Why Does "Fail Fast" Work?

Deconstructing Silicon Valley’s “Fail Fast” Using Baseball

Conclusion: Organizations that trade failure today for “feel” in the future create a lasting advantage over their competitors.

Explanation: When you expose yourself to failure, you also expose yourself to deeper orders of magnitude of problems, creating higher overall competence and value when you solve the problem.


It’s often heard that tech companies in Silicon Valley live by a motto of “fail fast” or “move fast and break things”. While many of these companies have gone on to create massive value, the mindset is still far from gaining widespread appreciation and adoption. So why does this “Fail Fast” mindset work? 

Surprisingly, we can look to baseball to better understand the value this attitude brings to create new and long-term value for teams.

Why Does “Fail Fast” Work?

Trade Failure for Feel

In the book “The Only Rule is that it has to Work”, the Ben Lindbergh explains a concept called “Feel”. In it, he describes how rookie baseball players make social mistakes on and off the field because they have “no feel”. Having “no feel” is the inability to conduct yourself in a setting.

When you start down a rabbit hole, you are trading the option of failure today for feel in the future. You can create a mental scaffolding of the situation and circumstances to “feel out” the situation in the future.

Obviously, most of us don’t want to find ourselves in “no feel” situations often, it can be the difference between long-term success and failure.

Orders of Failure

Which order mistakes are you making?

When you first begin attacking a problem, obvious solutions come to mind first. Things people without any specific knowledge can come up with. These are 0-order problems and 0-order mistakes. 

Unfortunately, anyone can come up with those solutions so the market tends not to reward these solutions. If you sit down and thoughtfully think through the problem, considering how others currently working on the problem thought through it, you may be on the first order. Reading books by experts in a field can lead you to this order of problem as well. These mistakes are slightly below the surface. You can probably build a business around solving these types of problems but you won’t get any sort of sustainable advantage if this is all you do. Fortunately for businesses, a very high percentage of people never take the time to solve this order of problems and gladly pay for their solutions.

If you go a level deeper and begin solving the problems that pop up within your solutions, you’re getting somewhere. We can begin to see how problems are nested within the orders of challenges, it’s a nonlinear adventure.

Companies that are willing to trade failure today for “feel” in the future can solve problems better because they have better “feel” for the problem space. They have been down the obvious rabbit holes and made the obvious mistakes. Stated otherwise, they’ve made the first order mistakes and are ready to solve second-order problems.

Since we now understand how exposing ourselves to new orders of problem sets exposes us to new business problems to solve, what else does it expose us to?

Tailwinds, your surface area of luck

When you step off the edge of your circle of competence, you’re in new territory. Most view this as a bad or scary thing. What this really means is you’re asking different questions to different people with different knowledge. This expands your surface area of luck. We define luck as good, unpredictable events that fall in your favor, typically driven by the actions of others. We want more luck, but not to be dependent on it.

When we explore new territories, we can visualize luck as a sphere. At any point within the sphere a lucky event can happen. As such we want as much area on the sphere as possible assuming luck is distributed evenly (which it not necessarily is). We don’t know how luck is distributed but we can say fairly confidently that people with smaller circles of competence generally seem to be less lucky. Some would even argue that you can grow your luck or productivity non-linearly with the introduction of new tools or fields.

To not confuse the map with the territory, we can understand our luck is not spherical but an asymmetric blob. The edges of our circles of competence in various fields define the edges of our surface area of luck. Push the boundaries of your circle of competence and you’re likely to find yourself luckier in the future.

Back to Failing Fast for Feel

The faster you can get to greater order mistakes and solutions, the more likely you can create and capture value. Since the entire premise of a company is to create, communicate, and capture value, this is where you want to get to. The length of time it takes is the opportunity cost you pay for feel. Companies who quickly pay the price not only have a culture oriented towards being comfortable with unfamiliar contexts, they also can begin extending their competitive advantage by working on deeper orders of problems. This rhymes with Paul Graham’s “we always ran upstairs when faced with problems”.


Pulling Away

Reading just 15 pages of a book a day totals to over 1.5 million words a year. If someone writes a 500 word reflection or blog post each week, they will have written 26,000 words in a year. You can imagine that these small habits can create a tremendous advantage when time is applied. Why does this matter? It’s tough to be consistently bad over time. For reasons that escape me, it seems hard for many humans to stay stagnant in skillset, especially when starting something new. I’d have to imagine that if you were to commit to these small habits requiring a few hours per week, you’d become at least a decent writer and reader over a span of 10 years. 15 million words later, you’ve been exposed to so many new ideas that it’s tough to be a “bad reader”. After writing over 250,000 words later, you might not be Hemingway but I can say with extremely high confidence you’ll have improved.

More importantly, progress is fun. Looking back and reviewing growth and progress smashes that dopamine “like” button. It’s a virtuous loop that begets itself.

The Bet You’re Making

Compare 15 minutes of reading daily to 15 minutes of TV. This TV compounds to 24 hours of commercials a year. Yes, that’s an entire day of your life per year dedicated to commercials. Go back and read “On the Shortness of Life” if you feel like that’s time well spent. 1.5 million words vs. a day of commercials is the bet you’re making. Not to mention you could trade that for with time spent with friends and family. Or you could choose to dig into deeper orders of business problems.

Pulling Away (In Business)

Take the lessons from the section above and apply them to business problems. Consider the impact that 15 minutes or an hour a day can have on the order of problem you’re solving. Not to mention that over time orders of problems suffer from erosion. (For a quick example, consider how easy it is to make a website today compared to even 5 years ago.)

What does the future look like without failure?

Hint: You’ll have no feel. Many wait until later in life to begin trying at the thing they claim they want to do. Unfortunately, they are trading the comfort of not failing for feel, and this is almost always a losing proposition, at the very least it’s disadvantageous. Small habits like the ones above go very far in advancing “feel”.


The Successful Traded Failure for Feel a Decade Ago

If you must compare yourself to others, don’t chase the people who are already successful. They traded failure for feel a long time ago and are likely orders of problems further along. They also may have a huge surface area of luck to go with it. The way you win is not by chasing the successful, but by resetting your time scale and extending it.

Don’t look at where others are, just get started on your own first million words.