The 100 Day Challenge: 100 Days, 100 Asks

Everyday for 100 days, I’m going to ask for something I want. 

I’m not talking about layup shots. I’m talking about making bold requests and asking for something I really want. Things that are usually deemed unreasonable. Asking for something that is scary for me to ask for. Asking for something from someone who intimates me. Asking for something that standard wisdom says I shouldn’t get. Asking for something knowing that what I’ll probably get is rejection.

In fact, the goal is to be rejected! So if I don’t get rejected, in theory I should actually try something else until I do.

Day 1 is September 23, 2014. Day 100 is December 31, 2014.

  • Do you want to join me in doing your own 100 day challenge? Let me know.
  • Or do you have any ideas for my daily challenge? Send me an email.
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  • Finally, to read the full backstory of why I’m doing this, check out this post.

[Day 25] Oct 18, 2014: Ask a Starbucks Barista If I Can Use Her Hand Lotion.

You can probably tell I hang out at Starbucks a lot.

I was ordering a coffee when I felt my hands and noticed: you guys are super dry. My first thought: I need hand lotion.

It’s funny how it’s getting easier to ask for things I want. I didn’t even think about it. After she handed me a coffee…

Me: “Do you happen to have any hand lotion? My hands are super dry.”
Barista: “Yeah, actually, I think I have some. Let me go check.” (Walks to the back room.)
Another barista walks out.

Barista #2: “
Here you go. It smells like pomegranates.”
(I can hear laughing in the back room.)
Me: “That’s fine, I’ll take anything right now. Thanks!”

SUCCESS. Lubed hands, ready to rock n’ roll.

 [Day 24] Oct 17, 2014: Ask a Facebook Friend to Take a Photo of Their Favorite Place in Their Hometown of Belgrade, Serbia.

This ask spawned from an ask directed at me.

I made quite a few virtual Serbian friends after my Huffington Post article about the flooding in Serbia hit viral status in Serbia. I’ve kept in touch with a few of these. One friend asked me for a favor, so I decided to flip the ask around and ask for something in return.

Facebook Friend in Serbia: “May I ask you a favor? I want a book. Is there a possibility that you buy it for me, when you come here, to Serbia? I can send you a money or give it to you when you come….”
Me: “Sure no problem… Now will you do something for me?”
Facebook Friend in Serbia: “Yes, of course…”
Me: “Will you take a picture of your favorite place in Belgrade and send to me? Maybe this weekend if you have time.”

SUCCESS! Here are pictures from Jelena’s favorite place in Belgrade, Top?ider Park:

[soliloquy id=”4777″]

 [Day 23] Oct 16, 2014: Ask for Help w/ Payment of a New Visa

Concurrently with the Greek stuff (Day 22, below), I’m also in the process of becoming sponsored to have the ability to work and live in the UK. I was putting the finishing touches on my Visa application. Up next: The payment.

A big fat number passed along the screen. I shot an email to the guys I’m working with. It was less of an ask, more of an…“You guys are gonna help cover this, right?!?”

SUCCESS. Thank goodness.

 [Day 22] Oct 15, 2014: My Big Fat Greek Ask: Asking for my Greek Citizenship.

I flew to Chicago for a 12-hour bender to move along the process of applying for my Greek citizenship. Long story short, it’s a loooong ass process to “ask” for my Greek citizenship. I have Greek lineage, so like with most European countries, if you can trace and prove it, it’s feasible to be granted dual citizenship. I had an appointment at the Greek consulate in Chicago to (hopefully) finalize my final paperwork from the US.

Things are moving. This was a big successful step in the process. SUCCESS.

Next up: Go to Greece and finish the process.

 [Day 21] Oct 14, 2014: Ask For an Arugula Salad — But Make it Kale. 

What a glaringly San Franciscan ask.

Me: “Hi, I’d like the Arugula Salad please. But instead of Arugula, can you please make it Kale?”
Dude at Cafe: “Sure.”
Me: “Oh. Okay. Thanks.”

Well, that was easy. SUCCESS. So I made a second ask that day, at the same restaurant.

