The plot thickens as I continue into the 2nd week of the Rejection Therapy Challenge. (I posted previously about week 1 rejections.)

A recap for new readers: I’ve taken on a 30 day challenge where I need to get personally rejected by someone every single day. I was inspired by to try it and thought it might be fun and help me get out of my comfort zone. I’ve been documenting this stuff on my blog.

INSIGHTS: I think the rejections this week are more interesting and more “real” than last week which I think is great (of course you can be the judge). I’ve also noticed that the challenge is making me more open to talking with strangers – because they might hold a rejection opportunity. It makes me more aware of my surroundings in general. I see that I’m exposing myself to serendipity, as Paul Buchheit recommends. It’s fun, a little stressful at times and as a fringe benefit, it’s makes for a great introductory story when meeting new people.


We were out for isocket team lunch and noticed a really nice, brand new Jaguar parked out in front of the restaurant. Later when we’re finishing up lunch we see the owner talking to someone and getting ready to drive off. I run outside and tell him I think he has a really nice car and ask if I could sit in it. He agrees. We talk briefly about why he got the car and how long he’s had it. As he push button starts the car, I ask if I could take it for a spin – he laughs and says no. REJECTION!


Today I got a free V8 with tea infusion from some promoter on the street. Later I run into a homeless guy who  asks for change. I offer the V8 bottle and he refuses! I even ask again “are you sure?” in my most persuasive voice – still no. REJECTION!

Later I was working at Starbucks before a Doctor’s appointment and ended up taking a 25 min phone call with a potential customer. When I ended the call, the old lady sitting across the table from me leaned over and said “I don’t mean to be rude, but I don’t think that phone call was appropriate.”

She then proceeded to lay into me about how Starbucks isn’t my home office and how phone calls ruin the coffee shop atmosphere. I took it all in good stride and she ended up shaking my hand as she left – I tried hard not to be say anything to provoke her. More amused than anything else at the UNPROMPTED REJECTION!


I was eating lunch at a small Vietnamese place in Burlingame and started joking with the owner about how maybe I could do the dishes instead of paying. She kind of went along with it at first, saying I’d need to wash 8 buckets in 2 hrs and dry them etc. Since that was not really a rejection, I decided to push it by actually pretending like I was going to do it.

At the end of the meal I said “OK, let’s do this!” I took off my jacket, put dishes into the tray and started busing the table. She’s lets me do all this and I start getting nervous. I walk into the back room to start washing the dishes and finally she’s says “Alright, you can stop! I was just joking!” I smile, and silently whisper thanks. REJECTED!

Later that night I was at dinner with friends in Palo Alto when I saw a girl who kind of looked someone I had met a while back. I tried saying her name and seeing if she responded. She didn’t. But she was so *almost* like the person I knew that I just went up to her group and asked if her name was Rui. “Nope it’s not.” she says.

I ask her name. She says she won’t tell me but shell let me guess. The guy next to her says it starts with a “J”. I guess Jessica. Wrong. Jennifer. Wrong. Then she tells me in a condescending tone that her name doesn’t even start with a “J”. EPIC GROUP REJECTION!

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I’ve been turned down, rejected and blown off for seven days straight. I’m thrilled.

In my last post on the Fear Scorecard, I discuss something I discovered via Hacker The site offers up a challenge with one rule: Get personally rejected by someone everyday for 30 days. The goal, according to its Creator Jason Cowlely is to reduce the fear and pain felt around rejection, encourage more open and “risky” social interactions and reap the many rewards that this comes with. (See the about page)

After reading it, I got really interested in doing it. I thought about how I even though I can tolerate a lot of physical pain and academic and career failure, I really don’t like being rejected. This is an area I’d like to tackle and conquer.

So I went for it. The results of just one week have been very interesting and I’ve decided to share them on my blog and see what happens. I dashed off emails of my rejection attempts each day to a couple friends to keep me on track. They’ve been tweaked for readability. Hope you find them interesting and they inspire you to give this a shot.


Warmup: asked a lady in airport store if she could “Get me one of these headphones in a different color.” She said no – that’s all they had. SOFTBALL REJECTION!

Main ask: on my Virgin America, I asked the flight attendants if I could fly first class. At first they said “You sure can!” and I followed with “For free” which they rejected. But they were nice about it: “It’s a short flight and even we don’t get free upgrades!”. REJECTION!


Asked a total stranger for their conference schedule guidebook because I didn’t get one. After a big “Pleeease?”, she gave it to me. Damn! But it started a nice conversation. REJECTION FAIL!

Then asked some other girl that my coworkers knew if I could have her Carwoo! sticker and she said “Nope!” REJECTION!

I was so happy! I told her about the challenge and she made me ask her friend out to dinner. Her friend thought about it and then said “I don’t eat dinner”. SILLY REJECTION!


Yesterday I was at Starbucks and their veggie sandwich was literally half the size of the turkey one, so I asked a Starbucks employee if i could have two sandwiches for the price of one. She said no. I decide after this that I’m going to try to avoid business transactions. REJECTION!


I went in for a hug with someone – and she rebuffed this advance. I was a little shocked, but then I realized I had told her about the challenge so it didn’t count. (She then gave me a hug afterward.) SORT OF REJECTION!

