Not content with the thought of being a mere parish priest, Wolsey landed himself a job as a chaplain with the Archbishop of Canterbury, Henry Dean. Once Dean passed away, he acquired a position with Richard Nanfan - the treasurer of Calais.
Wolsey worked for Nanfan from 1503 to 1507, and supposedly as a favour from him, Wolsey secured the position of Royal Chamberlain to Henry VII. Through this, he attached himself to people of influence including Richard Fox, the Bishop of Winchester and Sir Thomas Lovell.
While in this role, Wolsey completed various missions for Henry VII; some successful some not, but either way, Henry was clearly quite pleased with him and he awarded him the Deanship of Lincoln.
It's also around this time he is believed to have fathered two illegitimate children - a fact which comes back to haunt him in the future, when his enemies want to paint him as an immoral character.
In 1509, Wolsey became the almoner for Henry VII; somebody who is in charge of giving alms (money) to the poor. He fostered an alliance with Charles Brandon, Henry VIII’s close friend, and became popular with Henry VIII after his father died, as he indulged the young King’s desires to have fun rather than work.
In 1509 he became the Dean of Lincoln and Register of the Order of the Garter, and such positions continued to be awarded to him over the following years. His responsibilities increased and Henry's councillors started to grumble, noticing that Wolsey was becoming more like a King's chief minister, having positioned himself in between Henry and his council.
In 1513, Wolsey was made the Dean of York and in 1514, the Archbishop of York, though, it was in 1515 that received true recognition. As it was in this year he was made cardinal by Pope Leo X; a hugely important moment for Wolsey.
As part of being made a cardinal the Pope arranged for Wolsey to be sent ‘the red hat’ - a wide-brimmed galero - however, it took three years for this hat to eventually arrive. When it did, Wolsey arranged for the hat to have its own procession through London, in its own carriage.
Even though he had a seat in Lords, he didn’t have any official power in Parliament yet. Despite this, Henry clearly valued Wolsey’s opinion and judgement without question. In this year, Henry wrote to Pope Leo assuring him that when he speaks to Wolsey it is as to speak to him.
It’s not surprising really that when Princess Mary was born in the following year, Cardinal Wolsey was top pick for Godfather.