after retiring, cawley spent time obtaining all his coaching qualifications and obtaining a bsc in sports science and coaching. having worked initially at wimbledon fc's successful academy, he was recruited by laurie sanchez at wycombe wanderers. his stay here ended after a brief spell as assistant manager to tony adams. following adams' resignation in november 2004, cawley was sacked by the club. having been disheartened by his experience he went on to become a london black cab driver.