This is how I live my life now. Photo credits: Duncan Hull

Why Not Just Ask? Stop Doubting, Just Do It!

Cory Kennedy-Darby
Winning on 1%
Published in
2 min readOct 29, 2015

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This week I travelled to Montreal by train for a day trip to take a couple of meetings. Recently I’ve been baffled why some individuals are willing to push the boundaries of what they’re willing to ask for and others seem comfortable to not.

While heading to the train station, my thought process was along the lines of, “Why not always just ask? What is there really to lose? Just do it.”

True story, I listed to Shia’s motivation speech straight for an entire week once.

I get to the train station, and my train of thought sounds like:

Imagine if I just walked up to the counter and asked to be upgraded from economy to business.

Haha, the agent would probably think I was crazy. Can’t do that.

Actually, Why not? Nothing to lose, JUST DO IT! Ok! I’m going to do it.

With that in mind, I proceeded up to the counter and begun the conversation.

I know there’s no reason to do this. I’m having a long day and was wondering if there was any way you can upgrade my seat.

The agent at the desk looked at me, typed in a couple keystrokes, told me there were a couple empty seats; Some time passed, she passed me a new ticket and then told me to have a wonderful trip.

Economy to business class just by asking for it.

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