Becoming a giver: the most important lesson in a decade

May 2009: I’m 23 and eating breakfast with J*, a man who would go on to be one of the most influential people in my life.

J* is teaching me how to build a business.

In the middle of explaining a sales technique, he interrupts himself and says,

“You know, the real trick to business is being generous. Give as much as you can. The more good you do for the world, the better your life will go.

“Try to give the exact thing that you’re looking for. If you want to become successful, figure out how to help other people succeed. If you want happiness, spread happiness. That’s how it works.

“But there’s a catch: you actually have to care. You have to be generous for the sake of being generous, not for the sake of trying to gain something. If you can do that, everything will go better than you can imagine. I don’t know why or how this works; I just know it does. It’s really that easy.”


Last week I turned 31. Since I’m not one to miss an opportunity for reflection, I spent time contemplating the decade between 20 and 30. I realized that J*’s advice to be a giver shaped me more than any other advice I’ve ever received.

It’s difficult to overstate the power of investing in other people. In this article, we’ll cover how generosity affects the flow of your life, how it cultivates abundance, and a few ways I intend to continue practicing generosity in my life.

Using generosity to direct the flow of life

As far as I can tell the more generous you are, the better your life will go.

In business, proactively helping people has generated hundreds of thousands of dollars of revenue for me. While I was a professional speaker, someone sent me a long email asking about how to leave her comfort zone. Instead of dismissing her note, I made a cup of tea and wrote a lengthy response.

Several hours later, she wrote back. She happened to run a huge conference in Texas. Because she was so moved by my email, she wanted to book me to give a keynote.

Another example occurred last year when a friend of a friend needed free advice on how to build his business. I spent half a day teaching him the basics and proceeded to forget about it.  Today, that same friend of a friend is one of my biggest referral sources and has already sent two amazing clients to me just this month.

Hidden lessons in abundance

Practicing generosity trains you to understand that you already have enough. It also teaches you the importance of accepting help, something that many people struggle with.

If you’re one of the people who struggle to ask for what they want or need (like me), pause for a moment.

You feel good when you help other people, right? So do I. That’s normal.

If you’re reluctant to ask for something when you need it, you’re depriving people – often those you care about – of the joy that comes from helping others.

By refusing to ask for help, you’re making your life more difficult than it needs to be. By making your life more difficult, you hinder your ability to serve yourself and others. It forces you into a false feeling of scarcity and lack.

For the first few years of my 20’s, I was too poor to do much besides pay rent, work, and eat pasta. I was very self-conscious about being poor, especially since most of my friends were financially successful.

One of my best friends, W*, noticed this and paid for countless nights out for both of us.

Accepting W*’s generosity made me feel uncomfortable. I didn’t want to admit that I was barely getting by while most of my friends were doing just fine, but  today, I’m glad I stayed open W*’s kindness.

His actions increased my happiness and quality of life. And it wasn’t just my life that was affected. At the time, I was heavily involved with several non-profits. The increased happiness allowed me to dedicate more energy, care, and creativity to the people we served.

I still notice the ripple effects of W*’s actions.

7 acts of generosity

As I think about my future, I realize that one of the most important things to do is double down on the stuff that works. To these ends, I’m going to experiment with seven new acts of generosity. Admittedly, some of them are eccentric – even for me:

1) Spend at least one afternoon playing the “Make a stranger smile” game with a group of friends. The game is easy. As you move about your life try to make as many people smile as possible. You can tell jokes, give gifts, buy coffees, flirt, goof around, whatever. Whoever makes the most strangers smile, wins (B*, M*, you in?!).

2) Donate all of the proceeds from my one-off consulting calls to Ingenuity Prep.1 Speaking of which, if you’re interested in booking a call, mention this post when you apply, and I’ll give you an email retainer at no additional cost. You can learn more about booking a call with me here and more about Ingenuity Prep (one of the country’s most innovative and effective inner city schools) here.

3) Say, “I love you” to someone I love, but haven’t told yet.

4) Withdraw 100 one-dollar bills and pass them out to the next 100 people who ask for money.  From what I’ve been told, one of the worst parts of begging is being ignored. With that in mind, I’ll also do what I can to form a genuine – if fleeting – connection with the recipient.

Yes, I know that some of the money will be used for drugs and alcohol. Yes, I get that a buck won’t change a life. Yes, I’m aware that some beggars are con-artists.

