Are you stuck? You might as well enjoy it

Since I grew up deeply influenced by online media, I used to jump from interest to interest and opportunity to opportunity based on the latest trend. You know them, those bright shiny objects that lure the inexperienced because they have a nice ring to them: coworking, crowdfunding, blockchain, machine learning, etc.

After analyzing when and why my jumps happened, I realized it was whenever I felt I was stuck in a rut with my professional progression. Something new and shiny showed up and I jumped ship.

My problem was that I used to think that those moments when I felt I wasn’t making any progress were wasted time. Now I realize that they’re part of what’s needed to create things that matter, everything from a project to a personal relationship.

I have the opportunity to mentor entrepreneurs and sometimes they say they want to have a great team, sell a lot, and earn a lot of money, but they’re not willing to hear the hundreds of rejections that come along the way. They want the right to achieve big results in little time, but they don’t realize these results require hours upon hours of small learnings, learnings that at the time might feel insignificant. 

I wasn’t able to put this insight into words until I read the book Mastery by Robert Greene. The main idea I took from it is that the road to mastery has 3 stages:


We all know this one. It’s when we enter a new field with excitement and naiveté, without knowing exactly how much work lays ahead of us. We start learning the most important characteristics and tricks of the field, and we pretty much move forward by copying what others are doing. 

I like to think of this stage as the one where we learn the 80% of what there’s to learn. This is where fuck ups are sillier and seldom make a great story. 🙂

If we manage this steep learning curve and keep pushing forward, we start to gain fluency, and we master the basic skills which allow us to take on bigger and better challenges.


Eventually, we move from student to practitioner. We’ve got to grips with the basics and so we start dabbling and breaking things more purposefully. We use our own ideas and experiments, learning from feedback in the process. We develop our own takes on how things can or should be done. 

I like to think that in this stage we learn 15% more. Therefore, having 95% of knowledge in the area and having developed our own ways for years, we join the top tier. 


The keyword here is intuition. After much learning and practicing, we develop a systemic understanding of a field which allows us to innovate and break the rules without doing too much research, nor spending too much time on planning.

The first two stages are full of periods when we feel stuck. We keep doing what we’re doing but the project is not growing, we don’t have new insights, etc. 

The important thing to remember is that these plateaus are needed. They are where the important innovations and non-generic insights come to you. Sticking with it during the plateaus is what differentiates the amateurs from the people who actually might add something of differentiated value.

So, what was happened to me as I jumped from one thing to the next, looking for the next low hanging fruit? I’d say I was becoming the master of a lot of easy and stupid things that anyone can do.  I wasn’t developing a deeper understanding, nor mastery, because I was addicted to the highs that (supposedly) come from fast progressions.

Ok, but what can I do?

We need to find meaning in what we do in order to stick at it. But passion and purpose are not found, they are built. 

In order to embrace meaningful activities, we need to define what we value. Otherwise, we run like headless chickens behind new bright and shiny objects. 

Values → Meaning → Enjoying the Plateaus → Mastery

For example, I realized I didn’t really believe in equity crowdfunding when I realized that it was perpetuating systemic inequality because of where the money goes (mostly to white, privileged dudes from rich countries that want to build monopolies or addictive products). It was against the equality of opportunity that I value and in favor of the extreme consumer capitalism that I’m against. 

Sometimes preparation is mundane or repetitive and in itself feels far removed from success. In order to be patient and even enjoy the moments when we feel stuck, we need to be active in environments that align with our values and principles, even if they’re as weird as sharing stories of failure. 

In the long run, it will be deeply rewarding.

Pepe Villatoro

Pepe Villatoro

Fuckup Nights Co-founder

Pepe Villatoro is a globally awarded serial entrepreneur. He has created 5 companies, and was the WeWork Director for Latin North America. Currently, he is the co-founder and CEO of Fuckup Nights, a movement present in 330 cities in 90 countries, and collaborates with governments and companies to help create a shift in mindset. He loves travel, a good meal, and good conversations.