The 4 Hour Workweek Series: Defining the Nightmare and Living our Dreamlines

For this next part of the series I wanted to explore two of Tim Ferriss’s exercises in one post. When you read the book, the two exercises have their own chapters; but for this post we’ll go over both of them.

As was discussed in my last post, DEAL is the workflow acronym for the transformational journey of becoming a part of the new rich. And from the outset, it is key that we define what we don’t want to happen and what we do want to happen now that we have accepted that we are going to become a part of the new rich. Or, free our income from the tyranny of place and our direct input.

To do this, which is to become a part of the mobile elite, we have to come to grips with a truth that is a little unsettling: you are not the first, nor the dumbest, person to go on this journey of freeing income from place and action. What’s more, you could have done it a loooooooong time ago, you know lots of other examples of people who have done it, and it is something that you have always wanted to do. The question that I have for you: why haven’t you become a part of the new elite yet?

If you are like most people, and Ferriss asserts this as well, you are scared of what action might do to your life if you did what you were thinking of doing. It really is that simple.

What Tim proposes is a two-prong attack for preparing the launch pad into the new rich.

Define the Nightmare

The first exercise is called, Defining the Nightmare, and lately I have been asking people this question. When people talk about what it is that they want to do with their lives, or the big plans that they have, I ask them this simple question, “what is the absolute worst that could happen if you did what it is that you are thinking?”

Now, Tim advises that a person writes down the nightmare in gruesome detail, using as much feeling, color, and sensation as possible. But in conversation most people don’t want to sit and word vomit on a page and have a conversation. For me, I simply goad them on by asking them, “Really, what would be the nightmare if you did…”

My experience when asking people this question is that the nightmare that they conjure up actually sounds like a relief. Seriously, I asked an employee of mine this question with regards to her wanting to write a book. For her, the worst things that could happen is that people would discover that she writes like a hick, and that the nagging voice telling her to finish the book would go away. To this I simply say, “Doesn’t sound too scary after all when you think about it, huh?”

People are willing to live with self-doubt and self-criticism for years, decades even. And the reason for this is simple – people will tolerate familiar discomfort over investigating unknown excitement. Why they do this is simple, tolerating discomfort keeps you safe (for the most part) and investigating the unknown involves risks (sometimes). And for many, just helping them see through the ghost of the unknown, the proverbial nightmare tends to lose its power.

With that being said, just dispelling our nightmares is not always enough to get us to move forward. We also have to dream.


For the next exercise, Tim helps his readers understand that becoming a part of the New Rich, to undergo the transformational DEAL framework, is not about creating a vacuum of time. The purpose of freeing your income and person from place and responsibility is so that you can pursue what excites you. Ferriss is quite explicit not to use the word happiness because he believes that happiness is not motivating enough to get you to free your self. He would argue that happiness can be bought with a bottle of wine and a loaf of artisan bread. That’s where dreamlining comes in.

Dreamlining is the process of defining what will be true for you in the next six months. What will you have, what will you be, and what will you be doing now that you have become a part of the new rich.

What I love about this exercise is the emphasis on a short timeline (Parkinson’s Law), and the clear emphasis on being/doing instead of just having. So here is how it works. Take a piece of paper and you are going to write today’s date and the date it will be 6 months from today. Then you are going to create three columns, label them “Have” “Be” “Doing”, and turn on your thinking cap. What you are going to do is you are going to write down five examples of things that will change your life for you if they were true.

The litmus test here is Excitement, and much like Marie Kondo’s “Joy”, you have to feel the spark. What five things would excite you to have? What five things would excite you to be? And finally, what five things would excite you to be doing?

Here is an example of one of the Dreamlines I have made in the past. Once you are done with yours, I want you to circle the four things that excite you the most. The more unreasonable and outlandish the dreams, the more exciting and motivating those dreams become. (Mine are set in parentheses because I can’t circle them.)


(Less clutter)

A concubine

(Plane Tickets to Mexico)


(Less responsibility)


A captain

A fighter

A gymnast

A teacher

An Author


(Traveling Mexico to trace my English Roots)

Traveling to England to uncover my ancestor’s country

Starting a radically based academy

Posting a daily blog post

Consuming a lot of mushrooms in the desert

The four things that would excite me most were:

  • In six months I will have less clutter
  • In six months I will have Plane Tickets to Mexico
  • In six months I will have less responsibility
  • In six months I will have traced my English ancestry through Mexico

The key is not to do it all, but to limit what would make you most excited.

The next steps to Dreamlining are pretty simple. First establish a budget for each of those dreams; you can do the math of discovering what your Target Daily Income for those dreams needs to be if you want. Determine the actions you can take today, tomorrow and the next day for each of those four exciting dreams, and then do the first one today.

If you are ready to start becoming a part of the New Rich, you will need to first define you nightmare. Afterwards, you will be ready to define you dreams. Are you ready to start living your dreams?

3 thoughts on “The 4 Hour Workweek Series: Defining the Nightmare and Living our Dreamlines

  1. Pingback: Where I’ve been and what I’ve been up to | Alixander Court

  2. Pingback: You need to install a web-site blocker, a simple confession. | Alixander Court

  3. Pingback: The 4-hour Workweek Series: How to Eliminate Information and Interruption Overload – Alixander Court

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