkedin.com/in/annebenveniste/ 

Instagram: https://www.instagram.com/characterpod

Episode Highlights & Timestamps:

00:00 — Why we cling to old versions of ourselves (and how it weighs us down)

01:10 — How Anne uses tarot: intuition, alignment, and navigating change (not prediction)

02:28 — Workshop begins: the three themes—sparkle, release, and artistry

03:10 — Anne's story: chasing “success” (MBA/tech) vs. choosing what’s aligned

07:04 — Why tarot strengthens intuition: symbolism, unconscious knowing, and self-trust

09:25 — Workshop structure: themes → meditation → group tarot pull → Q&A

11:27 — The Empress: “follow your sparkle” and stop treating life like homework

13:23 — How numbing discomfort disconnects you from your inner yes/no compass

14:50 — Death card: releasing identities, beliefs, and behaviors you’ve outgrown

17:53 — The Magician: throw out the rulebook and create your own path

20:40 — Guided meditation begins: grounding in the heart and cultivating gratitude

25:40 — Reflection: what wants to be released from 2025?

29:00 — Reflection: what is your soul’s deepest desire for 2026?

31:40 — Mirror card: Eight of Cups (reversed) — resisting walking away from what’s “working”

33:40 — Challenger card: Two of Wands (reversed) — comfort, hesitation, and not dreaming big

34:55 — Helper card: Judgment — hearing the call and answering it

39:50 — Q&A: “There is no path until you walk it” and how transitions actually unfold

45:45 — Q&A: interpreting “the call” when you want a clear formula for what to do next

51:00 — Community reflection: boundaries, creativity, and making space for what lights you up

54:40 — Closing: Season one finale + what’s coming next for Character

Rob shows us what it takes to transition out of the structure and stability of the familiar path and embark on something creative and entrepreneurial. 

Raised in Kent in the south of England, Rob spent a decade working in partnerships for the Cannes Festival of Creativity before deciding to move away from the success and stability he’d built. Through a recalibration of his mindset, a reconnection to his values, and adopting a new approach to the process of evolving his career, Rob found his ideal next step as the founding partner of Super Okay, the creative design studio.

Outside of work Rob is a photographer, avid record collector, and occasional DJ. 

In this episode, we talk about:

- Leaving something successful, stable, and structured that no longer feels meaningful

- Letting go of classic markers of career success like title, brand-name, and money

- How he navigates the rollercoaster of entrepreneurship. 

- The power of vulnerability when building a business

- The mix of humility, humor, and curiosity that keeps you grounded

Rob is funny, vulnerable, and honest about the messy process of becoming yourself.

If you’re navigating change or craving more alignment, this episode is for you.

Timestamps:

00:00 – Intro

03:05 – Growing up in a creative household

04:03 – Early career: Cannes Lions & advertising

05:44 – Discovering creativity through business development

07:53 – Burnout, cycles, and the March 2020 pause

09:27 – Redefining success beyond money & titles

11:53 – Discovering personal and professional values

13:46 – The power of conversations & networking

15:18 – Breaking down old identities and rebuilding

16:10 – Personal work: alcohol, mental health & avoidance

18:46 – Acceptance, self-awareness & emotional regulation

20:26 – The roller coaster of self-growth

21:10 – Becoming an entrepreneur

22:24 – Separating self-worth from business success

24:30 – Fulfillment through people, clients & values

27:54 – Anxiety, fear & resilience in entrepreneurship

31:10 – Advice to his younger self

32:10 – Billboard message: “Know thyself”… or not

32:44 – “Make DJing cool again” hot take

34:14 – Closing reflections & gratitude

Subscribe to Character:  

YouTube: https://www.youtube.com/@characterpod  

Apple Podcasts: https://podcasts.apple.com/us/podcast/character-with-anne-benveniste/id1645863102 

Spotify: https://open.spotify.com/show/63UcUnBWGGxAjTiX9Q2RnN 

Follow Along:  

Substack: https://annebenven.substack.com 

Website: https://www.annebenveniste.com  

LinkedIn: linkedin.com/in/annebenveniste/ 

Instagram: https://www.instagram.com/characterpod

Julia makes reinvention look easy. And she credits it to staying curious, believing in people, listening to herself, and cultivating optimism. 

Growing up in the Soviet Union around the Black Sea, Julia’s curiosity, intuition, creativity, and tenacity eventually led her to local fame in Moscow as a music journalist for MTV Russia and early pioneer of internet television. She then reinvented herself as a techno dj in Berlin. In 2013 she moved to New York with no local community and without a strong grasp of English. She navigated this challenge by throwing herself into music production and launching her own record label, Jujuka Music. 

