Ever since July when I watched a man give away $100,000 in $100 bills to strangers he believed in, I decided it was time to challenge myself to be more of a giver — in bigger and bolder ways, in my business and my personal life.

The thing was, I sure as hell didn’t have $100-grand to give away.

And if I had to guess, you might not have those kind of funds on hand, either. :)

What do you suppose happens then? You start to feel like you’re not doing enough. 

Like you don’t have enough to give. Like whatever amount you can give won’t amount to a drop in the bucket. You start thinking, How much good could this possibly do? How much change could it really make?

And how could I ever make sure that what I want to give will be worth all of the effort, investment and risk I have to undertake to (hopefully) achieve it in the first place?


You’re Not Alone.

That’s one of those peculiar things about giving — it seems as if we’re more likely to give when the decision is spontaneous, not thought out.*

Most of us are more likely to donate to a cause on a whim — throw a coin in the bucket if it means a stranger’s smile, give a dollar to a beggar if we see ourselves in him or her, or say “Yes” to the $1 donation at the register because we feel a bit guilty over that new $100 toy we’re buying.

And on the flip side, we’re far more unlikely to give when we sit down, plot out an idea, think it through, dream of the impact, plan a course of action, begin to execute and ultimately deliver on our inner “want” to give.

Why do you think that is?

Think about it: what do you have to face when you’re sitting down and plotting a course of action to fundraise money for a cause, thinking of ways to reach out and communicate with people, planning courses of action, wondering what might go wrong and when and how you’ll have to deal with it — and then, when the thinking is all said and done, finally begin by executing upon a plan to deliver on your promise to give in “big and bold ways”?

There’s a whole lot of time to think. A lot of time to overthink.

Plenty to worry about. Plenty to fret over. Failure is one of them. Judgment is another.

You’ll fear that you don’t know what the hell you’re doing. You’ll realize at some point that there’s a whole lot of work to do — and maybe that you can’t pull it all off on your own. You might be risking something very real — money, time, resources.

You might fail in front of a lot of people — your friends and family — and don’t want to feel ashamed.

You’ll start thinking, “How do I deal with people rejecting me for donations?” even with people whom you love and thought you could count on to support the cause you love.

The list of worries, fears and mental-emotional elements is nearly endless. Those are the elements that dissuade even a devout, dedicated giver like you from going beyond your limits to give in big, bold, beautiful ways.


What Is Undermining Your ‘Want’ to Give?

When you understand your foe, you can defeat your foe. And sometimes, you biggest enemy is yourself.

It’s not you — we’re all guilty of undermining ourselves from time to time, because it’s a part of the human condition. Our higher levels of thinking, when unnoticed or left unchecked, results in those terrible feelings of self-loathing, self-sabotaging, and relinquishing to our fears and worries in spite of the amazing dreams, goals and desires that we have.

The worry-mind is the dreamer’s enemy.

And it has many weapons that undermine our goals. The worry-mind consists of the quiet, habituated patterns of thinking that you and I get accustomed to — and sometimes, rarely ever recognize: our brains are in a constant state of compare-and-contrast, we self-assess ourselves against others to see how we “measure up” and ask if we’re “good enough” when compared to others.

Those are just very fundamental, basic, biological and evolutionary traits that once kept our species together, united and alive. But in 2012, those traits can become the root of our dreams’ very undoing.

And what I didn’t realize earlier this summer was that the real challenge of “challenging yourself” is not in committing to a challenge, in spite of the uncertainty, unknown and fear.

The challenge is the uncertainty, unknown and fear that you continually encounter, battle and swim against after making the very commitment to begin with.

Sometimes, making a big, bold decision to take action is easy.

It’s the “I f*cking quit!” moment that we dream of when we’re stuck in a shitty job. It’s the inspiration we feel in our gut after a bold speech, a moving event or once-in-a-lifetime encounter that elevates the bar of expectation that we hold for ourselves — and instigates a new level resolve, determination and hope.

But most of the time, friend, the hardest part about sticking to your beliefs is as simple, lackluster and unexciting as living up to it. Over and over again. Over years and decades, and in tiny, small steps that few ever see — let alone praise, applaud or for which they might give you the credit that you’ve earned.

That’s what is so tough about giving.

But that is, altogether, what makes giving such an important endeavor. Such a worry and challenge. A teacher in itself and a way of life you want to live by — in spite of every unknown, any uncertainty, and even being misunderstood by people around you.


3 Reasons Why You Might Feel Like You’re ‘Not Doing Enough’

So, why do you feel like you’re not doing enough?

There are a few reasons why you might feel like an underachieving giver — but chances are, your self-beliefs or personal actions are simply out of alignment with what you so deeply believe.

1.) You’re Not Practicing What You Preach

Preaching is easy. Telling others what they ought to do, say, believe or feel is easier. And blogging about it, tweeting it, Facebooking it — even easier than that.

While tools like those are great for easily sharing messages and encouraging giving on all levels, it takes a whole lot of heart, guts and inner resolve to sit down, shut up, buckle in and do the work it requires to positively affect lives on a fundamental level — what really makes you a quiet leader worthy of emulation.

Remember that the social media or online aspect is a small, even trivial component of giving. To quell that feeling of “not doing enough” that’s haunting you, you need to consistently practice what you preach — especially when no one is looking. Do it often. Strive to make it second-nature; a routine. Don’t worry about the fanfare. Bring your actions into alignment with what you believe, and watch what follows.