 [Day 21] Oct 14, 2014: Ask For Someone’s Uneaten Food

Me (to the people at the table next to me): “Hi, are you going to eat those pickles?”
Girl 1: “No…they’re not even ours. They were here when we sat down.”
Me: “Oh I see. So…you’re not going to eat them?”
Girl 1 (laughing): “Um…no. Do you want them?”
Me: “Yeah, do you mind? Is that gross?”
Girl 2: “They’re all yours.”
Me: “Great. Score!”

Me (to my lunch partner): “Welp, guess I have to eat these now…Don’t judge me.”

SUCCESS — Pickles! SUCCESS — Acting like a homeless person in front of my lunch partner!  SUCCESS — Not contracting ebola!

 [Day 20] Oct 13, 2014: Ask for Clover Coffee Tour.

I was all up in Starbucks on Fillmore in San Francisco (big surprise). While waiting for my coffee, I noticed this giant “Clover” machine that the baristas keep trying to push. So I asked the lady:

“What’s the deal with this Clover Coffee thing? Can you explain how it works?”

A mini-tour of the clover coffee machine at Starbucks. Kinda boring. But a SUCCESS none the less.

 [Day 19] Oct 12, 2014: Ask Random People To Take a Selfie With Me.

I’ve been thinking about this one for a while, but have been too self-conscious to pull it off. Walking around San Francisco with my sister today, I decided I had enough encourage and moral support for it. Here’s the run down what happened.


Foreign couple on holiday (my guess: Russian), taking a photo of each other
Me: “Hi, do you want me to take a picture of you two?”
Woman: “Umm.. No, thank you.”
Me: “Would you mind taking a picture with me?”
(they start to agree and put their hand out for my phone).
Me: “No, I mean, will you take a picture with me? The three of us?”
Man: “Uhhh. No, No.”
Woman: “No…blah blah” Mumbling something in half-English.
Couple starts walking away from crazy guy.

Me: “Okay, thanks anyway. Have fun!”

Two elderly Asian ladies, walking along the sidewalk toward me.
Me: “Hello! Can we all take a picture together?
Elderly Asian Lady 1: Ignores me, keeps walking forward.
Me: “Just a quick photo, please?”
Elderly Asian Lady 2: Looks at me, disgusted. Appears to want to hit me.
Me: “No worries ladies, I’ll figure something else out.”

A pretty strong No and No from both parties. Two rejections off the bat. But then I really hit my stride.

Dude with a waxed mustache and a couple gnarly ear piercings.
Me: “Hi there, I have an odd question. Would you mind if we took a took a selfie together?”
Dude: “Uhhm, why?”
Me: “I just want to take a photo of myself with the Painted Ladies, but don’t want to take one alone.”
Dude (pointing at a light brown pit bull): “I’d rather not…but if you can get him to, you can take one with Jeffrey.”

Ladies & gents, Jeffrey:

Dog1 Dog2a  Dog2

Random young couple standing and admiring the Painted Ladies.
: “Hi guys, how are you? I have an odd request. Would you mind if we took a picture together, the three of us? A selfie?”
Guy: “Hmm. Yeah, Sure…”
Girl: “Haha…uhh”
Me (to the girl): “What’s so funny, is that weird?”
Girl: “Yeah, kind of…”
Me: “Okay, you’re right, it might be. You cool with it?”
Girl: “Yeah sure…”

Thanks for playing guys:

A couple trying to take a couple selfie of themselves.
: “Hey, do you want me to take a picture of the two of you?”
Guy: “Yes, please, thank you!”
I take a picture of the couple.
Me: “Where are you from?”
Guy: We’re from Italy. Milano.
Small talk about Italy, my family in Abruzzo, etc etc.
Me: Can we all three of us take a picture together. A little Italiano in San Francisco?”
Guy & Girl: “Okay!”

Grazie mille! Buon viaggio! Arrivederci! (I blame the sun for my face)


A group of youngsters up to no good.
: “Hey guys, where are you from?”
Guy 1: “We’re from Germany.”
Me: “Oh, where in Germany?”
Girl (looking at me like “you’re an American, there’s a 7% chance you know any German cities): “Hamburg…”
Guy 1: “But we’re studying in Long Beach right now. And just here for the weekend.”
Me: “Cool. Hey, can we all take a photo together?”
Group consensus: “Sure, why not…”

Again, with the face. Not sure why I look like a moron. Oakley’s probably touching my butt.


