Social life in Milwaukee was far more interesting than anything Herbert had experienced before. After Fred's departure Herbert roomed with other Normal students. Despite his sometimes cloistered study habits Herbert easily made friends among the students, men and women alike. Gertrude apparently slipped off of his list of preferred female companions. There was no lack of attractive young ladies to escort to dances, sleigh rides, and other entertainments at Wisconsin Normal. Besides, Gertrude was younger and still in Tunnel City.
Gertrude, perhaps sensing that Herbert was losing interest, then stunned him by announcing that she intended to teach. “She always swore against it,” he wrote his brother. “But so we do change. I think she will be a success with smaller children,” he added, not quite willing to grant Gertrude full credit for a career move that was identical to his own.43 Gertrude landed a job in suburban St. Paul, Minnesota.44 This was a bold move, revealing an unexpected streak of independence and drive in the small-town girl Herbert thought he knew. And she did not have to go to York to teach bumpkins, he no doubt noticed. His correspondence with Gertrude had dwindled (at least he seldom mentioned it to Fred), and he no longer regarded their relationship as a courtship, if he ever had. But Gertrude, well, Gertrude had other plans.
All the while, Herbert portrayed himself as a carefree youth playing the field. “Now I'm not in love—with anybody, but my Dutch and my Norwegian girls used to bother me somewhat, for I did not know which to please. I settled it by trying to please them both. Hope I succeeded.”45 One school incident hints that he was not quite the sophisticated lover that his letters made him out to be. Miss Faddis, an instructor at Normal, held regular classes in manners. Herbert attended infrequently, but decided to put in an appearance one day. He was the only man among fifteen young women for whom Miss Faddis was demonstrating the correct method of shaking hands, a procedure evidently more complicated in 1891 than it is today. Perhaps she failed to notice the lone gentleman in the room, or maybe she just forgot herself in the midst of a teachable moment. Whatever the case, in order to make clear the particularities of correct posture, she raised her dress “nearly up to her ___ ,” Herbert reported to Fred. This display of feminine pulchritude was too much for the blushing young brother, who left the room. He immediately reported the incident to Professor Mapel, but did not get the response that he expected. “ ‘Oh my dear boy!’ said he. ‘you don't like it because you are not interested. If Mr Gillan should give you the work you would do your best.’ ” Herbert evidently did not quite follow the gist of Mapel's remark. “I soon made him understand that he had told the truth for Gillan is a teacher, and Miss F. is not.”46 The boy from Tomah was not yet up to the droll humor of the urban sophisticates in Milwaukee.
The end of the spring semester 1891 found Herbert preparing for graduation and looking for employment. Fred was going to the University of Wisconsin in the fall, so Herbert needed a good job in order to support his brother's further education. The brothers put an amazing amount of time and energy into their search for employment. They seemed to know of openings in every school throughout the state and shared information about each place, who they knew there, and who could help them with a recommendation. Herbert's best chance for employment came from his brother's recommendation to replace him at Fairchild. He considered a position in Montello, but Professor Gillan thought it would go to a Catholic, so he advised Herbert to concentrate on Fairchild.47 Religious and ethnic prejudice worked both ways in the 1890s, as the Protestant Herbert learned.
With neither summer nor fall plans firmed up, Herbert looked forward to graduation. If not quite a lettered man, he at least would have a diploma that certified his professional standing among the ranks of Wisconsin teachers. He was relieved to pass this milestone in his diligent program of self-improvement and upward mobility.48
In July Fairchild finally decided to hire Herbert as principal at seventy dollars per month. At about the same time he learned about Fairchild, something else popped up. Gertrude, fresh from a year of teaching at St. Paul, wanted to study with him during the summer. He thought it would be a good idea, but the plan did not materialize as Gertrude had hoped.49 Herbert took a job as a traveling salesman of memberships in an association that sold books to members at discount prices. “Now if a man has time and wants a trip to California he can get there all right if he will work.”50 He liked the money, but selling on the road was not the path to status that he had in mind. A traveler did “not belong to any society, and of course” was “a fraud.”51 Herbert would find another way to get to California.
A letter from Gertrude found Herbert while he was on the road. She had heard about a teaching position at Fairchild and asked Herbert to help her get it. He was willing, but it turned out that the position had already been filled. Too bad, but Gertrude, a young woman of remarkable resilience, persistence, and determination, was not finished with Herbert yet.52
At summer's end Herbert went to Fairchild to take up his post as high school principal. He was twenty-one and only two years out of high school, yet now he taught pupils who were nearly as old as himself, managed the school, and oversaw teachers who were far older and more experienced than he was.53 Of course, he taught his own classes, so preparation was part of his day. As always, he worked at night for as long as the light and his energy held out. In addition to his myriad duties Herbert prepared himself to enter the University of Wisconsin, where Fred was now a student. Herbert would maintain this demanding schedule for two years, sending Fred whatever money he could spare.
It should come as no surprise that Herbert managed to do all of this work. By then discipline and labor were ingrained in him, but there was more to the principal's job than work. The management of older teachers who must have resented a mere youth as their new chief required sound judgment. Before long one of the teachers began to give him trouble, but he stood firm and eventually forced her to resign.54 “The one who wears the slipper can kick hardest and hurt most,” he observed.55 Despite his youth Herbert was willing to take charge, give orders, and insist that they be carried out. He did not like subordinates who challenged him. In his world, even in little Fairchild, status and authority went hand in glove. For the most part Herbert wore authority lightly, but he wielded it without compunction.
Principals had to deal with superiors as well as subordinates. The state school superintendent, Oliver E. Wells, had to approve the work done at Wisconsin high schools. He also had something to say about who taught summer institutes and was an ex officio member of the University of Wisconsin Board of Regents. Wells's win was something of a surprise in the 1890 election that swept him and other Democrats into office.56 Needless to say, getting along with Superintendent Wells was crucial for high school principals. Wells, however, was not well liked by the Bolton brothers. He hoped to revamp the University of Wisconsin to emphasize practical subjects that would better serve the people of Wisconsin, or so he believed. Fred wrote a critical newspaper article about Wells. “Good for you!” wrote brother Herbert. “I endorse your sentiment…exactly.”57
Herbert disliked Wells, but he had to cultivate him while he was in office. When finally he met Wells, Herbert ingratiated himself with pleasantries and good humor. In November 1892 Herbert voted against Wells, but the superintendent won reelection.58 Herbert had little choice but to go along cheerfully with a superintendent whom he happened to despise. This small incident foreshadowed a lifetime of pleasing the men who held authority over him. When in charge, Herbert expected to be obeyed; to his betters, he returned the favor with a smile on his face.
Success at Fairchild High School was important to Herbert, but it was a means to an end. He studied hard for the university and kept asking Fred for advice about his studies. The brothers were dreaming big dreams for farm boys with two-year teaching diplomas. They began to consider the doctorate as the consummation of their educational and social advancement. Herbert drew a figure at the bottom of a letter to Fred. At the left margin a fingerpost pointed to the right, followed by five arrows that ended at “Ph.D.”