What do you do when you see yourself in two Enneagram types — and can’t quite tell which one fits?

In this episode, we continue our Exploring Enneagram Types series with my friend and fellow entrepreneur, Claudia Richman. What started as a typing conversation quickly evolved into a deeper exploration of identity, ambition, autonomy, and what it really means to be seen.

Claudia shares her journey from high-powered leadership roles in advertising and tech to building her own businesses on her terms. We explore the tension between achievement and authenticity, the difference between success and autonomy, and how growing up in a highly controlled environment shaped her relationship with rebellion, control, and self-expression.

Along the way, we pause to discern between Type 3 and Type 8 — two assertive types that can get confused. Both can be competitive, direct, and independent. But the “why” beneath those behaviors is very different. We take a nuanced look at how to tell the difference by exploring the ways major familial influences shape our behaviors and examining the “thing behind the thing” to understand our motivations.

If you’ve ever identified with being the capable one, the achiever, the role model, or the person who holds it all together, this episode will resonate.

Want to explore this tool for yourself? Here’s my Enneagram Typing Self-Reflection Guide:

• I just want to download the doc
• I want emails to guide me through the process

Want to connect with Sandhya for yourself or your team? Here’s how:

• Set up a call with Sandhya

Resources:

• Follow Claudia’s work at wegrowforward.com
• Connect with Claudia on LinkedIn

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA

What happens when your sense of worth has always been tied to achievement—and you start to question whether that definition still fits?

In this episode, I sit down with my longtime friend and fellow entrepreneur, Arden Evenson, for a nuanced conversation about Enneagram Type 3 and the evolution of ambition, success, and self-worth. Arden reflects on how external validation, practicality, and being “the reliable one” shaped her early career and relationships, and why she’s been intentionally reexamining those patterns as her life and priorities have shifted.

We move beyond the stereotypical Type 3 narrative to explore achievement through caretaking, adaptability, and being easy to be with. I also share my own experience as a Type 3, including the tension between productivity and presence, the discomfort with stillness, and the fear that if we stop doing, we might stop belonging.

If you’ve ever felt pressure to earn your place, struggled to redefine ambition, or wondered who you are without your accomplishments, this episode offers new language and permission to practice compassion, embracing a softer way forward.

Want to explore this tool for yourself? Here’s my Enneagram Typing Self-Reflection Guide:

• I just want to download the doc
• I want emails to guide me through the process

Want to connect with Sandhya for yourself or your team? Here’s how:

• Set up a call with Sandhya

Resources:

• Connect with Arden on LinkedIn
• Episode 83. The Ambitious Person’s Guide to Working Less

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA

What if you treated the turn of the year as more than a reset button—and instead as a turning point in a much bigger cycle of your life?

In this New Year’s episode, I’m joined by my dear friend, professional astrologer and attorney Julie McGill, to look back at 2025 and ahead to 2026 through both a personal and astrological lens. We reflect on the intentions I set, how they unfolded throughout the year, and how Julie navigated her own shifts in work, identity, and rhythm. Julie breaks down some of the major astrological themes that shaped 2025 and offers guidance for what we may collectively and individually experience in 2026. We explore how to set intentions in a way that matches the moment, what it looks like to stay grounded when you can’t yet see the full picture, and the value of moving into the new year with presence, curiosity, and more compassion for yourself.

If you’ve felt like 2025 put you through the wringer, or if you’re sensing big change on the horizon without knowing what it is yet, this episode is meant to help you exhale. I hope it gives you language for what you’ve been experiencing, permission to be exactly where you are, and some gentle guidance for stepping into 2026 with openness instead of pressure to have it all figured out.

Resources:

• Pull your chart at astro-seek.com
• Learn more at thecosmicgem.com
• Follow Jules on Instagram: @julesthecosmicgem
• Listen to Episode 76. Tools to Work Your Way: Astrology
• Connect with Jules on LinkedIn

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA

Consistency doesn’t have to be so rigid.

In this solo episode, I share what I’ve learned about reimagining consistency in a way that actually works for creatives, entrepreneurs, and leaders. For years, I believed the traditional advice: stick to the same schedule, follow the proven and popular formula, just keep going no matter what. But what I found was that kind of rigidity often leads to burnout, shame, and misalignment.

Instead, I’ve discovered a more authentic approach. I walk you through the four principles that have helped me build momentum without losing energy: focusing on what lights you up, considering the impact you want to have, finding your own rhythm, and setting process goals instead of chasing outcomes.

Along the way, I reflect on the early days of launching Working Your Way, what I’ve learned from outsourcing vs. DIY, and how showing up with intention has created opportunities I never could have planned for.

If you’ve ever struggled to “stay consistent” or felt guilty for not doing enough, this episode will give you permission to let go of perfection—and design a version of consistency that feels aligned, sustainable, and uniquely yours.

