10 Things I Wish I Knew Before I Started Hand-Lettering

When I first started hand-lettering, I thought it was all about having nice handwriting and a steady hand. Turns out, I was wrong about a lot of things.

I've spent the last five years making signs, practicing letters, and figuring out what actually matters versus what I wasted time worrying about. Here's what I wish someone had told me before I started.

1. You're Going to Hate Your Work at First (And That's Normal)

My early attempts were rough. Like, really rough. I'd spend hours on something, step back, and think "this looks terrible." I remember one of my first signs; I redrew it four times and still hated it. I took a photo to compare it to other signs I'd seen online, and yeah, it was bad. I almost gave up multiple times because I assumed I just wasn't naturally good at it.

Here's what I didn't know: everyone's early work looks bad. You have taste before you skill, which means you can see that your work isn't great yet, but you don't have the experience to fix it. The only way through is to keep making things until your skill catches up to your taste.

It took me a few years before I stopped cringing at everything I made (sometimes I still do). Now I look back at those early signs and can actually see the progress.

2. Expensive Tools Won't Make You Better

I thought I needed the fancy brush pens, the premium paper, and the whole setup. I went to Hobby Lobby one day and spent $60 on markers and special pens, convinced that was the problem. Spoiler: it wasn't.

The truth? I do most of my work with basic chalk markers that cost like $5 for a pack. Yeah, they're finicky and annoying sometimes, but they work. Those expensive brush pens I bought? Still sitting in a drawer mostly unused.

Start with whatever's affordable and accessible. You can upgrade later once you know what you actually need.

3. Imperfection Is Part of the Appeal

This one took me forever to accept because I'm a perfectionist. I'd redraw letters over and over trying to make them perfect, and I'd get frustrated when they weren't exactly symmetrical or smooth.

I'll never forget the time I spent two hours on a single word, erasing and redrawing it obsessively, only to have a customer stop and say, "I love how handmade this looks." The thing I thought was a flaw might actually be what they liked about it.

But here's the thing: people don't always want perfect. Perfect can sometimes look sterile and mass-produced. The slightly wobbly lines and the hand-drawn quality; that's what makes it feel human and authentic. That's literally the whole point.

Now when I catch myself obsessing over a tiny imperfection, I remind myself that it's probably what makes the design feel real.

4. Spacing Matters More Than You Think

You can have beautiful individual letters, but if your spacing is off, the whole thing falls apart. Letters too close together? Looks cramped and hard to read. Too far apart? Looks disconnected and awkward.

I once finished what I thought was a great sign, put it outside, and immediately noticed from across the street that one word looked weirdly spaced. I had to bring it back in and fix it. Now I always step back at least 10 feet before I call anything done.

I didn't realize how much time I'd spend just adjusting spacing. Sometimes I'll erase and redraw the same word three times just to get the spacing right. It's tedious, but it makes a huge difference in the final result.

Pro tip: Step back and look at your work from a distance. What looks fine up close might look terrible from across the room.

5. You'll Develop Your Own Style (Don't Force It)

When I started, I tried to copy other people's lettering styles that I saw on Instagram or Pinterest. I wanted my work to look like theirs. I'd screenshot examples and try to replicate them exactly. But it never quite did, and that frustrated me.

Eventually I realized I was developing my own style without even trying. The way I naturally form certain letters and the little quirks in how I draw became my style. I'm much more confident in calligraphy and typography than I am in doodling, and that's just how my work looks now.

Your style will emerge as you practice. Don't force it to look like someone else's.

6. Some Days You Just Don't Have It

There are days when I sit down to make a sign and everything I create looks wrong. My hand feels stiff, the letters look awkward, and nothing flows.

Just last month, I had one of those days where I started a sign three separate times and scrapped all of them. I finally just closed up shop, went home, and came back the next day. Made the whole thing in two hours, and it looked fine. Sometimes your brain just needs a rest.

I used to think this meant I was losing my skills or doing something wrong. Nope. It's just part of the process. Some days your brain and hand aren't in sync, and that's okay. Take a break, come back later, or push through if you have to. But don't beat yourself up about it.

Creativity isn't consistent, and that's normal.

7. People Will Notice (In a Good Way)

I didn't expect anyone to really care about the signs I made. I figured they were just...signs. But people stop and take pictures, compliment them, and ask who made them.

One time, a woman came in specifically because she'd walked by the week before, saw the sign, and told herself she'd come back. Another time, someone tagged the store on Instagram with a photo of the sign I'd just finished that morning. It's wild.

The attention can feel uncomfortable at first, especially if you're still figuring things out. But it also makes you realize that your work matters more than you think. Even small creative touches leave an impression. (Check out last week's post!)

8. It Takes Way Longer Than You'd Expect

I spend anywhere from 3 to 6 hours on a single A-frame sign. Three to six hours! For something most people glance at for a few seconds.

When I started, I thought I could knock out a sign in an hour. The first time I timed myself, I looked at the clock after what felt like an hour, and it had been three. Between planning, sketching, erasing, redrawing, fixing mistakes, and adjusting spacing, it adds up fast.

But honestly? The time investment is worth it. Those few seconds of someone's attention can turn into them walking into the store or remembering your business later.

9. You Don't Need to Be Good at Everything

I'm way more confident in my lettering than my doodling. If you look closely at my illustrations, they're kind of silly. I recently attempted to draw a breakfast sandwich, just for it to look like a McDonalds quarter pounder. One time I was doodling a strawberry, and a kid pointed at it and asked what it was. Humbling.

But that's okay; I lean into what I'm good at. I focus on the typography and keep the doodles simple or just leave them out entirely.

You don't have to master every aspect of hand-lettering or design. Focus on your strengths and don't stress about being well-rounded. People will appreciate what you do well much more than they'll notice what you're not great at.

10. It's More Rewarding Than You Think

When I started, I just wanted to make decent-looking signs. I didn't realize how much I'd actually enjoy the process. The meditative rhythm of drawing letters, the satisfaction of finishing a design, and the little boost when someone compliments your work.

There's this moment when you finish a sign and step back and think, "okay, yeah, this is actually good." That feeling doesn't get old. Even on days when it's frustrating. There's something really grounding about making something with your hands in a world where everything is digital and automated.

If you're thinking about trying hand-lettering, just start. Your early work will probably be rough, and that's fine. You'll figure it out as you do. And eventually, you'll look back and realize how far you've come.

Key Takeaways

• Your early work will look rough, and that's part of the process. Everyone starts somewhere. Keep making things until your skill catches up to your taste.

• Tools don't make you good; practice does. Start with basic, affordable supplies. You don't need fancy equipment to create something people will notice.

• Imperfection is what makes hand-lettering feel authentic. Those wobbly lines and slight inconsistencies prove a human made it, which is the whole point.

• Spacing can make or break your design. Always step back and look at your work from a distance before calling it done.

• Your style will develop naturally; don't force it. Focus on what you're naturally good at instead of trying to be well-rounded at everything.

• Some days you won't have it, and that's okay. Creativity isn't consistent. Take breaks when you need them and don't beat yourself up.

• It takes longer than you think, but it's worth it. A few seconds of someone's attention can turn into them remembering your business or walking through the door.