Today Julia is renowned internationally for her innovative sound; The New Yorker called her music beguiling. She’s a regular at Tresor in Berlin and holds a residency at Public Records in New York where she also does programming focusing on modern techno and obscure club music. 

She’s also currently realizing a long-held dream of having a space where she can host friends, create events, and pour people drinks as the managing partner of the artist-run bar E-Flux Bar Laika in Clinton Hill in Brooklyn.

In this episode, we get into 1. How curiosity and tuning into yourself is the foundation for your evolution 2. The power of optimism and seeing life as full of possibilities 3. The opportunities created from seeing the good in people 4. Managing multiple major life transitions at once with no safety net 5. Julia’s philosophy on the duality required to be a strong artist 6. How experience helps your course correct in a more aligned way 7. Navigating an industry that will judge you first on your looks 8. The magnetic power of having character

Julia is warm, funny, and honest about her journey and what it takes to build a life with character, one that takes you to places you would’ve never imagined. 

If you’re considering a new transition, building a career based in creativity, or navigating a hard moment, this episode is for you! 

Timestamps:

00:00 – Listening to Yourself & The Challenge of Transition

01:49 – Childhood in the Soviet Bloc & Identity Shifts

02:32 – Success vs Experience: Julia’s Reframe

03:15 – Intuition as a Superpower

06:00 – Reinvention Series: Journalist → MTV Host → Blogger → Producer → DJ → Cultural Curator

09:14 – Anger, Negativity & How to Avoid Getting Stuck

11:43 – From “Somebody” in Russia to “Nobody” in NYC

13:09 – A New Poem for a New Chapter

14:47 – Looking Back at the Years of Disguise

15:42 – Toxic Work Environments & Energy Absorption

18:56 – Style as Practicality, Comfort & Movement

20:31 – The Pressure on Women in Electronic Music

22:47 – Collaboration, Trust, and Creative Partnerships

23:38 – The Hard Work Behind a “Lucky” Career

24:56 – Community, Dance Floors & Cultural Responsibility

27:24 – What She’s Working On Now

28:15 – Advice for Anyone in a Transition

29:32 – What Character Means to Julia

Do you ever feel like the career you built is the one you thought you wanted - but then you wake up one day and realize it’s no longer clicking?

That’s where Caroline Witmer found herself. Brown grad. Columbia MBA. Wealth management. Private equity. She’d ticked all the boxes, jumped from chapter to chapter with ease, externally she was ‘crushing it’… but never looking inside to ask herself, are you happy? Is this really what you want?

In this episode of Character, I sit down with Caroline—who's actually a former coaching client of mine—to talk about her journey from finance to founding Tuck Shop, a handcrafted chocolate company capturing the spirit of your happy place.

Caroline shares how she’s building something meaningful while raising three kids under four without the pressure and intensity that colored her career in finance.

In this honest conversation about career change and building a life with character, we explore:

- How do you know when it’s time to leave a career that looks good on paper? 

- Letting go of other people’s opinions. 

- Giving yourself permission to play. 

- Building a business while raising babies. 

- What it takes to let go of the pressure and hold things looser.

Connect with Caroline and Tuck Shop:

Website: https://shoptuckshop.com/

Instagram:

@shoptuckshop https://www.instagram.com/shoptuckshop/

Timestamps:

00:00 Introduction & Early Aspirations

01:33 Path into Finance

03:38 Finance Career Growth

05:15 Business School & Transitioning Roles

07:04 COVID & Life Changes Triggering Reflection

09:08 Coaching & Transitioning Mindset

12:43 Shifting from Finance to Entrepreneurship

16:25 Founding TuckShop

20:01 TuckShop Growth & Operations

24:24 Learning Operational Skills

27:14 Spirituality & Grounding Practices

29:18 Balancing Motherhood & Entrepreneurship

32:38 Impact of New York City on Career & Creativity

34:53 Advice to Younger Self & Key Takeaways

SUBSCRIBE NOW:  

YouTube: https://www.youtube.com/@characterpod  

Apple Podcasts: https://podcasts.apple.com/us/podcast/character-with-anne-benveniste/id1645863102 

Spotify: https://open.spotify.com/show/63UcUnBWGGxAjTiX9Q2RnN 

FOLLOW ALONG:  

Substack: https://annebenven.substack.com 

Website: https://www.annebenveniste.com  

LinkedIn: linkedin.com/in/annebenveniste/ 

Instagram: https://www.instagram.com/characterpod

What happens when you build something you thought would work and then it doesn’t? And there’s no plan B.

