Confidence Bordering On Entitlement

I probably should blame myself more.

And I’m honestly not sure how much this is innate or because of my bad parenting but…

Vlad has a level of Personal Confidence that easily wanders into Entitlement.

To be frank, I find the way that Vlad asks for anything––and you could substitute other verbs for “ask” ranging from “insists” to “requires” even “demands”––impressive and also slightly intimidating.

All obstacles to his desire are irrelevant.

That includes, for example, personal conversations you might be engaged in, or even the rare occasions when the ball escapes through the fence.

He knows exactly what he wants…and he doesn’t hesitate to ask for it.

And that’s what’s inspired this month’s new meditation theme––Asking––HERE.

(Vlad assuming correctly that I’ll retrieve his blue ball)

Having spent the last month diving deep into Clarity (particularly by re-reading Essentialism), I’m not surprised that I’ve honed in on exactly what I want to create and receive next in my life.

I’ve looked beyond what’s the smartest, most strategic Next Move into what’s actually deeply important to me.

I’ve made some difficult choices that have allowed me to narrow and concentrate my focus.

Yes, there’s a sweet rush of energy coming from my newfound conviction but at the same time there’s also new corresponding levels of resistance.

Having coached dozens of creatives (including myself) through these pre-Breakthrough waters, I know this is par for the course.

Even so, partly because of the Big League nature of what I’m launching next––more on that soon enough––I find myself musing about the nature of Asking itself. 

Why it’s often so difficult for us…

What deep emotions it brings up…

Our inner (and outer) dialogue with worthiness..

The stigma that’s often attached to asking…

And the immense rewards it offers.

Thus, I’m re-reading two books with wildly different takes on the topic this month.

The first: The Art of Asking by the alt-rock, dark cabaret, cult hero Amanda Palmer.



If you’re not familiar with Amanda Palmer, you might start by watching her Ted Talk (which has over 20 million views worldwide) HERE.

Please also allow me to summarize it.

After graduating from Wesleyan, before her music career took off, she spent several years busking as a living statue called “The Eight Foot Bride.”

Painted white and never speaking, she took the character around the world, asking for donations in Harvard Square and Berlin, from Edinburgh to Australia.

When people gave her money, Amanda offered them a flower.

If they did not accept the flower, she offer a lingering sad gaze.

After years of couch surfing while touring and (literally) crowd surfing during her concerts, Amanda Palmer truly earned a PhD in the Art of Asking, the title of her book.

And, in an astonishing demonstration of this, in 2012 when she decided to raise $100,000 via crowdfunding to independently produce her album, she ended up raising $1.2 million…at the time, the largest crowdfunding of a music project.



Just FYI, the other book I’ve decided to re-read this month is one of the cornerstones of New Age thought, Ask & It Is Given by Esther and Jerry Hicks.

Having read it first in what seems like several lifetimes ago, yet not having picked it up for many years, I’m curious what I’ll think of it in 2023.

Will it seem refreshing and pure…or simplistic and naive?

I am very, very curious to find out.

You’re invited to read/re-read it along with me.

One of the best moments in Amanda Palmer’s Ted Talk is when she reframes the paradigm around asking.

It’s NOT about GETTING people to pay money for music, she tells us.

It’s about LETTING them pay.

Exactly along these lines, I’m reminded of an indelible moment I experienced many years ago.

After a flirtation with getting an MFA in filmmaking right after college, I was living in LA briefly.

While attending a blur of screenwriting meetings that never amounted to a paycheck, my survival gig was at a leading advertising agency.

Even though I was just a temp, I somehow got invited to the Christmas Party.

It was held at the Santa Monica Airport which has interesting event spaces near the runways.

I was working for a Sr. VP with a wicked sense of humor.

She asked me to research if it were possible––and how much it would cost––to hire a pilot in a private plane to taxi down the runway, stop outside the entrance to the party, so she and a friend could exit the plane in evening gowns.

(Clearly, she really wanted to make a red carpet-level entrance.)

I managed to find a pilot who thought it was a hoot and agreed.

Although I can’t remember the exact price he quoted me––maybe $100 to cover the fuel––when I told my boss, she immediately responded with “Really? Tell him, I’ll double that!”

Amanda is right: Sometimes people really do WANT to pay…you just have to let them.

My primary interest around Asking is exploring what holds us back, ie. how we can do it better and more freely.

And YES, the ultimate goal is to be even 50% as unapologetic about declaring my needs and desires as Vlad is.

At the same time, I’m also reminded that perhaps part of this involves something that Rilke famously teaches us:

Part of mastering the Art of Asking is that we must…

Try to love the questions themselves like locked rooms and like books that are written in a very foreign tongue.

In fact, the poet goes on to say:

“Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything.  Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”

To be honest, I definitely want most of my answers BEFORE that distant day.

And more importantly, I want to be more clear and confident in my asking right now.

Thus, I invite you to join me on this journey.

Again, you could start with the new meditation HERE.

And perhaps consider watching Amanda’s Ted Talk HERE or reading either book along with me.

Or simply reflect on what you’re asking for and how you’re doing it these days––and also where and why you’re not asking at all,and why that is.

Perhaps as Rilke advises we may come to love the questions…but wouldn’t it be even more astonishing if (in the near future)we also came to love the Asking?

Namaste for Now,

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