The Power of Asking for What You Want: Being an Enneagram 8 in a World of Choices
As a 30-year-old millennial woman, I’ve come to realize that one of the most powerful things you can do is ask for what you want. Sounds simple, right? But for someone like me, an Enneagram 8 (The Challenger), asking for what I want isn’t just about getting my way—it’s about decisiveness, control, and a need to assert myself in situations where others might hesitate. For those unfamiliar, Enneagram 8s are known for being bold, assertive, and confident in their decision-making. We aren’t the type to sit back quietly or go with the flow just to keep the peace. We feel empowered when we know we’ve made a decision based on our values and beliefs.
Now, compare that to my husband, an Enneagram 7 (The Enthusiast). Sevens are spontaneous, fun-loving, and always seeking new adventures. They avoid discomfort at all costs and can sometimes struggle with making decisions because they don't want to miss out on any opportunity. For example, I'm all about directness if something goes wrong at a restaurant. If my order is wrong, I'll ask for it to be corrected without hesitation. I see it as a simple exchange of expectations. But my husband might worry that bringing it up will ruin the fun or lead to unnecessary awkwardness. This situation occurs all the time in our decision-making, and I've learned that knowing what you want and asking for it isn’t about aggression—it’s about clarity and self-respect.
This dynamic came into play recently when we purchased a new home. Touring potential homes is always a journey, but I pretty much know from the second I step inside if a house is going to be “the one.” This drives my husband insane, as he’s so open-minded and sees the possibilities in everything. If this weren’t my second time using our realtor, I’d be certain she would want to strangle me! Long story short, we found our home, put in an offer, and it was accepted. Then came negotiations. I don’t hold back—I put it all out there. This also included the selling of our current home. When the decision was made that we were taking listing photos, I had every basic repair done, the house professionally cleaned, the landscaping touched up, and the house staged within three days. When it was all said and done, my realtor posted on social media, “She’s smart, confident, she knows what she wants. She’s efficient, outspoken, and doesn’t mess around…it’s my client.” Secretly, I think she’s an Enneagram 8, too, but her words were so validating. I am those things, and there’s nothing wrong with that. I just have to ensure I manifest those traits appropriately in the right situations and at the right time.
Step 1: Do It Brave – Don't Be Afraid to Speak Up
One of the first things I’ve learned is that asking for what you want requires bravery. For women, especially, there’s often an underlying fear of “causing a scene” or drawing too much attention to ourselves. Society still conditions women to be agreeable, quiet, and non-disruptive. But if you want something—whether it’s a raise at work, better coffee in the breakroom, or more respect for your time—you must be willing to step out of that comfort zone.
Fun/True Story: When I first moved to Raleigh, NC, at 22, I had no friends, and meeting people after college was hard. The small firm I worked for only had team members twice my age. One day, I went shopping, passing the time. In the dressing room, I came out to check my outfit in the mirror, and a woman approached me with the advice that the top I had on was gorgeous, but just too big. I was confused and asked if she worked there. She quickly replied, “No.” This stranger, who gave an ounce of care about what I looked like, started a conversation with me, and we realized we lived in the same apartment complex. Hillary and I have been friends ever since.
Over the years, I’ve watched Hillary pursue her career, sometimes feeling lost but always landing exactly where she needs to be. She oversees sales, marketing, and merchandising at a fine jewelry company and travels the world for work—from Miami to Dubai. She’s the type of person who can get a room upgrade simply by asking. I’ve watched her command a room, befriend a chef, and get meals comped, not because she’s trying to take advantage of anyone, but because she exudes a directness and warmth that makes people want to be around her.
Hillary is a powerhouse—strong, direct, and never afraid to ask for what she wants. She’s probably an Enneagram 8, at least a winged. When we moved into our new home, she came over and immediately got to work organizing closets, bathrooms, and everything in between. She took the initiative at the Container Store and found discounts I would have never known about because she asked the store associate what the best deal was for the items I needed. Something I would have never done. She’s a mentor and a friend, someone who embodies the spirit of asking for what you want with boldness and grace. Someone who is in my corner to remind me that I can be bold and brave, too.
The truth is, being brave doesn’t mean you aren’t afraid. It means that you acknowledge the fear and still go ahead and ask anyway. I think of women like Mary Barra, the CEO of General Motors. She didn’t get to where she is by staying silent or fearing the repercussions of her decisions. She’s been vocal about wanting to change the culture at GM and has spearheaded efforts to lead the company into a new, more sustainable era. Women in leadership positions don’t shy away from asking for what they want—they lean into it. Because, quite frankly, if you don’t ask, the answer is always no.