 [Day 18] Oct 11, 2014: Ask a New Friend to Pee Outside With Me.

Apologies if this sophomoric Ask offends you. But sometimes when you catch me a little tipsy + tired of serious Asks – I need to have fun with this. Here’s the ask in a short & choppy fashion:

Fleet Week. San Francisco. Rooftop Party. Bathroom. Long Line. Gotta Pee.

Outside. No Line. Little Nook. Green Grass. “Wanna Go?” “No…No.”


 [Day 17] Oct 10, 2014: Ask for Sponsorship (Again).

Following Day 14’s rejection, I drafted up another Ask to another organization who I think (hope) will (could) be interested in sponsoring me to deliver a talk at the Travel & Adventure Show.

Stay tuned…

 [Day 16] Oct 9, 2014: Ask for Career Advice from Someone I Admire.

On the surface, this may not seem like a hard one. But please know that in general, I have a hard time asking for help. Including advice. Especially from someone I admire. Even if that person is a friend.

Today, I was texting with Amber Rae about her latest project The World We Want. Amber is one of those people who seems to know everyone — not just everyone everyone, just the everyone worth knowing. Not in an entitled way — just in a way that they’re usually the people crafting up cool projects and making huge impact on the world at the intersection of art and business. Everyone I’ve met through Amber is someone who I instantly connect with.

What I’m saying, basically, is that Amber is the shit, and I respect her opinion.

I need to make some big work, career and life decisions pretty soon. And I realized that I could stand to take some advice from people I respect. So I texted Amber:

“Do you have any time to chat on the phone later today? I would love your advice on some stuff, work/career wise…”

And of course, because she’s Amber, she said “definitely.” SUCCESS. Thank you, Amber.

[Day 15] Oct 8, 2014: Ask to Have Conversation About Work/Career 

Again, on the surface, not an monumental ask. But, again, my tendency is to be all “go-along, get-along” (as Stephen Markley described of me in Tales of Iceland). This is fine for most things. But on big topics it can be devastating.

I asked to continue a big conversation with the guys leading one of the big projects I’m working on right now.

SUCCESS. I knew this had a pretty good chance of a non-rejection — but it was important for me and all of us to make sure we continued the conversation.

 [Day 14] Oct 7, 2014: Ask for Icelandair to Sponsor a Talk.

You may recall that my ask on Day 5 was to pitch myself as a speaker at the Travel & Adventure Show, a US travel trade who. I was offered 2 dates: Philadelphia & San Francisco! Cool!

It’s great for promotion. It’s great for practicing public speaking. And it’s a great opportunity to meet some great people — last year I made friends with Patricia Shultz, creator of 1,000 Places to See Before You Die, and Pauline Frommer of Frommer’s Guidebooks, to name a couple). Plus my buddy Rick Steves will be there this year.

The problem is, this ain’t no paying gig. So in order to help pay for my travel & lodging to make the trip worth it, I need to get creative on how I get to Philly and SF.

Since the talk I plan to give is about Iceland (and promoting Tales of Iceland and the Tales Of travel series), I decided to reach out to a contact at Icelandair and see if they’d like to collaborate on a promotion…AKA sponsor me to deliver the Iceland talk! So I asked.


“We actually have already committed our budget for promotions and shows, so we unfortunately don’t have any additional funds for promotions beyond the show registration.”

Or is it a rejection? Maybe more like an obstacle? Or a “not now, maybe later?” I’m a persistent little devil. Stay tuned…

 [Day 13] Oct 6, 2014: Ask an Actress Friend for Some Movie Scripts

This was an Ask that I actually asked a little bit ago, but it came to fruition in full force today.

Basically, I’m curious how a written screenplay looks when compared to how it actually looks on screen. I’ve never actually looked at a written screenplay before. So I sent a note to an actress-friend I recently met in LA and asked if she could help me find a copy of some screenplays, or better yet, if she could send me some.

Today, she sent me A BUNCH of screenplays. Thank you & SUCCESS!

