For a number of years, Mr. Cutting was associated with his father and brother in the general store, but, as time went on, he became ambitious to enlarge his activities. He, therefore, assisted in the organization of the New England branch of the Sheldon School, of Chicago, and was its manager for a number of years. When he first undertook this work, Mr. Cutting had never made a public speech in his life, and, while he was interested in politics and ambitious for success along this line, he felt greatly handicapped by what he considered to be his inability to face an audience acceptably. It was at about this time that we first formed the acquaintance of Mr. Cutting and, upon consultation, informed him of his natural aptitudes and talents. He immediately began a careful study of public speaking, supplementing this study with actual practice both in politics and in his capacity as manager of the Sheldon School. In 1908 and 1909 he was a member of the House of Representatives for the State of Massachusetts, gaining credit for himself as a member of important committees and rendering to his own constituency unusually faithful and efficient service.
As manager for the Sheldon School, Mr. Cutting selected and trained a number of salesmen and assistants in the leadership of whom he did excellent work, he himself delivering lectures before boards of trade, chambers of commerce, trade conventions, and other such bodies in all parts of New England. He has since, however, given up this particular line of work to devote himself to politics, to his civic duties, and to the management of his growing mercantile business. He is, at present, chairman of the board of selectmen for the town of Weston, an office which he has held with distinction for five years. He is also a member of the executive committee of the Republican Club of Massachusetts. In 1913 he was the Republican candidate for representative in Congress for the thirteenth district, at the special election held during that year to fill the vacancy caused by the promotion of the Hon. John W. Weeks to the United States Senate. This was the year when the Progressive vote was very large and the Republican candidate for governor in Massachusetts was thousands of votes behind the Progressive. Notwithstanding this unusual political situation, Mr. Cutting, though not elected, led his Progressive opponent by more than 3,000 votes, and, by his splendid leadership, helped lay the foundation for the Republican victory in the same district the following year. At this writing, Mr. Cutting has just won a notable victory at the polls, having been elected a member of the board of county commissioners for Middlesex County by a very large plurality. He carried every district in the county except two, and in nearly every district he ran far ahead of his ticket.