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The Dip

Starting the journey into The Valley of the Unknown

Recently, I’ve been talking to a lot of entrepreneurs about The Dip — The really hard part of starting something new, where it feels like nothing is going for you. Seth Godin has written about The Dip and why it is an important part of the journey. If you feel like it’s you against the world at the moment, read on.

It can feel like the world is ending when you’re in The Dip

The Dip is something that anyone who ventures out beyond the walled garden of a corporate job will encounter at some point. The concept is paralleled in the Initiation phase of Joseph Campbell’s concept of the Hero’s Journey (pictured below). As an entrepreneur, it’s important to understand that a lot of the criticisms that you will receive from investors and potential clients will likely dissipate if you’re able to traverse The Dip. As Seth Godin points out,

“Extraordinary benefits accrue to the tiny minority of people who are able to push just a tiny bit longer than most.” Rather than fight it, embrace The Dip.

The Initiation

For background, the Initiation phase of the Hero’s Journey has several smaller parts (there are other iterations of the stages but for the most part this sums it up well):

  • Tests, Allies, Enemies: A series of tests that a hero must undergo at the beginning of the long and perilous path of conquests.
  • Approach to the Innermost Cave: The Hero makes final preparations before taking the final leap into the unknown. The Hero will face doubts and fears that had originally surfaced at the start of the journey.
  • Ordeal: The Hero must draw upon all of the skills and experiences that were gathered on the journey to overcome the final test.

After this, the Hero receives the Reward and begins the Return. As you can see from the above diagram, a majority of the journey happens in the Unknown. This is an area that isn’t visible to people externally. Typically, everyone will see the subsequent success and envy it. Those people won’t understand the trials and tribulations that were faced.


Frequently, I find myself consoling entrepreneurs that are negotiating The Dip in one form or another. Media provides a highlight reel of the good times, giving a distorted perception of the struggles that are necessary the fruits of success can be tasted. The Dip is an opportunity to prove yourself. A common set of questions that early-stage entrepreneurs may face are, “Why you? Why now?” Realistically, few people are just going to fund a hope or some idealistic ambitions. There are far more people that are interested in funding people that have solved difficult problems and come through the other side.

For this reason, it’s important to be resilient but at the same time, listen to what the market is telling you (even your advisors might not have the right answers). In the early stages, keep the burn low. This will give you more time to make mistakes and journey through the valley of darkness.

“If you can keep going when the system is expecting you to stop, you will achieve extraor­dinary results.”

Build from a small base

This might feel frustrating in an age that worships consumption and growth at any cost. Why take the time to get the basics right when the opportunity is so simple for you to see? What if someone copies the idea and gets out ahead of you, taking the market from under you?

Momentum starts slowly. Jim Collins’ concept of starting the flywheel is apt. It takes a massive amount of effort at the beginning and the indications of success will likely be missing. However, when compounded over time, all of the small actions add up. Momentum can build up from a freakishly small base

“It is so easy to overlook how powerful it can be to take something small and hammer away at it, year after year, without stopping. Because it’s easy to overlook, we miss the key ingredients of what caused big things to get big.”


Don’t get angry or annoyed when faced with any of the problems that you face at the early stages of a business. Treat them as challenges, problems to be solved, just like any other. The times that frustrate you in the early days will probably be some of the most fruitful and enjoyable times in hindsight.

In the words of the SEALS:

“Fast is smooth, smooth is fast”

Get the basics right and prove that you can execute. The competitors that you’re benchmarking yourself against may not even be there when you come out the other side of The Dip.

Read more at endeavour ventures




thoughts on early-stage investing and life generally

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Sam Gibb

Sam Gibb

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