(I’m keeping her identity private as it may be frowned upon for her to send them to me. They’re safe in my hands, promise).

 [Day 12] Oct 5, 2014: I Failed Today.

I didn’t ask for something today, and I feel horrible.

These 100 days of asks is becoming more difficult than I anticipated. Some days I’m tired and just don’t feel like asking for something!

I failed you today. SELF-REJECTED.

[Day 11] Oct 4, 2014: A Private Ask

This one isn’t for public consumption. But just know that I asked. SUCCESS.

 [Day 10] Oct 3, 2014: Ask For a Free Sample at a Restaurant (After I Finished My Meal) 

I had dinner at a BBQ joint in Napa, CA late last night (I’m here for a wedding). There were two items that looked especially delicious: the pulled pork sandwich and the slab of ribs.

I chose the pulled pork. It was delicious, and while I chomped down, I certainly didn’t regret the decision. But after the meal, I began to wonder…did I make the right choice? Did I miss out on the ribs?? And what if the future lives of my children’s children would be wrought with depression and despair because I so nonchalantly chose pulled pork?!?

This was a heavy burden I was not prepared to bear. So I pulled my waiter aside:

Me: I have a question. The pulled pork was great. But I can’t stop thinking about those ribs — they looked delicious. Is there any way I can have a taste of them?
Waiter: Uhhh…hmmm. Man, I don’t think so. Those ribs are already prepared, and they just come in a giant slab. Pretty sure we can’t just cut one piece off.
Me: Maybe just like one little sliver of a rib or something?
Waiter: Trying to think what we can do…but no, I don’t think it’s possible. But yeah, those ribs are good.
Me: Okay, thanks anyway.

REJECTED. Sorry great grandchildren. I tried — I really did.

[Day 9] Oct 2, 2014: Ask Someone on Tinder to Go For a Run.

Like most of its millions of users, “I don’t really use Tinder.”

And like the 30% of people who don’t really use Tinder, the primary reason I still have it on my phone is because “it’s entertaining / like playing a game.” So naturally I thought it might be the forum for a creative Ask.

I was planning to go for a run later in the evening. So I decided that the next person I matched with I’d ask them cold and straight up — will you go on a run with me tonight? And that’s what I did:


I was certain this was going to be a rejection. Who would say yes to this? Would you? Maybe you would. I’m not judging.

The afternoon passed. I went on my run later that day. Rejected and alone. Thanks a lot, Courtney.

And then I got a response later that evening.

SUCCESS? REJECTION? A little bit of both I suppose. It feels like success though.

(Side note: In doing research on Tinder, I came across a hilarious site called Hello Let’s Date. Please invest in your immediate happiness and dedicate the next 30 minutes of your life to that site.)

 [Day 8] Oct 1, 2014: Ask a Friend to Help Me With a Publishing Project.

I met up w/ my good buddy Mike to catch up on life, love and everything in between (or “Bojo” if you’ve read Tales of Iceland).

Long story short, we started talking about Tales of Ecuador — the 2nd book in the “Tales Of” series friend & author Stephen Markley and I are working to build together. Basically, I’d been so preoccupied w/ building The Escape School that I’ve been neglecting the publishing of that and have been putting it off. It’s written and almost ready to go

Bojo: “Dude, what’s up with Tales of Ecuador?”
Me: “Ahhh I know! Man, don’t get me started. It’s been on the back burner and it bugs me every day. I just need to get it out there.”
Bojo: “Do you need any help?”
Me: “Um…. Yes! Will you please help me finish the publishing process…the ebook and paperback formatting?!? I think you’ll really dig the process. And you’ll be good at it.”
Bojo: “Sure man. Happy to do it.”
Me: “Oh! And that’s going to be my ask today! Asking you to help me with the book.”
Bojo: “But actually I asked you…”
Me: “Bojo, shut up. I asked you. You’re remembering it wrong. No one will believe you.”

RESULT: SUCCESS! Bojo is going to design the book interior for Tales of Ecuador (Even though technically he gets ‘killed off’ in Tales of Ecuador. Spoiler alert.)


