The law degree was no longer hanging on the wall, instead collecting dust in a cardboard box in the corner of the garage, while the wine shop business was beginning to sour.
It was a long ragged road to the law and the story of what it took for Central Otago's Tim Cadogan to seriously consider practising at nearly 40 years old is far from a text book case.
Mr Cadogan gained his degree from Otago University over a quarter of a century ago, but it wasn't until 2005 that he was admitted.
"When I graduated in 1990, it was still pretty grim times following the 1987 stock market crash. There wasn't a lot of work. I wound up getting a job working in student radio in Dunedin as a sales manager," he says.
While working in student radio as a salesman in Dunedin he also landed a few on-air radio presenting shifts.
Life behind the microphone
Mr Cadogan and his first wife and young child eventually left Dunedin for Queenstown and he fell into a similar job, with a local commercial radio station in the lakeside resort.
"The job came looking for me. I recall a phone call and it sort of went like this – would you like to come and work for us because we've had a couple of announcers leave," he says.
And so the accidental radio career began to blossom and the possible law career was shelved for a decade.
"It's funny how life works out. It was never something that I planned. The job at student radio was simply one of necessity, and I basically drifted into being on-air."
The lure of the microphone eventually saw Mr Cadogan move to Alexandra, where his law office is now based.
But when he landed there in the early 1990s, law was occupying an increasingly distant corner of his mind as the shift to the Central Otago town renowned for its annual blossom festival was to write radio commercials for Radio Central, something that he turned out to have a knack for.
"I'd written one or two commercials during my days with student radio and within a short time I'd won national radio awards for my copywriting. It was an 'I didn't know I could do that moment'," he says.
Mr Cadogan also rose through the ranks to become both the now closed down station's breakfast host and programme director.
"Looking at radio from a law perspective, it gives you a good grounding and certainly being a creative writer doesn't hurt the process of being a court barrister."
How radio helped shape a law career
Mr Cadogan says when he eventually hung up his microphone and headphones for a legal career, standing up and talking to a crowd of people was a skill he had mastered.
"Radio was a brilliant background to have for learning how to deliver a message with a start and finish and vital information in the middle.
"It gave me the confidence certainly at the outset. However the first time you stand in front of a judge, to do a plea in mitigation for somebody, it's downright terrifying," he says.
Mr Cadogan says during his time in radio he conducted hundreds of on-air interviews and those skills have proven to be an excellent legal tool.
"In some ways it's not that different to cross-examination in court because you've got a path that you want to go down, a story you want to tell but you just don't know how the other person is going to react.
"It's the same as if you're cross-examining somebody – you've got to bring them back to where you need them to be, so without knowing it, my radio days were a loose training ground for me," he says.
Rebirth of the law degree
Mr Cadogan's law degree had found a new home in a box in the family garage during his radio days.
It was slowly become a relic of his past.
"I used to get a bit upset because as the years went by I thought, I'm just not going to get to use it, but what I didn't appreciate was that the radio background has enabled me to do the more vocal parts of practising law as opposed to conveyancing or commercial law," he says.
Gold rush heritage town Alexandra has a population of just over five thousand. It's like the Tuscany of Central Otago, better known these days for its abundant fruit orchards and vineyards than glittering nuggets. The actor Sam Neill's "The Last Chance Paddock" vineyard produces a rare pinot noir each season there.
Mr Cadogan ended his radio career in 2002 and opened a wine shop on the main street of Alexandra, which proved an unlikely catalyst for a legal comeback.
"My wife and I had the wine shop for about one year and it didn't work out," he says.
It was at that point Mr Cadogan decided it was time to try and use his degree in law.
"By chance there was a lawyer in our wine club and I approached her to see what I might have to do to get started.
"I was prepared to do anything, even pick grapes for a couple of years and retrain if it meant I could finally use my law degree," he says.
As luck and timing would have it, the law firm the woman worked for wanted to employ a law clerk and she thought that Mr Cadogan might be ideal because he was local and had a few years under his belt at nearly 40.
In other words, he could bring a little worldly experience.
Starting out again
"When I went for the job interview, I said frankly I don't remember a hell of a lot, but I was told, it doesn't matter, the degree shows you can think like a lawyer," he says.
Getting up to speed was a hard slog because many areas of the law had changed since he had graduated from university all of those years ago.
But it paid off and he was employed by the law firm Bodkins for five years before establishing a sole practice.
"I've had my own practice for six years. I went from nothing to this, specialising in family, criminal and employment law. I'm also the Dispute Tribunal referee for Central Otago and Queenstown Lakes," he says.
Life experience means honest empathy
Drawing from his own personal experience of a difficult end to his first marriage, including self-representing through court proceedings, Mr Cadogan can say hand on heart that he understands a person's civil battle, when practising family law.
"I went through a fairly untidy divorce, arguing over children and so forth, so what I try to bring to my clients is a sense of empathy that I've been there when their whole world is suddenly upside down and the future they expected to have just isn't going to happen," he says.
It's the fight for a person's life that Mr Cadogan says attracts him to family law the most.
"Because I've lived it, I wouldn't have these skills if I'd come straight out of law school, so the gap has benefited my work, although sometimes I do have to remind myself that I am a lawyer, not a counsellor.
"I have about 20 files sitting in front of me, and every one of them is the most important thing happening in that person's life right now. When they're resolved, it might not be exactly what they want but I'm able to use a little life experience and maturity to tell people what the likely outcome could be, particularly in a family matter."
Mr Cadogan laughs and says thankfully he hasn't had any life experience with criminal law.
"Perhaps I committed a few radio music crimes, playing the band Atomic Kitten on the radio during my broadcasting days," he says.
Advice to people considering law later in life
"If I can do it, you can. It's a tough road but if you want it bad enough, you'll succeed."
And while he is concerned about the lack of young law graduates getting into family and criminal law because of cuts to legal aid funding, he sees it as opportunity for the more seasoned law graduate.
"It could cause a vacuum where spaces in family and criminal law just won't be filled, but then perhaps older people with a little more life experience could be ideal for working in these areas. That's been my experience."
Choosing small town over city law
The children have all left home and at 51, if he wanted to, Mr Cadogan could set his sights on the bright lights of the big city, but he isn't.
"Living in a small town, radio gave me the chance to get my name out there, so it's not just another name in brass on a plaque decorating a wall. I've got lifestyle here, golf, it's incredibly important at this stage of my life and I just paid my $330 annual green fees where I live in Clyde.
"On a good day, I am a drive and a nine iron from the number one tee," he says.
Tim Cadogan's drive to help people doesn't stop with the law. He is a member of several community trusts and boards and is standing for Central Otago Mayor in the upcoming elections.
And leadership runs deep in the family bloodline as his brother Bryan Cadogan is the Mayor of South Otago town Balclutha.