But this bravery isn’t limited to boardrooms or high-stakes meetings. Sometimes, it’s as simple as asking for that extra PTO you deserve or requesting flexibility in your work hours. You’re not being difficult; you’re advocating for yourself. Luvvie Ajayi, in her book Professional Troublemaker, (I love this book and will reference it multiple times in this blog) reminds us that “being a professional troublemaker means being the person who is not afraid to speak up for what is right.” This isn’t about causing chaos—it’s about making sure your voice is heard in the spaces where you work, live, and love.
Step 2: There's No Right or Wrong Way to Be You—But Don’t Be Demanding
One of the things I love about being an Enneagram 8 is my ability to confidently stand in my truth. But here’s the thing: while there’s no right or wrong way to be yourself, how you ask for things matters. Just because you know what you want doesn’t mean you should bulldoze your way through every conversation. People don’t respond well to demands—they respond to persuasion.
I’ve learned this lesson through experience. Early in my career, I thought the best way to be heard was to be firm and unwavering. While that approach works sometimes, it doesn’t always yield the results I hoped for. Over time, I realized that presenting my case with well-thought-out reasons and a collaborative mindset worked better than issuing ultimatums.
Let’s take the example of asking for a raise. Instead of demanding more money because you feel you deserve it, present your case: show your accomplishments, outline the value you bring to the company, and demonstrate why a raise is a logical next step. The power of persuasion is real, and when you approach a conversation with openness and facts, you increase your chances of getting a favorable response.
Here’s a tip: Be prepared. Luvvie Ajayi says, “Fear has a lot of us acting like we’re just happy to be in the room. No. Get in the room, ask for what you want, and be prepared to back it up.” Don’t just ask—explain why your ask matters. Whether you’re requesting more vacation days or a change in the office dress code, come equipped with facts, examples, and a solid rationale. It’s not about being demanding—it’s about making your case in a way that others can understand and support.
Step 3: Be Ready for “No” – Decide What You’re Willing to Compromise
Here’s the tough part: Sometimes, the answer is no. It’s inevitable. Whether you’re asking for a raise, suggesting a policy change, or requesting that your meal be fixed, not everything will go your way. The real power comes in how you handle that rejection.
Before going into any conversation where you’re asking for what you want, decide whether “no” is an acceptable outcome. Are you willing to compromise, or is this a non-negotiable for you? If you’re willing to budge, think about what concessions you’re willing to make. If it’s a hard line in the sand, be prepared to stick to your guns—but know that doing so may come with consequences.
For example, in the workplace, let’s say you’re advocating for a more flexible work-from-home policy. You might ask your boss to consider letting you work remotely two days a week. If the answer is no, are you willing to accept one day a week as a compromise? Or is this a situation where you feel the flexibility is non-negotiable, and you’ll need to start looking for a new job if they refuse? Knowing where you stand beforehand can help you navigate the conversation more confidently and avoid unnecessary frustration.
In less consequential situations—like receiving the wrong order at a restaurant—you have to decide whether it’s worth the hassle of asking for it to be corrected or if you’re okay just eating what was brought out. I would absolutely send it back, while my husband might just eat the meal as-is to keep things moving and avoid making a fuss. And that’s okay, too! There’s no one-size-fits-all approach to advocating for what you want.
You Are Not Too Much—You Are Enough
Obviously, there are times and places where asking for what you want isn’t an option. No matter how much confidence you have, there are still rules we have to follow and job duties we’re responsible for—even if we’d prefer not to do them. You’re not going to walk into a courtroom and ask for a free pass on a traffic violation after going 65 mph in a school zone. Sure, you could apply my previous argument: “If I don’t ask, the answer will always be no,” but in this case, you can go ahead and prepare for that "no."
Throughout this blog, I’ve used a variety of examples of how asking for what you want can manifest in your life, and I loosely tied it back to work because I want you to start thinking of all the ways—big and small—that you can start speaking up for yourself. Whether asking for better coffee in the breakroom or advocating for a change in the dress code, these moments are just as important as the big ones because they reflect how much value you place on your voice.
At the end of the day, don’t let anyone make you feel like you’re “too much” for asking for what you want. In the workplace, at home, or out with friends, your desires, opinions, and needs matter. My last Luvvie quote, “You cannot be afraid of your own voice. You cannot be afraid of using it.” Asking for what you want isn’t selfish—it’s necessary. However, let’s be real: time and place matter. My favorite phrase is, “read the room.” If your company just announced budget cuts due to a decrease in revenue, that’s probably not the best time to ask for that raise you’ve been eyeing.
Being an Enneagram 8 has taught me to be decisive and clear, but it’s also shown me that there’s power not just in what you ask for but in how you ask. The key is to approach every situation with confidence, clarity, and a willingness to listen. So, go ahead and ask for what you want—and never let anyone tell you that you’re asking for too much.