[Day 8] Sept 30, 2014: Ask for Honest Feedback From our Members/Customers About a Course We’re Running at Escape the City.

On November 8 in London, we’re running a course for people who are interested in learning how to make a living from writing, led by all-star blogger/author/entrepreneur Joanna Penn: How to Build a Business from Writing.

So many times when we (the universal we) offer products / services to customers, we’re often afraid of feedback. Because — what if the feedback is negative? My default mode is to make an offer — but not ask for honest feedback on whether what we’re offering hits the mark and satisfies a need.

In an email, I sent this to a subset of people who we think might be interested in the new course:

“Finally, I have a small request. If you’re not ready to take the full-day course w/ Joanna at this time — would you mind sharing with me why not?

In our mission to build and grow The Escape School, we’re trying to learn as much as we can about the types of courses you want and how to best deliver them to you all. Please feel free to respond to this email and let me know why this course doesn’t appeal to you at the moment. Any/all feedback helps immensely.”

No response yet.
UPDATE: Only about 8% of the people I emailed responded. And about half of those responded w/ a small piece of negative feedback. Lots of REJECTION going on!

(Sorry these asks aren’t as sexy or entertaining as having a stranger scratch my back.)

 [Day 7] Sept 29, 2014: Ask a Professional Photographer if I Can Spend an Afternoon Learning from Them.

The response to my “There are 100 Days Left in 2014” post on Medium was incredible. Through it, some fascinating people have reached out to me. One of those people is a professional photographer who has some jaw-dropping work (

I’ve dabbled in photography. I even bought a starter DSLR a couple years ago. I think I have a decent eye. But I’ve never learned the techniques behind photography.

So when I learned we both will happen to be in San Francisco next week, I asked her last night if I could spend an afternoon learning some of her tricks of the trade and how she’s become so great at her craft.

No response yet.
UPDATE: After a suspenseful few days, she (hesitantly!) said Yes. SUCCESS but with a brief scare of REJECTION… 🙂

[Day 6] Sept 28, 2014: Ask a High School Student If They’ll Ask Their Teacher If I Can Speak to Their Class

A very meta Ask, I realize.

First, I’ll be honest and say that thinking of something to Ask for everyday is already getting more difficult than I anticipated. In theory, it’s not difficult. But my default mode is to think:

“You’re good! You don’t need anything else right now. Why don’t you just appreciate what you already have? Work on making good on the things you’ve already asked for.”

In a way, I’m absolutely right. Always wanting more, wanting something other than what we already have, wanting something that’s better, is not necessarily the secret to a happy and fulfilling life.

But then again, this was the challenge I set for myself. To force myself to think bigger, braver. To challenge myself to desire something everyday and ask for that something.

The balance, I believe, is to always be grateful for what you have, and to be content knowing that whatever you have now is enough. But at the same time, to also always know that you’re capable of much more than you realize, that personal growth is a never-ending journey, and the moment you stop pursuing something (the moment you “arrive”) is the moment you risk fading away.

Okay. Enough of that. Onto the Ask.

It was 11:55pm, last night.

I was responding to emails about the 100 Day Challenge.

One was a note from a girl who attends the high school I went to (years ago…) outside of Cleveland, Ohio. She suggested about 15 “Asks” for me to do. Things like: “Ask a stranger to switch shoes with him/her (forever).”

Good ones like that.

I thanked her for her suggestions. Then, knowing I had 5 minutes left to complete my Ask for the day, decided to ask HER for something:

“Will you please ask one of your (coolest) teachers if I could speak to your class about my 100 day challenge? I can come in on Tue, Wed, or Thu this week, or sometime during the week of October 20-24.”

No word yet from high school student. I will keep you posted.
UPDATE: The student asked her teacher, and the teacher reached out to me! Plus, ANOTHER teacher in the area reached out to me and asked if I would come speak to her class. SUCCESS x 2.

[Day 5] Sept 27, 2014: Ask My Mom to Make Me Breakfast

“Hey mom, will you make me breakfast?”
Mom: “Is that your big ‘Ask’ for today?”
Me: “Yes…”
Mom: “Okay. Here’s mine: Will you empty the dishwasher?”

Okay, that didn’t count.

