If your project requirements include items that lack a proven approach at the time you are estimating, you need to schedule them early in the project. Those are the things that will send you back to stakeholders to beg for increases in the budget and extensions of the schedule. Worse, if they are turn out to be unachievable, they may threaten the viability of the entire project. If you're going to have to pivot, you want to know that was early as possible.

Google has a helpful mental model for this - monkeys juggling torches on top of pedestals. Stick with me on this for a minute.Their innovation lab X (not the identically named Elon Musk company) focuses on moonshot projects. Each project they take on has three key criteria:

1. It has to be a huge problem affecting millions or billions of people.

2. The potential solution has to be so radical as to seem impossible today.

3. There has to be a reasonable prospect of a technology breakthrough that would make the solution possible in 5-10 years.

Those criteria select for extremely high risk, extremely high reward projects. There will always be more opportunities than can be funded, so early detection of projects that will ultimately fail the third criteria is critical. The only way to guarantee that sort of detection is to work on the hard parts first.

This is where the monkey comes in.If your project was asked to deliver a monkey juggling flaming torches while standing on a pedestal, where you would start. Most people would go for the easy win and start on the pedestal. You could probably run down to the home decor store and buy one. BOOM - the project is 50% done, right? Now we just have to find the monkey and train him.

If you started with the monkey first, you're probably going to come to the conclusion that the whole requirement needs to be rethought. Kudos to Annie Duke for turning me onto this example in her latest book, Quit: The Power of Knowing When to Walk Away and for swapping out X's monkey reciting Shakespeare for one juggling torches. Annie also provides the great example of the California high speed rail effort. The project has already spent $10B and is completely focused on the easy, flat sections of track (the pillars), with no clear plan for how to cross the mountain ranges (the monkeys) that make it hard to connect San Francisco and Los Angeles.The X website includes a lengthier discussion of their vision for moonshot thinking (https://lnkd.in/ezQP2jfD) that you may find interesting.

Ironically, Google failed to heed their own advice. Two days before Ms. Duke's book was published, Google announced that they would be shutting down X. In retrospect, creating the development model for a moonshot product was the pedestal. Creating the funding model was the monkey. In the days of free capital, a long path to positive cashflow from an investment was fine. Now that we're back to a more historically normal cost of capital, "Where's the money going to come from?" is an unavoidable question.