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- Manual laborer: Cottage landscape work, circa 1967
- Wood chopper: Cottage work, circa 1967/8
- Photographer: First “pro” work, circa 1968
- Landscaper: Tree planting, 1971
- Part-time student jobs
- Computer hacker: No sinister intent, circa 1972
- Programmer: TypeSet — a revolution on a mainframe, 1975
- Teacher: Concordia University (while in Masters program)
- Author: Published Computer Paper, 1976
- I.T. Professional: Carleton University Computer Center, 1976-80
- Geek: Personal Computer owner, 1976-79
- Entrepreneur: business attempt, MicroDynamics circa 1979-81
- Computer Analyst: Litton Systems Canada, 1980-1992
- Software Designer: Soft Touch Systems, 1985-87
- Computer Room Designer: Litton, 1988-89
- Brickworker: home improvements, 1989
- Consultant: Soft-Touch Systems Consulting, circa 1989-92
- Entrepreneur: Matol Botanicals, MLM, 1991-1993
- Entrepreneur: Office in a briefcase, 1991-1992
- Computer Analyst: Abbott Labs, 1992-1994
- Computer Analyst: William Mercer, 1994-1995
- I.T. Manager: VP Unix Systems, Information Resources Inc, 1996-2001
- I.T. Manager: First in Chicago to adopt Blackberry pagers, 1997
- I.T. Manager: IRI Y2K project, 1999-2000
- I.T. Manager: IRI, the EDT project, circa 1997-2001
- Consultant: IRI lead-up to exit, 2001-2002
- Entrepreneur: Best Value Guide, circa 2003
- Photographer: Hershel Belkin Photography (take one: kids), 2001-2006
- Teacher: Bnos Rabbeinu Girls High School, 2006-2017
- Website work: Bnos Rabbeinu High School, 2006-2016
- Photographer: High School Seniors, 2007-2017
- Photographer: Hershel Belkin Photography (take two: Kids, weddings, events), 2007-2020
- Entrepreneur: Search Engine Optimization, circa 2009
- I.T. Manager: Jewish Educational Toys, Chicago, circa 2004-2017
- Entrepreneur: Jewish Stock Photos, circa 2011-2012
- Entrepreneur: My-Headshots, circa 2013
- Teacher: School Fire lesson, 2015
- Entrepreneur: Skadget online sales, 2016
- Sales and Bookkeeper: Aspaclaria Judaica, 2017-
- Author: A book that took 20 years to print, 2021
- Photographer: Goldleaf Portraits, 2021-