He grew up in Teaneck, New Jersey, and after a brief stint in the U.S. Navy, attended M.I.T., studying chemical engineering, and Harvard, where he graduated with a B.A. in Physics, cum laude. He attended General Theological Seminary (Episcopal) in New York City, from which he graduated with a Master's Degree in the New Testament. After ordination, he served as a Fellow and Tutor at the Seminary, and then served churches in New Jersey. Following this, he served as Canon Pastor of Grace Cathedral in San Francisco. He also served on the National Staff of United Ministries in Higher Education for a number of years,

Honors

He has received many honors. He was the 2006 recipient of the National Samaritan award, joining such prestigious company as Karl Menninger, Peter Drucker, Norman Vincent Peale, Betty Ford, and Sir John Templeton. The Library of Congress in 1996 named his book as one of 25 that have shaped reader's lives. His book has appeared on the New York Times best-seller list (paperback non-fiction) a total of 288 weeks.

Bolles makes public speaking appearances and leads workshops around the United States. He releases updated editions of his Parachute book every year, as well as working on new titles. The latest title is "The Job-Hunter's Survival Guide", a short 100 page book. He has had various co-authors for some of his other books, including Howard Figler, Carol Christen, Dale Brown, and one of his sons, Mark Bolles. Mark is the principal author of their book Job Hunting on the Internet ISBN 1-58008-652-7. He is also a member of high-IQ society Mensa.

He lives in the East Bay of the San Francisco Bay Area and is married in 2004 to the former Marciana Garcia Mendoza Navarrete, who is from Cavite in the Philippines see dedication for his 2009 edition of What Color is Your Parachute. He has four children by a previous marriage, and his wife has two.