Why my “perfect” plan flopped

Let’s talk about that moment every business owner dreads: pouring your heart (and a chunk of your budget) into something you’re sure will be a hit, only to watch it flop.

You know the feeling. You do everything “right,” follow the playbook, and… take a big L. It’s like throwing a party and realizing you forgot to send the invites.

I’ll admit, I’ve been there more times than I’d like to count. A while back, I launched what I thought was a killer workshop. I’d spent weeks planning, built a fancy landing page, lined up some testimonials, and even roped in a few friends to help spread the word. I hit “send” on my email, cracked open a cold drink, and waited for the signups to roll in.

Except, they didn’t.

Not a single one that first day. I refreshed my inbox so many times I thought my keyboard would give out. Day two, nothing. By the end of the week, I had a grand total of three signups, two of which were from people who’d already bought from me before. It stung.

Here’s the thing: I’d fallen for a classic trap. I assumed my audience cared about my offer just because I did. I skipped the part where I actually listened to what they needed right now. I was so focused on what I wanted to teach, I forgot to check if anyone wanted to learn it.

So, I did something that felt a little awkward at first: I started asking questions. This was not a survey or poll but rather a series of informal conversations. I reached out to a handful of folks who’d been on my list for ages but had never bought anything.

A couple of them ignored me, but most were happy to chat. Turns out, my timing was completely off. They weren’t looking for a deep-dive workshop. They wanted quick wins — tiny, actionable tips they could use on a busy Tuesday.

That single insight changed everything. I scrapped the big workshop idea and started sending out short, punchy tips instead. And wouldn’t you know it, engagement shot up. People replied. They shared the emails. Some even asked for more.

A few months ago, I did do the workshop, and it was quite successful. But I’ve learned the lesson (the hard way): don’t build in a vacuum.

If you’re feeling stuck or your audience isn’t biting, take it as a signal, not a failure. Get curious. Ask real questions. You might be surprised by what you hear.

If you want to try this yourself, here’s what worked for me:

1. Pick five people from your list who’ve never bought from you.

2. Send a short note, something like, “Hey, I noticed you’ve been around for a while. Mind sharing what you’re struggling with lately?”

3. Listen more than you talk. Resist the urge to pitch.

4. Look for patterns. If three out of five mention the same headache, you’ve found your next topic.

You don’t need a big audience to get this right. You just need a few honest conversations and the willingness to adjust course. Trust me, it beats guessing.

If you have a similar story or would like to share what has been effective for you, please feel free to reply. I read every mail and always learn something new.

— Shashank

Marketing ideas for marketers who hate boring

The best marketing ideas come from marketers who live it. That’s what The Marketing Millennials delivers: real insights, fresh takes, and no fluff. Written by Daniel Murray, a marketer who knows what works, this newsletter cuts through the noise so you can stop guessing and start winning. Subscribe and level up your marketing game.

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