In the spring of 1840 Henry left home again in search of work away from his family. He ended up working as a chain holder for a survey company in New York. They were laying the route for a train from New York to Philadelphia.

When the surveyor line reached Philadelphia, he got a job at an auction house Myers, Claghorn and CO. as a clerk. His tenacity, hard work and cheerful disposition eventually landed him a job as an auctioneer.