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Home » NC Weekly 3: Stumbling on the right path – How randomness, algorithms and climbing can help you find your way in a complex world.

NC Weekly 3: Stumbling on the right path – How randomness, algorithms and climbing can help you find your way in a complex world.

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(Note: This post was initially published as part of my newsletter. )

Hi, hope you’re having a great Sunday!

Today we’re getting a bit geeky.

How do you choose the right path? How do you know which skill is the right one to learn at any given moment? What should you dedicate time to over something else?

I’ve been dealing with these questions over the past couple of weeks as I try and juggle several balls at a time. Agency work, affiliate site, this newsletter (and blog), reading a mountain of books, learning (html, css, poker, something else?), exercising and on and on.

If there’s one thing I’m glad this lockdown did, it’s that it removed any FOMO (fear of missing out) I had. At least on traveling, social commitments etc.

I’m stuck at home and dedicating time to all those activities got “easier”. But then you start accumulating stuff and FOMO is replaced by thoughts on opportunity cost. When you have more time, more options, it’s tough to know what to focus on.

Enter Hill Climbing

Chris Dixon wrote a great article where he suggests that the Hill Climbing algorithm could help you find your career path. In computer science, Hill Climbing is used to find the best possible solution between alternatives. This quick video is great for understanding the concept:

Dumbing it down would be: not sure you’re in the right direction? Just try a bunch of different things and see what sticks.

The problem with simple Hill Climbing is that you can get stuck on peaks (local maxima) that are not the tallest (global maxima). In addition to that, in the real world our career paths, our learning plans, are not simple 2D graphs.



It’s more like 3D. Hence why things are messy and complex.

Plateaus, ridges and greedy bastards

What happens when you’ve been climbing and climbing and suddenly you reach a big ass flat valley? Is it the end? The best you can do?

You have no idea. This is called a plateau, an “area of the state space where the evaluation function is flat”. Here, our poor algorithm has no idea which way to go to optimize its search. It’s the same when you start going up a ridge.

You’re blinded by your upward trajectory.

To make matters worse, the hill climbing algorithm is greedy as fuck (it’s actually called “greedy approach”), because whenever you’re climbing it always chooses a point that’s higher up than the previous one. He doesn’t care if momentarily going downhill would allow you to hop on a taller mountain. Bastard.

How to find your way in a complex, 3D world full of distracting hill tops

There are a few solutions to these issues that make hill climbing still effective in a complex reality and I think they can be applied to any endeavour whether our careers, learning, and even relationships.

Add in randomness

A more efficient version of the algorithm is called “Random Restart Hill Climbing”. It takes the standard process, where you look at two neighbouring points and always pick the uphill one, but adds in an element of randomness once you’ve found the temporary optimal solution. Then it restarts the process all over again (with the hope of finding the tallest peak).

Randomness here is what allows you to make sure you are not overlooking other, potentially better solutions. It gives you multiple tries to find the best possible starting point.

What can you do to spice things up? How can infuse whatever you’re doing with some randomness? For me it’s as simple as following a ton of different breadcrumbs when I’m researching or reading. Sometimes I find that I’m hating the article I’m reading but a link sends me to something else that’s excellent. Random, but perfect.

Allow sideways moves

Whenever we reach a plateau or a ridge, the common thing to do would be to keep going forward if we got there from climbing up, but remember this is a 3D world. So, what if we started stepping sideways? I think about this as changing careers.

When I left my job as a software engineer, I had just started dipping my toes into copywriting and UX. it was an entirely different world. A step sideways. Same when I decided to look into the basics of html and css a while ago.

As long as the move you make is not completely out of your current landscape (like jumping into a portal to another world), when you think it’s time because you’ve been plateauing for while you shouldn’t be afraid of making a step sideways. This is true for changing jobs, niche, learning a new, seemingly unrelated skill or reading a fiction book when you’ve been binging on non-fiction all your life.

Downhill doesn’t mean it’s the wrong way

Another improved version of Hill Climbing, called Simulated Annealing, allows you to move downhill as well as uphill. It’s the opposite of greedy because it forgoes short-term gains in the hopes of long-term ones. Another way of putting it is that it alternates “exploiting” with “exploring”.

It can mean for example taking a pay cut, but maximizing for learning…

It’s really important to approach what we do daily with an open mind and the willingness to explore with growing curiosity.

What we previously thought of as the wrong path, might instead lead us to the top of an even taller hill. We just couldn’t see it from where we stood.


That’s it for today. I hope this gives you something to think about and sparks some interesting ideas. I’m curious, what has helped you maintain the correct course in your life?

Here are this week’s top finds:


Passive income for the soul

  • Short and fun read. For some reason when you decide to drop all your goals and expectations for something to happen, you start appreciating the process a lot more. As a consequence you end up moving in the right direction towards your previously set goals. Weird but true.


Exploring Ayahuasca

  • I started listening to this series of podcasts where the Far Out guys talk about Ayahuasca. I’ve always wondered what the fuss was all about and this (plus another few episodes) goes in depth into what participating in a ceremony looks like. Very interesting.


How ‘The Last Dance’ changed our perception of Michael Jordan

  • If you didn’t watch “The Last Dance” Netflix documentary I recommend you do. Here, former NBA players Tracy McGrady and Richard Jefferson talk about how the documentary changed their perception of Jordan and how the series can inspire younger generations.

Have an amazing week!


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