Around the Ladder

Erika Steinberg
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Welcome to Around the Ladder – the podcast where we explore the twists, turns, and unexpected detours of career journeys. Many of us are familiar with the phrase ”climbing the corporate ladder,” but what happens when your path doesn’t follow a straight line? I became fascinated by the idea of going around the ladder – carving out a different kind of career path. My own journey took this route. After 25 years as an employee, I stepped away for a year and emerged as a consultant and business owner. And along the way, I realized I’m not alone. There are so many people out there whose careers have taken unconventional, surprising, and inspiring directions. In this podcast, you’ll hear conversations with people who have traveled paths of all shapes and sizes. Sometimes you backtrack or move sideways; other times, you need someone to lift you up or simply sit with you right where you are. No matter where you are on your journey, you’re not alone. So, whether you’re rethinking your next step or just curious about the many ways a career can unfold, you’re in the right place. This is Around the Ladder – let’s explore the journey together.

  1. Aug 27

    Three Alumni, Three Decades, One Unexpected Throughline with Haley Gray and Isabel Angeli

    What happens when three George Washington University alumni from different generations sit down to compare notes on college, career pivots, and the experiences that shaped them? In this special episode of Around the Ladder, host Erika Steinberg welcomes Haley Gray, financial planner and founder of Valora Wealth, and Isabel Angeli, a legal marketing communications professional, for a conversation about the lasting influence of George Washington University and Washington, DC. All three began with different expectations for their careers. Haley and Isabel arrived at GW drawn to journalism, while Erika imagined a future in academia. But through internships, city living, group projects, early professional exposure, and a few hard-earned lessons in class registration, each discovered that careers rarely follow a straight line. Together, they discuss the value of being proactive, building resilience, taking smart risks, embracing career changes, and leaning into the connections that come from an alumni network. From cold LinkedIn outreach that leads to a job opportunity to taking a step back professionally in order to move forward, this conversation is a reminder that the people, places, and challenges we encounter early on can stay with us for a lifetime. Whether you are a GW alum, a current student, a recent graduate, or someone navigating a career transition of your own, this episode offers encouragement to look through every open door—and trust that you can figure out the next step. In This Episode Why GW’s location in Washington, DC, created an environment where students learned to become professionals early. How internships, jobs, and real-world access can be just as formative as coursework. The unexpected paths from journalism into financial planning, legal marketing, and legal-industry communications. What living in a fast-paced city teaches you about resilience, independence, and paying attention to the world beyond your immediate circle. The importance of asking for help, being proactive, and learning from mistakes—including registering for the wrong class. Why career pivots can require humility, patience, and sometimes taking a step back to build toward the right long-term opportunity. How a cold LinkedIn message to a fellow alum helped Isabel land a pivotal legal marketing role. The enduring power of alumni communities, local events, and professional relationships. What each guest would tell her freshman-year self about stress, opportunity, relationships, and enjoying the journey. Connect With the Guests: Haley Gray: Website- Stellarix Group LinkedIn- Haley Gray   Isabel Angeli: LinkedIn- Isabel Angeli

  2. Aug 13

    Business Plans, Big Feelings, and Better Boundaries with Elissa Hecker

    When small business attorney Elissa Hecker had her first child, she expected to go back to her in‑house role, hire a nanny, and keep climbing. Instead, a miserable work environment and a powerful “this can’t be it” moment pushed her to bet on herself and build a remote law practice—back in 2004, long before it was cool. In this episode, Elissa joins Erika to talk about the very human side of starting a business: the fear, the relief, the identity shifts, and why your personal story is never as separate from your business as we like to think. Along the way, she shares the practical legal building blocks every founder should consider, what really happens when “business partners” need a “business divorce,” and why she tells clients to “blame the lawyer” to protect important relationships. If you’re sitting in a role that feels safe but miserable, or you’re thinking about starting something of your own and keep finding reasons to wait, this one’s for you. In this episode, we talk about: How becoming a mother—and being unhappy at work—pushed Elissa to open her own practice instead of going back in‑house What it was like to run a fully remote law firm in 2004, and how people reacted when she said she worked from home The difference between being great at your craft and actually knowing how to run a business around it Why your personal growth and your business growth are almost impossible to untangle The “lawyer/therapist” role and how Elissa holds space for the emotional side of entrepreneurship Why she tells clients to “blame the lawyer” to preserve friendships and family relationships in tough negotiations Connect with Elissa  LinkedIn: Elissa D. Hecker  Website: The Law Office Of Elissa D. Hecker

