Embracing Rejection: The Power of Audacious Requests

Washington DC, United States Jul 14, 2026 ALN: One big consequence of our fear of embarrassment is that we’re almost all overly sensitive to rejection. We haven’t built up our acceptance-of-rejection muscles, and this is a major impediment to agency.

I’ve found that the most efficient way to build these muscles is to make audacious requests.

Most of us carefully assess which requests that we might make are acceptable and which go too far. We avoid any request that’s likely to generate social friction, behaving as if it would be immediately fatal to have a request denied. “I just moved to the city, want to show me your favorite lunch spot this weekend?” “No.” Zap, dead, via bolt of lightning. What a tragic and premature demise!

We also really don’t like the feeling of being told “no,” of receiving what feels like a judgment that we’ve overestimated our worth. Hence, we opt out of requesting.

Yet, simultaneously, we know that if we try to prevent ourselves from ever experiencing rejection, we miss out on many opportunities in life. If you are determined to avoid rejection wholesale, you will likely never:

• Ask someone on a date who might be out of your league.
• Ask someone in a field where you have no experience for help getting a job.
• Ask someone you admire for mentorship or feedback on your work.
• Ask someone to fund your startup, research, or art project.
• Negotiate for higher pay.
• Deepen a friendship or relationship by talking about risky subjects.
• Publish creative work on the internet.

When we treat rejection as an existential hazard, we are limited to a predictable existence.

A more helpful point of view is that rejection is a form of information. When you experience rejection, you’ve learned that a given request won’t work. That avenue is now shut off, freeing you to try something else.

The high-agency mindset about rejection takes things even further. It says that you should seek out rejection, or at least welcome it. Congratulate yourself on hearing no. Remind yourself that if you don’t routinely encounter rejection, you are not asking for enough—you’re only making requests that are extremely likely to receive a yes.

How do you get comfortable with the high-agency approach to rejection? Alas, it’s exposure all the way down. The more times you hear the word no and notice that it’s not lethal, the less aversion to rejection you’ll feel. You can speed this up by seeking it out.

I suggest that you start by asking for a few unreasonable things.

The Art and Science of Asking Big

I believe in asking for “unreasonable” things for many reasons, beyond the emotional training.

One: If you habitually avoid rejection, you are not going to be well calibrated about what’s reasonable—which might be more than you expect.

When I started training myself to make bolder asks, I found it helpful to think of myself as wearing rejection-sensitivity goggles, which I had to figure out how to take off. The goggles limit agency in many ways. By trying to shield us from rejection, they steer us away from approaching people who could be of huge help.

The goggles don’t just cause us to overrate the severity of rejection. They also make us overestimate how often we will be rejected.

In a series of experiments, researchers Frank Flynn of Stanford and Vanessa Lake of Columbia University got students to ask strangers for help. Requests included “Can I borrow your cellphone?” and “Can you fill out this questionnaire for a study I’m doing?” They asked the students to predict how likely people would be to help, and found that they underestimated by 50%—about twice as many people as expected agreed. Flynn and Lake concluded that the students displayed an “egocentric bias,” focusing too much on their own feelings. They imagined that because asking for things felt awkward, it must also be awkward for the people receiving the requests.

But of course, it often feels pleasant to be asked for a favor that you can capably grant. We just forget this when we ask for favors, acting like we’re visiting a curse on an innocent person rather than giving someone an opportunity to demonstrate their capability and generosity.

When we take off our goggles and start asking, we free ourselves from this bias. We’re then able to engage in a new, accurate training process, where asking for what seems unreasonable generates data about where the lines really are.

Two: When you train yourself to be less afraid of rejection, you will find your requests are granted more often, because you’ll make them with greater confidence.

Human beings are subject to emotional contagion. If you’re scared to ask someone for a favor, they will feel your fear and take it as a cue: They’re scared to ask this, so it must be a really big deal. I should say no!

If you don’t signal fear, they’ll be more likely to consider the request reasonable.

Three: Unreasonable requests can open the door to reasonable requests.

This effect was documented in a classic study by Robert Cialdini. When the large request came first, the likelihood of the strangers agreeing to the smaller, fallback request tripled.

According to Cialdini, it’s because of the social norm of reciprocity, which says that if someone makes a tacit concession (“You’re right, my ask was way too big”) we should reciprocate with a concession of our own.

One great way to use this effect is in salary negotiations.

Four: Unreasonable requests can be a filtering mechanism.

The point is that most people will say no, but a few interested clients will say yes. It not only ensures you’re paid a “cheerful price” but also acts as a filter for the most motivated clients.

Making a request that 99% of people will say no to is a fantastic way of finding the 1% of the population you’re most aligned with.

Five: Unreasonable requests can lead to productive conversations.

I think it’s fair to say that asking to be appointed to head an organization you’ve never worked for is flat-out unreasonable. Sending this, I knew the recipient might regard me as delusional.

The recipient never responded directly to my email, but I still consider my message a success: A few months later, when the organization was spinning up another major project, she reached out to see if I was interested.

Finally: Making requests helps build your muscle for imagination.

When you start wondering what you could ask for, you build your imaginative muscles by asking the simple question, “What else is possible that might currently seem unreasonable?”

Don’t Hedge or Hector

A key thing about audacious asks is that you can’t do them hesitantly or halfway. Ask for what you want, straightforwardly.

It’s also vital to take rejection gracefully. Be sure to say something to the effect of, “I understand, thank you for hearing me out.” If you sense a no isn’t necessarily the end of the conversation, you can ask: “Okay, I’m not trying to convince you to change your mind—but could you tell me why it’s a no for you?”

This was a lesson that Jia Jiang learned in his one hundred days of rejection, and he ended up adopting it as a major principle: Don’t run, ask why. He found out what few bother to learn: that there is an enormous difference between our stories about why people turn us down and why they actually do.

When making bold asks, keep in mind that agency is all about breaking through the fictitious barriers of your life and letting yourself be limited only by real barriers. A firm no is an actual barrier. Show respect for that, and tell yourself that you are now that much more aware of another limit, and free to pursue another ask.

Excerpted from the book YOU CAN JUST DO THINGS by Cate Hall with Sasha Chapin. ©2026 by Caitlin Hall and Alexander Chapin. Used with permission of Harper Edge, an imprint of HarperCollins. .