$100 Tip

In my wallet I always carry a $100 bill.

If my posting this leads to me being mugged, so be it!

Come and get your Benjamin, you cranky little thief.

I have it there as a “just in case” for when a credit card has some issue, the power is out at a store and I have to pay in cash, or I need to pay for parking at a pay station and they ask me for a smaller bill and we stare at each other since I don’t have anything else…and they let me park for free.

But it’s MOSTLY there for one reason – on occasion I feel inclined to leave it hidden under the final bill receipt at a diner, bar, or restaurant, usually late at night, after a successful event, as I am starving from a long day.

When I notice extra thoughtful service rendered, I feel it’s a cool thing to leave for a hard worker.

I don’t film this or post selfies about it. 

I have yet to do a party where everyone gathers around to watch me give this money, to be celebrated online for my “charity”.

Most of the time my family never even knows I’ve done this with or without them to witness it.

2 times in the hundreds of times I’ve done this, the server will come running after me once we’ve exited the building, to the shock of my children, as my new best friend hugs and thanks me and yells, “Praise The Lord! Thank you, Thank you!”

It’s awkward, but it’s special, and it’s the reason I carry a $100 bill.

Giving away $100 is way better than making it.  

I don’t know how or why this began, but I believe I can trace it back to doing an event years ago where I realized I had just made $100 per minute on stage.

I never thought in high school I would someday even be able to make $100 per day in my future career, but after this gig I was feeling extreme gratitude for the fact that I had stumbled into such a blessing as making a living doing what I love, and being paid extreme amounts for the value.

As I sat watching my server give their all, I remember she cleared the table next to mine, a party of over 10, and looked at the receipt, only to see the portion for a tip was left empty, and I could see her visibly crushed by this.

She and I barely spoke, I know nothing of her story, but that moment made me realize how hard she was trying and literally keeping The Promise for everyone around her, and the last table didn’t even have the decency to acknowledge her efforts.

And here I was on the heels of a standing ovation for doing something that felt like very little effort.

After paying my bill, I reached in my backpack and found a $100 bill, and snuck it under the receipt on my uncleared table.

I left quickly, and walked outside, looking in the window to see if she’d get it.

It took a while for her to return to my table, but I could tell, due to the way I was dressed (I was in my post show clothes after getting changed, which essentially were pajamas), she wasn’t expecting much on the tip of the receipt.

She looked down and saw that I had left 25% on the receipt and I saw a look of relief on her face.  She was grateful.  She cleaned the table and then moved the receipt.

There sat the $100 bill.

Suddenly she carefully set the plates back on the table in shock.

She bent over with her head down and silently



breathed a sigh of relief

wiping her tears

she resumed clearing the table.

She then briskly walked to the kitchen, where I saw her tell her co-workers, and they all were stunned as well.

Remember, this was years ago, before social media posts and promotions of charity, as I don’t think this sort of thing happened back then as much.

But it had a profound affect on me to do this secret service.

I stood in the parking lot watching all of this unfold, as I didn’t know how it would be received.

In that moment, I made a promise to always carry $100 in my wallet for the opportunity to surprise and bless someone who was keeping the promise in their work.

I turned and walked away into the night.


I believe every person that reads my blog does something like this for others that pretty much no one knows is your thing.

It’s your secret promise of kindness.

I hesitate to even share this, as I’ve done it in secret for almost 2 decades and have never written about it.

Whatever yours is, if you want to share, please inspire us with your ideas of how you do it.

And if you don’t share with us, please promise to continue doing what you do, which is your private Signature Move of blessing lives, and keeping The Promise to those blessed by your heart.


~ Jason Hewlett

Husband, Father, Writer, Mentor, Hiker

  • Speaker Hall of Fame * Award-Winning Entertainer * Coach & Mentor
  • World’s Only Keynote Speaker utilizing entertainment, musical impressions, and comedy to Create Legendary Leadership through the Power of Commitment
  • Author of “The Promise To The One”



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28 thoughts on “$100 Tip”

  1. Great story. Love it.

    Let’s start a new Secret Service. We’ll all be incognito like the folks protecting the president (the photo of you in dark glasses is perfect) and we’ll go about doing service in secret.

  2. Your article made me cry — your big-heartedness and about what happened to the server with the table of 10 and no tip (and what you left her). Something I’ve done when I’ve seen a need at a restaurant, is to secretly leave money with the manager or owner to pay for the table’s bill. The most rewarding a while back took place when a family with 14 children ate at my favorite Chinese buffet. It was a very rare outing for them due to the prohibitive cost. My husband and I anonymously paid that bill. Also, I’ve prepaid someone’s bill at Starbucks and at a tollbooth.

    I think the giver gets the most reward. It’s often the little things that count and where we can do the most, such as opening the door in a public place for someone who would otherwise struggle with it. Spreading the love…

    1. Andrea! This is so awesome. I love that you’ve done this for others! Well done and thank you for sharing some of your secret giving.

