His convictions for criminal breach of trust and other money-related issues had hurt his career moves before.
He failed to become an insurance agent because of his record. And he did not get a taxi licence, having chalked up many demerit points. Then, the business management graduate found his niche in real estate, with monthly earnings of up to five figures.
But his past caught up with him again, when he lied - he did not declare his criminal convictions - in his application to obtain a property agent's licence, under new rules put in place earlier this year.
The man, who asked to be known only as S.H. Ang, recalled that after he became a property agent in 2007, he sold more than 100 properties and hit a monthly wage of $12,000.
But under new rules set this year by the Council for Estate Agencies (CEA), he cannot deal in property now, as he has no licence to do so.
Mr Ang, 34, had run afoul of the law on a few occasions. One was a case in 2006 involving criminal breach of trust, when he worked in the food industry. For that, he was sentenced to a year behind bars. He claimed he was released within four months due to good behaviour.
But he lied to the CEA in his recent application. A check with the council showed that Mr Ang was one of the 440 property agents who did not declare their criminal convictions. When asked why he did not make the declaration, as required, he replied: 'I asked my peers and they all told me no one would know if I did not, so I decided to try my luck.'
Mr Ang has been the main income earner in his family.
Both his mother and his wife are working. He has no children.
'Being a real estate agent was my calling and now that's being taken away from me. How can I compete with new graduates at my age?' he asked.
As of Jan 7, a total of 31,288 property agents had submitted their names to the CEA for approval. Some 92 per cent - 28,766 people - got its approval. The rest were rejected for various reasons, such as not meeting certain criteria or having undeclared criminal convictions. About 813 property agents who submitted their applications after the Nov 30, 2010 deadline or whose forms were not in order were provisionally allowed to handle properties till the end of this month.
In a statement to The Sunday Times, the CEA said that since property transactions typically involve large sums of money, it was 'important that salespersons are qualified to render their services professionally and ethically, and provide confidence to consumers'.
It also said that as long as an offender had been charged and convicted in court, the applicant had to declare it in his application, and that police warnings do not constitute a criminal conviction.
The council said it does not permanently disallow individuals from becoming real estate agents. 'Individuals who have kept a clean record will be allowed to re-enter the industry after a period of time.' This depends on factors such as the severity of the offence committed.
In Mr Ang's case, the CEA said he has appealed to it for reconsideration. It also said Mr Ang's CBT charge was a repeat offence, and that he had two earlier criminal convictions.
Meanwhile, Mr Ang is in the midst of gathering past clients' feedback and is planning another appeal to the Appeals Board (Estate Agents) on his own should the CEA's ruling prove unfavourable to him. The fee for Mr Ang's appeal is $1,000. The board is independent of the CEA and comprises professionals with relevant experience.
The CEA also said it is assisting rejected applicants with criminal convictions by referring them to the Employment Assistance Unit of the Singapore Corporation of Rehabilitative Enterprises (Score) for employment assistance.
It will also discuss with property firms the possibility of hiring these applicants for administrative jobs.
Industry practitioners are generally supportive of the CEA's methods so far.
Dennis Wee Group director Chris Koh said everything boils down to the nature of the offence committed.
'If the salesperson had gone to jail because of a cashback or moneylending charge related to the real estate industry, then the law ought to come down hard. If not, however, then I think there should be a second chance. So far I think the CEA has been very flexible,' he said.
Most of the 19 ordinary people The Sunday Times spoke to favoured the CEA's stance. Five said it was too harsh.
Home owner Margeret Tan, 35, who bought her house in Geylang early last year, said: 'It is good that such agents are gone. I won't feel comfortable letting those who are criminally dishonest with money handle my deals.'
But prospective home buyer Vincent Poh, 26, said: 'We always talk about giving second chances. We could let them practise under stringent guidelines.'