As a boy Watt seems to have been always a dreamer, building castles in the air and planning great schemes of business and adventure. Because of these dreams of verdant fields and herds of cattle, he desired to join the movement for the settlement of Texas, then being effected under the leadership of Sam Houston, and was prevented only by the ill health of his father and the large family which needed his aid. As a sort of compromise his father agreed to migrate to Missouri in 1838. This move resulted only in hardship and privation, and soon young Watt was turning his thoughts again toward the prairies of Texas. In the winter of 1840 and 1841 he started south, stopping in the country of the Creeks and Cherokees to earn money at his trade of carpentering. It was at this time that the Oregon country was coming prominently before the people in Missouri. Watt became interested and returned to his home with the intention of migrating to Oregon. On his way through the southwestern part of the State in the spring of 1843 he came in contact with many who were planning to start that year. Senator Lewis F. Linn, of Missouri, had introduced a bill into the Senate in 1838 providing for the settlement of Oregon and offering six hundred and forty acres of land to each settler. Watt read all that he could find upon the subject, listened to everything which he could hear and talked much with his associates. By the spring of 1843 he was ready to start, but his father had become equally anxious to better his condition and proposed that the whole family prepare to go the following year. By the spring of 1844 it was clear that the expense of so long and difficult a journey could not be met, and Watt, unwilling to defer his hopes longer, started with two companions, expecting to earn his way across the plains by driving the teams or cattle of well-to-do emigrants. The assets all told with which he started on this long journey were $2.50 in cash and a stock in trade of a pair of new boots, some pins and fishhooks, to be used in trade with the Indians.