The analytical lawyer and the creative entertainer do indeed share something: an appetite for words and a desire to persuade. This is certainly the case for stand-up comedian James O'Loghlin who, from being a corporate hot shot at Blake Dawson and busy criminal lawyer to working in the TV industry, has learned a thing or two about playing to an audience.

That’s a good question and I still don’t know the answer. I was one of those people who got a decent HSC mark and thought I shouldn’t waste it. I was an “artsy” person, not a “sciencey” person, so I decided to do Arts/Law, a wonderful general degree, and all of sudden five years later I was a lawyer. I’m sure some people have a certainty that they want to be lawyers, but there are a lot who just “became lawyers” and I was one of them.

Where was your first gig as a lawyer?

Blake Dawson Waldron. I started in 1991 as a corporate lawyer but it wasn’t really my thing so I moved to a small criminal and immigration firm the next year and worked for Legal Aid as a criminal lawyer from 1994 to 1999 - the last couple of years of which were part time.

Why did you take your first job?

Right through uni it was collectively assumed that the best thing to do was to get a job with a big corporate firm. If I’d taken five minutes to think about what I was interested in and good at I would have realised that it didn’t suit me. I’m far more interested in dealing with people. I’m fascinated by criminal law and it was my favourite subject at uni.

What did you love about law?

As soon as I started doing crime [laughs] I realised it was what I wanted to be doing, I wanted to be standing up in court and talking. As a duty solicitor at Legal Aid for five years, everyday I was getting up seeing who had what sort of problems and going into court being their mouth. I really loved that.

What else did you do whilst practising law?

Through the ‘90s I was doing stand-up comedy, initially as a hobby and then I started to get work and was sort of running [law and comedy] in parallel. My first gigs were at the Harold Park Hotel in Glebe and the Comedy Store (then in Cleveland Street, Surry Hills). Around 1997 I went three days a week at Legal Aid, then two days a week and then, in 1999, I realised it was probably a good idea to commit fully to one or the other.

What’s the common ground between law and comedy?

You are performing and your job is to get the attention of the audience, be it 100 people or one magistrate, and get them to see the world in the way you’re trying to portray it, whether that’s to make them laugh or get them to understand why someone committed a particular crime.

Which occupation is more important?

As a stand-up comedian, if you fail you feel humiliated and bad and worthless, but nothing bad happens to anyone. As a lawyer, if you stuff up other people can bear the brunt of that. That said, if you stuff up as a lawyer, there’s a lot of people who are still learning when they are representing people. Magistrates, in my experience, understand that and can often work out what should have been said.

You are the author of How to Balance your Life. What’s your experience of work/life balance?

Corporate lawyers mostly admit that their industry has terrible work/life balance. My experience is from 20 years ago, but I do a lot of speaking at events with lawyers [the most recent of which was the Lawyers Weekly Awards last Thursday] and it seems things haven’t changed much at the big end of town. The expectation that you were there for very, very long hours was not something I was too excited about. The hours weren’t bad at all at Legal Aid though, because when it was on, it was on, and when it wasn’t, you had to wait for it to start again. You’d get to court about 8.30am and meet everyone who wanted to be represented and it was “Go, go, go!” but by mid afternoon, all the advocacy was done.

Did you find any creative fodder in law?

Every time you do a plea for someone, a bail application, a hearing, try and cross examine someone or make a submission, there’s an opportunity to do that in the same old way that the magistrates have heard before, or to try and make them sit up, listen, take notice and see your client as a flesh and blood person, rather then number 68 on their list. So I do think there are opportunities for creativity.

Was it difficult to leave law?

It was difficult to make the jump. I was really lucky that at Legal Aid I could work part time. I was really scared to leave because of the security factor and I still get nervous about that now. I’m in a very insecure industry with no guarantees, especially with a family. So far it’s been great, but who knows what will happen in the next few years.

How did you make the jump?

I think it was when I was going to two days a week at Legal Aid and I’d come into the office and people would go, “Oh, you still work here do you?” It was becoming a smaller and smaller part of my life.

Would you ever go back?

Yes, if the media and [stand-up comedy] stuff sort of ran out. If I could get back into crime [laughs], that could be a job I think I would still like. It wouldn’t be my preferred option, but if I need to go back I will.

What do you do when you’re not working?

I’ve got thee young children so that’s pretty much the answer. A bit of exercise, read a few books and work on various unfinished projects which may never be finished ... At the moment I’m trying to write a kids novel, so that should be out in 2018.

Click on the images below to find out why some Australia's most noted entertainers took the leap from law to the land of showbiz: