His first summer job was playing trumpet at a children’s church camp and later picking fruit (raspberries, cherries, and peaches) during the summer while in high school. Pattison had many jobs while in high school, including selling doughnuts in the school parking lot, selling seeds door-to-door, delivering newspapers, and working as a page boy at the Georgia Hotel. He graduated from John Oliver Secondary School in 1947.

During a break from University in summer 1948, Pattison was selling cars at Richmond Motors in BC, although his primary duty was washing cars. In summer 1949, he worked for Kingsway, a used car dealer in Vancouver. “I worked there all summer and then [my boss] gave me a car to drive to university. So I then started to sell used cars at UBC,” Pattison told a reporter.

By 1961, using his sales skills, he was able to persuade a Royal Bank manager to lend him $40,000, significantly more than the branch’s lending limit, to open a Pontiac dealership on Main Street near his elementary school. To complete the funding, he also sold his house, assigned the cash surrender value of his life insurance policy to General Motors and took a loan from GM for $190,000 for preferred shares in the company. A quarter-century later, he was selling more cars than anyone else in Western Canada.

On February 15, 2008, Jim Pattison Group announced the purchase of the GWR organization, the company known for its Guinness World Records franchise. Its annual book, published in more than 100 countries in 37 languages, is the world’s best-selling copyrighted book. Pattison, who owns approximately 30% of the shares of Canfor, was in a dispute over governance with money manager Stephen A. Jarislowsky, whose firm owned 18%. Pattison won and ousted CEO Jim Shepherd over Canfor’s poor performance and declining share price, replacing him for the interim with Jim Shepard.

Imagine Canada rated the Jim Pattison Foundation in 2008 as the eighth largest giver of charitable grants by a private foundation in Canada.

On April 16, 2009 Jim Pattison announced that Save-On Foods had donated $100,000 to CBC Television in order to rent high-definition television trucks for away games during the Vancouver Canucks’ 2009 1st round NHL playoff series versus the St. Louis Blues. Prior to this donation, CBC stated that it would not broadcast high-definition away games in St. Louis due to the cost of renting high-definition equipment during the current tough economic times and major cuts to funding for the CBC by the federal government.

Pattison is a well-known philanthropist, and an article in The Globe and Mail noted, “He has always given away 10% of his income.” In July 2013 he donated up to $5 million to Victoria Hospitals Foundation (Victoria, British Columbia), to support its “Building Care Together” campaign to purchase new equipment for the new patient care tower at the Royal Jubilee Hospital. In recognition, the hospital named the ground floor lobby of the patient care tower “The Jim Pattison Atrium and Concourse.” In 2011, Pattison contributed $5 million to add his name and to match public donations for a $10 million 100-day fundraising campaign in Surrey, British Columbia for the new Jim Pattison Outpatient Care and Surgery Centre run by Fraser Health. Other donations in the past included $20 million Vancouver General Hospital in 1999 and $5 million to the Lions Gate Hospital in 2008.

He was involved with the committee for the 2010 Vancouver Olympics. Among other honours, Pattison is an Officer of the Order of Canada and a member of the Order of British Columbia. He was also listed as No. 177 on the 2015 Forbes list of the world’s richest people. He was also listed then as the richest Canadian.

At a Los Angeles auction on November 17, 2016, Pattison purchased (for $4.8 million) the Jean Louis dress worn by Marilyn Monroe when she sang “Happy Birthday, Mr. President” to President John F. Kennedy at a celebration of his 45th birthday. At age 90, Pattison enjoyed playing the piano, organ and trumpet.

On March 28, 2017, Pattison donated $75 million to the construction of the new St. Paul’s Hospital in Vancouver, a Canadian record for a private donation to a health care provider. On May 30, 2017, Pattison and the Jim Pattison Foundation announced they were donating $50 million, the largest private donation in Saskatchewan history, to the new Children’s Hospital of Saskatchewan in Saskatoon, Saskatchewan which is expected to open in 2019. It was also announced that day the new hospital would be named Jim Pattison Children’s Hospital in his honour.

His company owned 25 car dealerships as of March 2018, Peterbilt truck dealerships, Overwaitea Foods, Save-On-Foods, Quality Foods, Ripley’s Believe It or Not!, Guinness World Records and radio and TV stations in British Columbia, Alberta, Saskatchewan and Manitoba. Pattison entered the media business when he bought Vancouver AM radio station CJOR with five partners. The Broadcast Group was Canada’s largest western-based radio and TV company in 2018, with 43 radio stations and three TV stations. Pattison Agriculture is the second-largest John Deere dealer in Canada, with 19 locations in Saskatchewan and Manitoba.

In late 2018, Pattison was still working full-time, making a tour of Pattison Agriculture farm equipment dealerships across the west, for example, driving a pickup truck thousands of kilometers to do so. When asked by a Bloomberg reporter whether he ever took a vacation, Pattison replied, “Well, I get 365 days. If you like your work, it’s not work”.

Pattison married Mary Hudson, whom he met at the Swift Current church camp when both were 13. Hudson was from Moose Jaw. Some 66 years later in 2018, Pattison commented, “The secret [to a successful marriage] is to marry somebody from Saskatchewan. Then you won’t have a problem!” The couple has three children.

In October 2020, at age 92, Pattison is continuing to look for fresh investment deals. At that time, a news item stated that “Jim Pattison Group Inc. had $10.9 billion in revenue and employed 48,000 people”.