Ask!: On Seeking Rejection as a Life Skill

This is how I learned to seek rejection, and because of it; get more out of life.

I watched Amanda Palmer’s TED talk when it first came out a couple of years back. In her talk, she spoke of how learning the art of Asking had helped her both in crowd funding her post-Dresden Dolls project The Grand Theft Orchestra and with her life as an artist in general, and although it had resonated with me, I had never fully field tested Asking as a habit in my own life.

Until now.

As a socially awkward child who blossomed into an even more socially awkward young adult, making asks of people was scary because it entailed one big thing: rejection.

In 2013, the University of Michigan released a study that essentially stated that you experience rejection like you experience physical pain, so you weren’t the only person who felt like they were punched in the gut when they found out they didn’t get into their dream school or that cutie that they’d been crushing on for a while didn’t feel the same way.

I’ve tried to avoid rejection as much as possible because of that pain and the feelings of inadequacy that it brought with it. But because of this avoidance, I was missing out on a lot of what life had to offer. I was letting friendships, relationships, academic opportunities and jobs pass me by because I was too afraid to ask for them.

That changed when I started dating again after the end of my 2 and a half year long relationship.

“Buy me a drink.”

Initially, when I started dating again, I was going about it in a very “conventional” sense. I would wait until some guy would walk up to me at the bar and chat me up first, or message me first on any of the litany of apps I was on at the time (barring, of course, Bumble).

But after going on a couple of drink dates with men who would ask first, I found that I was not getting the kinds of people with whom I could sustain a prolonged ~thing~ with.

So I decided to start asking.

My first experience in asking was after a first date with a Tinder guy who seemed to tick all the boxes for promising ~thing~ prospect: a recent grad who worked consulting for Deloitte, was passionate about economics and wanted to get into a PhD program in a couple of years and cute in a way that reminded me of a hamster I had as a 9 year old.

I thought drinks had gone well, and after a couple of days of mustering up the courage to ask, I texted him about my interest in seeing him again.

Hours pass, and I agonize over my decision of hitting send. At the end of the day, just as I was leaving the office, I get his response.

“Hey Gabby, whats up? I think you’re a great girl and you’re certainly very attractive but I’m just not feeling it and I don’t think it’s gonna work. Sorry and best of luck.”

Getting that response sucked. Big time.

Adam knows what’s up.

But even as getting rejected did elicit all familiar feelings of “not good enough” and “should I have worn a different outfit?”, something strange happened.

I found that while it did put a damper on my Thursday night; the feeling did not linger any more than that, which being a naturally anxious person was something new and novel to me.

So I did it again.

I started going up to guys first when I went out with friends, I started messaging them first on the various apps, I started asking more.

But because of this, I started encountering rejection more frequently. From blunt rejections to ghosting, asking became a master class in seeking rejection and how to deal with after the fact.

Getting rejected better (Or How I Learned to Add Value)

And as frequently as I was being rejected, I had started to learn how to iterate and make my asks of people better, clearer and even add value to persuade them to act on those asks.

One other way getting rejecting taught me how to make better constructed asks was asking Starbucks baristas to give me my coffee order for free. I got the idea from Jia Jiang’s 100 Days of Rejection project.

I would pass 2 particular Starbuckes on my way to work, and this is where I would field test the Coffee Rejection exercise*. I would alternate making my asks between Starbuckes, so I could give the baristas a rest from my persistence, and also to A/B test the way I made my asks.

In both scenarios, my heart would pound as I got closer and closer to taking my turn to order, but that’s about as similar as the two experiences get.

At Starbucks A, I would ask the barista to give me my flat white directly. I kept the fact that I had a rewards card and had nearly enough points to get myself the coffee. After a week of asking the same ask, I finally decided that the baristas of Starbucks A were not going to give my order for free.

I tried a tweaked approach with Starbucks B. Instead of just asking for it like I did at Starbuck A, I tried to add value to my ask. I tried to find a point where the barista could meet me half way.

I started asking Starbucks B baristas what ways I could potentially get my drink order for free. Most times, especially when the line was too long, the barista would politely shoot me down.

After attempting for 2 weeks, I got my breakthrough when one of the baristas I had been frequently been asking sighed and jokingly asked if I had a rewards card. I told her I did but did not quite enough points to get my flat white. She told me to hand it to her and rung my drink order through; regardless of lacking the right amount of points for it.

Every “No” Brings You Closer to a “Yes”

At this point, rejection has become a part of my daily routine; and I genuinely feel my life is better for it.

Yes, getting rejected and the feeling that comes along with it still sucks, and I don’t think that will ever change; but by having the willingness to make asks of people and opening myself up to rejection, I am also opening myself up to more opportunities, both personally and professionally.

Both as an aspiring entrepreneur and as a human being, learning the skill of seeking rejection has served me well thus far, and I expect this is something that will not change anytime soon.

*I totally made this moniker up.

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