Around the Ladder: Resumes, Realizations, and the Road to Reinvention with Anne Ryan

In this episode of Around the Ladder, host Erika Steinberg sits down with Anne Ryan, a resume and LinkedIn coach who has helped thousands—from students to executives—unlock their unique strengths and land meaningful roles. Anne shares her unconventional journey from two decades in tech to entrepreneurship, her passion for helping others find purpose, and the superpowers she’s discovered along the way.

Key Topics Discussed

• Anne’s Career Pivot: Anne recounts her transition from a 20-year career in software and tech to resume coaching. As a hiring manager, she noticed how many qualified candidates were overlooked due to poorly crafted resumes, inspiring her to start offering workshops and eventually launch her own business1.

• From Rejection to Success: Anne shares a powerful client story: someone who sent out 300+ job applications with no luck. After working with Anne to reframe his resume for the tech industry, he quickly landed interviews and a job offer. Anne emphasizes the importance of marketing your skills in the right language1.

• Entrepreneurial Fears & Lessons: Both Erica and Anne discuss the fears and hesitations that come with starting a business. Anne introduces her concept of “FOMAM” (Fear of Making a Mistake) and recounts the advice that helped her move forward: “You’re going to launch wrong, but do it anyway.” She highlights the support she received from entrepreneurial friends and the transformative effect of the COVID-19 pandemic on her career path1.

• Superpowers & Coaching Philosophy: Anne credits her yoga teacher training for teaching her the importance of “holding space” for clients—creating a supportive, encouraging environment. She aims to make professional development fun and approachable, and values the feedback that she inspires and energizes her clients1.

• Favorite Audiences & Workshops: Anne has a special place in her heart for working with students and young professionals. She shares stories from her workshops, including a creative session at the Society of Women Engineers conference where she presented a resume workshop themed around Ken from the Barbie movie—complete with costume1.

• Defining Moments: Anne reflects on the pivotal moments that pushed her to entrepreneurship, including encouragement from mentors and the ease of officially starting her business. She describes entrepreneurship as “the most fun I’ve ever had, and the hardest I’ve ever worked”1.

Memorable Quotes

“You’re going to launch wrong, but do it anyway.” — Advice that helped Anne overcome her fear of making mistakes and start her business1.

“I want to make resumes and LinkedIn profiles fun. If you have to do it, you might as well have a good time.” — Anne Ryan on her coaching philosophy1.

“It’s the most fun I’ve ever had, and it’s the hardest I’ve ever worked.” — Anne on being an entrepreneur1.

Connect with Anne on LinkedIn