Prior to joining Food Network Canada, Olson was a pastry chef at Inn on the Twenty in Jordan, Ontario for seven years. Working in a winery type restaurant appealed to Olson. The fact the Inn on the Twenty used local and seasonal ingredients also appealed to Olson. While at Inn on the Twenty, Anna soon met her future husband Michael Olson.
Anna was born in Atlanta, Georgia. Her parents immigrated to Canada, more specifically Toronto, Ontario where Anna would grow up. Although cooking was not her first choice she soon realized it was her passion. Before cooking came along, Anna earned her degree in Political Studies and Sociology from Queen’s University in Kingston, Ontario. While discovering her passion for cooking, Anna worked for a time in a bank in downtown Toronto. It was during her lunch breaks that she would wander the St. Lawrence Market searching for different ingredients and inspiration for her next dinner party. That was when she knew cooking was her true calling.
Anna Olson then enrolled in the culinary program at Johnson & Wales University in Vail, Colorado. She never second guessed this choice. Upon her graduation for the culinary institute, Olson set out and travelled across the United States in various states and cities such as Texas and New Orleans. She would eventually find her way to Niagara Falls.
Aside from working in television, Olson has also explored print media. The Inn on the Twenty Cookbook was co-authored by her husband Michael and published in 2000. Anna also published a cookbook called Sugar in 2004. It was a companion to her popular TV show by the same name which can be found on Food Network Canada. Anna Olson co-authored another book with her husband which was released in October 2005. The book is called Anna & Michael Olson Cook at Home: Recipes for Everyday and Every Occasion. This is a menu driven book which highlights how Anna and her husband cook at home. It also includes tips and tricks for entertaining and weeknight dining. Olson is writing another book with recipes derived from "Sugar", called Another Cup of Sugar slated for release in late 2006. While Anna is not in front of the camera or writing a book, she can be found freelance writing for many different publications such as Vines and LCBO Food and Drink.
While away from the camera and the stroke of a pen, she can be seen at Olson Food and Bakery in Port Dalhousie. Port Dalhousie is a historic lakeside community in St. Catharines, Ontario. Olson Food and Bakery opened its door in August 2004. The shop has an open kitchen right on site and sells many different items such as fresh baked goods which are made fresh every day, artisanal cheeses and gourmet pantry items.
Olson also participates in various fundraisers in and around her region, but Anna supports a local program called the Niagara Women’s Enterprise Centre. The centre basically provides training in the hospitality sector to women who might not have that opportunity, plus her end-of-the-day product is graciously given to a local YWCA women's shelter or Out of the Cold Program.