Resources:

• Episode 27. Creating Harmony in Work and Life with Sam Parvin
• Episode 50. Behind the Scenes of Working Your Way | Celebrating One Year
• Episode 55. Beyond Resolutions: How to Set Meaningful Goals for 2025
• Episode 74. Working For Yourself: What You Need To Know

Produced by NOVA

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA

We’re revisiting a powerful conversation with Edina Kalamperovic, SVP at Publicis Group, one of the largest communications and digital transformation companies in the world, and Founder of CareerJig, an online career development and mentorship platform. Edina’s story is one of resilience, authenticity, and staying grounded in her values—even in high-pressure environments.

As a first-generation American and child of immigrants, Edina shares how her upbringing shaped her perspective on success and character. She opens up about the challenges of working in environments where stagnation and status quo held her back, and how stepping away gave her the clarity to return with renewed focus and impact.

In this episode, we dive into Edina’s reflections on burnout, leading with authenticity, and fostering trust on her teams. She talks about bringing a startup mindset into large organizations, the importance of direct yet caring communication, and why “growth moments” matter more than “gotcha moments.”

Join us for this inspiring conversation about finding your purpose, building resilience, and leading with integrity in today’s workplace.

Resources:

• Download the Energy Inventory Worksheet
• Read Edina’s work on Substack: edinakalamperovic.substack.com
• Connect with Edina on LinkedIn
• Sign up for CareerJig
• How to Restore Yourself from Burnout with Dr. Christina Maslach - How to be Awesome at Your Job

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA

We’re excited to revisit one of our earlier episodes featuring the inspiring Jill Lyons. As the SVP of Creative Operations at Maximum Effort, Jill has built a remarkable career by following her curiosity and embracing new possibilities. From her beginnings in journalism and traditional TV production to leading creative operations at an innovative media firm, Jill’s story is a testament to the power of exploration and adaptability.

In this conversation, Jill shares how her diverse experiences created a strong foundation for her career—what she describes as building a wide pyramid base before narrowing in on the work she loves most. She also opens up about her challenges with perfectionism and predictability, and how learning to surrender to possibility has shaped her growth as a leader.

Join us as we learn from Jill’s journey and gather practical advice for embracing creativity, curiosity, and self-trust in your own career path.

Resources:

• Learn more about Jill at jilllyons.com
• Connect with Jill on LinkedIn
• Read Find Your Zone of Genius by Laura Garnett
• Read Designing Your Life by Bill Burnett & Dave Evans
• Reflected Best Self Exercise™
• Listen to 24. How do I define my personal brand? | Career Questions

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA

Discomfort isn’t always a bad thing—in fact, it’s often where the most meaningful growth happens. In this solo episode, I’m sharing why getting uncomfortable is essential for building confidence, deepening relationships, and becoming the person you want to be.

I’ll walk you through the “learning zone” model to help you identify whether you’re in your comfort zone, stretching in a healthy way, or pushing yourself into the panic zone. We’ll talk about how to discern between discomfort that helps you grow and the kind that harms, why avoiding difficult conversations keeps us from developing critical skills, and how my own core values of growth and connection guide me in these moments.

Along the way, I’ll share stories from my own life—from stepping onto a stage at The Moth to tackling emotionally vulnerable conversations—that show how discomfort, paired with self-compassion and support, can transform your capacity and your connections.

If you’ve been avoiding a challenge because it feels uncomfortable, this episode will help you decide whether it’s a moment to lean in, step back, or find a healthier way forward.

Resources:

• Listen to Episode 35. Are You a People Pleaser? | Let’s Talk About Labels
• Listen to Episode 08. Being Bold & Creating Belonging with Eduardo Placer
• Learn more about Fearless Communicators
• Watch my talk: My Story: The Pursuit Of Belonging
• Learn more about The Moth

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA

Somewhere along the way, many of us realized that chasing every goal, promotion, or dollar didn’t actually make us happier or healthier. My friend Arden Evenson, founder of Firefly Advising (and a regular here on Working Your Way), and I regularly discuss how we can reject the “rise and grind” mentality, and we wanted to bring that conversation to you. As we get honest with ourselves and each other, Arden and I compare notes on ambition, letting go of hustle culture, and what it takes to design a career around joy, flexibility, and enoughness.

We get into how becoming a parent (or simply changing priorities) can challenge your definition of success, why “good enough” can be the most sustainable business strategy, and how neither of us wants to sacrifice well-being for the next rung on the ladder. We talk about giving up perfectionism, resisting comparison, and setting boundaries that actually stick—even when the old pressures flare up.

If you’ve ever wondered what would happen if you worked less but cared even more, this episode is for you.

Resources:

• Connect with Arden on LinkedIn

Connect with me:

• Instagram
• LinkedIn
• YouTube
• selfatwork.com

Produced by NOVA