The Coffee Challenge
How a cup of coffee taught me to ask for what I don’t deserve
I used to think that starting a business meant doing complicated stuff like market research or assessing product-market-fit. But I recently learned that it’s much simpler than I thought.
Noah Kagan, CEO of AppSumo and author of Million Dollar Weekend, suggests that the best way to start a business is by taking on four challenges:
The Dollar Challenge - Asking for a $1 investment
The Now, Not How Challenge - Asking for a business idea
The Freedom Number Challenge - Calculating the money needed to live comfortably
The Coffee Challenge - Asking for a 10% discount on a cup of coffee
Each of these challenges is designed to build momentum and exercise the ability to ask. Asking, in particular, is an incredibly powerful skill and has served me well in the past.
For instance, when I decided to become a writer, I knew that joining the Write of Passage (WoP) course would elevate my potential and set me up for success. But I couldn't afford the $3995 tuition. So, I reached out to the WoP team and made a proposal to let me join the next cohort in exchange for working on a data project for free. They agreed, and this led me to the most transformational 5 weeks of my life.
For any aspiring entrepreneur, mastering the skill of asking is crucial. After all, the only way to make sales is by asking customers to pay for the service or product being offered. I've found that the best way to develop this skill is by taking on Noah’s four challenges, so I pushed myself to complete all of them.
While I was able to breeze through the first three in less than a day, the last one—the coffee challenge—would always make my feet as cold as ice cream. Although ice cream is fun, this challenge certainly isn't.
The coffee challenge requires me to ask a stranger for a discount—for no reason at all. I thought this was crazy because unless there’s a special occasion, nobody would say yes to that. But perhaps that was the point. I needed to learn how to ask for something and get comfortable with receiving a no. I needed to conquer my fear of rejection.
So, after three long weeks, I decided it was time to finally do it.
Facing My Fears
My Coffee Challenge Day, as I like to call it, was on a Friday afternoon. I decided to go to my favorite café located near the middle of Catbalogan City.
When I arrived at the café, I felt a resistance to step inside, but I mustered enough courage to open the door. I saw a few people sitting on the tables and felt relieved when nobody was lining up at the cashier.
The last time I went to the café was around December. At the time, only three people were situated at the counter. This time, there were six. The counter was small, too, so if I were to ask for the discount, there’s a chance that all six of the staff would hear me make my ridiculous request.
What would they think of me? Will this be the last day I step foot in my favorite café?
Maybe I should just take on the challenge another time. There will be plenty of opportunities. I can start drinking coffee thrice a week instead of just once!
But I didn’t want to back down.
If I couldn't ask for a 10% discount, how could I ever expect myself to start my own business?
I clenched my teeth as I walked to a spot right beside a window where sunlight could enter. I dropped my backpack on a brown sofa, and gave a distant look outside the window.
I turned my back to walk up to the counter at a pace that was slower than usual. As I approached the cashier, I greeted her good afternoon and took a good look at the menu.
"I’ll have one matcha strawberry and a garlic toast."
The lady behind the cashier told me the total was ₱250 (roughly $4.50). I pulled out my phone to pay via GCash, but the app took time to load, so I pulled out my wallet instead. My hands started being covered in cold sweat as I was mentally preparing myself to ask the question.
I asked the lady to remind me how much the total was. I could still remember the amount, but I wanted to buy myself time.
“It’s ₱250.”
“Oh,” I said in a low voice. “Is it possible to ask for 10% off?”
The question took her by surprise. “You mean a discount?” she asked with a puzzled look. I gave her a slight nod.
She asked one of the staff if they offer any discounts, and they both ended up being confused. They whispered to each other, trying to assess how to handle the situation, and I was left there hoping they didn’t say anything mean about me. About 20 seconds later, the cashier faced me to give the answer I was waiting for.
“Sorry, we don’t have any promos running right now.”
“Oh, that’s alright.”
Then, I handed over the payment and waited patiently to get my change. After saying thank you, I seated myself on the sofa.
I felt my face turn red, but thankfully, nobody could see me. I stared out the big window again before turning my attention to my laptop to make myself appear busy.
I felt like a huge weight was lifted on my shoulders. And strangely, I found myself smiling unconsciously. As weird as it may sound, I was celebrating getting a rejection.
But I couldn’t lie about how I was feeling. I felt proud because I finally did it. I completed the coffee challenge.
Decaffeinated Reflections
I learned quite early that if I wanted something, I needed to work hard to obtain it.
I remember my parents giving me my first Game Boy when I ranked at the top of my class in 3rd grade. I played Power Rangers SPD all afternoon that day, and my parents allowed me to skip studying because they said I deserved it.
This has been the theme of my life as a kid: I get rewarded when I achieve good grades or earn a shiny gold medal. This served me well growing up as it taught me the value of hard work, but as an adult, it's a lesson I needed to revisit. This learning was the reason why the coffee challenge was so difficult for me.
Even though I knew about the power of asking and how important it is to confront my fear of rejection, I still struggled to take on the challenge. Whenever I made an attempt, I’d hesitate and tell myself, “Why should I ask for a discount if I know I don’t deserve it?”
But then I wondered, do I really need to deserve something before I can ask for it? I don’t think so.
Having the right to ask for something does not need to be earned. So I should allow myself to ask for things even if I don’t feel like I deserve it. Because by doing that, I’ll be able to view the world with more possibility.
If I could imagine myself getting a discount for no reason at all, I could see myself aiming for bigger things. I could be confident that I could start my own business and give my family financial freedom. So I’m going to ask a lot more, and I’ll do it in this essay.
Even if I don’t feel like I deserve it, I ask that you support me through this journey.
Thanks to for taking on the challenge of giving feedback on the 2000-word version of this essay.
How It’s Going:
🎉 — Recently did the The Wheel of Life exercise and found that I haven’t been paying enough attention to my body, finances, and friendships. The next month will focus on these areas.
🎮 — The Steam Spring Sale got me this year. I bought Naruto Ultimate Ninja Storm 3 & 4, Unravel Two, and Need for Speed Heat. I’m learning to fall in love with games again, which is honestly a great change for me this year.
🔖 — Started getting into biographies by listening to Steve Jobs by Walter Isaacson. Anyone got some good recommendations?
💭 Conversation Starter:
What is something you fear doing, but believe that you must do anyway?
Congratulations on accomplishing the Coffee Challenge, Linart! Lately, I am reminded of my fear of taking examinations, because I usually fail. But I'm again learning to feel more confident about my capabilities. And thank you for reminding me that I can ask and pray for things even when I think that I don't deserve it.
The Dutch actually have a lot of sayings actually that are in favor of trying stuff against all odds. One translates to 'you already have 'no' but you could get 'yes'', another to 'if you never made the shot it is always a miss'. Like the quote "You miss a 100% of the shots you don't take". It's all very true, but I'm like you - not believing anyone would actually say yes (or in my case, that anyone would ever pay to read a personal Substack).