Around the Ladder

Erika Steinberg
  • 5.0 (5)
  • Careers
  • Updated Weekly

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. 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

    39 min

  2. 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

    38 min

  3. Apr 30

    Around The Ladder: Listening to Your Body, Rewriting Your Career With Teah Iosebashvilli & Aleena Abrahamian

    In this conversation on Around the Ladder, host Erika Steinberg talks with Teah Iosebashvilli and Aleena Abrahamian about what happens when work, health, and identity begin to shift at the same time. Both guests share candidly about burnout, perimenopause and menopause, and the decision to build careers that support their energy, wellbeing, and priorities instead of working against them. Their conversation is honest, funny, and deeply relatable for anyone reassessing what success really means. Teah reflects on leaving a long corporate career after realizing she could no longer keep pushing through in the same way, especially as health challenges made full-time work unsustainable. Aleena shares how a combination of intense work demands, illness, and perimenopause forced her to slow down and rethink how she wanted to work moving forward. Together, they discuss the freedom and flexibility of fractional work, the value of experience, and the importance of setting boundaries that protect both health and momentum. This episode also explores the emotional side of reinvention: letting go of old expectations, becoming more comfortable saying no, and accepting that ambition can still exist alongside rest, flexibility, and self-care. The result is a thoughtful conversation about career changes, midlife clarity, and building a version of success that feels sustainable. Connect with Teah and Aleena Teah Losebashvilli Teah is a fractional marketing strategist who helps professional services firms and companies elevate their brand, generate demand, and drive revenue. She brings nearly two decades of experience leading marketing at Big Four consulting firms and Am Law 50 firms, and now works with clients to position them to win in competitive markets. LinkedIn: Teah Iosebashvili Website: Four 1 Five Aleena Abrahamian Aleena is a growth operator and fractional CMO who helps consumer brands build and scale new revenue engines. She has led product marketing and partnerships for brands including Calm, MyFitnessPal, Charlotte Tilbury, and Finch, with experience spanning startups to billion-dollar global businesses. LinkedIn: Aleena Abrahamian

    1h 1m

  4. Apr 16

    Around The Ladder: Building Success Without a Traditional Ladder with Caitlin Harrison

    In this episode of Around the Ladder, Erika Steinberg speaks with Caitlin Harrison, founder of Firmly Studio, about what it means to build a career without a traditional ladder. Caitlin shares how her path through small design companies, print publications, and digital work led her to launch her own business in 2020. What began as a leap during an unstable season turned into a clearer vision for the type of work she wanted to do and the clients she wanted to serve. Together, Erika and Caitlin explore: What it means to build a career when no clear ladder exists. How the pandemic and family life shaped Caitlin’s decision to go out on her own. Why niching down brought clarity to her business. What many law firms misunderstand about websites and online marketing. How simple, trust-building design helps convert visitors into clients. The role of networking, relationships, and flexibility in growing a small business. How Caitlin now defines success through freedom, family, and meaningful client work. Caitlin also shares how her business has evolved from general design work into a focused service for solo and small law firms, while still offering branding, print design, and website care plans. Connect With Caitlin Website: Caitlin Harrison Creative Tour link: Firmly Studio Tour LinkedIn: Caitlin Harrison Instagram: Caitlin Harrison Creative

    28 min

  5. Apr 2

    Around The Ladder: Letting Go Without Losing Control with Ariana Tenine

    In this episode of Around the Ladder host Erika Steinberg sits down with fractional COO and operations strategist Ariana Tenine to talk about what happens when your business is “working” yet you feel maxed out mentally and emotionally. Ariana shares how she accidentally discovered operations as her zone of genius and how she now helps multi six and seven figure visionaries cut their day to day decision making in half through her Restructured Method.​ Together Erika and Ariana unpack why so many entrepreneurs normalize mental overload, especially women and neurodivergent founders, and why resistance to systems is often a quiet fear response rather than a tech issue. They explore what a supportive business actually looks like, how to stop building around old corporate expectations, and why the first honest question to ask yourself is “but do I have to do this.”​ In This Episode We Talk About The feeling of “flying by the seat of your pants” and what is usually underneath it before systems ever enter the conversation.​​ How holding everything in your head becomes invisible mental labor and why so many high achieving women assume it is just part of the job.​ The hidden fear behind “I can do it faster myself” and how lack of trust in your offers or messaging can show up as resistance to systems.​ Why constant pivoting makes it impossible to trust your data and how consistency reveals what is actually working.​​ What a supportive business feels like day to day, from clear objectives to assigned tasks and realistic timelines for your team.​ How quarterly strategic planning can become your North Star when you are overwhelmed or tempted to chase every new idea.​ Why Ariana recommends starting with operations before hiring a VA so you are not onboarding people into chaos.​​​ Connect With Ariana TikTok: ArianaTenine​ Instagram: arianatenine_doo​ LinkedIn: Ariana Tenine Website: ArianaTenine.com