[Day 5] Sept 27, 2014: Ask to Speak at the Travel & Adventure Show

THE REAL ASK: Pitch myself as a speaker at the Travel and Adventure Show.

A few days ago, I decided to send an email to a contact at the Travel & Adventure Show, one of the leading travel shows in the US, to ask if I could speak at a show this year.

My email:

“…Just wanted to check in and see if you had open speaker slots for any of the upcoming shows this year? Really enjoyed being part of the Dallas show last year and speaking on Iceland. And would love to work with you again if there was an opportunity. I can speak on Iceland, Ecuador, or Serbia…”

Today, I received an email response back:

“…I can definitely you on the destination stage in Philly—so plan on that. And, I would like to include you in San Fran…”

SUCCESS! 1 or 2 new speaking opportunities. Now I just need to figure out if I am actually available to speak on those dates…!

[Day 4] Sept 26, 2014: Ask a Stranger to Scratch My Back

I was having drinks with some high school friends at my buddy’s new bar in Cleveland, Jukebox. I’d been putting off the ASK challenge all day, and of course, the more I thought about it and put it off, the more difficult it became.

I looked at my phone: 11:30pm. Shit. Only 30 minutes left! Gotta move.

Walked up to the physical Jukebox. A girl walks up next to me. We’re paging through the albums, each looking for a song to play. I strike up some idle chitchat:

Me: “So…what song are you going to play?”
Girl: “Probably a Wilco song if they have it. What about you?”
Me: “Hmm… not sure. Oh! They have Sam Cooke! Definitely Sam Cooke.”
Girl: “Cool.”
:::awkward silence:::
Me: “Hey… so I have this really big itch on my back that I can’t reach. Would you mind scratching it for me?”
Girl (cocking head, half-smiling, sizing me up): “Umm….sure?”
Me (turning my back to her): “Oh God, thanks so much.”
Girl (while scratching my back): “So is this your thing or something?”
Me: “Um, yeah, sure… a little higher please. Ahh that’s great, thanks.”

A scratched back. SUCCESS!

Okay, so I can already hear your criticism:

“Stop asking girls for these things! Of course it’s easier for you to ask a girl! If you’re really looking for rejection, try asking some burly dude to scratch your back.”

I get it. Of course it’s easier for me. But hey! It’s day 4. I have 96 to go. I’m trying to ease into this thing.

More bold things to come…

[Day 3] Sept 25, 2014: Ask For a Taste of a Stranger’s Drink

I don’t know why, but I was especially nervous to do this. I talk to strangers all the time, traveling and at work. But just randomly going up to someone when I don’t have a real reason made me uncomfortable.

Me: “Hi, that looks good! What kind of drink is it?”
Tattooed Girl w/ Jet Black Hair: “Yeah, it’s good. I don’t usually come here. My friend ordered it for me. I think it’s a Pumpkin Latte or something.”
Me: “Do you mind if I have a taste?”
Tattooed Girl: “Yeah, sure!”
Chitchat for a while, then she leaves with her two friends. 1 minute later, her friend walks back in.
Friend: “Could I get your number for my friend? She didn’t ask me to do this, she’s just kinda shy.”

DOUBLE SUCCESS! Sip of a pumpkin spice latte + a phone number.

[Day 2] Sept 24, 2014: Ask to Go Behind the Counter at Starbucks

I ordered an Americano at my hometown Starbucks (normally I just get regular filter coffee), and then asked if I could go behind the counter and watch her make it.

REJECTED! & SUCCESS! “For liability reasons we cannot let customers behind the counter. But if you can see from there, I’ll show you.” I strained my head past the register to watch the lady press a button on Starbucks’s fancy coffee machine. They sure don’t make coffee like they use to do!

[Day 1] Sept 23, 2014: Ask for a Free First Class Upgrade on an International Flight

Asked to be put in first class in the middle of my flight from Madrid to NYC.

The flight was completely full — so maybe this shouldn’t count?

[Day 0] Sept 22, 2014: Ask to Upgrade to Bigger Bed

Asked to be upgraded from a twin bed to a bigger bed at my hotel in Lisbon for no extra cost.

SUCCESS! Was upgraded with no problem.