Two negative questions every Operator should ask.

mindset Nov 06, 2025

I gave a presentation on Thursday about some new products we’ve been developing behind the scenes. 

But at the start, I wanted to share a quick insight about who we are as a business and where we’re going in the future. 

One of the slides was titled: 

What Pisses Us Off About The World…

And as I said those words aloud and got a few giggles in the audience, it occurred to me that this isn’t a normal thing to say during a presentation to clients and partners, but it's also a unique lens to look through.

As it flashed up, I thought for a split second I'd made a mistake. I thought I should have used more approachable words.

But it was too late for that, so I leaned in.

It just felt normal for me to view the world and speak from this perspective.

I finished the presentation and we had a great discussion at the end. People were pleased to hear how we approach things and see the outcomes.

As I walked back to the car afterwards, I realised how powerful that lens is. 

The Negative

But not to be negative

Rather, to inspire action. To light your fire. To wake you (or others) up and find solutions. 

When you look at what’s shit in the world you normally have a visceral reaction that compels you to want to do something about it. 

Applied to your life, your business, or your industry, it offers a great villain for entrepreneurs to go up against and fix shit.

When you’re genuine about negativity and use it positively, it can be a compelling motivator. 

And if you want my honest opinion, we’re all told too much to "stay positive". Visualise the win. Manifest success. Only good vibes welcome here...

In my experience, lovely vibes aren't always what drives you to solve interesting problems.

I don’t know about you, but for me, focusing on the negative has helped me more times than visualising the win… 

Especially when you spend time thinking about what could go wrong (without it becoming crippling worry). 

I’m talking about preparation and anticipating possible outcomes. Or more formally, premortem discovery.

Here's what I mean.

Instead of asking “How can we succeed?”, you ask:

  • What would cause this to fail completely?
  • If we lost everything 12 months from now, what would have caused it?
  • What blind spots are we ignoring because we’re too optimistic?

This isn’t about instilling fear in your team.

It’s about building antifragile businesses—ones that get stronger because of the hits, not in spite of them.

Which is exactly the type of thing you need to survive these days.

The same type of thinking can be applied to nearly anything. 

A marriage. A business. A project. 

So here are two valuable (negative) things worth trying this week:

  1. Ask what pisses you off about the world, your industry, you life, your product. Then make a plan to do something about it. 
  2. Pick one major goal, project, or assumption you’re betting your future on, then list the top 3 ways it could completely fail. Then build a system to make sure that doesn’t happen.

It might be clunky to begin. Uncomfortable even. 

But often, that discomfort is where the best solutions come from. 

I hope it helps you as much as its helped me in the past.