But if I have something that I can easily give to someone who wants it, who am I to deny the flow of things?

Hat tip to my friend Z* for coming up with this idea and practicing it on a monthly basis.

5) Get involved with at least one political or social activism campaign. I used to feel like I could trust my government to make good decisions about the fate of my country and its people. Today, it’s become abundantly clear that I was wrong; the US government cannot be trusted to safeguard humanitarianism, democracy, and equality. Instead of watching from the sidelines, I’m going to get involved.

6) Spend two hours in a crowded place (maybe the airport?) silently wishing happiness for the individuals that pass. I first came across this idea in Chade-Meng Tan’s book, “Joy on Demand.” The process is to focus on a specific person, breathe in, connect to the energy in your body, say, “I wish for this person to be happy” in your head, and breathe out.

I understand my more cerebral readers may find this to be a futile practice, and it may be. I can’t prove that energy or intention directed at others affects anything. But if you’re skeptical, I invite you to wish happiness for two random people near you. Did you notice a weird shift in energy or connection?

7) Volunteer at a Title 1 School to teach one of the following topics: self-compassion, self-love, meditation, or entrepreneurship.

Postscript: want to give me a birthday gift?

If you’d like to give me a birthday gift, my request is simple: increase your generosity, and do it in a way that makes your life better too. The more you enjoy the process of giving (as opposed to feeling like you’re making a sacrifice) the better.

If one of the ideas above resonates with you, steal it.

If none of the ideas feel right, find something that does and do that. It doesn’t have to be big, enduring, or perfect. It just has to be sincere and designed to help someone else.

As far as I can tell, doing so will tap into a forgotten truth about the human experience: the more generous we are, the better our world – and individual lives – will be.


  1. Ingenuity Prep, by the way, was founded by my close friend W* – the same guy who paid for nights out when I was too poor to pay for myself. I’m biased, but if you believe that the way to build a better world is by building better leaders, contributing to Ingenuity Prep is one of the best investments you can make.

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9 thoughts on “Becoming a giver: the most important lesson in a decade

  1. Happy birthday Jason! And thanks for the great story,… I use that make a stranger smile a lot, I use it while shopping, in business, everywere. Best thing, after a while, it doesn’t feel generous at all, it almost feels selfish cause it makes YOU feel good. That initial energy invested is paid back 10 fold 🙂

    Next up, get 100 euro coins and give them in people of need! Awesome advice!

    1. Dude, Timon! You’ve made my day. And I’ve had the EXACT same experience with make a stranger smile. It starts as something a bit outside my comfort zone, and then ends up being something I fall in love with. That’s awesome you’re doing the 100 Euro thing too. Can’t wait to hear how it goes for ya. And thanks for the birthday wishes. 🙂

  2. What an amazing post! I knew a woman years ago that would always carry $5 with her. Whenever a kid would come to her door selling something, she’d always give them the $5, even if she didn’t buy what they were selling. She wanted to reward the bravery it took for a child to approach an adult and talk to them, let alone try to sell them something.

    I always loved that idea and told myself I should do it myself, but never followed through. This post reminded me of that story and inspired me to go get $5 for the next kid that comes to my door.

    Thanks for the insight and happy birthday!

    1. Thank you! And what a cool story. I’m so happy to have helped you remember to follow through with supporting the bravery it takes for a child (really, anyone) to go out into the world. That’s beautiful. And thanks… so far 31 has been the best year of my life. 🙂

  3. Cheers to your generosity, Jason!

    I like the attitude of giving what you can, paying it forward, finding unique ways to be generous. All good things. In addition to building up a sizable donor advised fund (which I highly recommend), I support the Rockstar Giving Fund, making the world a brighter place $20 at a time.


  4. Wow, really great article!

    I’ve known several people who always seem to be giving and who also seem to have the best “luck” such that good things are always happening to them in return. I’ve talked to them about it and always that there was a karmic aspect to it.

    Lots of cool and easy tips that I’m going to put into action immediately.

    1. Hey Sundeep – Glad to hear you like the article and that it’s applicable to you. 🙂 I’ve noticed the same thing: many of my most generous friends seem live these charmed lives filled with luck and serendipity. Perhaps it is a karmic thing. I look forward to hearing how it goes for you!

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