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I’ve just told a young man I’ve been working with to pursue his dream of becoming a pilot. Overall, he’s been a decent enough worker who has done what’s asked of him. However, he only seems to come alive when he talks about being a pilot. He’s learnt the various call signs and radio signals involved in the process. Yet, somehow, he’s never made it close to flying school.

So, when I look at him, I get frightened for him. He’s going to be a good boy who does as he’s told and takes the safe route, which in the Singapore context means getting a good degree and working in a safe and predictable office job, which in itself is not wrong, but when I look at him, and he admits to me that dealing with files is not his thing. While some parts of the investigation work in forensic accounting excite him, it’s clear that he doesn’t have it in him to be a lawyer or a financier.

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I’ve told him that a decent degree is nonnegotiable today. He cannot neglect his studies. I’ve also told him to keep his job with us as he builds his finances, as flight school is not cheap. However, he needs to give his heart and soul into trying to get into an airline that will give him the chance he needs to prove himself. I have also stressed to him that SIA isn’t the only airline on the planet, and he should knock on every door available until he gets behind a cockpit.

He’s trusted me and called me a “father figure,” which I cannot take lightly in all good conscience. I guess I am officially a “terrible parent figure” by telling him to chase his dreams.

However, what’s the alternative? To push him into something that he has no heart to do? Sure, there’s a good chance that he may not achieve his dream – but he needs to give it his best shot. Think of it, way too many of us end up becoming old and bitter people because of all the things we loved and dreamed about but never gave it a shot because it was the risky option.

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Seriously, at the end of the day, what’s going to matter? Steve Jobs said it best: “There’s no point being the richest man in the cemetery.” Since all of us will end up in the same place, we should make the journey the best possible. So, as an older person, I believe I need to encourage young kids to follow their dreams. Sure, an element of practicality needs to be involved. After all, we all need to earn a living.

However, there’s no point in being a slave to your living if it kills you to do it. Best to pursue your dream, and even if you don’t “make it,” there are ways of modifying that dream. Heck, I grew up in the advertising industry, which is staffed by people who would have loved to be in creative arts (movies) but found alternative ways of making a living doing what they loved.

Thanks to AI, the presence of machines in the workplace will only grow. There is no way you can be more of a machine than a machine, so we all need to play to our strengths and bring passion to our jobs in the way that only humans can.

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A version of this article first appeared at beautifullyincoherent.blogspot.com