Start Here: Why Keep Asking Exists

One question at a time, we learn to hear our own voice again — and live with more clarity, calm, and intention.

Jan 17, 2026

You’ll spend over 15 years of your life consuming content.

Scrolling. Streaming. Listening. Reading.

According to Pew Research, the average adult consumes six hours of media per day.

That’s 15 years of consuming other people’s voices over the course of a lifetime. And, that doesn’t even count the in-person voices trying to get your attention (family, friends, colleagues, supervisors, neighbors, etc.)

We know what the algorithm recommends.

We know what our friends are watching.

We know what every expert is shouting.

We know so many other voices.

We make space for so many other voices.

Can you even hear your own voice anymore?

Keep Asking is about making space for that voice again.

In 2020, I was invited to speak to a group of high school students about “life skills.”

I asked them what they thought the most important life skill was.

My “scientific” poll of 250 eleventh graders came back clear:

“How to do taxes.”

To be fair, you can actually end up saving a lot of money if you know how to navigate that world well. But taxes are not exactly my specialty.

So I took a different path.

I tried to think about skills that have the biggest positive ripple effects across the rest of life.

“What’s the one skill I could develop that has the biggest positive impact on everything that comes after learning it?”

My hypothesis?

The ability to ask better questions.

That’s how Keep Asking was born.

One question a week.

Every week.

What began as a test is now my own personal quest. There are so many positive side effects of asking better questions that I’ve continued pursuing this project for over five years now.

How My Life Is Better (And Why Yours Might Be Too)

Over the past five years, this practice has quietly changed almost everything about how I think, act, and relate.

Not because of the answers.

But because I’ve learned how to ask — and how to listen to the answers that show up.

Here’s how my life has changed:

I’m more intentional.

Questions create space.

They interrupt my autopilot and force me to pause — to really consider what matters.

Sometimes that pause is just a beat before I respond.

Other times, it’s a long stretch of reflection before I make a decision.

I’m a better listener.

When I was younger, I talked a lot.

Like... a lot.

But spending years thinking in questions changed how I enter conversations.

Now, I’m not trying to win the moment.

I’m trying to understand the person.

It’s helped me build deeper relationships.

I’m more self-aware — and, maybe more surprisingly, more self-compassionate.

Here’s something I didn’t expect:

Asking hard questions hasn’t made me more self-critical.

It’s made me a better friend to myself.

“All of humanity’s problems stem from man’s inability to sit quietly in a room alone.”
Blaise Pascal

We live in a world where silence is terrifying, so we scroll, tap, distract.

But questions have helped me sit in that space and actually listen to myself.

Not all of the answers are pretty.

But they’re mine.

And I’ve come to respect that voice more than ever.

I think like a strategist.

Robert Greene calls it the “Grand Strategist” — the kind of person who makes decisions with the long-game in mind.

That’s what this project has helped me do.

I’m not just reacting to what’s urgent.

I’m aligning with what matters.

Questions like “Who do I want to become?” or “What’s the real cost here?” have helped me zoom out and live more intentionally.

It also helped us make one of the biggest decisions ever—quitting my job!

I’m more peaceful.

I’m not immune to stress or anxiety. I still have my moments. (lots of them)

But now, I’ve got tools to navigate everything from the big crises to the small everyday inconveniences.

These don’t erase the hard stuff.

But they reframe it. They help me respond with clarity instead of spiraling in confusion.

Thanks for reading Keep Asking! This post is public so feel free to share it.

A moment I’ll never forget

I once guided a simple mindfulness exercise with a group of high school students.

Nothing fancy. Just sit quietly and breathe.

Afterwards, several students said:

“don’t make us do that again.”

When I asked why, they said:

“Because we’d rather do homework and be productive or be distracted with something else.”

That hit me.

I wonder how many of us are doing the same thing. We unintentionally (or maybe intentionally) busy our minds on any and everything else possible, instead of making the time and space needed to listen and learn from our own voice.

That’s what Keep Asking is about — helping you reconnect with that voice again.