  3. Jul 30

    Why Soft Skills Are Actually Strategic Skills With Bushra Khan

    In this episode of Around the Ladder, Erika Steinberg sits down with Dr. Bushra Khan to explore why the skills that matter most in today’s workplace are often the ones that are hardest to measure. As AI takes over more of the technical, repeatable parts of work, the conversation shifts to what still sets people apart: communication, emotional intelligence, trust-building, and the ability to lead through uncertainty. Bushra makes a strong case for retiring the phrase “soft skills” and reframing them as strategic skills. She breaks down how self-awareness, relationship management, social awareness, and emotional regulation affect everything from leadership and change management to conflict resolution and career growth. The episode also digs into why AI is raising the bar at work, how leaders can keep teams grounded during change, and why human connection is becoming even more valuable. Erika and Bushra also talk about the importance of team-based training, shared language, and creating organizational buy-in instead of relying on one-off coaching or individual development alone. Bushra closes with a practical reminder: when work feels uncertain, return to your own track record and remember the hard things you’ve already done. In this episode, you’ll learn: Why emotional intelligence is a strategic advantage in the AI era. How trust and human connection still drive leadership and influence. Why change leadership matters more than change management alone. How AI is reshaping expectations, pace, and burnout across industries. Why resilience and self-awareness are essential for navigating uncertainty. Connect with Bushra Khan: LinkedIn: Dr. Bushra Khan Website: Leading with BK Instagram: leadingwithbk

  4. Jul 16

    Around The Ladder: What If the Detour Was the Point? With Matt Plavnick

    In this episode of Around the Ladder, Erika Steinberg sits down with Matt Plavnick to talk about the unexpected turns that shaped his path, from teaching and writing to time in Antarctica, freelance work, and eventually a long career inside law firms before launching his own business. Matt’s story is a reminder that not every move needs to look strategic in the moment to become meaningful later. What can feel like a gap, a detour, or a series of happy accidents may actually be the foundation for the work you’re meant to do. What we talk about How Matt describes his career as a series of “happy accidents”. The role travel, writing, and wilderness work played in shaping his perspective. Why he didn’t feel “behind,” even when his path looked unconventional. What he learned from stepping into law firm life in his mid-30s. How parenting and work forced him to rethink creativity, ambition, and priorities. Why storytelling and critical thinking became such important parts of his work. How naming and framing can help people recognize the strengths they already have. Why he believes many people are more prepared for change than they realize.   Matt’s journey is a reminder that clarity doesn’t always arrive first, sometimes it shows up after the experiments, the pivots, and the unexpected yeses. No matter where you are on your journey, you’re not alone. Connect with Guest LinkedIn: Matt Plavnick Website: Axis Blog: Legal Marketing AF

  5. Jul 2

    Around The Ladder: Financial Planning for a Career Pivot With Haley Gray

    In this episode of Around the Ladder, Erika Steinberg sits down with financial planner Haley Gray to unpack one of the most emotionally charged parts of career change: money. Haley shares how financial planning intersects with fear, freedom, identity, and the very real practical concerns that come with leaving a stable job or starting something new. Together, they discuss what people are most afraid of when considering a career move, why money is often more emotional than logical, and how to build more financial flexibility before making a leap. Haley also explains the common surprises that catch people off guard, including healthcare costs, irregular income, and the need to separate personal and business finances. The conversation also explores the differences between proactive and reactive career transitions, why a side hustle can be a smart way to test an idea, and how generational attitudes toward work and risk shape these decisions. If you’ve ever wondered whether you’re “ready enough” to make a change, this episode offers both reassurance and practical guidance. Connect with Haley: LinkedIn: Haley Gray, CFP, AIF Website: Stellarix Email: hgray@financialguide.com

