The Leadership Risks Most Worth Taking

Why Ask for What You Want is now Great Leaders Take Risks

Why exactly am I so endlessly fascinated with the nuances of asking for what you want effectively? It’s a question I’ve asked myself frequently as I’ve shared these ideas with you over the past year. Not just for myself, but for all of you: I want to share the heart strings it plucks in me so perhaps yours too will resonate in harmony.

Is it about getting what you want? Finding safety, freedom, love, happiness, or success? Certainly we all want those things! But it can be deeply satisfying to ask for what you want even if you don’t quite get the results you were looking for. Is it about achieving integrity? Sure, better expressing your desires can help you feel more whole. But I doubt you think of yourself as lacking integrity—or lacking the ability to ask for what you want, for that matter.

These are things we all already do! It’s not like I invented the idea of pursuing our desires. If anything, we can’t help but ask for what we want, it’s programmed into us at a deep level.

So perhaps the more interesting question is why we so often don’t ask for what we want. We keep our mouths shut instead of speaking what’s in our hearts. We repeat the same ineffective asks for years and blame others for their indifference—instead of accepting the answer is NO and changing our approach.

When I reflect on what clients have told me over the years, often they’re waiting to be sure. Waiting to be sure their dream is achievable before they pursue it. Waiting to be sure what they say will land before they speak it out loud. Waiting to be sure their new approach will work before they abandon the old one. Stressed out by all the risk and uncertainty around them, they decide to wait until they’re sure to act.

But the world isn’t getting any more predictable, that’s for sure! If anything, it seems more uncertain than ever as waves of change transform everything around us: COVID, AI, Trump, tariffs. What will come next? I don’t know, but I’m pretty sure it’s not a return to a world of calm, predictable certainty.

The world has always been full of uncertainty—and thus risk. Our current era just keeps prodding us with ever more potent reminders of that uncomfortable reality. And long ago our bodies adapted to that reality with the stress response. At the first hint of danger, we pump chemicals into our bloodstream, activate our nervous system, and jump into fight, flight, freeze, or fawn! Pondering what we truly want and how to get it is the last thing on our mind—safety first.

So while pursuing our desires is programmed into us at a deep level, so too is avoiding risk—and avoiding risk nearly always takes precedence when the two come into conflict. If we do take risks, often it’s not out of excitement to create change at all. It’s out of fear we’re not good enough as we are today.

Maybe you’re already asking for what you want in life. But do you ask when the stakes feel high? When failure doesn’t feel like an option? When you might lose your job? Or people might judge you harshly? These are the risks that hold us back from asking for what we want. Our bodies react to them just like physical danger, but mostly they’re not dangerous—just stressful.

So as I’ve reflected on what asking for what you want means to me, to me it represents embracing risk. Trusting yourself enough to ask even when the stakes feel high, even though the world is uncertain—because you know you can handle the consequences.

Our society glorifies risk-takers, exactly because we mostly avoid risks in everyday life. Entrepreneurs, artists, athletes, adventurers, and revolutionaries. But you don’t have to take giant risks to learn to build comfort with risk-taking.

On the contrary, you learn to embrace risk by taking small risks every day—and building your comfort over time. Like asking for what you want instead of holding back. Or accepting when your ask fails and trying something new.

That’s why my newsletter (and book and framework, eventually) has a new name: Great Leaders Take Risks. Because we’re all asking for what we want to some degree, but often we’re not taking the risks necessary to achieve greatness. We’re waiting to be sure and missing our big opportunities.

With my writing, I hope to inspire you to take those risks. Not because you’re not good enough as you are (and you are!), but because the potential for greatness lives inside each of us. In my experience, there are four key risks that great leaders take again and again:

1. Great leaders risk pursuing their boldest ambitions.
   They don’t wait for a sure thing or compromise too soon.

2. Great leaders risk asking for help.

   They don’t coerce others or do it all themselves.

3. Great leaders risk admitting when they fail.
   They don’t blame others or deny their failures.

4. Great leaders risk changing how they lead.
   They don’t just stick with what’s familiar or give up entirely.

So what risks aren’t you taking right now? What do you think of the new name? Would love to hear your thoughts. Feel free to say hello and share where you are on your risk-taking journey.