The Rejection Therapy Challenge: Week 1

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!

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Jason Shen

Jason is a tech entrepreneur and talent expert. He is CEO of a performance hiring platform called Headlight, a Fast Company contributor, and an advocate for Asian American men. Follow him on Twitter at @jasonshen and subscribe to his private newsletter.

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    • @jasonshen you are my hero, love how you make things sound easy. I will give a shot this week and get one rejection at least.

  1. Congratulations on getting rejected! Lots of my attempts at rejection therapy are through email, and it’s difficult to get rejected if no one replies to reject you. Maybe that’s a form of indirect rejection.

    Incidentally, I’m a writer, and in the writing world, getting a rejection letter is celebrated. It means someone actually paid attention enough to send you something. Bonus points if the sender wrote a personal note.

  2. I was waaaay too amused by this post :) Great stories for sure, but I think you can step it up. It almost seems like you wanted to get rejected just to fulfill the goal. Think you can put yourself out there a little more and go for something big? It’s a great exercise and I’m loving your experiences. Can you take my challenge? I’m thinking about following in your footsteps, and it’s nice having you do it as a example crash course.

    • @jennalanger You know, this challenge isn’t easy – in part because most people are willing to do a lot of things if you ask the right way. I am trying to push myself, while also making sure that I don’t miss a day. Promise that next week will have better rejections!

    • @jasonshen Ya, I’m just giving you a hard time. It’s a challenge to go out of your comfort zone and I applaud you for it. Seems like this is also an exercise in persuasion, and you’re killing it!

  3. Awesome post. I’ve read of similar “programs” and I think they’re an incredible idea and you seem to be making the most of it!

    Thanks for sharing. Some of this stuff is absolutely hilarious, but it’s cool that you can appreciate the hilarity and the benefit of such a “program.” I look forward to reading more from you!

  4. Jason. I’m totally amped by this post! The Rejection Therapy challenge is “gut-wrenching fun” as I like to say :)

    I’m going to be taking the Rejection Therapy challenge again soon, and podcasting about my experiences on the site. I would be extremely happy if you would join me on a podcast… let me know if you’re up for that.

    Thanks for the inspiration Jason. Let’s keep in touch!

    • @rinkjustice Hey man – yeah, I’d love to get in on this podcast with you. How frequently do you think you’ll be doing it? The things I’m trying to do to get rejected just keep getting more funny. =)

    • @jasonshen This is all very cool Jason. re. the podcast, I’m thinking weekly. We should talk via Skype sometime. Hash this thing out :)

  5. This is really fantastic Jason. Cracked me up. I do, however, think you aim to get rejected in some of these, when it seems to me that the true point is to always be aiming to succeed, but get rejections through the sheer number and sometimes seemingly unobtainable goals (the idea being that you’ll surprise yourself). Think about it. I love it, man. Keep up the good work .

    • @joshuagoldman Thank you Joshua.

      Rejection is a necessary life experience. We can’t get stronger as individuals without resistance and adversity.

      Comfort is the true enemy of personal progress, not rejection :)

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  9. Whoa, awesome, dood! There are so many times we want to do something and we don’t because we’re afraid. That’s cool that you’re challenging that pattern and documenting it.

  10. Hi Jason thank you for this post, I currently work from home selling export goods online, but recently I have been wanting to market my own little invention, just a cosmetic. Do you think its better to buy locally or buy my stuff abroad? Thanks. 

  11. In university we used to play a game called ‘watch me get shot down’ the rejections were epic as were the results.

  12. This is amazing and made me laugh out loud several times (with you I promise).  I appreciate your sense of adventure and humor; and clearly are a talented writer to convey it all so well!  Excellent work, I am officially inspired.

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