Bradley was born July 10, 1868, in Boston, Massachusetts to Aaron Bradley and Sarah Rowland. At the age of 12 he obtained a job as an apprentice for a weekly newspaper — the "Iron Agitator", later known as the "Iron Ore" — in Ishpeming, Michigan. He had moved there with his mother to be with family after the death of his father. He left at 17 for Chicago, Illinois, where he held a few brief jobs as a wood engraver and typographer before dedicating himself to freelance graphic design. He moved back to Massachusetts and set up the Wayside Press, where he served as an illustrator, editor, typographer, designer, and press manager for a magazine he named "Bradley, His Book". The periodical usually contained compilations of poetry, stories, and sketches, and his work received a warm reception. He had achieved financial success, but the stress of managing so many projects at once began to damage his health, and he collapsed at the age of 28. He recovered quickly, but he was forced to sell the Wayside Press.