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Howard Cockburn began their work experience in 1997 as an assistant director at Brewin Dolphin, where they worked for almost 15 years. During their time there, they assisted with investment decisions, communicated with clients, and worked with trusts. In 2012, they joined JM Finn & co as an Investment Director, where they currently manage investment portfolios for private clients, trusts, and charities, based on their risk profile and investment objectives.

Howard Cockburn attended Rugby School from 1986 to 1991, but did not earn a degree or pursue any specific field of study during that time. Howard then went on to attend Newcastle University from 1992 to 1995, where they obtained a Bachelor of Science (BSc) degree in Agricultural Economics.