Your Webinar Wipeout Fix: A 4-Part Rescue Plan

I’m trying something new! A bonus email article based on the poll last week, let me know what you think.

Last week’s poll results are in—thank you for weighing in! Turns out the first two challenges listed were clear winners, which honestly doesn’t surprise me at all. Curious which one you picked? Here’s what the full poll looked like, to jog your memory:

Virtual events are fascinating creatures, aren’t they? One minute you’re crafting what feels like the perfect presentation, and the next you’re staring at a registration page with three sign-ups (two of which are your mom and your colleague who felt sorry for you).

I learned this the hard way, back in 2013 when I launched Typography Dojo with nothing but a webcam, earbuds, an iMac, and enough nervous energy to power a small city. Thank god I had my friend Nikki Villagomez willing to be my first guest, and generous design community members who showed up to support what was essentially me figuring it all out in real-time.

But here’s what those early, terrifying sessions taught me: most of the chaos you’re experiencing isn’t personal failure—it’s predictable challenge. And predictable challenges have solutions.

After 12 years of hosting virtual events and watching other brilliant professionals wrestle with webinars, here are the four most common roadblocks and what works to fix them.

1: “I’m shouting into the void—no one’s RSVPing!”

You know this feeling. You’ve designed a solid event, written compelling copy, and posted across your networks. Yet that registration counter moves about as quickly as a government website during tax season.

In those early Typography Dojo days, I made every promotional mistake in the book. I focused on optimizing event times, tweaked registration page layouts, and posted them on Facebook multiple times a day. What I wasn’t doing was sharing why typography mattered to me personally, or why I was willing to fumble through technical difficulties to talk about it.

The shift that changes everything: Stop promoting. Start storytelling.

Instead of leading with features and benefits, share why this topic keeps you up at night. What client conversation sparked this idea? What mistake did you make that others could avoid? People don’t register for bullet points—they register because something resonates.

Try this: Your next promotional email should read like you’re writing to a friend who asked for advice over coffee. Personal, specific, and genuinely helpful before they even show up.

The reminder that doesn’t feel like spam: Skip “Last chance to register!” Instead, try “I was reviewing my notes for tomorrow’s session and remembered something you might find useful...” Context matters more than urgency.

2: “I’m terrified people will get bored and ghost mid-event."

There’s nothing quite like the sinking feeling of watching your attendee count drop in real time while you’re mid-sentence (especially when the counter is live, like it was in Crowdcast). It’s like watching people leave your dinner party through the kitchen window.

I’ll never forget my Typography Dojo session, where I watched the attendee number drop by 15 during what I thought was my guest’s hilarious presentation. Brutal lesson, but it taught me something crucial: engagement isn’t about being entertaining—it’s about being genuinely interested in your audience’s experience.

The engagement secret: Turn your audience into co-creators.

You don’t need fancy breakout rooms or elaborate production. You need moments where people feel seen and heard. Ask questions that matter to them. Use quick polls not as filler, but as genuine curiosity about their experience.

When someone shares in the chat, acknowledge them by name. When you see people engaging, call it out: “I love seeing these responses—this is exactly the kind of method that leads to more clients.”

The honesty approach: Break the fourth wall occasionally. “I know some of you are multitasking right now, and that’s fine. But this next part addresses the exact question three of you asked in the question tab, so you might want to tune back in.” Acknowledging reality often brings people back to the room.

3: “The tech, the timing, the chaos—I’m in meltdown mode.”

Running a live webinar can feel like conducting an orchestra while juggling flaming torches. Screen shares, audio levels, guest introductions, your own presentation anxiety—it’s a lot of moving pieces for one human brain.

Those early Typography Dojo sessions were held together with digital duct tape and prayer. I once spent the first five minutes of a live session trying to figure out why my guest couldn’t hear me, with 30 people watching me click frantically through audio preferences. Not my finest moment, but it taught me the value of ruthless simplification, and no fancy microphones were allowed on my show after that. (He ended up calling me on the phone and we talked on speakerphone for the rest of the livestream.)

The sanity-saving solution: Simplify ruthlessly.

Look at your run of show and ask: “Does this serve my audience or just make me feel busy?” Cut anything that doesn’t directly support your core message. Script your opening three minutes word-for-word. Know exactly what you’re clicking when, and in what order.

The confidence builder: Schedule a 15-minute tech rehearsal 48 hours before every event. Even for your tenth webinar on the same platform. Even when you’re presenting solo. That dry run catches the gremlins your stressed brain will miss under pressure, and it builds the muscle memory that keeps you calm when you’re live.

4. “What the heck am I even going to talk about?"

Content paralysis is real. You have expertise, experience, and insights worth sharing. But staring at a blank outline can make you question everything you know about your own field.

When I started Typography Dojo, I thought I needed my guests to teach everything about typography in every session. The result? Overwhelming prep work for my guests and confused audiences. It wasn’t until I started focusing on what they want to know, “How do you do what you do best?” that my content started clicking.

The content breakthrough: Teach what you already repeat.

Your best webinar content is hiding in plain sight—in your email responses to clients, in explanations you give colleagues, in the advice you find yourself giving repeatedly. What question do people want answered? What concept do you explain so often that you could do it in your sleep?

Start there to recruit speakers and craft the content that serves your audience.

The topic test: Can you summarize your idea in one clear question and three concrete takeaways? Can you tell a two-minute story that illustrates the main point? If yes, you have a talk worth giving.

The Reality Check

Here’s your practical cheat sheet:

• Low attendance? Share the story behind the topic, not just the topic itself

• Poor engagement? Create moments for participation, not just consumption

• Technical overwhelm? Simplify your setup and rehearse your flow

• Content paralysis? Teach what you already know by heart

The truth about webinars is this: everyone has something that trips them up. The professionals who seem effortless? They’ve just figured out their particular brand of chaos and built systems around it.

Those early Typography Dojo sessions were messy, imperfect, and occasionally disaster-prone. But they were also genuine, helpful, and supported by a handful of creative community members who showed up because they believed in what we were building together. That’s what made the difference—not perfect production values or flawless delivery.

Your next virtual event doesn’t have to feel like a high-wire act. With some intentional planning and a healthy dose of self-compassion, it can feel more like a meaningful conversation that happens to be broadcast to multiple friends.

And that’s a much more manageable way to think about it.

You made it to the end! Here’s the next poll! Put in your vote.👇