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There were some things, he reckoned, that were ''in the blood'' and, in his case, that was teaching.
A seventh-generation teacher, Mr Gilbert (42) - not to be confused with his namesake and father, former Otago and Highlanders coach and school principal Tony Gilbert - is now back in the city where he grew up.
He is chief executive of Arinui Ltd, a new Dunedin company which provides an online appraisal system for schools.
For nearly three years, it has been a joint project between Dunedin-based technology company The Tarn Group and nationwide educational consultancy Evaluation Associates.
Now it has become its own entity, built on the software platform Bracken which was developed by The Tarn Group.
The Tarn Group, which started as a video analysis company founded in Dunedin by Joe Morrison in 1997, under the name Siliconcoach, now provided technology-based solutions working with businesses, sports organisations and educational providers.
The driver behind Arinui's development and implementation was to help teachers navigate the recently implemented Standards for the Teaching Profession in a way that helped improve practice and, ultimately, outcomes for pupils.
Aimed at primary, secondary, kura and early childhood education centres, it had been developed in conjunction with institutions themselves and educational experts, including Evaluation Associates chief executive Anna Sullivan.
Arinui is used by more than 450 schools, kura and ECE centres in its project phase, and aims to increase the number of its users across New Zealand.
Its purpose - and his role - was to create something that allowed teachers to be able to focus on what was important - which was teaching and learning - and make that environment better for them, Mr Gilbert he said.
And when it came to improving that environment, he said he was very similar to his father who, whether it was rugby or school, always considered himself an environment manager.
For Mr Gilbert, the role encompassed commercial, education, appraisal and a leadership role, so it ''ticked all the boxes''.
Surrounded by education from a young age - his mother Marg was a new entrants teacher and his father a school principal for years - he was educated at Logan Park High School before studying at the University of Otago and completing his primary school teacher training.
He got a job in Auckland, before shifting to Australia briefly and then returning to teach in Wellington and then Coromandel.
In Waihi he trained as an ambulance officer, combining teaching with ambulance night-shifts on a Friday, along with the demands of his own small children.
From there, Mr Gilbert went to Auckland as head of dance and drama - he also eventually ran the music department as well - at Onehunga High School.
He then became deputy principal of Green Bay High School, one of the first schools where everyone was called by their first name, and with a different model of pupil-led learning.
Having finished his post-graduate study, he was offered a job with New Era which provided ICT support solutions for schools throughout New Zealand.
That was to be an ''incredible learning curve'' around the commercial world and allowed him an understanding between it and the education sector, but also the synergies.
In January this year, Mr Gilbert and his partner Abby Clark, a clinical educator in midwifery, and their young daughter Arabella, who is about to turn 3, moved to Dunedin, something the father of five had relished.
''Being back is being home and that's what I love about it. Dunedin is soulful and solid - but people can't park properly.''
Mr Gilbert acknowledged there were aspects of hands-on teaching he missed.
He had to resolve that his influence was on the teachers and that in turn affected the pupils.
In the commercial world, that became removed again but it was ultimately all about being there to support and serve those young people, he said.
A avid actor, Mr Gilbert was keen to do some improvisation and also teaching of that. He had toured the United States twice, doing improvisation and won a world improvisation title.
He also auditioned for Whose Line Is It Anyway?