    31 min

  6. Mar 19

    Around The Ladder: Leaving “Safe” Work to Tell Bigger Stories with Steven Heumann

    In this episode of Around the Ladder, host Erika Steinberg sits down with storyteller and founder of Super Heumann Creative Steven Heumann to unpack what happens when “safe” stops feeling right and comfort starts to feel like a trap. Steven shares how he spent 15 years in television rising from intern to senior producer then realized the growth he wanted would only come if he took a risk on himself. Erika and Steven dig into the idea of “test trial or trap” and how to know whether you are experimenting stretching or simply staying stuck because the familiar feels easier than the unknown. They explore the discomfort of leaving a long held role the messy middle of entrepreneurship and why our expectations about how a risk “should” turn out can be the very thing that keeps us from taking it. If you have ever stayed too long in a role because it was familiar or questioned whether a setback meant you made the wrong move this conversation will help you see your own story differently. You will walk away with a reframed view of failure a deeper understanding of your own “tests” versus “traps” and a reminder that your story is worth telling even before you feel like it is finished. In this episode we talk about How Steven went from “I cannot make money as an artist or writer” to building a storytelling agency of his own. The moment he realized the risk he wanted his company to take would have to come from him instead. The difference between a test a trial and a trap when you are making career moves or life changes. Why comfort can feel good and bad at the same time and how to listen when it starts to feel wrong. What “failing until you succeed” looks like in real time including a lead generation investment that did not go as expected but still transformed his business. How legacy storytelling can help you see the value in your own journey and create deeper connection with others. Connect with Steven Website (storytelling and legacy work): superheumann.com Fiction site and signed paperbacks: stevenheumannauthor.com LinkedIn: Steven Heumann

    41 min

  7. Mar 5

    Around the Ladder: From Winning on Paper to a Life That Fits With Jennifer Gillman

    In this episode of Around the Ladder, host Erika Steinberg sits down with legal recruiter and author Jennifer Gillman to talk about what it really takes for lawyers to move from “surviving” to truly thriving in their careers and lives. Drawing on years of conversations with law firm partners and rainmakers plus insights from her new book The Happy Rainmaker, Jennifer shares a practical framework for building a successful practice that does not cost you your health or your relationships.​ Jennifer explains why so many lawyers who look like they have “made it” on paper are exhausted, isolated and stuck in perfectionism cycles that keep them chained to their desks. She introduces her Six Pillars to Becoming a Happy Rainmaker starting with caring for yourself so you actually have the mental and physical capacity to design a more sustainable practice.​ You will hear concrete examples of how rainmakers can use business development to gain more control over their time, structure their practices around what matters to them and have better conversations with firm leadership about the support they need. Jennifer and Erika also talk about what thriving looks like in real life from taking real vacations to showing up for a child’s award ceremony to having something meaningful to retire to rather than being the 87 year old partner who has nowhere else to go.​ The episode is full of small, doable ideas built around Jennifer’s mantra that “0.1 is enough to get started” whether that means taking a six minute walk, making a doctor’s appointment or adding ten minutes of sleep. They also explore how associates can begin setting boundaries early, how accountability can make new habits stick and why law firms benefit when lawyers are healthier more engaged and more intentional about their careers.​ If you are a lawyer who is winning on paper but feeling the Sunday scaries, living on vending machine meals or constantly on the apology tour at home, this conversation will give you both language and tools to start changing your path one small step at a time.   Connect With Jennifer:  LinkedIn: Jennifer Gillman  Website: Gillman Strategic Group Book: The Happy Rainmaker

    37 min

  8. Feb 19

    Around The Ladder: Owning Your Story With Janet Falk

    In this Episode media strategist and former academic turned Wall Street analyst, nonprofit leader and legal PR pro, Janet Falk has built a career by refusing to climb a single ladder in a straight line. In this episode, Janet joins host Erika Steinberg to talk about control in media relations, the six Ws every communicator should use, and why you are always in the “business of your own name.”​ In this episode How Janet navigated academia, Wall Street, nonprofits, legal services and entrepreneurship to create a portfolio career that fits who she is.​ Why you never truly control media outcomes, and what you can control instead through Janet’s “marketing RBI” framework.​ The six Ws of communication (including the often forgotten sixth W) and how they guide more effective marketing and PR.​ How to turn one article or speaking gig into a snowball of conferences, media quotes and new business.​ Practical networking strategies, including how to “warm up the room” before an event so you never walk into a cold crowd again.​ Why lawyers and other professionals must see themselves as being in the “your name” business and get comfortable being visible.​ Connect with Janet Website: Falk Communications and Research ​ LinkedIn: Janet Falk Janet's Books & Newsletter Create and Monitor Your Marketing RBI (price $9.99)   Three Steps to Improve Your Networking Success Write Your Case Study with P A RI (Problem, Action, Result, Impact)

    46 min
See All (37)

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
    37
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Around the Ladder

You Might Also Like