🧮 Solving the fear/opportunity correlation

Ten minutes before going live online, I’m sitting in my Dublin hotel room—comfortable overall, but bland as expected, and with the lighting conditions of a serial killer’s basement.

I’m staring at my laptop’s WiFi indicator, and I’m thinking: “I should have said no to this.”

The workshop I’m about to give is for The Roost—Louis Grenier’s community of exceptionally smart marketers who have zero tolerance for BS. And I’d been dreading this moment since first checking into my room two days earlier.

Not because I didn’t know my stuff. But because I couldn’t control the variables.

The date for the session couldn’t be moved, so I knew I’d be away from my carefully controlled home office. And hotel internet is… well, you know.

Let me save you the suspense: things went wrong, and everything was OK. But the whole story is a good reminder about the important relationship between fear and opportunity.

The cost of playing it safe

It would have been so easy to decline this webinar when Louis and Diana first invited me.

New uncontrollable environment. Too much risk. Easy to justify as the “responsible” choice.

But I stopped and reminded myself that the opportunities that scare us are often the ones most worth taking.

Every time we optimize for comfort over growth, we’re making a trade. We avoid temporary discomfort. But we also avoid proof of what we’re capable of handling. And all the benefits of handling it well.

And here’s the kicker: the opportunities that make us most nervous are usually the ones that could move us forward the most. Imperfect circumstances let you showcase your work to high-caliber audiences we’d love to connect with and impress.

These are exactly the experiences that build our professional confidence. But only if we say yes.

The regret of “what if I’d said yes” tends to last longer than any momentary anxiety.

When your “worst case” becomes reality

About 15 minutes into the session, my screen froze mid-sentence.

At least Zoom had the decency to drop me from the call almost immediately.

The exact scenario I’d been dreading was happening in real time.

But here’s the thing: I’d prepared for this. I had a Plan B connection ready. I switched over, got back online, and delivered the rest of the session without another glitch.

The “worst” happened. And I survived it.

Actually, more than survived—the session went great. People were engaged, asked smart questions, and genuinely appreciated the content.

The difference between fear and preparation

There’s a gap between catastrophizing and contingency planning.

Catastrophizing is: “The hotel internet will fail and I’ll look incompetent and ruin my reputation.”

Contingency planning is: “Hotel internet might fail. I’ll have a backup connection ready and a plan to switch quickly.”

You can’t control everything. But you can prepare for likely scenarios without letting fear stop you from saying yes.

Here’s what helps: identify what you’re actually afraid of. Not the surface worry, but the real fear underneath. For me, it wasn’t really about the internet—it was about looking unprepared in front of people I respect.

Once you name that fear, you can ask: what would make this manageable? Not perfect. Not risk-free. Just manageable enough to say yes.

Sometimes it’s having a backup plan. Sometimes it’s adjusting your expectations. Sometimes it’s simply acknowledging that if the worst happens, you’ll figure it out in the moment.

The goal isn’t perfect control. It’s adaptability. And the confidence that you can handle things when they don’t go as planned.

***

The real win from that Dublin hotel room wasn’t the successful workshop.

It was reminding myself that worst-case scenarios are survivable. That the fears we construct in our minds are often more paralyzing than the reality of things going wrong.

And that we’re all one “yes” away from discovering what we’re actually capable of handling.

The leap matters,

📆 Save the date

Visual Branding for Marketers

Does your design align with your brand strategy? Do you know how it plays into your sales funnel? And can we, non-designers, get a proper sense of the different visual assets that play into a memorable brand? I’ve asked my hands-down favorite brand designer Sarah Hart to join us for a live session and discuss all of these questions.

Register for free here →

👌 Handpicked stories for you

Here are some interesting things I stumbled upon this week while reading, writing, researching, and being a generally curious marketing person on the internet:

💼 Three for work

How to Create a CTA that Gets Clicked (and an AI prompt that helps) | A good primer on CTA best practices and persuasion principles at play. I’m definitely testing the AI prompt from the post, but I’d also give the model some directions on my USPs, not just the target persona description.

The tells that reveal you’re not ready for the next level in content marketing | The truth is not every content writer is a good content marketer. This list covers important points from both a writing and a higher-level strategy and leadership perspective.

How to Turn Audience Research Into Content Ideas | If you’re stranded for content ideas, this workflow can help you find new perspectives worth exploring. It’s not complex, and that’s the beauty of it!

👀 Two for fun

This exploration of our need for purpose | We’re always looking for meaning, and the truth is, this is a search doomed to fail. What can make us feel better is getting comfortable with uncertainty.

This statistical analysis of life-changing books | This is a pretty cool look at numbers that can help us find meaning. It’s also a great exercise in statistics.