Failing Successfully – A Short Guide On How To Fail

**I wrote this blog post several years ago for a different project, I felt like re-sharing it here.**

There was a moment in history, we as people looked up for the very first time [at the stars] and never would it be the same.

We brought our own relevance and capabilities into question with a majesty that, to this day, maintains an unrelenting hold on our lives.

As sophisticated as we may feel we have become, as progressive as we may imagine we are, rest assured most of us find ourselves petrified by the thought of failure.

We are convinced that the world has an unforgiving memory and if we fail in the eyes of the world – however we define our world – we may never have the opportunity, the time or worse, the right to redeem ourselves.

I grapple with this concept everyday; in my businesses and in the conversations I have with friends, family and acquaintances alike.  There is an undertone in all of my conversations that inevitably reveal some form of fear of failure.  

To make a long story short; this fear of failure is often unwarranted.


Do you fear failure?


Do you fear the time it would take to recover from the failure (personal / professional image, lifestyle, etc)?

As soon as I made this distinction for myself, things began to change for me and you can do the same.

There are 3 very powerful concepts I would like to share with you, that I feel will help you arrive at my perspective.

Concept 1: Failure vs Time

Time Night Cap

Our fear of wasting time, ironically, can cause us to waste time.

Don’t take your time to fail.  Fail quickly. 

This advice is not to say throw due diligence out the window. But it is to say that there will be a moment you find yourself sitting on an idea, an idea that you have hammered out to the best of your ability, and you cannot seem to improve it any further – act on it.

You can either wait longer and hope you receive more insight through osmosis or you can simply start.  More often than not, you will come to observe the shortcomings of your idea much quicker and more thoroughly by starting.

I would rather start and understand the flaws in my idea in 3-6 months rather than try to anticipate every variable for a year only to learn I have flaws in my idea that I need to work on.

Concept 2: The Pedestal

Gore Vidal - No Consequence - Logicrat.jpg

“It is of no consequence what others think of you.  What matters is what you think of them.  This is how you live your life” Gore Vidal On Charlie Rose

On April 10th, 1998, Gore Vidal gave this piece of advice on Charlie Rose and it sticks with me to this day.  When we sit back and honestly evaluate how we tend to live our lives, we may come to find that we operate based on how we value our ourselves in relation to other people.  Our perception is paradoxically our greatest strength whilst also being our greatest weakness.

If you fear the potential recovery time it may take from a perceived failure, you are valuing someone else’s perception of you higher than your own goals and aspirations.

Understand that you are doing this….and…stop it.

Concept 3: Re-Framing Failure – The Dark Room Analogy

Dark Room 0 Night Cap blue

Imagine you are interviewing two potential candidates and you are asking them about their success in the “dark room experiment”.  The dark room experiment being put in a pitch black room with the task of finding the exit door out of the dark room.

C1 (Candidate 1) tells you about his experience.  He crept slowly across the floor, gradually inching his way to a wall.  After finding the wall, C1 traced the room with his hands on the wall.  Eventually, C1 bumped into a bookshelf.  Not intimidated, C1 slowly traced around the bookshelf and inevitably found the doorknob and exited the dark room.  C1 accomplished the goal in 5 minutes.

The second candidate (C2) tells you his story.  He also began to walk at a gradual pace and began feeling around the room – arms out.  C2 bumped into a chair, then a table, then the same bookshelf C1 did; constantly feeling around in the process.  C2 bumped into everything you could possibly bump into in this room but eventually found the doorknob but he did not exit right away.  After finding the doorknob C2 traced the entire room before finding the doorknob again before walking out.  This person accomplished the goal in  15 minutes.

Question: Imagine you have to partner with one of these two people (or hire them), who would you feel is more likely to succeed?

Society values time more than anything else.

It is our most finite resource.  In fact, we are just beginning to see companies monetize our time (think Uber and AirBNB).

Any company that can help us save time and bring that product or service to scale will undoubtedly experience exponential growth and success in the coming decades – but we are not companies.

The traditional perspective on failure and our value on time would endorse the 5 minute candidate over the 15 minute candidate.

Do you know why I would be more interested in the 15 minute candidate?

Because while the 5 minute candidate can boast that he accomplished the task in 5 minutes, the 15 minute candidate can tell me about every single piece of furniture in that room (every mistake that can be anticipated); perhaps even the materials they were made of (how detrimental each mistake could be).

The 15 minute candidate could also confirm for me that there is only one way out of the room (no alternative methods of achieving the same goal).

You see what I began doing there?  I began reframing the perception of “failure”.


To be able to extrapolate from what would traditionally be referred to as “failures”, you have in fact redefined the event or artifact all together.

Because at the end of the day, if you or a potential partner can extrapolate valuable information from their “failures”, are they bringing baggage to the group or project?

Or are they about to save you a hell of a lot of time?

You know…that thing we value so much?

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Powered by WordPress.com.

Up ↑

%d bloggers like this: