Trust your knowing.

How letting the questions in is the key
to moving from your head to your heart

We’ve stopped asking questions.
And that’s the problem. 

I was on the treadmill listening to a podcast and thinking about the state we find ourselves. And the thought came to me:

We live in a world where asking questions—be it deep or tactical ones—makes us look less than. Creating a feeling of being watched, judged, seen in our not knowing. 

And because knowledge has been, and in some places continues to be, the currency of success, not knowing, ignorance, is a demotion. 

So we’ve learned to tuck away our deeper, more abstract questions, the ones that don’t have a clear answer. And we’ve taken the tactical, straightforward questions to AI. All so we can maintain some semblance of being one who knows. 

But at what cost?

In listening to Arthur Brooks on 10% Happier with Dan Harris, he said, “Human life is about asking, not about answering, and that’s what we forget. You want to be a real human, fully alive, ask more questions.” 

Answering questions isn’t what makes us uniquely human. Asking questions is.

And I thought about the work I do with Dare to Lead—where one of the hardest things for CXOs sitting atop the largest companies struggle with is asking for help–allowing themselves to be seen in their unknowing. What they do instead is armor up.

(Click the image below to see some of the ways armor shows up in leadership.)

I think it’s one of the reasons Barack Obama felt like a breath of fresh air in leadership—because he made it a point to say he didn’t have all of the answers. He surrounded himself with people who were smarter than him in their relative domains, and rather than co-opting their intelligence, he let them lead. Taking credit only for having the wherewithal and good sense to hire them and get out of the way. He was okay being seen in vulnerability, in his willingness to ask the hard questions and commit to looking for the answers, and rallying us to live in the possibility that they could be found.

But lately, there’s been a subtle movement away from asking towards “knowing.”

And I put “knowing” in quotation marks because, in this case, I mean the knowing that happens in the brain, not the knowing that happens at one’s core. 

And that shift from devaluing the questions in an attempt to maintain status, how we are perceived, the illusion of success—needing to “know,” is what’s keeping us from the answers that truly matter. 

We’re stuck in our heads when what we are looking and longing for is deeper, and fortunately (or unfortunately) not something we’ll have words for when we find it. 

I was working with a client who was gearing up to leave her job to start her own practice, and she was struggling with what to call herself. Not because she didn’t know what she did and who she wanted to serve in her business, but because she couldn’t fit that into a nice, neat soundbite for marketing purposes. 

We talked about how she found her way to me. She’d been talking with a friend about the challenges she’d been facing, the questions she was wrestling with, and her friend said, “I think you need to talk to Aisha.” 

When she and I had our first conversation, it was just that—a conversation. Not a sales call. Not even a discovery call. It was just two people exploring the questions. 

She left that call knowing she wanted to work with me. 

So in our session, I asked her, How did you decide to work with me? 

I just knew.

That was enough. 
You trusted your knowing.
What did Ashley call me?

She didn’t. 

And I bet if you asked Ashley what she would call me, she would say she didn’t know exactly what to call me. 

If I asked YOU what you’d call me, what would you say?

She laughed, “I have no idea.”

That’s not because I haven’t tried to fit what I do into a neat box—it’s because I’ve stopped trying to.

What I do is bigger than I can articulate. It’s deeper. And trying to squeeze it into a soundbite or a neat “I help” statement diminishes the significance of the work.

So I don’t. 

And she wasn’t the only one. 

Another client who joined me at my last retreat, sent me a text on day two:

And yet, at the end of that retreat, she said she could have come to the resort on her own and been rested, but it wouldn’t have been transformative like this. 

The things that are transformative, life-changing don’t come from things we “know” in our heads. They come from things we feel and know with our bodies.

Those moments of clarity, meaning, human-ing, come when we sit with the questions, when we let them linger and wander among them together

When we feel the answers that ring true in a deeper place, that space beneath our ribs just above our stomach, the feeling that we can’t put into words or justify in our minds, but that we know in our core.

When we listen to, trust, and act on that feeling, that truth, that is how we begin to shift from our heads leading the way to our intuition–from knowledge being the currency and the makings of success to knowing being the current and lifeblood of significance. 

Questions for you:

What questions have you be turning over in your head rather than letting them exists in the open?

What if instead of pushing them away, you let them in?

An invitation:

Close your eyes. Take a deep breath. Exhale slowly. And another one. Now while keeping your eyes closed, ask yourself the question. Then sit quietly with yourself and the question until you have what you need: peace, an answer, clarity, or whatever comes up for you.

That's your knowing. Trust it.

I’m a trusted coach and partner to executives and entrepreneurs, who despite being the first, the only, and the underestimated, have achieved extraordinary success. And now, they are ready to live a more expansive life beyond it.

Through retreats, private coaching, and my signature program Beyond Success, I can help you live and lead with more margin, meaning, and joy.

Hi, I’m Aisha—

If you’re craving a sacred, supported space to do your deepest, most important work of sitting with the questions, start here.