What nobody tells you about being a PM

by Jack Dunn

Here's a secret: half the time, we're making it up as we go along.

Actually, it's probably more than half.

Not because we're unprepared, but because navigating the intersection of technology, business, and human psychology is like trying to predict the weather – theoretically possible, practically maddening.

The allure of being a PM

I didn't set out to work in Product. For many years, I worked in marketing and became fascinated by PMs. They seemed to occupy this magical position where they could gather all the inputs about a product, combine it with a business strategy, and orchestrate talented teams to bring solutions to life.

It looked like the ultimate leverage point—a role where you could impact millions of customers' lives. If any job resembled wielding a magic wand while playing Oprah ("You get a feature! You get a feature!"), product management appeared to be it.

The day-to-day reality? Vastly different from the glossy perception. Yet that hasn't diminished its appeal—I've been a PM for over 5 years now, completely hooked on the challenge.

You do get to witness incredible products come to life, but the true joy comes from embracing the uphill battle required to get there.

Decision making under pressure

During the pandemic, while working at a marketplace connecting travelers with attractions and museums, our metrics didn't just decline—they collapsed overnight. Our partners looked to us for support while facing existential threats themselves.

We had to pivot quickly with limited data:

Instead of facilitating far-flung adventures, we reimagined our value proposition around local exploration—helping people discover hidden gems in their own cities.

One feature I worked on directly addressed a major concern: booking ahead and losing money if COVID restrictions forced a change in plans. We created a flexible cancellation upsell that entitled customers to their money back if it didn’t work out.

This seemingly small change removed a massive psychological barrier and significantly boosted conversion rates. What started as crisis management became a permanent part of our value proposition, contributing to the company's current success.

The lesson? Sometimes the best decisions don't require months of debate. Just as AI can reason itself away from the right answer, we can also over-think ourselves into paralysis. Great product management often means making decisive moves and course-correcting along the way.

Embracing the beautiful mess

Here's the truth about being a PM: We're all navigating uncertainty.

Our role involves simultaneously steering the ship in the best direction while patching leaks below deck. It's more art than science—a continuous improvisation requiring equal parts vision and pragmatism.

To normalise this reality at my company, I host a regular "Product Show and Tell" where we explicitly invite people to "embrace the real, gritty experiences that make us better PMs" rather than just celebrating wins.

These moments of vulnerability and shared challenges help us recenter, declutter our thinking, and focus on what truly matters.

The chaos never disappears—you just develop a more graceful dance with it. And in that dance is where the true magic of product management happens.

You can find Jack here: https://www.linkedin.com/in/-jack/

Do you have any ideas you would like to share? Get in touch on LinkedIn 👇

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