Suddenly evicted by his landlord, he was homeless for the first time in his adult life. He spent nights huddled on park benches, trying to sleep. He was abusing sleeping pills and drinking heavily.
"It's like your whole world goes black. You can't plan ahead. It's like you can't see anything," the 60-year-old said.
Upper never thought he would end up on the streets. Moving to Saskatoon two years ago, he had a steady job at a local aviation company. He says he hadn't had problems with alcohol or drugs since his early 20s.
The downward spiral began when was kicked out of his home after a disagreement with his landlord. Soon after, he underwent heart surgery that involved eight bypasses. He was unable to work. With no job and no place to sleep, he turned to drinking and prescription drugs.
"It was something to turn to when you can't cope with reality. You create your own reality with the drinking," he said.
He spent a night in the police detention cells and at the mental health centre at Royal University Hospital. But even with the supports there, he ended up back on the street.
He said the drugs and the drinking only exacerbated his mental health issues.
When he was at his worst, he showed up at the doors of The Lighthouse and was admitted to its brand new stabilization shelter. The shelter offers a safe place for men and women who are drunk or high, but don't need to be incarcerated, taken to emergency services or watched by a health official at the health region's Brief and Social Detox Unit. While the Lighthouse had a shelter before, it would not admit people who were under the influence.
Upper, who was in the throes of intoxication but wanted to sober up, was the perfect candidate.
"They ask questions, but they don't turn you away. They ask questions out of concern. There is no prejudice or criticism," he said.
After spending a few nights in the shelter and accessing the addictions counselling and services provided by the staff there, Upper was offered an opportunity he'd thought he would never get again: a place to live.
Last weekend, he moved into a new affordable apartment at the Lighthouse.
"I can't describe the look on his face," said Holly Lucas, the Lighthouse housing coordinator.
"The words I got to him were 'Welcome home.' At that point we all burst into tears."
Lucas said Upper is the first person to successfully transition from the stabilization unit into the affordable apartments the Lighthouse provides. His place looks like any other bachelor-style apartment. There's a tidy kitchen, clothes in a closet and a couch where he can watch TV.
Upper says his stay at the shelter and his new home have given him a new perspective on life and the people he used to just pass by on the street.
"You see those people out on the street? I was one of them. I have an empathy I didn't have before," he said. "You can get trapped in a cycle if you don't find a way out of it. This was my way out of it."
Upper is continuing with counselling through the Lighthouse and hopes to return to work as soon as his doctor says it's okay. Even though he is slowly getting his life back together, he doesn't plan to leave his new home anytime soon.
"It's like heaven. It's perfect," he said.