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Build the Scary Stuff First

Fear is a reaction. Courage is a decision. – Winston Churchill

Every great product leader I have worked with is fearless. Whether it’s a war room, a pivot, or a company-wide strategic shift, they always do something utterly frightening that changes the trajectory of the company. Seems to be a job requirement.

Why is the average product manager quite fearful then? Part of the answer is in the spirit of our frameworks:

  • MVP - build as little as possible to deliver the minimal value

  • Value/Complexity prioritization - quick wins trump all

  • Agile - everything must fit into a 1-4 week sprint

Tactically, these are invaluable frameworks, but they can easily destroy your mindset and make you fearful. A fearful mindset means thinking small, optimizing for the short-term, and avoiding large/unknown efforts.

Throughout human history, fearful people changed the world 0 times. Neither the pyramids nor SpaceX was built thinking “is there an easy quick way to do this?”

By doing a few things differently, you can be fearless too.

Nothing but Value

The essence of every product and company is to deliver value. Customers, revenues, growth, success, fame, and getting rich are all downstream effects of creating value. It is the hardest and most important thing, and the vast majority of products never achieve this.

The effort and time invested in creating real value are not important for 2 reasons:

  • If you’ve failed at this then you’ve got nothing

  • At scale, those big efforts diminish in light of the many customers you are now delivering meaningful value to. Think of Amazon and their massive supply-chain investments

Obsess about creating maximal value, not about avoiding effort.

High-Hanging Fruits are Yummy

You’ve recently been in a brainstorming session where all the ideas were boring and the one big idea got shut down within 30 seconds. Fear drives this behavior and your job is to fight it.

High-hanging fruits are often the real game changers. The feature that takes 6 months to get right but makes your product irreplaceable. The problem that seems unsolvable but becomes the reason people give you money.

By no means should you ignore the low-hanging fruit, but every option needs to be on the table. Scan the entire option tree first, then optimize for maximal value, and only then prioritize based on effort, risk, and other factors.

You can’t do everything, but you definitely can do anything.

Embrace Huge Efforts

How accurately can one estimate non-trivial efforts? Let’s put this question to the test.

You are the operator of the Washington Monument. The foundations have been eroding and you need to deal with it. How much effort will this take to fix?

Turns out that the foundations erode because harsh chemicals are being used. These chemicals are used to clean off bird poop. The bird poop is there because the birds come to eat the spiders. The spiders are there to eat the insects. The insects are the because of the night lighting. The night lighting is there because…?

The fix is to turn off the lights at night. An effortless fix.

You can never tell the true effort something will take until you commit to it. If you fear it, you’ll never find out. If you tackle it, you’ll find ways to scope it, break it down, and often you'll learn that up close, the devil is actually a cute puppy.

Sparking Innovation and Creativity

Do you know that guy at work who’s always working on the small easy stuff?

He wasn’t always like that.

Innovation and creativity rise to the surface when we tackle projects that are difficult and big, something that demands creativity and innovation, something that scares us.

But when we avoid effort and constantly work on the small easy stuff, we slowly but surely become lazy incrementalists. It is human nature to conserve energy and do as little as possible.

Remember, what you prioritize doesn’t only impact what you build. It impacts how things are built, and the spirit of every team member.


Fear used to keep us alive in the wilderness, now it gets in our way of building world-changing products.

The best product people are not literally fearless, they simply control their fear instead of it controlling them. They do this in 4 ways:

  • Nothing but Value - The essence of every product is to deliver large meaningful value. Without value, you’ve got nothing. Obsess about creating maximal value, not about avoiding effort

  • High-Hanging Fruits are Yummy - Your team will shut down ideas that scare them. You can’t allow this to happen. Let every idea be heard and confronted without emotions

  • Embracing Huge Efforts - Huge scary efforts often unlock the most value. They seem scary from far away but become smaller as you get closer. Any effort can be managed through scoping, breaking things down, and the ingenuity of your team

  • Sparking Innovation and Creativity - No matter how amazing your team is, they will become lazy incrementalists if all they work on is small incremental stuff, yet they’ll blow your mind with innovation and creativity if they get to work on challenging risky projects. Which one is scarier, a team of lazy incrementalists or tackling a complex and risky project?

This is how you train your fearless mindset: always put one scary, big, and ambitious rock into your priority jar. Put it in first, and the easy stuff will fit nicely in between.

If you have to fear something, fear a future in which you're not creating massive value.


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