Step Out of Your Comfort Zone to Level Up Your Woodworking Skills

Step Out of Your Comfort Zone and Level Up Your Woodworking Skills

There’s a quote floating around—maybe from Robert Allen—that goes something like, “Everything you want is just outside your comfort zone.” There was a time when I would’ve dismissed that as something motivational speakers say to sell books. But honestly? It’s true. If you want to improve—whether it’s in woodworking, fitness, cooking, or any creative pursuit—you’ve got to get comfortable with being uncomfortable. And it must be true, because without it, I wouldn’t be able to make a dumb Willy Wonka meme about it. So let’s delve into why I believe you should step out of your comfort zone to level up your woodworking skills.

The Fastest Way to Get Better at Woodworking

When you’re new to woodworking, the best way to learn is to dive headfirst into a project and figure things out as you go. Sure, you might feel like you’re dog-paddling at first, but before you know it, you’ll be cruising along with smooth strokes (synchronized swimming skills optional).

The biggest mistake I see beginners make is staying in “practice mode” for too long. Practicing dovetails on scrap wood is great, but nothing beats the experience of actually using that skill in a real project. Even if your first attempt isn’t perfect, I guarantee someone in your life would love to own something you made by hand. And here’s the bonus: when you succeed, you reinforce your skills. When you fail, you learn in a way that sticks—because nothing teaches a lesson quite like having to redo a mortise you cut on the wrong side of the workpiece.

Why I Still Push Myself (Even After 20 Years of Woodworking)

As a woodworking educator, I naturally stick to what I know. Confidence comes with experience, and it’s hard to teach something you’re still figuring out yourself. But here’s the beauty of online woodworking content: we can mess up. And honestly, people prefer seeing the struggle.

Watching a master woodworker execute a perfect joint is impressive, sure. But watching someone wrestle through a new technique? That’s relatable. That’s how you will have to learn, too—by troubleshooting, adjusting, and occasionally uttering words best left out of a family-friendly blog.

After nearly 10 years of making woodworking videos and publishing my first book (Hybrid Woodworking), I have to remind myself to embrace this process. My best content comes from showing both the victories and the inevitable hiccups along the way.

The Woven Panel Hamper: An Exercise in Uncertainty

Case in point: my recent Woven Panel Rolling Hamper project. I decided to design on the fly, something I used to do often in older builds like the Sculpted End Table and Gadget Station. The woodworking itself was straightforward, but the woven panels? Completely new territory.

I designed it in SketchUp (shoutout to my buddy Scott Seganti for the assist), but software doesn’t exactly factor in real-world challenges—like the difficulty of weaving a panel while connecting multiple legs, rails, a bottom panel, and a back panel. I took a risk. If it failed, I would’ve wasted time, materials, and an embarrassing amount of camera footage.

But, much like a college student who writes a brilliant paper the night before it’s due, I sometimes do my best work under pressure. And guess what? It worked.

How to Push Past the Fear of Failing

The hamper wasn’t a high-stakes gamble, but it’s a great example of why you should step outside your comfort zone. Want to level up your woodworking? Start experimenting with:

✔ New joinery techniques (ever tried a bridle joint?)
✔ Unfamiliar materials (bamboo, epoxy, even leather!)
✔ Complex designs (curves, angles, inlays, oh my!)

Of course, do some research first so you don’t end up doing something unsafe or ridiculously impractical. But don’t let “analysis paralysis” keep you from taking action. Pick a project, design it well enough to get started, and make some sawdust. You’ll be surprised at what you’re capable of.

Find Your Comfort Zone—Then Step Just Beyond It

Not everyone learns the same way. Some people need more hand-holding than others (which is why we offer step-by-step instruction in the Wood Whisperer Guild). But this principle applies no matter your skill level:

👉 Find your comfort zone.
👉 Set your next goal just beyond it.
👉 Do this with every project, and you will improve.

So, what woodworking challenge have you been avoiding? A tricky joint? A new tool? A project that intimidates you? Drop a comment and tell me what’s outside your comfort zone—and then go build it.