The Game of No: Why Rejection is Harder Than You Think

Chasing rejection has taught me two things: most things are negotiable, and I need to learn to say no more often.

Rejection is weird.

You spend most of your life avoiding it, ducking out like you just made accidental eye contact in an elevator. But the second you seek it out? Turns out, rejection is surprisingly hard to get.

That’s what I’ve been learning in my Rejection Neutrality Challenge, where I actively try to get rejected 10 times just to prove (to myself) that a "No" isn’t the end of the world.

And so far? Let’s just say the world isn’t cooperating.

So let’s recap my list of Nos so far:

• The airline upgrade that didn’t happen. You already know this one.

• A sold-out TEDx event. I emailed, asked for a spot anyway. Didn’t get it, but the organizer and I promised to keep in touch. Not all bad.

• An online course. I asked for special conditions for more flexibility. Got a no, but also got valuable info on options I didn’t even know existed, like picking my own start date. Unexpected win.

Then, I took this mindset to work. I spent the week pushing the limits, actively seeking a "No." What’s surprising? I had to work really hard to actually get one.

In the process, I ended up getting more help, more resources, and more support on things I never would’ve asked for before. Things I thought were off-limits were actually just… sitting there, waiting to be claimed.

The Unexpected Side Effect: More Yeses Than Nos

The funniest part? I braced myself for rejection, but instead, I got an embarrassing number of yeses.

Especially from the people closest to me: colleagues, my training group, friends, my partner. Turns out, I’ve been dramatically underestimating how much people want to say yes.

So now I have to admit: seems like I’ve been playing it too safe in this rejection game. Time to turn up the heat.

New Rejection Strategy:

✅ More in-person asks.
✅ More asks to strangers.
✅ Bigger, bolder asks. Time to get uncomfortable.

We’re 4 rejections down, 6 more to go.

Biggest Takeaway So Far? The World is Friendlier Than You Think.

This challenge started as a way to get comfortable with rejection, but it’s turning into something else.

Turns out, most people genuinely want to help. Almost everything is negotiable if you just ask.

But this week, I also ran into an entirely different problem: my own inability to say no.

---

When You Can’t Say No (Even When You Should)

I had some workers at my place fixing things. As they were leaving, one of them asked to use the bathroom.
Of course, I said yes and pointed to the guest bathroom, right there, easy to access.

And then?

The guy completely ignored my instruction, stormed into my bedroom, and used MY bathroom.

I stood there in stunned silence. My brain short-circuited:

• Did he misunderstand?

• Is he checking something before going to the right bathroom?

• Wait… is this actually happening?!

By the time I realized my privacy had just been completely bulldozed, it was over. He came back, I paid, they left. And I said nothing.

Not when he took the wrong turn.
Not when he walked into my personal space.
Not even after, when I could’ve asked why.

Instead, I spiraled: Am I overreacting? Am I being weird with this bathroom thing and the fact that is a blue collar worker? Should I have been clearer? Am I just too dramatic about privacy?

But what bothered me most wasn’t what happened, it was that we both knew it wasn’t supposed to happen, and I still didn’t speak up.

---

Ask More, But Also Protect Yourself

In summary: go out and ask for more. If you’re like me, you’ll probably get way more yeses than expected.

But also, practice saying no.
Because if last week taught me anything, it’s that people-pleasers need rejection therapy just as much as they need a boundary bootcamp.

So, back to the mission: 6 more rejections to collect. Let’s go.