Why I am asking the hard questions

and why you should too

You’ll never grow if you’re not willing to ask the hard questions.

And by hard, I don’t mean complicated. I mean uncomfortable. I mean the kind of questions that don’t guarantee a flattering answer… the kind that poke at blind spots we didn’t even know we had.

These are the questions that stretch us.

Recently, I wrote a Substack post about a friend I met in Colorado. I mentioned my wife in it too… it was a personal piece, and I felt good about how it turned out.

But after I hit publish, I still had that voice in the back of my mind reminding me I’m not where I want to be with this newsletter. I’m just trying to get better. And that doesn’t happen all at once. It happens through small, consistent shifts.

So I did what I try to practice often: I asked the hard question.

I sent the post to my wife. Told her I had mentioned her and asked for her thoughts. After she read it, I asked her directly, “What do you think I can do to get better at this?”

She was honest. She told me to go deeper. To write more stories. To let it breathe a little more… maybe even go longer with my posts.

And I’ll be real with you: part of me pushed back. I wasn’t sure how many people actually read a post from start to finish these days. I didn’t want to overdo it. But I knew her feedback came from a place of care, and deep down, I agreed.

She said she liked it… but she also said there’s room to grow. And I didn’t take that as criticism. I took it as clarity. Not a sign to quit. A sign to keep building.

The next day, I sent the same post to the friend I had written about. We hopped on a call and I asked him too: “Hey man, what can I do better?”

It felt risky. He’s been writing a long time, and I knew he could easily point out things I missed. But I asked anyway.

That’s the part most people skip. Because when you ask questions like this… real questions… you open yourself up. It’s vulnerable. You invite feedback you might not be ready to hear.

But that’s the point. The answers to these questions don’t come from you. They come from someone seeing your work, your life, from the outside.

We all have blind spots. I’m too close to my own thoughts, my own process, to see everything clearly. Sometimes you need someone else to hold up a mirror.

That’s something I’ve been learning for a while now.

At work, I’ve always tried to ask what might seem like a dumb question. I’ve been the one who says, “Hey, I don’t actually understand what we just talked about. Can someone break it down?” Not because I’m slow. But because I want to learn. And I’d rather be honest than stay confused.

It doesn’t mean I don’t belong in the room. It means I care enough to want to grow in it.

That’s what qualifies you… your willingness to ask the uncomfortable questions. The ones that help you see what you didn’t before.

Right now, my goal is to publish daily on Substack. I don’t know if I’ll hit it every single day. But I do know I want to keep showing up. I want to get a little bit better, in writing and in life.

So let me ask you: What’s the hard question you’ve been avoiding?

Who could you ask — a friend, a family member, a coworker — to help you see what you’ve been missing?

Where in your life are you ready to grow, but haven’t yet asked how?

This is a challenge to myself as much as it is to you.

What’s one uncomfortable question you can ask today?