The Art of Asking — Amanda Palmer

This is my first attempt to consolidate notes from books I’ve read, starting with Art of Asking. I love love love underlining words on the page so I can savor it more the second time; when I can’t underline, I take pictures of the text, leading to my phone filled up with unsearchable screenshots.

As part of my goal to remember and better package information that can be distributed, I want to do this for the books that I want to reread or recommend to others. Inspired by Corey Breier’s amazing write-up on Black Hole Focus.

To be honest, I was a bit skeptical about the raving recommendations for this book at first. I thought, “I already know and ask for things often. I also really like asking questions. Why would I need to read a book on how to ask when I’m asking everyday?”

As someone who customized my own education and found a job in SF through asking (for intro calls, stories, referrals, favorite startups, etc.), I thought I knew everything in this realm. Yet there are still things I struggle with asking for, like a promotion or raise. Asks that touched on my self-worth made me feel especially vulnerable.

This book surprised me with its writing, personal voice and depth of the concept of asking. I devoured the whole book on the 8 hour plane ride from Iceland, so this is a great way to parse through and crystallize lessons learned.

Insights —

on asking:

1. Why people are afraid to ask for help

“Asking for help requires authenticity and vulnerability”

• From Amanda’s TED talk, it seems that everyone struggles with asking not in the act in itself, but what it might potentially mean because of two things:

1. fear of putting yourself out there and getting rejected
2. thinking that we’re not good enough and undeserving of help

• Often times, we’re very attached to the outcome, and when someone rejects our ask, we take it very personally, as if anything other than a yes is an attack on our character.
• Example: just recently, I experienced this when introducing two friends to each other. I really wanted them to get along, I felt anything less than instant connection and laughter as a “fail”. Yet afterwards, I realized that interactions are not so binary as a pass / fail. The two friends are individuals; I have no control over their chemistry and how they would interact. I thought I was wanting the best for them, but after deeper reflection, I realized that it was out of my own selfishness as wanting to be seen as a good friend.
• Usually when we care about the result, it’s because it’s something that we really want and we feel that it’s a reflection of us. However, our value as a person isn’t tied to those outcomes. By the default nature of asking (you ask someone a question you don’t know the answer to), you’re giving that person the option to say yes or no. Or else it would be simply demanding them to do something.

2. Asking for help isn’t shameless

• Amanda crowdfunded her own music, using Kickstarter to raise $1 million and created an alternative way to how the music industry traditionally worked — by cutting out the label / middle man between artists and audience. Right now, there are also additional platforms like Patreon, where you can help artists directly.

“Effective crowdfunding is not about relying on the kindness of strangers. it’s about relying on the kindness of your crowd.”

• People denounced it as shameful that she was “begging” for money from her fans. In reality, for crowdfunding to effectively work, you need a strong foundation of people who you care about and who cares about you. For Amanda, that took about a decade to build and nurture with genuine thoughtfulness.
• Additionally, it was not a case of charity because she’s providing something in return, in this case, her album. She notes that it’s important to understand that artists and their audience is a two way exchange in an ecosystem. And “that shame pollutes an environment of asking and giving that thrives on trust and openness.” After all, her fans had an option to choose whether to contribute to her album or not, and they wholeheartedly did.

3. Asking is a foundation of any relationship

• We ask to better understand the other person and to better understand questions like: Can you help me? Can I trust you? Do you love me?
• Thus asking is hard because it conveys the core of the relationship, and when we are rejected from our asks, we may not feel loved.
• Asking is also a form of collaboration. In terms of power dynamics:

→ asking with shame = you have power over me

→ asking with condescension = I have power over you

→ asking for help with gratitude = we have power to help each other

• Those who ask convey two things: I deserve to ask and you’re welcome say no. Asking is a gift, a partnership, a mutual acceptance of each other’s differing willingness to act, without assuming what the other person wants. It’s an open dialogue because “the ask that is conditional cannot be a gift.”
• As mentioned earlier, when letting go of the outcome, it makes asks less daunting. Additionally, when you’re feeling afraid to ask, notice that it’s something that means a lot to you and let that fuel you to take action. Sometimes the process of asking is more important than what happens afterwards because during the process, it strengthens the relationship between you and someone else.

on street performing:

1. Amanda worked as a white veiled bride, gifting a flower to anyone (along with an elaborate dance when it’s cold) to whomever offered payment

• She’s changed my perspective on street performers. I’ve often averted my eyes when coming across them, because I was taught growing up that they’re only out to get me and my money. Even though I’ll chip in a dollar or two whenever a performer stops me in my tracks, those were the exceptions. Amanda has shifted my mindset on street performers in a completely new and different way. In her own words:

“Being a statue was a job in which I embodied the pure, physical manifestation of asking: I spent five years perched motionless on a milk crate with a hat at my feet, waiting for passerby to drop in a dollar in exchange for a moment of human connection.”

