The Art of Experimenting By Always Asking

Personal finance

If you don’t ask the answer is always going to be no. You miss 100% of the shots you don’t take (classic Gretzky quote).

What I’m getting at is that you need to get into the habit of asking. This post is coming to your directly from Puerto Plata. On top of beautiful weather and unlimited drinks, there’s something else I can brag about. I got upgraded to a junior suite.

How much did this upgrade cost? It was completely free to be honest. Well I did tip the gentleman a few dollars for his time and for looking out for me. My brother and I got to our room and there was only one bed in it. One bed in a room is fine for a couple, but not for two guys that weigh over 180lbs. We immediately went to the front desk to complain. Instead of being rude we were polite and pleasant. We kindly asked if he had anything available with a small tip provided.

After a few minutes of just browsing around, the clerk at the front desk said that there would be a two room suite available for us the next day. We accepted and were pleasantly surprised when we saw our room the next day. It wasn’t a room, it wasn’t even a suite, it was like an apartment. There was a living room, kitchen, two bed rooms, a washroom, and a flat screen tv (not that we watched it at all).

If we never asked or said anything, we would have been stuck in this tiny room with one bed in it. Instead we spent the week in a pretty sweet suite (you like that?)

I’ve been doing something different the past few years. I’ve made it a habit to experiment by always asking.

What are some examples of how you can start asking?

  • Ask for discounts. Whenever you’re making a purchase, large or small, it makes sense to ask for discounts. The person on the other end is trying to make a sale. To gain your business they’ll likely be willing to lower the price a bit. You have to remember that you work hard for your money, so others should work even harder to get your money. You can negotiate everything in life in my opinion.
  • Look for better offers. There’s always a better deal out there. It makes sense to at least ask to see what options are available to you. Companies are working hard to keep customers these days. You never know when a better offer is waiting out there.
  • In your dating life. I used to be worried when it came to getting a girls number or escalating things. Then I learned that if you don’t try, you’re never going to know. Instead of stressing about failure, why don’t you ask that nice young lady at the gym out for a cup of coffee? Success isn’t about perfection. Success is about execution.

You have nothing to lose from asking. The worst case scenario is that you’ll get a no. I’ve been turned down so many times in my dating life and in general that I wouldn’t even try to guess how many times it has been. I don’t care any longer because I know that I have nothing to lose. If you want to be financially successful you need to be bold. To be bold you need to ask questions. If you don’t ask for a lower rate or another option, you’ll be stuck with the standard option. Do you want just the standard option or do you want more? I think that you want more. Go after it.

“Trying and failing is better than merely failing, because trying makes you an artist and gives you the right to try again.” – Seth Godin


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