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

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 [https://thestillwandering.substack.com/] * Company: Rumbo [https://www.rumbocareers.com/] * LinkedIn: Alex McCann [https://www.linkedin.com/in/alex-mccann-ba1718230/]

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 [https://www.linkedin.com/in/laura-guy-2412b910/]

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 [http://linkedin.com/in/teah-iosebashvili-261b591] * Website: Four 1 Five [https://four-1-five.com/] 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 [https://www.linkedin.com/in/aleena8/]

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 [https://caitlinharrisoncreative.com/] * Tour link: Firmly Studio Tour [https://firmlystudio.com/tour/] * LinkedIn: Caitlin Harrison [https://www.linkedin.com/in/harrisoncaitlin/] * Instagram: Caitlin Harrison Creative [https://www.instagram.com/caitlinharrisoncreative]

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 [https://www.tiktok.com/@arianatenine?_t=8V8YRRemOQY&_r=1] * Instagram: arianatenine_doo [https://www.instagram.com/arianatenine_doo/] * LinkedIn: Ariana Tenine [https://www.linkedin.com/in/ariana-tenine/] * Website: ArianaTenine.com [https://arianatenine.com/]