4 steps to fail at anything

Ethan Steininger
4 min readFeb 22, 2018


Wait… what? Why would I want to fail?

There are an endless number of quotes, motivational sayings, videos, etc that preach how failure is the path to success, you just have to get back up and learn, yadda yadda yadda.

Cartoons always have the most quotable sayings (Jake the Dog — Adventure Time)

Most of us are familiar with the phrase “fail fast”, but what does it really mean and how can it be applied to business, hobbies, and even relationships?

Paul Graham of YCombinator has been preaching this mantra since the early stages of Silicon Valley and it’s grown to be the foundation of the fastest growing companies like Facebook.

Zuck said himself that Facebook has thousands of different versions live at any point in time. The goal here is to determine why each versions fail, so the organizer can answer: how do we get slightly closer towards success next time?

In order to be successful in any new endeavor, you must construct a framework for short-lived experiments whose goal is to fail with minimal time investment.

My goal with this article is to outline the steps taken in order to construct a short-lived failure-centric experimentation framework and then how to take the findings and apply them to your north star.

1. Define your success criteria

This is your north star. What are you looking to achieve? Be it your startup, established business, relationship, hobby, anything, you have a goal. Define this goal and quantify it.

Suppose you love to write Medium articles in your free time and your goal is to have 100 “claps” in a week since posting in order to drive more consultations to your firm. Or if you’re a startup and your goal is to have at least 50 signups per month in order to grow. What do both of these have in common? They are SMART.

No, they don’t have a high IQ, they follow the SMART framework:

Specific: clear and concise target (e.g. one sentence goal)

Measurable: quantifiable (e.g. 100 claps)

Achievable: it can be done (e.g. I’d hope so)

Relevant: it brings you closer to your goals (e.g. driving more consultations to my firm’s website)

Time-bound: realistic time frame (e.g. one week interval)

It’s important that your goal follows this framework so that you have a clear method of what to look for in a binary yes/no review after the fact.

I apply this same framework when I create my To Dos. My strategy for designing To Dos is on the backlog of stories to write, so be patient.

2. Construct the experiments

Alright now you know how to measure, it’s time to figure out what you want to measure.

In the example above, I want to increase the amount of claps so as to drive more consultations to my website. My goal is ultimately to drive more consultations but a precursor is to have 100 claps.

My experiments will consist of writing 4 different articles spanning wide ranging categories. These will be independent variables for those middle school science experiment memories.

My method of measuring is to monitor the “claps” each day following an article post. By day 7, I’ll record the total claps.

Different types of article categories experiment

I see the personal growth category has the most positive reaction and know that it

3. Fail fast

An article is a very quick way to gauge the results of an experiment. Other methods of conducting a fast experiment can be a simple Tweet.

Say you want to know the book title that has the highest click through rate for your next book about personal growth. A fast way to fail would be a blog post with different titles and content bodies, but even faster could be a tweet.

Different tweets could indicate different titles and the tweet/title that has the best like/retweet/comment rate could be your winner.

The key here is to create an experiment that has the fastest turn around time to yield the most learnings so you can move onto the next one, fast.

4. Document a post mortem and share key findings

The experiment is over and it’s time to write up and compile your findings into actionable insights for the rest of the organization.

Hopefully you have some sort of document repository in your business, life, etc. if not it’s time to start! I use Evernote for personal experiments and Confluence for business.

Share your findings with the rest of the organization or your future self. What did you experiment with? What was your independent variable? Did you learn anything new? How can it be applied in the future?

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We started VirtueTheory.com to guide founders, companies, and teams in their product development journey. We apply the above tactics and industry best practices to build a prototype and scale it, maximizing your odds of success.