Plan vs strategy, non-linear growth, climbing the wrong hill

Happy Sunday! Welcome to Work Less issue 42.

I'm in Kuala Lumpur for a weekend yoga event with my wife. Took the opportunity to visit Tsutaya Books, a new—and very cool—bookstore in town.

Tsutaya books

Plan vs. strategy

A plan is a set of steps you want to take based on the resources available to you. They are usually the best practices with predictable—sometimes guaranteed—outcomes. Everyone follows a plan because it's easy.

A strategy is different from a plan. A strategy is a set of things you want to do based on logic about how the world works and how it will turn out in the future. They are assumptions. The outcomes are uncertain.

Coming up with a strategy and seeing it through is tough because no one has done it yet. You could be wrong, and it's scary. But if logic is right, a strategy will change your business and life forever.

Growth doesn't happen linearly

Often, the best strategy to go up is to go down. To get to the highest mountain, you need to be willing to go down from your current peak into the valley and work your way up again to the next peak.

I experienced it throughout my fitness journey. To build muscle and bulk up, you need to be willing to gain some extra body fat. And to get lean and shredded, you need to be willing to lose some muscle mass.

The same applies to the exchanges of resources. If you want more time, energy, or money, you need to be willing to have less time, energy, and money for a while.

Climbing the wrong hill

On the same note, here's one of my favorite analogies from Climbing the Wrong Hill by Chris Dixon:

A classic problem in computer science is hill climbing. Imagine you are dropped at a random spot on a hilly terrain, where you can only see a few feet in each direction (assume it’s foggy or something). The goal is to get to the highest hill.

Consider the simplest algorithm. At any given moment, take a step in the direction that takes you higher. The risk with this method is if you happen to start near the lower hill, you’ll end up at the top of that lower hill, not the top of the tallest hill.

A more sophisticated version of this algorithm adds some randomness into your walk. You start out with lots of randomness and reduce the amount of randomness over time. This gives you a better chance of meandering near the bigger hill before you start your focused, non-random climb.

Another and generally better algorithm has you repeatedly drop yourself in random parts of the terrain, do simple hill climbing, and then after many such attempts step back and decide which of the hills were highest.

Archery, rip currents, and tall trees

The same analogy applies to many things in everyday life:

  • To shoot an arrow, an archer must pull the bow backward first.
  • To get back to the shore when caught in a rip current, let the current pull you away and swim sideways.
  • For a plant to grow taller and stronger above the ground, its roots need to grow deeper and wider underneath the ground.

More recommended reads

Get my email delivered to your inbox once in a while

Three to five things I learned—that will help you work less, earn more, and live a better life. (Also get notified of new posts and masterclasses)

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

👆 Join 3,100+ leaders, creatives, and knowledge workers today.

Dean is a strong voice in the self-mastery space. His newsletter consistently delivers insightful ideas on how to become a better version of yourself and is the only newsletter that I always read.

Sebastian Kade

Head of product and engineering