Moving From Wall Street to Wilderness: The Career Pivot of a Tech Professional to a Full-Time Hiking Guide

Initial Steps in the World of Finance

Goldstein began his professional journey as an intern on Wall Street, influenced by his peers. His career in finance continued to thrive as he took up roles at the notable firms Credit Suisse and Goldman Sachs. While the finance world fascinated him, the demanding nature of the industry started to interrupt his work-life balance.

Transitioning to the Tech Industry

By 2013, at the age of 27, Goldstein decided to take his first career pivot and ventured into the technological domain. Although he found the environment at tech startups to be intense, his desire to lead hiking groups around the Hudson Valley and the Catskills remained unwavering.

Realizing the Dream: A Full-Time Hiking Guide

“I’d always thought that if I were ever in the financial position and had achieved enough in my corporate career, I could finally give myself permission to pivot,” Goldstein shared with Business Insider in September 2025.

Fulfilling his lifelong dream, Goldstein made his career pivot as a full-time hiking guide in 2023 after achieving his savings and investment goals. This decision brought immeasurable happiness and contentment to his life.

Dive deeper into Goldstein’s fascinating career transition journey from Wall Street to the wilderness.

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