Sutian Dong, Partner at Multitudes and Co-Founder of Global Women in VC, is fascinated with creating products, technologies, platforms, services, and communities that move humanity in a positive direction by not changing how we do things, but the way that we think and feel.

After years of lucky breaks and things always just working out, Sutian found herself in uncharted territory when her original concept for Multitudes failed and she had no idea what came next. That moment of disorientation became the catalyst for profound self-inquiry that ultimately sparked the insights that created her new venture, Multitudes, which invests in and incubates ideas that explore the edge of human consciousness.

On this episode of Character, Sutian joins me to talk about:

- Why running a business is one of the rawest forms of self-expression

- The modalities Sutian used to move through processing failure and figuring out what came next

- Navigating discomfort to support your growth

- The relevance of spirituality in the modern world

- Using tools like astrology, tarot, and aura photography to access self-connection and build community

- The second-order effects of AI

- Multitudes’ approach to investing in initiatives at the edge of human consciousness

This episode was recorded at Love Letter, an aura photography studio, on the Lower East Side. 

Learn more about Sutian’s work: https://www.sutiandong.com/

Learn more about Love Letter: https://www.loveletter.nyc/ 

TIMESTAMPS:

00:00 — The Power of Pause

00:52 — Meet Sutian Dong

02:10 — Childhood Dreams

04:17 — Growing Up Entrepreneurial

05:30 — From Structure to Self-Reliance

07:34 — When Success Stops Working

09:56 — Forced Introspection

11:50 — Feeling the Feelings

13:57 — Tools for Healing

16:35 — The Gradual Sunrise of Change

19:16 — Compounding Change & Self-Advice

20:58 — Redefining Venture Capital

23:01 — The Power of Belief Systems

24:08 — Following Curiosity

25:57 — Flux and Rebirth

27:10 — Searching for Meaning in Chaos

SUBSCRIBE NOW:  

YouTube: https://www.youtube.com/@characterpod  

Apple Podcasts: https://podcasts.apple.com/us/podcast/character-with-anne-benveniste/id1645863102 

Spotify: https://open.spotify.com/show/63UcUnBWGGxAjTiX9Q2RnN 

FOLLOW ALONG:  

Substack: https://annebenven.substack.com 

Website: https://www.annebenveniste.com  

LinkedIn: linkedin.com/in/annebenveniste/ 

Instagram: https://www.instagram.com/characterpod

What does it mean to build a life around authenticity, intuition, and joy—even when it defies expectations?

Ariel Palitz, nightlife veteran, entrepreneur, and former NYC Nightlife Mayor, joins me for a conversation about defiance, self-discovery, and designing a life by trusting what feels good. Growing up in Manhattan, Ariel found herself drawn early to the freedom of nightlife as a place where she felt most alive. From experimenting with PR and music, to opening her own nightclub, to ultimately creating a career at the intersection of community, culture, and advocacy, Arielle’s story is one of resilience, intuition, and flow.

On this episode of Character, Arielle joins me to talk about:

• Growing up in a New York household that was glamorous but disconnected, and learning to rely on her own inner compass
• Discovering the authentic energy of nightlife as a place of freedom and expression from a young age
• Why experimenting with different jobs and industries was essential to finding where she truly fit
• The leap from working in PR to opening her own nightclub and later shaping NYC’s nightlife policy
• How she stays connected to herself through meditation, creativity, and joy-centered practices
• Lessons on trusting flow, protecting your peace, and the spiritual side of nightlife

SUBSCRIBE NOW:  

YouTube: https://www.youtube.com/@characterpod  

Apple Podcasts: https://podcasts.apple.com/us/podcast/character-with-anne-benveniste/id1645863102 

Spotify: https://open.spotify.com/show/63UcUnBWGGxAjTiX9Q2RnN 

FOLLOW ALONG:  

Substack: https://annebenven.substack.com 

Website: https://www.annebenveniste.com  

LinkedIn: linkedin.com/in/annebenveniste/ 

Instagram: https://www.instagram.com/characterpod

What does it take to leave behind security and familiarity and start over in pursuit of purpose?

Brandon Ross, a former flight attendant turned massage therapist and founder of Romie Massage in New York City joins me for a story of reinvention, courage, and self-acceptance.