• You may be wondering — what human connection? I realized that there’s a difference between being looked at and being seen. And through actually paying attention to the passerby and looking at them in the eyes, Amanda wordlessly conveys the message I see you.
• I was amazed at the extent of heartfelt reactions, and how touched they were by this gesture of flower and attention exchange. So many of us go through the day without being really seen or acknowledged for our existence, floating amidst people on the commute to work, avoiding contact with strangers, with most of our eye contacts made in business-y meetings. I think it was powerful that she was able to make and give that genuine connection.
• Personal note: We all want to be seen, actions are our cries for attention. Interactions are bids for affection.

2. Why it’s easier to connect with strangers

• conditional love is: I will only love you if you love me
• unconditional love is: I will love you even if you do not love me
• It’s easy to love strangers unconditionally because they have a limited effect on you since you don’t know each other well. You haven’t formed an attachment to them or a specific outcome.
• It’s hard to love someone unconditionally when they can hurt you, hence the fear surrounding commitment. Feelings of pain, insecurity and a myriad of others are at stakes here. Yet that’s what makes asking unconditionally so beautiful — it’s not a reflection of you or on you, only a process that you and the other person go through (since the other person is also an individual being with their own thoughts, etc.), strengthening your relationship as a byproduct.
• Unconditional asks is similar to / tied with unconditional love.

On marketing / startups:

1. How to be scrappy starts with asking questions

• When she first started out, Amanda didn’t have much so she had to be scrappy. Through asking, she learned about things she would’ve have never known about otherwise and received a lot of help. She formed friendships with the florist and got leftover flowers for a discount, and saved a long commute by storing the costume at her barista job. In the asking process, people found out about her and supported her by offering free coffee for life, a place to rest, etc.

2. Authenticity

• Amanda is literally the OG of authentic marketing. It’s really inspiring to hear about her efforts to get closer to her fans, solely for the sake of connecting deeper with them. As a marketer, I’ve become a bit jaded by all the focus to scale and acquire users as much and as fast as possible. Compared to buying lists and scraping data, organic growth like Amanda had for for her mailing lists that grew slowly over time by word of mouth seems much more genuine. The way she used email and social media to communicate with her fans more has made me look at digital marketing in a more refreshing way. (for example: thinking of providing value not in terms of blasting out this post, and keeping your followers updated).

3. The fan as a significant other

• We hear about great customer service all the time. Amanda takes it to the next level by thinking of them as a significant other in a committed partnership. When she crowdfunded millions of dollars for her album, that wasn’t the work of an overnight — it was the result of a decade. She was cultivating and nurturing those relationships, not because she had an end goal in mind or wanted to get as much money as possible out of people, but rather she cared for them as humans and wanted to genuinely connect with them.

4. Free content

• The freemium model is pretty popular: offer something free now, and upsell later. Marketers also give away content to capture email addresses. Amanda sees it as: “Giving away free content for me, was about the value of the music becoming the connection itself. It’s about the value coming from the taker of the flower, the hearer of the song, the heart of the beholder”.
• She likens it as a gift that is passed around, in constant motion. This is similar to the mindset that what we’re given is suppose to be given away again, not kept, a forever reciprocation among people that touches many and goes around and around. Euphemism perhaps? I think thinking about creations like this is quite beautiful.

On being an artist:

1. You’re an artist

• When you have this urge to connect the dots that share what you’ve brought together.

“When artists work well, they connect people to themselves, and they stitch people to one another, through this shared experience of discovering a connection that wasn’t visible before.”

• You’re an artist when you say you are. Labels such as college degrees are only surface level credentials, at the end of the day, it’s up to you to believe whether you are an artist or not.

2. Humans collect, connect and share

An artist makes someone seen and accepted. A great example is Amanda being the white bride maid. People were drawn to her because from that moment of connection with them, they felt understood and believed.

3. No one really knows what their doing

Even the pros are winging it. So much is about actually going out and doing it and seeing what happens. Life is a series of experiments that you reiterate and retest the next time.

Takeaways + Applications:

“when you ask, there’s always the possibility of a no on the other side of the request. If we don’t allow for that no, we’re not actually asking, we’re either begging or demanding.”

• I want to work on how to ask “constantly, creatively, compassionately, gracefully”. Understanding that the process itself is so incredibly important and letting go of the attachment to an outcome. Making space for that potential no.
• It’s comforting to know that the most powerful people have asked. Amanda pointed out that when Steve Jobs worked in his parent’s basement, he probably had to ask his parents if he could live at home and crash, even though he was already a grown man.
• When in fear, asking myself: “is it because I’m afraid of no? Or is it because I don’t believe I deserve it?” Rejection therapy and self-affirmation exercises would help these fears, respectively.
• Read Thoreau’s Walden
• And wondering, when will I love my craft so much that I’ll bleed on to the page?*

*especially relevant since I’m currently reading War of Art