2.) You Haven’t Done Enough ‘Risking’ in a While

You want to give in bigger, bolder, more meaningful and truly impactful ways. But how can you achieve that if you’re not willing to risk more — even if it’s just every once in a while?

Giving in significant ways is naturally “risky” feeling. That’s precisely because you and I don’t have $100,000 readily on hand to give away to charity, whether attendees at your conference or to a big-name charity that everybody knows. Giving in bigger ways means risking in bigger ways. And, eventually, you will have to face up to the mental and emotional challenges of uncertainty, fear and unknown in order to overcome your feelings of “not doing enough” to give in the ways that you desire.

3.) You Need a Bit More Self-Confidence

When you’re living misaligned from your values, you’re bound to feel a deep sense of inner conflict and unfulfillment. Those are corrosive to your self-confidence.

When we lack a feeling of meaning, purpose or fulfillment — both in the day-to-day, and the big picture — we fall into a haze of confusion devoid of clarity to guide our feet and the necessarily motivation to carry our thoughts, dreams, beliefs and desires through to a state of action, commitment and pursuit.

The way that you rebuild your self-confidence is to commit to an intentional practice. What makes you feel fulfilled daily? Make a short list of 5 values that give you the feeling of purpose and meaning in your everyday life. By starting small and building your confidence from the inside-out, you begin to feel more aligned and “on purpose” — which helps you give in bigger, bolder ways.


Thank you, NYC: We ‘Did It In A Dress’!

On short notice and a whim-and-a-prayer, I pushed myself to risk more and do something I had never done: host a fundraising event to benefit one of my favorite charities, One Girl, in New York City on October 19th on behalf of their annual fundraising spectacular, the Do It In A Dress campaign.

As of this writing, the global campaign has raised an epic $248,373 that will provide basic education to more than 1034 girls in Sierra Leone, West Africa — forever changing the course of their lives, directly improving small and developing communities, preventing the spread of HIV/AIDS, underage marriage, teenage pregnancy and prostitution.

That. Is. Remarkable!

For my fundraising event, I combined an easy-sell idea with great people on behalf of a good cause — an open bar with proceeds benefiting One Girl, with the help of my amazing friends, friends of friends, volunteers and other awesome contributors.

Together, we raised $1,076 that will provide 4 girls with education next year!

I have loved One Girl since they came on my radar in 2011 because of the profound, positive, life-changing effects they have in the lives of young people who so desperately need it.

To think that just over a year ago, I was chatting with co-founder Chantelle Baxter on an idea for a campaign — this campaign — that would explode with popularity just a few months later. I am grateful and proud of all of the hard work of these men and women do in Sierra Leone and across the globe.


With Gratitude, Thank You To…

Special thanks to my pal and an all-around amazing guy Daniel Jarvis for his very generous $200 donation to the event.

Another big thank you to is owed to my fellow Young Entrepreneur Council member Michael Sinensky for assisting us with an amazing venue and the help from his incredible staff and crew at SideBAR N.Y.C.

And, another very big thank you is owed to the wonderful Antonella Saravia, photographer-extraordinaire, for donating some time from her weekend to kindly photograph our event.

If you’re in the New York City area and looking for a photographer, look no further than Tone — she is amazingly talented and highly recommended.

Thank you also to all of our fundraiser attendees and contributors including Kristen Fleming, Bridget Kluger, Jane Ursillo, John Vouyiouklakis, Carrie Kinsella, Nicola Brune, Lucy Foster, Mike Mulhern, Rob LaPolla, Peter Foglio, Katie Spinelli, Andrew Manning, Colin McSherry, Blanca Del Castillo, Carlos Perez, Ray Klein, Madeline Pfau, James Varsam, Ali Gigante, Miguel Fernandez, Marlon Teki, Helen Murphy, Kaitlyn Paul, Kara Evans, and the more than two dozen more attendees who joined us live at the event.

And, thank you to donors who couldn’t attend but who were so generous as contribute to our $1,076 total, including Pat McGuire, Lindsey Angione, Stephanie Angione and Lindsay Van Winckle. You guys rock!

Speaking of giving more, my latest book is now available in paperback for the first time — and a limited number of autographed copies are on sale today to help benefit another amazing cause:

Yes, that’s right!

I’m very excited to announce that my second book, God Whispers on the Wind — a collection of 81 heart-stoking poems — is now available in an utterly gorgeous, 140-page paperback edition. And, I’m putting just 30 special copies on sale for you: a limited, author-signed edition — personalized and made out to you.

Better yet, a portion of proceeds from every sale of this limited edition will directly benefit Housing Works, a charitable and advocacy organization whose work benefits local communities including the homeless and those living with HIV/AIDS. Your price is $30, and shipping is included:


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Can’t see the buy box? Visit the blog to purchase here.


Housing Works operates thrift stores and bookstores in New York City — one of which I frequented with old clothes donations and even a donation of books, including copies of Lead Without Followers. And this week, when you buy a new and beautiful paperback of God Whispers on the Wind for yourself or someone else, you’ll be helping the good people at Housing Works help more people in the greatest city on Earth.

So, there you have it. Just one more effort to do some giving :)

I hope you’ll pick up your signed copy of God Whispers on the Wind today. If you miss your chance to get a limited copy, you can always head over to Amazon and purchase the paperback or for Kindle.

Until next time, friend — keep shining.

* Footnote: I’m admittedly having a hell of a hard time Googling for supporting evidence on the notion that we are more likely to donate when it’s spontaneous and not planned. I believe it’s a fairly well-known element of psychology and recall reading it in various studies. If you have any links to articles on hand, please send me an email and let me know. :)