Around the Ladder

Around the Ladder
Podcast Description
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.
Podcast Insights
Content Themes
The podcast covers themes of career development, personal growth, and entrepreneurship, with episodes discussing topics such as career pivots illustrated by Anne Ryan's transition from tech to coaching, the importance of reframing resumes, and creating supportive environments for personal development.

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.
On this episode of Around the Ladder, host Erika Steinberg welcomes Erin Alli, founder of Essential Assistance, to discuss the realities of entrepreneurship, the importance of operational support, and how to build a business that allows for true freedom. Erin shares her journey from sales and management to becoming a fractional COO and operations expert, and offers actionable advice for business owners at every stage.
Key Topics & Highlights
Erin’s Career Journey
From sales and management to entrepreneurship, to be available more for her family.
Launching Essential Assistance to help CEOs and founders reclaim their time.
Nearly 30 years in operations and leadership, with 20 years as a business owner.
About Essential Assistance
Virtual support for CEOs and business leaders: operations, leadership, and more.
Focus on small and midsize businesses, providing tailored strategies and systems.
When to Seek Help
Common signals: overwhelming inboxes, constant overwork, lack of effective delegation.
The value of a trusted operations partner to break down projects, set realistic timelines, and ensure continuity.
Coaching and Personal Support
Erin’s approach blends operations expertise with her coaching expertise to offer a unique benefit to those that work with her.
Addressing mindset blocks, perfectionism, and self-care for entrepreneurs.
Building personal relationships with clients to support both business and personal well-being.
Building Effective Teams
The power of regular team meetings-even virtually-to foster connection and collaboration.
Creating a safe environment for team members to share struggles and needs.
Encouraging mutual support and cross-collaboration among team members.
Essential Systems for Growing Businesses
Early implementation of Standard Operating Procedures (SOPs) for business continuity and smooth onboarding.
Leveraging automation for tasks like email, scheduling, and social media to save time and reduce bottlenecks.
Advice for Overwhelmed Entrepreneurs
Start where you are and break tasks into manageable steps.
Use brain dumps and project lists to organize thoughts and priorities.
Reach out to your network for support, even if you’re not ready to hire help.
Embrace time-blocking and minimize multitasking for greater focus and productivity.
Personal Reflections
Both Erika and Erin discuss the freedom and challenges of entrepreneurship, including the importance of authenticity and letting go of fear of others’ opinions.
Advice to their younger selves: stop overthinking, don’t hold back, and don’t worry about what others think.
Notable Quotes
“We go into business for the freedom, but as an entrepreneur, you know that you don’t have that-unless you have someone else to support you.” – Erin Alli
“You can’t be everything to everybody. I write things in a way that reflects me because I know I’m not for everybody, and everybody’s not for me.” – Erika Steinberg
About the Guest
Erin Alli is the founder of Essential Assistance, a virtual support company for CEOs and business leaders. She is also the co-host of the Mastering Business Skills podcast, co-creator of the Ultimate Lead Nurturing and Sales Conversion Guide, and co-leader of Virtual Skills Master.
Connect with Erin Alli
Thank You for Listening!
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