  6. Jun 18

    Around the Ladder: What If the Ladder Isn’t the Answer? With Shabnam Irilian

    In this episode of Around the Ladder, host Erika Steinberg sits down with Shabnam Irilian for an honest conversation about what happens when a career that once felt right starts to feel misaligned. Shabnam shares her experience of stepping away from a successful, linear career after realizing that burnout, exhaustion, and a lack of fulfillment had taken over. Together, they explore the emotional weight of leaving behind a path that others may see as successful, even when it no longer feels sustainable from the inside. The conversation goes beyond career change and into the deeper stories we tell ourselves about work, worth, and success. Shabnam opens up about the beliefs that kept her going for so long, the idea that hard work would always be rewarded, that gratitude should keep her from asking for more, and that being dependable meant carrying more than she should have. Erika draws out thoughtful reflections on burnout, identity, and the pressure many high-performing professionals, especially eldest daughters and first-generation women, carry throughout their careers. They also discuss the shift toward building a portfolio of income instead of relying on a single job or title. Shabnam talks about creating a more intentional life through consulting, board work, teaching, and creative projects, while Erika reflects on the importance of choosing work that feels aligned and sustainable. The episode closes with a powerful reminder that career clarity often begins by paying attention to what does not feel right, asking better questions, and giving yourself permission to choose differently. Connect with Shabnam:  LinkedIn Website

  7. May 28

    Around The Ladder: The Growing Disconnect Between People and Their Jobs With Alex McCann

    What happens when your career looks good on paper, but still feels off? In this episode of Around the Ladder, Erika Steinberg talks with Alex McCann about career pivots, the pressure to “have it figured out,” and why so many people are questioning the old rules of work. Alex shares the through line behind his own shifts from engineering to music to marketing and now to founding Rumbo: curiosity, experimentation, and a willingness to test assumptions about himself. He and Erika also dig into his viral essay, The Death of the Corporate Job, and why it resonated with so many people who feel disconnected from the jobs they’re supposed to value. The conversation explores the gap between how work looks and how it actually feels, the role of social media and comparison culture, and why “imposter syndrome” may not always be the right language for what people are experiencing. They also discuss AI, automation, and what happens when white-collar work becomes increasingly easy to simulate or obscure. Later in the episode, Alex explains how his experience with a career coach inspired Rumbo, a platform designed to help people move beyond tactical job-search advice and get clearer on strategy, direction, and what they actually want from work. The episode closes with a thoughtful reminder: if something feels wrong in your career, it may be worth stepping back and connecting your work to a problem you genuinely care about solving. Connect With Alex Substack: Still Wandering Company: Rumbo LinkedIn: Alex McCann

  8. May 14

    Why High Achievers Struggle Without Structure with Laura Guy

    In this episode of Around the Ladder, Erika Steinberg sits down with licensed clinical social worker Laura Guy to explore what can surface when high-achieving professionals step off the traditional career path and start building something of their own. What often looks like freedom on the outside can also bring up a surprising amount of uncertainty on the inside, especially for people who have long relied on structure, external validation, and clear markers of success to feel grounded and secure. Laura and Erika dig into the connection between achievement and anxiety, and why so many overachievers are also anxious overachievers. They talk about how perfectionism, imposter syndrome, hyper-responsibility, and the need to “get it right” can become deeply ingrained coping mechanisms, often shaped by childhood experiences, family dynamics, and environments where performance was heavily rewarded. The conversation also touches on how these old patterns can show up in adult professional life, from reacting strongly to unclear emails to feeling like one mistake could undo everything. One of the most helpful parts of the episode is Laura’s reminder that uncertainty tolerance is a skill, not just a personality trait. Together, Erika and Laura discuss practical ways to work with anxiety instead of fighting it, including noticing the feeling, naming it, creating a little distance from it, and taking small values-based steps forward anyway. If you’ve ever wondered whether the voice in your head is really your adult self or an older, younger part of you trying to keep you safe, this conversation offers a thoughtful and validating framework for understanding it. Connect With Laura LinkedIn: Laura Guy

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Ratings & Reviews

5
out of 5
5 Ratings

About

Welcome to Around the Ladder – the podcast where we explore the twists, turns, and unexpected detours of career journeys. Many of us are familiar with the phrase ”climbing the corporate ladder,” but what happens when your path doesn’t follow a straight line? I became fascinated by the idea of going around the ladder – carving out a different kind of career path. My own journey took this route. After 25 years as an employee, I stepped away for a year and emerged as a consultant and business owner. And along the way, I realized I’m not alone. There are so many people out there whose careers have taken unconventional, surprising, and inspiring directions. In this podcast, you’ll hear conversations with people who have traveled paths of all shapes and sizes. Sometimes you backtrack or move sideways; other times, you need someone to lift you up or simply sit with you right where you are. No matter where you are on your journey, you’re not alone. So, whether you’re rethinking your next step or just curious about the many ways a career can unfold, you’re in the right place. This is Around the Ladder – let’s explore the journey together.

Information

  • Creator
    Erika Steinberg
  • Years Active
    2025 - 2026
  • Episodes
    43
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Around the Ladder