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How flying makes me a better barrister

Working as both a barrister and pilot has offered Damien Toohey different yet complementary lessons and experiences, allowing him to live life to the fullest.

user iconKace O'Neill 04 February 2025 Big Law
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Tom Cruise once played the rookie lawyer Lieutenant Daniel Kaffee in the movie A Few Good Men, he also played the iconic Pete “Maverick” Mitchell in the movie Top Gun – yet never did so simultaneously.

However, a recent guest on The Lawyers Weekly Show may have cracked the code on balancing both the “danger zone” and “wanting the truth”. Damien Toohey of Selborne Chambers in Sydney is both a certified barrister and a professional and commercial pilot.

Between being a barrister and pilot, Toohey has determined what skills and experiences are able to be intertwined between the two vocational pathways and what others need to be kept separate.

Toohey expressed some of the key differences between the two professions, labelling flying as the “ultimate test of character”.

“I suffer a little bit from impostor syndrome, and the way I normally deal with that is to research my way out of it and prepare my way out of it. One thing I learned about flying is that if you can’t do it, just put your hand up and say you can’t do it because you will get found out.

“Whereas with law, often you can BS your way through things and you can say, ‘oh, yes, I’ve done plenty of those or whatever’, but I don’t do that because I know that it’s not right and also I’ll get found out,” said Toohey.

“For me, it’s the ultimate test of character because the persona, I often say to people, I’m going to put my suit of armour on, which is my uniform, because when I put my uniform on, it actually strengthens my mind to the task at hand.”

Despite the differences, Toohey has similar approaches to each of his professions, using a strong attention to detail.

“As a barrister, I tend not to leave any stone unturned. And that helps a lot with flying. But it’s cross-pollination because in flying, we use an acronym called GRADE, which is gather, review, analyse, decide, and evaluate. So I try to bring that sometimes to flying and to law because I think ‘gather’ is a very important stage of the decision-making process. One often informs the other,” he said.

However, Toohey is often cautious about how he carries himself as both a barrister and a pilot, as he’s seen negative characteristics often arise in the role of a barrister.

“You’ve got to be a bit careful because sometimes, as a barrister, you can become what appears to be a little bit dictatorial because you’re in a decision-making role and people need to be sort whipped into shape a little bit if they’re going foaming off at the mouth about something that’s important to them. So, sometimes, I have to stop myself and think, OK, now just being a bit arrogant here, maybe there’s something you’re missing. Start listening,” he said.

In reflecting on his journey in both spaces, Toohey expressed gratitude towards the experiences he’s had, claiming that life in itself is a “sweet experience”.

“Life is a really sweet experience, and it requires forgiveness, motivation, calculation, dedication and all those things. And being a good person, you know, like all those things, they sound trite, but they’re so true. Forgive often. Be kind and be nice to people,” said Toohey.

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