I Wonder What Would Happen If... (The Curiosity Trick That Got Me Writing)

ADHD
#procrastination#productivity#getting-started#executive-function

I've been meaning to start this blog for months.

Not in the casual "yeah, that'd be cool someday" way. In the "I have six half-written posts in my drafts folder and I think about this every single day but somehow never actually do it" way.

You know that flavor of procrastination? Where the task sits there, getting heavier, while you find increasingly creative ways to do literally anything else? I reorganized my entire project management system twice. I built features for my app that weren't even on the roadmap. I deep-cleaned my home office (which, let's be honest, is DEFCON 1 level avoidance for an ADHD brain).

The blog sat there. Waiting. Judging me a little.

Then this morning, something clicked.

The Reframe That Actually Worked

My ADHD coach, Chelsey, and I have been working on this curiosity-based approach for getting unstuck. The core idea: when you're avoiding something, the way you're thinking about it might be the actual problem.

Here's what I did today:

Old framing: "I need to write blog posts."
New framing: "I wonder what would happen if I built a system to help me generate content."

That's it. That's the whole trick.

And holy shit, it worked.

Within an hour, I was setting up my blog infrastructure. Within two hours, I was writing this post. The system? Claude Projects with writing personas for each topic, blog infrastructure with Next.js. Turns out making it a technical challenge was the hook my brain needed. And yes, I'm using Claude to help write this. That's part of the system. The curiosity wasn't about writing—it was about building something interesting that helps me write. The thing I'd been avoiding for months suddenly felt... interesting? Doable? Like something I actually wanted to explore?

Why This Works for ADHD Brains

Here's my theory (backed by exactly one successful attempt and Chelsey's professional experience, so slightly more than a grain of salt):

The phrase "I need to..." triggers obligation mode. And obligation mode, for many ADHD brains, is like kryptonite. It creates pressure. Pressure creates resistance. Resistance creates avoidance. Avoidance creates guilt. Guilt creates more pressure. You see where this goes.

But "I wonder what would happen if..." triggers exploration mode.

ADHD brains LOVE exploration mode. We're novelty-seekers. We're curious. We like figuring things out, tinkering with systems, seeing what happens when we try something new. That's the mode where we accidentally spend six hours learning everything about 18th-century shipbuilding because one Wikipedia link led to another.

The curiosity reframe hijacks that tendency and aims it at the thing we've been avoiding.

Instead of:

  • Obligation → Pressure → Resistance → Avoidance

We get:

  • Curiosity → Interest → Exploration → Action

Same task. Completely different emotional pathway.

It's Not Magic (But It Feels Like It)

Look, I'm not claiming this is some revolutionary breakthrough. I'm literally writing this post on the same day I discovered it worked. I have no idea if it'll work tomorrow, or for other tasks, or for other people.

But here's what I DO know: after months of getting nowhere with "I should write blog posts" and "I need to start this blog" and "why am I not doing this thing I said I'd do," a simple reframe got me moving TODAY.

That feels worth sharing.

How You Might Use This

Think about something you've been avoiding. Not the hard stuff (we'll get to that), but something relatively straightforward that you just... can't seem to start.

Now try swapping the framing:

Instead of: "I need to organize my finances"
Try: "I wonder what would happen if I spent 20 minutes building a simple tracking system"

Instead of: "I should clean out my inbox"
Try: "I wonder what would happen if I treated this like a game and tried to get to inbox zero in one session"

Instead of: "I have to prepare for that client meeting"
Try: "I wonder what would happen if I mind-mapped all the possible directions this conversation could go"

See the pattern? You're taking the same task but:

  • Removing the obligation language ("need to," "should," "have to")
  • Adding curiosity language ("I wonder," "what if")
  • Sometimes making it more specific or game-ified
  • Focusing on the process/system rather than the outcome

The Critical Part Nobody Talks About

This doesn't work by making the task easier or less important. It works by changing your brain's relationship to starting.

You're not lying to yourself. You're not pretending the task doesn't matter. You're just finding a side door into doing it that doesn't trigger your avoidance circuits.

For my blog, I genuinely AM curious about building a content system. That curiosity is real. But I couldn't access it while I was stuck in "I need to write posts" mode. The reframe helped me see what was actually interesting about the project.

This Won't Work Every Time

I'd love to tell you this is the solution to all ADHD procrastination. But I've been doing this long enough to know: there are no universal fixes.

Some days, nothing gets you moving. Some tasks are genuinely boring no matter how you frame them. Some obligations can't be reframed because they're time-sensitive or have real consequences.

This is one tool. Not the whole toolkit.

But it's a tool that worked for me this morning when nothing else had worked for months. And on an ADHD entrepreneurship journey, you take the wins where you find them.

Your Turn

Here's the action step: Think of one task you've been avoiding. Just one.

Write down how you've been thinking about it ("I need to..." or "I should...").

Then rewrite it as a curiosity question ("I wonder what would happen if...").

Don't try to force yourself to do the task. Just see if the reframe changes how it feels to think about it.

If it works, great. If it doesn't, that's data too. You're learning what moves your brain.

And if you're reading this post right now, that means this curiosity reframe worked well enough for me to actually publish something. Which means I'm writing this from the future of about three hours ago when I was still stuck.

Progress, not perfection. Tools, not rules. And sometimes, the right question is better than the right answer.

What are you avoiding right now? Send me an email at hello@keithgstewart.com or tag me on LinkedIn—I'm genuinely curious. (See what I did there?)

P.S. - If you're looking for ADHD coaching support, I can't recommend Chelsey Summers enough. Working with her has been a game-changer for figuring out which strategies actually work for my brain vs. which ones just sound good on paper.