The Top Five Things Holding You Back from Asking for What You Want
If you’ve been following my newsletter over the past month, you may have noticed a theme—situations where I landed opportunities many dream of but never get:
A front-row VIP experience to see my favorite comedian—for free.
Three trips to the Super Bowl—without tickets.
Access to a private conference where my favorite author spoke—without a pass.
Maybe you read these stories and thought, “How boastful!” Or maybe you thought, “How do I learn to do that?” If you’re in the latter camp, keep reading.
I’ve been in sales my entire career, and one of its most fundamental skills is knowing how to ask for what you want—and get it. There’s an art to this, but it’s a teachable one. The only prerequisite? Motivation.
Everyone Is in Sales
People often tell me, “I could never do sales!” My response is always the same: Everyone is in sales. Whether you’re selling yourself to a future employer, a romantic partner, or an opportunity you want, you’re engaging in an exchange—your time, money, energy, or experience– for something of value. Like it or not, that’s sales.
This last comment tends to split rooms into two groups of people:
Deniers – Those who believe hard work alone will get them noticed and rewarded.
Acceptors – Those who recognize that the fastest way to get what they want is to ask for it.
Acceptors quickly embrace the idea that Asking is a skill worth mastering. If that’s you, keep reading. If not, I won’t judge you for clicking away—but if you stay, you might learn something that could change your life.
Since you’re still here, let’s start with the real question:
What’s Stopping You from Asking?
Sales is a two-player game. The most fascinating part, to me, is the psychology—your mindset colliding with someone else’s. Oftentimes, the biggest hurdle isn’t persuading others; it’s getting past your own fears.
The Five Biggest Reasons You’re Afraid to Ask
As a sales leader and mentor, I’ve coached countless people through their fear of Asking. It usually boils down to these five reasons:
1. Fear of Rejection
What it sounds like in your head: “If they say no, I’ll be a failure, ruin my one shot, or embarrass myself.”
How it’s holding you back: You take rejection personally instead of seeing it as part of the process. But here’s the truth—sometimes you need 10 “no’s” before you get a “yes.” If you quit after the first, you’ll never get what you want.
Reframing your fear: Ask yourself, “What’s the worst that could happen?” Then follow up with, “And if that happens, what will I do next?” You’ll realize rejection isn’t fatal—and you’ll come back stronger.
Action: Challenge yourself to make one low-risk Ask today.
2. Fear of Being Seen as Selfish
What it sounds like in your head: “What will they think of me for asking?”
How it’s holding you back: You assume asking makes you greedy or pushy, but in reality, people spend 99.9% of their time thinking about themselves—not you.
Reframing your fear: Shift your mindset. Instead of focusing on what you gain, ask, “How does the other person’s world improve if they say yes?” If their world is better after giving you a “Yes,” you’re not being selfish—you’re offering value.
Action: Rewrite an Ask you’ve been hesitating on, this time focusing on the benefit for them.
3. Fear That You’re Not Enough
What it sounds like in your head: “Who am I to ask for this? I don’t have enough experience, influence, or knowledge.”
How it’s holding you back: You fixate on what you lack instead of recognizing what you bring to the table. But tradeoffs exist in every negotiation—for example, how many times have you seen hunger and drive can outweigh experience?
Reframing your fear: Ask yourself, “Who do I know that was less qualified but still got what I want?” Then, “What would have to be true for the person on the other side of the table from me to say ‘yes’ despite my self-identified shortcomings?”
Action: Stop deciding for the other person. Let them evaluate the tradeoffs and determine if you’re worth it.
4. Fear That You Don’t Know How to Ask
What it sounds like in your head: “Even if I wanted to ask, I wouldn’t know how.”
How it’s holding you back: It’s not that you don’t know how to ask—it’s that this particular Ask feels important, and you want to get it right. That pressure makes you hesitant because it puts you in a vulnerable position.
Reframing your fear: Shift your focus away from yourself and toward the other person. Consider how they’ll experience your Ask: Is it simple or complex? Will it require significant effort on their part or minimal? Does it come with a strict deadline or flexibility? Understanding these factors helps you craft an Ask that aligns with their perspective and increases your chances of getting a “Yes.”
Action: Structure your Ask using this framework:Acknowledge their current challenge or situation.
Clearly explain how saying “Yes” will resolve that challenge or improve their situation.
Provide a specific, time-bound request for a response.
Refine and revise your Ask until it sounds natural and considerate, ensuring it reflects the tone and urgency you hope to convey.
(Note: this may be oversimplified, but it’s a great starting point).
5. Assuming The Answer Is Already “No”
What it sounds like in your head: “There’s no way they’d go for this.”
How it’s holding you back: When you assume rejection before even asking, you do one of two things: you don’t ask at all—removing yourself from the opportunity—or you water down your request to something smaller than what you actually need. Either way, you lose before you even try. As one of my college professors used to say, “Assume = Making an ASS out of U and ME.” Let the other person decide for themselves.
Reframing the fear: Instead of assuming a “no,” flip the script—imagine they said an enthusiastic “yes!” Now ask yourself: Why would they agree? List three reasons why your Ask benefits them or aligns with their interests.
Action: Use those reasons to reframe your request. Present it in a way that highlights the value for the other person, making it easier for them to say “yes.”
The Bottom Line
Most people don’t fail because they lack skill or talent—they fail because they don’t ask. Whether it’s fear of rejection, lack of confidence, or not knowing how to ask, these roadblocks only sabotage you.
The key to Asking? Realizing the Ask isn’t about you—it’s about the other person and the value they receive by saying yes. When you shift your focus to them, your fear loosens its grip, and you move from “I want to ask” to “I’m ready to ask.”
In my next article, we’ll dive into the three reasons why asking for what you want is the fastest way to get it. See you next week!
