Why is it so hard to ask for what we want?

No matter who you are, what your dream is, or what you hope to change: You can ask for what you want. Don’t believe me? 

In this moment, I suspect there's at least a part of you thinking this work isn't really for you. That you already know how to ask for what you want—it’s other people who won’t give it to you. Or really you shouldn’t have to ask at all! You might tell yourself that what you want is pretty unlikely, so why bother taking the risk? Or that you're just fine sticking with the status quo. You might even think asking sounds great for the privileged few—if you were a rich white guy, you would go for it!

All these sentiments are not just welcome here, they're integral parts of the process of asking for what you want. Asking itself is easy: we articulate our desires, ask for them intentionally, accept the response, and try again. Working through our own resistance to those steps is what's hard. That’s why so much of my work with leaders—and the AFWYW framework—is about getting to know that unique individual resistance. There are risks and challenges to asking for what we want, but there are also risks to holding back: we suffer when we sacrifice our integrity by hiding our true desires. And the rewards of asking can be a radically different life than the one you’re living now. Asking for what you want effectively is about working through the fears holding you back and embracing the dreams drawing you forward.

The Parts that Hold Us Back

I remember so clearly my first weeks after I joined Slack 10 years ago: I was thrilled to walk through those doors every morning. Building a product that customers loved at a tiny startup with some of the best people in the industry? It was my dream job. Yet it was clear within the first month that the CEO didn’t trust me—and I had no idea how to earn that trust. What I desperately wanted was to build that relationship so we could do the best work of our lives together. 

But that desire was drowned out by all the fears in my head. 

What if I asked how to fix our relationship and the conversation didn’t go well? What if he fired me? What if I lost my stock package worth millions? What if everyone knew I’d failed? Would this dream job actually be the end of my career? My focus became avoiding those fears, and my dream of a better relationship with the CEO was all but forgotten. In the end I achieved neither: I lasted a year before finally being let go for good, and those fears haunted me far longer. 

While we all have parts of us that are excited to follow our dreams, we also have parts that have grave concerns with that path. They’ll actually argue against following your dreams to keep you safe! Maybe they feel safer being content with what they have, and aren't comfortable wanting something they might never get. Maybe they believe it's irresponsible to ask, that the risk of negative consequences will be too great or the chance of success too slim. Or maybe they feel entitled to getting what they want no matter what, so to them it feels dangerous to accept a no or adjust their ask based on the feedback. All three of those stories were in my mind often during my time at Slack, and I believed them.

To understand our resistance to each step of asking, we need to figure out what stories you tell yourself when you’re not getting what you want. 

Embracing Your Resistance

Let’s get to know the parts of you that get scared and the stories they tell. I’ve heard many stories of resistance in my work as a coach, and I’ve grouped the parts of us that tell those stories into two broad categories: people-pleasing parts and the control-freak parts. 

First, the people-pleasers. These parts of us seek others’ approval to feel safe. What stories do yours tell? Maybe you decide you’re fine as-is, convince yourself you can live with the status quo. Maybe you know what you want, but tell yourself asking for it is impossible: too risky and unlikely to succeed anyway. Or maybe you even get up the nerve to ask, but give up after one try, telling yourself no means no and that’s it. . 

Pleasing others gives us a temporary sense of safety, but it comes at a high cost. People pleaser parts sacrifice pursuing their desires to maintain strong relationships. So testing that strength by asking for what you want can feel really scary, especially if you’re a woman, person of color, or come from a culture where directness is considered rude. For these parts the challenge tends to be to ask more: to dream bigger, to ask more boldly, to keep asking even when they get a no, to not give up on their dreams just because pursuing them comes with risk.

Then there are the control-freak parts. These parts of us seek to control outcomes to feel safe. They tend to ask for what they want loudly and often—in fact, their asks often sound more like demands. The problem is this entitled strategy usually doesn’t go over well with others. So what stories do you tell when you’re not getting what you want despite your best efforts? Maybe part of you blames others for being unreasonable when they won’t comply. Maybe you tell yourself you deserve this, that others have no right to deny you. Or maybe that you shouldn’t have to ask at all. 

Asserting control gives us that temporary sense of safety, but it comes again at a high cost. Control freak parts sacrifice strong relationships to pursue their desires. When we feel so entitled to a certain outcome, our asks aren’t very skillful and tend to work against us. We don’t hear all the no’s we’re getting, don’t learn from that feedback and revise our approach. In fact, accepting that other people don’t owe us anything—direct reports, partners, and children included—can be extremely upsetting. For these parts the challenge tends to be to accept more: to thoughtfully revise both what they want and how they ask for it based on the responses they get. Respecting others’ autonomy can be exactly what helps build the strong relationships necessary to unlock true influence.

The Path Ahead

Recognize a bit of yourself in these parts? Good! That means you’re a human being. And you’re certainly not alone. But you don’t have to sacrifice strong relationships or pursuing your dreams: you can achieve both. In fact, that’s what the AFWYW framework is all about. The more you practice asking for what you want—and working through whatever resistance arises in you—the more skillful you’ll be at both asking and making peace with the results. 

My clients are startup leaders, and startups are never done: they’re perpetually full of potential, always in the process of becoming the best version of themselves. That very much describes personal growth as well: we too are full of endless potential. And the practice of asking for what you want is a great way to unlock it.

I’ll be sharing more resources and stories in the months ahead to help you work through your own resistance and ask for what you want effectively, so comment below with your questions and let me know what you want to explore next.

In the meanwhile, make sure you’re following me on LinkedIn and subscribe to the AFWYW newsletter to stay in touch. Finding meaning in this work? Please share it with your network so we can build this community, I look forward to the conversations!