From a delayed blooming growing up gay in a conservative Christian household, to an angry rebellion as he built his first career as a flight attendant, and then switching it all up to create an entrepreneurial career around what energized him, Brandon’s story is one that anyone who dreams of more can learn from!

On this episode of Character, Brandon joins me to talk about: 

• Navigating his love for dance and choreography while growing up in a strict religious household that didn’t embrace this self-expression

• The freedom and adventure he found as a flight attendant — and why it ultimately left him searching for more

• How he discovered massage therapy through years of travel, curiosity, and noticing the artistry of touch

• The leap of faith it took to leave corporate stability and build his own practice

• Lessons on identity, devotion over discipline, and the importance of surrounding yourself with people who believe in your vision

TIMESTAMPS:

00:00 – Meeting Brandon at a Buffalo party

01:15 – Wanting to be a choreographer

04:50 – Growing up in a strict household

08:10 – Flight attendant years & freedom in travel

14:30 – Discovering massage therapy

19:20 – Taking the leap into entrepreneurship

22:30 – Staying committed through challenges

26:20 – Devotion vs discipline

27:50 – Flow and alignment through massage

28:50 – Tools for reconnecting with self

SUBSCRIBE NOW:  

YouTube: https://www.youtube.com/@characterpod  

Apple Podcasts: https://podcasts.apple.com/us/podcast/character-with-anne-benveniste/id1645863102 

Spotify: https://open.spotify.com/show/63UcUnBWGGxAjTiX9Q2RnN 

FOLLOW ALONG:  

Substack: https://annebenven.substack.com 

Website: https://www.annebenveniste.com  

LinkedIn: linkedin.com/in/annebenveniste/ 

Instagram: https://www.instagram.com/characterpod

What if finding true connection had less to do with swiping on apps—and more to do with romancing yourself and showing up authentically in the world?

Amy Van Doran — matchmaker, CEO, and founder of The Modern Love Club — joins me for a deeply inspiring conversation about love, identity, and why community and spirituality matter more than ever.

On this episode of Character, Amy shares:

- How her unconventional childhood shaped her unapologetic sense of self

- Why loneliness can be transformed into a gift that fuels connection

- The parallels between careers and romantic relationships — and why both require risk, curiosity, and play

- How creating community might be the real antidote to our modern dating crisis

SUBSCRIBE NOW:

YouTube: https://www.youtube.com/@characterpod

Apple Podcasts: https://podcasts.apple.com/us/podcast/character-with-anne-benveniste/id1645863102

Spotify: https://open.spotify.com/show/63UcUnBWGGxAjTiX9Q2RnN

FOLLOW ALONG:

Substack: https://annebenven.substack.com

Website: https://www.annebenveniste.com

LinkedIn: linkedin.com/in/annebenveniste/

Instagram: https://www.instagram.com/characterpod

How does an Argentinian psychoanalyst and sommelier with no formal design training build a beloved fashion and bridal line in New York City? We dive into Delfina’s journey in the first episode of Character and discuss: 

• The culture and influences that shaped her early career and life in Buenos Aires

• Making the move to New York and exploring a variety of careers

• Using intuition to guide the launch of her first collection and the launch of her widely successful non-traditional bridal line

• The powerful role ayahuasca played in her ability to navigate this growth and tap into her authentic self-expression and creativity

• The lessons learned from 14 years living in New York and building her own brand

Subscribe to the Character Substack for:

• My deeper analysis as a coach of what’s helped Delfina thrive

New York City is full of characters: unapologetically authentic people who create the vibe that make this city great. People who have thrown out the rulebook and become the artist of their life.

We dive into the messy, unpredictable journey towards fulfillment and authentic self-expression. We talk to creatives and artists, entrepreneurs and change-makers about where they came from, who they’ve become, and what it took to get here. These are honest, intimate conversations, where we explore taking risks, trusting your intuition, career twists, creative awakenings, and the role this intense and powerful city played in shaping their path. We explore the structures and tools they used to support them - from psychedelics to therapy, spirituality to community. 

We get real. We have fun. We go deep. Always in the quest to leave you wiser and more inspired. This show is about the character it takes to build an authentic and fulfilling life that feels uniquely your own.

SUBSCRIBE NOW: 

YouTube: https://www.youtube.com/@characterpod 

Apple Podcasts:

Spotify: https://open.spotify.com/show/1D1jloreKR7qwgqEKp2buU

FOLLOW ALONG: 

Substack: https://annebenven.substack.com

Website: https://www.annebenveniste.com 

LinkedIn: linkedin.com/in/annebenveniste/ 

Instagram: https://www.instagram.com/characterpod