If you’ve ever rehearsed asking for a raise in the shower and then chickened out once you got to the office, you’re also not doing yourself any favors, according to rejection expert Jia Jiang.
Jiang, the entrepreneur behind the viral “100 Days of Rejection” experiment and author of the new book Easy Discipline: An Unconventional Way to Achieve Ambitious Things, joined Jean Chatzky on the HerMoney podcast to talk about why we’re so bad at asking for what we want, and how to get better at it, especially when it comes to money.
Why We’re Afraid to Ask For A Raise
Jiang says the fear of asking for a raise (or a promotion, or a networking introduction) usually comes from a false assumption: that if our boss hasn’t already offered us more, there must be a reason.
“Sometimes we always have in our mind that we shouldn’t ask because my boss or the company already know [what I want]. If they’re not giving me this opportunity, there’s a good reason,” Jiang said. “But that’s not the case.”
He argues the opposite is true and that the act of asking is itself valuable, whether or not you get a yes. “Sometimes asking itself is showing what you got. It’s showing your medals, right? And then that increases your value in the other person’s eyes, so opportunities will come to you,” Jiang explained.
Chatzky agreed, pointing to one of her own longtime money rules: “If you don’t ask, the answer is always no.” She added that even a “no” can shift how someone sees you going forward: “It can change the perception that the other person has of you… maybe they gave you a no this time, but they’ll think of you for the next opportunity.”
It’s About the Process, Not the Outcome
Jiang’s advice extends beyond how to ask for a raise to two other places people often feel stuck: job hunting and saving for the future.
On the exhausting process of job searching, Jiang suggests reframing the goal entirely. Rather than blasting out resumes into an AI-filtered void, he recommends setting a goal to have real conversations. “Set up a goal to talk to 100 people in 100 days,” he said. “Find people in the companies that you want to work for, talk to them. Networking is a much better way to find jobs than [sending out thousands of resumes].”
On investing, Jiang described himself as a “love investor,” someone who invests in companies whose products he genuinely uses and enjoys, like Costco. That emotional connection, he said, has helped him stay invested through downturns including the 2008 financial crisis and COVID.
“By having fun with investing and saving, now I don’t have this fear,” he said. “Everyone knows it’s not about timing the market; it’s time in the market. And how do you have time in the market? Have fun, love the process.”
The Bottom Line: How To Ask For A Raise
For Jiang, learning how to ask for a raise isn’t about salary scripts or negotiation tactics; it’s about rewiring your relationship with rejection itself so the fear of “no” stops running the show.
As he put it, once you stop bracing for rejection and start engaging with the conversation itself, the process becomes the reward.
Asked how to sum it all up, Jiang kept it simple: “Get pleasure from the process, not the result.”
MORE ON HERMONEY:
- How To Ask For A Raise (And Actually Get It)
- Ask Jean: “I see Apple is launching a new option for leasing iPhones. Does it make sense financially?”
- HerMoney Podcast Episode 319: Moving Past Rejection
