Why Do We Make Giving So Complicated?
– Rik Roberts
Welcome to the Relentless Generosity Blog. Where we flip our mindset from that of a reluctant giver to being relentlessly generous. I’m Rik Roberts, and I’ll take the journey with you—sometimes as your passenger, sometimes as your guide—but always focused on “giving while living” until we reach the other side.
Quote of the Day
“We make a living by what we get, but we make a life by what we give.”
— Winston Churchill
We all kind of know how to make a living, but making a life? That’s worth some thoughtful consideration. Sometimes it’s easier to gain perspective by looking back rather than looking forward.
When it’s all said and done and our funeral friends gather around, what will they say?
You might think, “Why would I care? I’ll be dead!”
Well, true. But if that’s honestly your first thought, you should stick with this blog — because your funeral may not be so much about what you did, but about what you didn’t do.
What is “Relentless Generosity?”
To me, relentless generosity means giving without pause, hesitation, or expectation of return. It’s a mindset—one where kindness isn’t dependent on convenience, wealth, mood, or audience.
It’s relentless because it perseveres—through fatigue, busyness, or doubt—and generous, because it flows from abundance of heart, not abundance of stuff.
It’s consistent, not conditional. Relentless generosity doesn’t wait for the “right” time or person. It becomes part of your daily rhythm—small acts, quiet gestures, steady grace.
It’s just as much about patience, encouragement, and forgiveness as it is about money or possessions. Giving from who you are, not what you have
And it’s a force that changes both giver and receiver.
Over time, relentless generosity reshapes how we see the world—not as a competition for resources but as a shared opportunity to create good.
At its core, it’s pursuing kindness with the same persistence that others pursue success. It’s living life with open hands—and keeping them open, even when it’s uncomfortable.
Living vs. Winning
Somehow, life has turned into a competition—power, possessions, real estate, wealth—it’s all about winning.
But what if Living is Giving?
What if life is about sharing what we have and making others’ lives better? I’m not talking about some hippie commune where everyone shares the same toothbrush. I mean living in a way that brings joy and value to others while you’re still here.
There are countless reasons we should be doing this already. Yet, we create even more excuses for why we haven’t started. Excuses are just reasons with an escape hatch. Instead of escaping, let’s investigate what keeps us from following a more generous path.
The Whataburger Incident
As a stand-up comedian and speaker for over 30 years, I’ve spent a lot of time under the spotlight. But off-stage, I’m the opposite—laid back, low-key, and always seeking out a way to be comfortable. When I travel, I am not one to impress with my wardrobe. I’m not “hobo chic” as U2 as once was called, but I’m not in suit and jacket, either.
My speaker friends always dress up for travel days—”You never know who might see you, Rik!” I get it—it’s good business. But when I’m off-stage, I’m off stage.
So, if you see me at an airport, I’ll probably be dressed in tactical black cargo pants and an old, beat-up sweater—the kind you wear around the house because it’s so comfortable (and probably a little “holey”).
A few weeks ago, I was flying through Texas and saw a family of seven in front of me at Whataburger in the Dallas Love airport. Chaos doesn’t begin to describe it. Kids were whining, one was rolling on the floor like a tumbleweed in a tornado. They were taking so long to order I thought I might miss boarding my flight. I kept glancing at the family, my watch, and he menu.
I heard the dad said to one kid, “You can’t have an extra-large Coke. It’s a waste of money. You’re getting water.” Then he noticed how loud he said it, glanced at me and looked embarrassed. I shrugged it off but thought about slipping him $5 and saying, “Hey, the Coke’s on me. Let’s just keep it moving.”
I didn’t—because, let’s be honest, no kid about to board a plane needs an extra-large Coke!
After they ordered their food, I stepped to the counter. The cashier looked up and said, “It’s paid for.”
“What?”
“That man there with the five kids gave me $20 and said you can get whatever you want.”
At first, I thought, that guy thinks I’m broke! Maybe the speakers were right about dressing up! Then I thought – woo-hoo! I’m getting myself an extra-large Coke!”
Then it hit me—this was an act of generosity. No strings attached. No announcement. Just kindness. I ordered and stepped aside with everyone else while we waited for our names to be called.
When I thanked the father, he said, “Sorry for making you wait. It took forever to get our order together. It’s the least I could do.”
I was relieved he didn’t think I was penniless—and then found myself scrambling to “repay” him somehow. But I stopped. I thanked him sincerely and left it at that.
How About You?
Have you ever had a moment like that—where you thought about helping someone but didn’t act, only to have someone else show generosity first?
How did you feel afterward?
What did you learn?
From that Whataburger moment, I learned seven lessons about why we make giving so complicated.
- We Think With Our Heads Instead of Our Hearts
I wanted to do something kind but overanalyzed it. The father didn’t. He just acted. Pure heart, no hesitation. We need to quiet the “head noise” that talks us out of good deeds.
- Resist the Urge to Deflect Generosity
I almost refused the free lunch out of pride. Accepting kindness—even when you don’t need it—teaches gratitude. It’s okay to simply say thank you.
- No One Needs to Know “Why”
I almost asked him why he paid for my meal. But the truth is—it doesn’t matter. Not every good deed needs an explanation.
- You Don’t Have to Get Even
We live in a transactional world. It’s okay to let kindness stand alone. True gratitude shouldn’t feel like a debt.
- You Don’t Need Permission to Be Generous
Generosity isn’t something to negotiate. If your heart moves you to act, do it—no permission slip required.
- Model Generosity With Simple Acts
The father gave quietly, even his kids may not have noticed. But when I accepted his kindness, they saw gratitude and thoughtfulness in action. That’s how we teach generosity—by living it.
- And Finally…
No one needs an extra-large Coke before a flight. Trust me… 140 passengers, two bathrooms, 84 ounces of caffeine—it doesn’t end well!
Recap
Giving is instinctual, but it’s not always natural. It takes practice—like strengthening a muscle.
The first step from reluctant to relentless generosity is simple: follow your heart more than your head.
Generosity doesn’t have to be complicated. Usually, our first instinct is right—and second-guessing only adds layers of hesitation. Don’t let a past reaction dictate future action.
Snap Into Action
Start your generosity journey with these small, actionable steps:
- Act on Your First Generous Impulse
When you feel the nudge to help someone—do it. Don’t rationalize it away.
Try this:
Write down one generous thought you had recently but didn’t act on.
Next time it happens, act immediately.
Remind yourself: Generosity doesn’t need permission.
- Practice Receiving Without “Getting Even”
When someone blesses you, don’t rush to balance the scales.
Try this:
Simply say thank you and mean it.
Reflect on how their kindness made you feel.
Let gratitude inspire your next act of giving.
- Start a “Small Acts” Challenge
You don’t need big gestures—simple, everyday kindness matters.
Try this:
Do one unannounced act of kindness daily this week.
Keep a short “Generosity Log” of how it made you feel.
Let those small actions remind you that giving is simple, heartfelt, and contagious.
Rik Roberts is a clean stand-up comedian and speaker who performs for fundraisers, volunteer appreciation events, corporate gatherings, and conferences. Learn more about his comedy and speaking programs to see if he is a good fit for your next event.
