Young Stedman did grow to be an extraordinary man. He lived a varied life as a poet, critic, advocate of copyright law, and influential voice in the world of American letters. Yet, he often struggled financially. He assumed that he would inherit a substantial sum of money on his 21st birthday but a newer will from his grandfather was found.
Stedman often used his birthday as a test of his progress from year to year. In 1864, for example, he noted: "My thirty-first birthday. Since October 8, 1863, I have published my second volume, made $10,000, which came like the shadow of a great rock in a weary land... It has been the happiest year of my toilsome, turbulent manhood." By his 37th birthday in 1870, however, Stedman was despondent:
[I] have passed the fatal — to poets — 37th year, and begin to think I am no poet: only a poor, gray haired, unsuccessful dreamer, trying to get fat by feeding on the wind. Am as poor as on my 20th birthday... O, how poor, and how precarious the future! And how my genius, whatever it may be, is cramped, warped, and gradually atrophying away.
In fact, Stedman had turned away from a life of literature and put it aside as a hobby. His new career was on Wall Street. On his birthday in 1866, he reopened a brokerage business, concluding "Am now obliged to leave Art again and take up the Muck Rake." Ultimately, he worked on Wall Street for some 35 years.