Astley was born in Norfolk and grew up in a military family, his first experience of war was at the tender age of 18 years when he joined an expedition to the Azores in 1597 under the command of teh Earl of Essex and Sir Walter Raleigh.
In 1598 he joined Maurice of Nassau and Henry of Orange in the Netherlands, where he served with distinction in the Dutch Revolt. Afterwards he fought under Gustavus Adolphus in the 30 Years War.
In 1622 Astley joined the household of Elizabeth, daughter of James I of England and her husband Frederick, King of Bohemia serving as military tutor to Frederick's son Prince Rupert.
His characteristic battle-prayer has become famous: "O Lord, Thou knowest how busy I must be this day. If I forget Thee, do not thou forget me" which he followed promptly with the order "March on, boys!"
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