  3. I also have a secret giving I was inspired to do years ago. A few of my work associates found out about it and began giving me $5 bills to carry on with. I couldn’t do $100, but I gave away hundreds of $5’s. One day, I happened to have $20. It was all the money I had at the time, but I felt drawn to give it away. I did and watched as the man unfolded the bill and then wept. At that moment I knew it wasn’t the money that caused him to weep, but the fact that he had been seen, that his need had been seen. I will never forget the look on his face as he looked back at me as I drove away.

    This being said, money isn’t the main thing I give. I send cards and letters, hundreds a year, to those who have spoken in a way at church or other events that moved me, a service that was rendered, or in acknowledgment of a pain they are suffering. It is old-fashioned, I know, but it has helped many, and frankly, it helps me. We all keep the promise to see, hear, and respond in whatever way we can and it does make a difference. Thank you for sharing this. It heartens me. : )

    1. This is why I wrote this article. Thank you my friend for sharing. The power of giving any amount is truly as you say, to let them know they’re seen. Well said! And yes, be it money, letters, anything that can serve another, it is worth giving.

  4. This made me cry. My aim is to be a Secret Santa and be able to do that for many during Christmas season. Thanks so much for sharing and being an inspiration

  5. Thank you for this. I am heading across country in a couple days for a meeting, and will pack a $100 bill! I can’t wait to use it! Raleigh has a place called A Place at the Table https://tableraleigh.org/, Raleigh’s first pay-what-you-can cafe. They sell wooden coins, now called Place Cards, for $10, and the person in possession of it can exchange it for a hot meal. I have loved buying these and handing them out to those on the streets and at the stop lights. It’s a wonderful way to provide a meal and ‘community’ for our homeless, and we feel good knowing it is going to a hot meal. It has gotten great publicity if anyone wants to research it for their town!
    Thank you again for sharing this!

  6. What a great idea! You’ve inspired me to do the same thing, and to be more intentional in observing those around me who might be in need of a lift. Thank you!

  7. Thank you Jason for inspiration to do good in the world. There is so little of this and it is so needful for others to recognize how many kind hearts there really are. Funny how I see how much alike you and my husband are. Being blessed certainly obligates one to pass it along. There is no greater joy than knowing you were God’s hands for one of His children in need. Love you Brother.

    1. Mindy, I love and appreciate you and Dave so much. Thank you for this comment. I feel very connected to him, and honored to be like him in some way.

  8. Hi Jason,
    I’m a regular reader, have been enjoying your blog for a long time, and learn from you almost every time you post your thoughts.
    That being said, this is the best post you have ever shared with us. It’s a fabulous idea that I’m going to start doing immediately. I think it’s good enough to be a speech, a book, a consulting practice, and more. And you’re just the guy to deliver it masterfully.
    Thank you for sharing such a valuable, life-changing idea.
    Your friend,
    Bruce Turkel

    1. Oh wow my friend! I’m thankful for your words, they have really touched me, as there are few who’s opinions I respect more. Thank you.

  9. I love this story. I also hesitate to leave mine. It’s not nearly as generous but I do look forward to it every payday. I go through the Dutch Bros line and pay for the order of the car behind me. Sometimes it’s just one drink. Sometimes the worker comes back and asks if I’m sure because there are 4 or 5. It’s all good. I never look back. I never wait for an expression of gratitude. It’s just a wonderful blessing to start someone’s day off with a small surprise.

  10. Jason, I also leave really big tips. Whenever possible I buy less food and leave more of it as a tip. Last weekend my daughter and I split a huge Mexican meal and we left the same amount for tip as the meal cost, just under $22. When it’s just me eating it’s usually $10 or so, and I always leave another $15-20 for the waiter.

    I’ve enjoyed this for years and I also don’t like to tell people about it.

  11. Thank you for your super secret awesome sauce that you’re doing Jason! I’m excited for when I’m earning the amount of money to where I can comfortably do this.

    For now, I think about times like when I returned a wheelchair bound Uber rider their phone after being 20 minutes away. (And such a situation where it didn’t feel right to submit for a lost item to Uber to be reimbursed.) And am inspired to continue the super secret awesome sauce moves!

  12. this is fabulous! Mine is not secret, but definitely heart warming. I met Earl around Christmas time digging in a trash can. He was a giant man and he asked me for money. I said “what for” and he said “diapers”. I told him I would take him to buy diapers but he wasn’t riding in my car and I showed him where to walk. I drove to the store and Earl met me. I alerted the guards at the front (not a good area of town at all) that I’d be coming through with Earl and shopping. They just shook their heads. Earl proceeded to buy everything his kids could possibly need. But he’d pick up sugary things and put them down because he new they were bad for their teeth. When we were done he gave me the biggest hug and slobbery kiss (yes Earl had been drinking) and he skipped home to see his kids that he probably had not seen in months because I am sure he could not afford diapers and wasn’t allowed back without them. Merry Christmas Earl. I hope you are well.

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