The couple rear and graze their own young stock, plus 700 sheep and a small Hereford stud.
Reuben grew up farming sheep and beef and worked for six years as a block manager in the dry stock industry after leaving school, before going sharemilking near Cambridge.
Deb grew up on a dairy farm in Ohaupo and holds a Bachelor of Teaching (ECCE) from Waikato University.
The couple has four children – Laura, 7, Vanessa, 5, Zoe, 4, and Isla, 2 – and a fifth due in June.
Trying to balance their busy on-farm life with a young family, the Dairy Industry Awards, Young Farmer of the year contest and Covid restrictions, meant it was often "controlled chaos" at the Connollys, Reuben joked.
"If we do something, we'd like to do it well. We're certainly busy with farms and family and bits and pieces, but it's about giving everything a go."
Entering the awards was like continuous improvement, Reuben said.
The couple told the DIA judges that sharemilking with little prior dairy knowledge had been a huge challenge, overcome with advice from other farmers, DairyNZ discussion groups and industry professionals.
One such industry professional is the couple's Ravensdown Agri Manager, Te Awamutu-based Brenna Coleman, who they met through the Dairy Industry Awards (DIA).
Soon after, they became a Ravensdown customer and then a shareholder.
"We had been with another firm, but are grateful for Ravensdown's and Brenna's support of the industry and of us," Reuben said.
He had also learnt a lot from his parents, Brian and Bev.
"I obviously look up to them and see all the hard work they did before us."
Future farming goals for Reuben and Deb include farm ownership.
Reuben said he went dairy farming because of the apparent lack of progression in the dry stock sector.
"There's no real ladder to climb. You're either working, managing or the owner. We saw the dairy industry as more of a way to get ahead. So we gave it a go, and the rest is history.
"If you want to be a dry stock farmer, you have to find a way of getting there. We went for dairy and it worked for us, but whatever you decide, you have to be prepared to work hard and adapt to change.
"You can't go past being an honest, hardworking person; you can learn the rest."