Later we were trying to unload our isocket tshirts to people at the conference. Most people were happy to take a shirt, but I approached a few people who had absolutely no interest in a free shirt. REJECTION!


This day was tough. A girl I had met the night before had given me her phone number and told me to call her to get a drink the next day. I didn’t really want to call, but my coworkers said I had to. So I called and left a message and she never responded. SORT OF REJECTION!

Then at the airport I told the TSA people that I had a knee brace before I walked through the detector and it didn’t go off. They said I still had to do a scan. I asked if I could skip it since there was no alarm but they said because I disclosed, they had to. What else would you expect from the TSA? LAME REJECTION!


Was going to ask a girl on the train for her number, but there were a bunch of other people there and I didn’t want to make her feel awkward (aka I was being a wuss). FAILED REJECTION!

Then at lunch I complimented a woman on her sunglasses and asked if we could swap. She refused and said that her sunglasses wouldn’t look good on me. REJECTION!

More interestingly, I then decided I would ask another cute girl on the train for her number. This time, I end up sitting across the aisle from her and had a conversation with her (which was mostly her getting nervous energy out because she had forgotten to validate her caltrain ticket). By the time we got off the train and I went to ask for her number, we had connected enough that she said “Sure!” Not bad at all. FAILED REJECTION!


I wanted to knock my rejection out right away so when I was at the Caltrain station, I was looking for opportunities to get rejected. Then I spied a guy eating a croissant and decided to ask if I could have some. Who gives strangers a piece of their croissant? He kind of looked at me funny and pointed at the coffeeshop where he got it, but I insisted that I wanted a piece of HIS croissant. When he asked “just a little piece?” my heart sank. He ended up giving me his croissant. I had to eat it, smile, and then slowly back away. FAILED REJECTION!

Later in the evening, I was at a bar in SF at a bar – I introduced myself to two guys and they were like “Whoa you’ve changed!” Apparently they had run into another Asian guy named Jason at this bar. So I started joking that we needed to fight until there was only ONE! And I asked one of the guys if he’d be my 2nd. You know, in case I died. He said “Yeah, I don’t think I’m down.” REJECTION!

My non-duel partner friend then said “I’ll think about it though if you introduce me to that cute girl over there.” He pointed at someone. I didn’t know who she or any of the five guys she was talking to were. But I said “Ok” and just walked over there, introduced myself to the group, started talking with the girl. After a second, I asked her “Have you met Eric?” After seeding their conversation with a few hooks I took off and let Cupid do his thing. NOT REJECTION BUT STILL AWESOME!

This is part of an on-going series of posts on learning Ruby on Rails. It’s a bit technical but not too much so. If you’re interested in startups and are a “business guy” it definitely wouldn’t hurt to understand everything I write here, as I’m pretty much a total noob, but was willing to learn. Enjoy!

While Ruby on Rails prides itself on requiring few dependencies, there are still a couple of things you need to install/setup in order to actually start doing anything in Rails.

  • Xcode Tools (the Apple developer toolkit)
  • Ruby (the most up-to-date version)
  • Ruby Gems (the package manager)
  • Rails (the framework itself)
  • Sqlite (one of the preferred database engines)

While there are apparently some auto-installers out there, I chose to use Hivelogic’s guide to installing Ruby – which is also referenced as a guide from the official Ruby on Rails site. I figured I’d do things manually so I could better understand what was going on – also none of three I looked at (Locomotive, MacPorts, Finks) seemed that very user-friendly, so might as well go with the pure install.

Note: In hindsight, I probably would have used the setup recommended by the Ruby section on – it makes you install RVM (Ruby Version Manager) and Git but still it looks pretty easy.

What ended up happening was that things were a little bit trickier than I anticipated, and also because it is still so new, some stuff in Rails 3 wasn’t working exactly right, so it took roughly 4 hours for me and I’m still not 100% convinced I did it right. But anyway, here’s how it went:

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I’ve been fascinated about building things on the web since the late 90’s. Remember Geocities? Yeah, I had a site there. I remember learning HTML for a back in middle school (late 90’s, early 2000’s) to build a webpage (no sites yet!) with animated construction gifs and guestbooks. I learned a bit of Java and Ti-83 BASIC in high school and some Python in college, but never got very into it because I had little interest writing really basic programs that weren’t useful.

I’ve watched the web develop, continued learning about HTML, and later CSS, and how to navigate my way around a WordPress installation. It seems like now with libraries like jQuery and symfony and web frameworks like Django, symfony (thanks smentek!) and Ruby on Rails, it is easier for people to build useful web apps without years of experience as a developer and/or thousands of hours of coding.

I do hope someday to found a web/tech startup and while I’ll never serve as CTO, I know understanding more about web development will be critical to our success. I also have a few ideas for web apps that I’d like to build. And to be honest? I’d love to gain some street cred as a geek. Hey – just being honest.

You can learn more about my adventures with Ruby on Rails here.

This was a project I did with Crystal Yan

What’s Next is a collaborative book project on the power of youth.

Inspired by Seth Godin’s What Matters Now, it showcases the stories & insights of 25 bright young voices from around the world. Designed for students, parents, educators, and employers, What’s Next shows us how Generation Y is shaping tomorrow, today. What’s Next is a production of Crystal Yan, Jason Shen and a host of incredible young people.Read the beta version now.