The heart, the hook, and the hustle: Lessons from 20 years in digital content

My first real content job was in a busy newsroom, where “going digital” meant copy-pasting into a clunky CMS and hoping the headline fit.

In the mid-2000s, “online” was still the side hustle of newsroom, not the engine. Headlines were written for page layout, not SEO. Articles were pushed live manually, often in a panic, and audience data meant counting comments. Two decades later, content isn’t just part of the business—it is the business. It drives leads and builds trust, and is often the sharpest tool in the box for small businesses trying to stand out in a crowded market.

Over the years, I’ve written and edited everything from war coverage at major news outlets to PPC copy for business software. I’ve built teams from the ground up and scaled content engines across markets and time zones. I’ve built and sold a media startup, led as CEO, and run dozens of scrappy experiments in between.

Here’s what I’ve learned—and what might help you make your own content work harder.

1. Everything is emotional – even B2B

Let’s get this out of the way: business decisions are emotional decisions. Yes, even for enterprise software. Yes, even for CRM integrations.

As editor in chief of The Cannigma, a science-backed cannabis education platform, we had to build trust with audiences that ranged from new users to medical patients to industry professionals. That trust didn’t come from facts alone. It came from emotion – relief, confidence, safety.

More recently, fuelled by hours-long conversations with my colleagues in the office and my ever-insightful partner at home about performance marketing, I’ve been formalizing this insight into something we call emotional driver mapping. Start with the pain (not just the problem). Ask: What fear is motivating this buyer? What desire? The fear of wasting money. The need to feel competent. The frustration of falling behind competitors.

Whether you’re selling mattresses or payroll software, if you can articulate your customer’s emotional state better than they can, they’ll assume you’ve got the solution too.

2. Structure sets you free

In my early career, I worked in breaking news at The Jerusalem Post, one of Israel’s major English-language dailies. The pace was relentless, the stakes were high, and we often filed stories before our coffee had time to cool. What kept things functional? Process.

Later, as I scaled the content team at a growing marketing firm in Tel Aviv, I saw the same truth play out: creativity thrives when operations are strong. I’m talking editorial calendars that actually get used. Templates that clarify, not constrain. Briefs that include a word count and a goal.

Even solo business owners benefit from content structure. A simple system for repurposing blog posts into email sequences can save hours. A standing review checklist can eliminate most of your revision rounds. You don’t need to become a project manager—but a little structure goes a long way when your time and budget are tight.

3. People before platforms

There’s always a new tool. AI content assistants. All-in-one CMSs. Campaign analytics dashboards with 74 filters.

And yet, I’ve never regretted investing in people more than tech. Whether building a brand or scaling ads, your success often depends on clear communication: strong briefs, aligned expectations, and editors who can sharpen a message without flattening the voice.

At Goodnet, a wellness and positive impact media brand I led as Editor-in-Chief, I helped grow a cross-cultural editorial team. We didn’t always have the best tools. But we had good feedback loops, shared goals, and a culture of trust. That’s what moved the needle.

If you’re running a business, focus first on your messaging team – even if it’s just you and a freelancer. Are you aligned? Are you clear on audience pain points? Is someone double-checking for jargon? Tools don’t build momentum. People do.

4. Don’t just track – listen

In B2B marketing, we’re trained to optimize. Track open rates. Compare CTRs. Run A/B tests.

That’s great, but data without insight is just noise.

I’m a proponent of a “sonar” approach to content testing. You send out a wave, for example five versions of a headline, three versions of an offer, and wait for the echo. Which ones resonate? Which ones bounce?

Then you zoom in. You rewrite based on what’s working emotionally, not just numerically. That’s how you build marketing that actually speaks to people’s needs, not just their inboxes.

For example: In one PPC campaign, the line “Scared your business might fail?” outperformed “Get paid faster today.” Why? The first speaks to fear. The second speaks to utility. And in that moment, fear won the click.

Small business takeaway? Monitor your numbers – but don’t forget to ask what story they’re telling. Don’t just track engagement. Feel it.

5. Breathe, then write

Let’s be real, content creation can be a grind.

There are weeks when you rewrite a homepage twice, brainstorm blog headlines over dinner, and send one last edit to your designer at midnight. And that’s if things are going smoothly.

Perhaps that’s one of the reasons I leaned more deeply into mindfulness meditation around the same time I started writing professionally. I now use insights from my practice daily in writing, leadership, and strategy. (I also finished my meditation teacher certification a few years ago.)

Stillness isn’t just a wellness thing – it’s a content thing. When I pause, I write more clearly. When I reflect, I edit with more empathy. When I stop trying to sound smart, I say what matters.

This doesn’t mean you need to meditate, per say. But before you hit “publish,” try taking a breath and asking: “Does this piece of content achieve its aim? Does it speak to the intended audience? Does this help someone feel more confident, informed, and in control?” If the answers are all yes, you’re on the right track.

What I’d tell my 2005 self

If I could go back to my first week in digital – newsroom chaos, blinking CMS errors, half-written headlines – I’d tell myself this:

“The tactics will change. The tools will get fancier. But at the end of the day, you’re writing for a human being with a problem, a goal, and a messy, emotional brain. Speak to that person and you’ll always be relevant.”

And if you’re a business owner juggling your first content hire, your fifteenth LinkedIn post, or your fourth attempt at a newsletter that doesn’t sound robotic, know this: your words matter more than your formatting.

Speak with purpose. Write like a human. Build something worth clicking.