The Worst Time To Ask For Something

The other day I turned on to the freeway and I saw a hitchhiker holding a sign asking for a ride. It took less than one mental snapshot to know that, not only was I not going to pick him up, but he would be waiting there all day long. 

How did I know he wouldn’t receive a ride, you ask?

Did he look deranged? No, he was well kept and wasn’t holding a human head or doing anything that screamed, “villain from the Saw movie franchise”. 

Was he unclear on where he wanted to go? No. His sign was very clear. It was simple and said “I-10 E” in big letters. Signifying that he wanted to go to the I-10 freeway going east. He even put a fun smiley face in the 0. 

Was he asking for too much? No, the location he needed to go was less that 5 miles from where I entered the freeway. Not too much to ask at all. 

So how did I know he wouldn’t get a ride?

Because he was set up halfway down the freeway’s on ramp. He wasn’t right on the corner where he could actually get in the car of someone willing to pick him up. He was standing on the side of the road almost all the way to the entrance of the freeway. 

Even if his mother was driving by and saw him, it would be too late for her to give him a ride

Which reminds me of a very important aspect of asking for something. Timing

In the past I have written that studies show that one of the biggest reasons people give, is because they were asked. But as my hitchhiker friend illustrates, we need to know when to ask. To put it more clearly, we can’t ask for something when it is too late. 

Children who ask for a list of toys on December 26th will get laughed at by their parents. A man who asks his high school crush out on a date when she is married with 3 kids is going to be shot down. And a hitchhiker who asks for a ride when doing so would cause a 10 car pile up is going to get left in the dust. 

Timing is a critical part of asking for something. 

Because I am a freeway-half-full kinda guy I like to think that I just caught this man at the wrong time. Maybe he was working his way up the on ramp and just stopped to catch his breath. Maybe he was trying to improve his positioning and eventually he set up his smiley face sign at the corner. 

For his sake I hope that’s the case. Because where I saw him, he had everything going for him but one vital detail. Timing.


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