Brighten Your Day: Take The Bob Challenge

A smile is a curve that sets everything straight.Phyllis Diller

I like to make people smile, but I can’t compare to Bob.  He can make anyone smile.  Bob probably isn’t his real name.  He just looks like a Bob to me.  I pass him most mornings on my way to work.  As people walk by on their morning commute, Bob throws out hilarious one-liners, compliments and witty observations.  He always sits in the same spot along the sidewalk with a small cup awaiting donations.  Bob is homeless.

Last week as I passed by, Bob called out to a woman, “I’ll make you smile one of these days.”  The professional looking woman had a scowl on her face, obviously dreading the day ahead of her.  I don’t know if he ever made her smile, but if she walked by Bob regularly, my guess is that he did.  Most people who hear Bob’s voice or see his grinning face can’t help but smile back.

I have often wondered just how many people’s days have been brightened because of Bob.  Hundreds of people pass him every day.  Thousands every week.  Hundreds of thousands every year.  In the five or six years I have seen Bob working his magic he must have conjured up millions of smiles.

I have watched Bob to see how he does it, and it’s not that hard.  You don’t need a sharp wit or a great joke to inspire a smile.  In fact, it is often the easiest and most subtle things that turn the edges of someone’s mouth upward.

Here are 5 simple ways to bring a smile to someone’s face:

The easiest way to make someone smile is to smile yourself.  Give it a try.  Walk down the street or through your workplace and flash smiles at those around you.  Even strangers will smile back.  Smiles are contagious.

Compliment someone
Everyone loves to receive a compliment.  It makes us feel good about ourselves.  Compliments don’t have to be elaborate, but they should be sincere.  Like someone’s tie? Say so.  Admire a colleague’s work?  Tell them.  Pay someone a compliment and you’ll see how easy it is to create a smile.

Be courteous
Courtesy is a dying art.  The simple act of holding a door for someone is becoming an unfortunate rarity these days.  Perhaps that is why it will elicit a smile so easily.  Even a simple please or thank you between strangers can brighten someone’s day.  Be courteous and spread some smiles.

Be generous
We all have something to give.  Maybe you have used goods or clothing that a shelter can use?  Maybe you have time to share with family or friends.  Or maybe you have a skill that can be put to use volunteering.  Whatever it is, give generously.  Generosity creates smiles.

Spread some love
Tell someone you love them.  Nothing fuels our souls more than knowing we’re loved, cared about and appreciated.  Whether you choose to say the words or to show your love through actions and affection, love will bring a smile to someone’s face.

Yesterday I decided to take the Bob Challenge.  I wanted to see how many smiles I could create.  Could I even come close to creating as many smiles as Bob does every day?  I gave it a shot and before long I had random strangers on the street returning my smiles.  A bank teller smiled at my friendly attitude.  Colleagues smiled at some sincere, but unexpected compliments.  My wife smiled when I held her tight and told her I loved her.  A partner at a volunteer organization smiled when I scheduled time to help them out.  And although I didn’t see it, I know that the donation I made to a local charity will help bring a smile to someone’s face in the future.

I did pretty well with the Bob Challenge and was quite proud of myself.  But I have to say that the most rewarding smile of all was the one on my face at the end of the day when I realized I had spread a little joy to others.

How do you make people smile?  Are you up for the Bob Challenge?


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  1. Jason,

    I love the introduction to Bob…. I love that you were inspired to act by him…… what I would really like to know is “Bob’s” backstory…

    Have you thought of taking some time to interview him and find out why he does what he does?

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