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?

The 4-hour Workweek Series: Defining the New Rich – their goals, objectives, and beliefs

Defining the New Rich

For most, escaping the 9-5 lifestyle is simply a dream that will never come to pass. But for those who do attempt to live like a millionaire without having to be a millionaire first, there is a predictable and repeatable process for breaking the shackles. While it was key that you understand the principles of 80/20 and Parkinson’s Law, it is imperative for you to learn the DEAL to being a part of the New Rich.

In order to take advantage of the shift in the new global economy, we have to unpack the process it takes for a person to enter the strange and unfamiliar world of the New Rich. From here on out, you are going to be a DEAL maker and conveniently this will also serve as the structure of our new workflow. DEAL is an acronym: Define, Eliminate, Automate, Liberate.

Today we are only going to focus on the first step in the personal transformation process: Define.

To be a part of the New Rich we first have to explore the difference between what the New Rich (NR) value as compared to Deferrers (D). A deferrer is a person who works their whole life for the pot of gold called retirement at the end of the rainbow. But retirement is only one objective/goal that differentiates the New Rich from the Deferrer. Let’s look at some of the other key distinctions that Tim elucidates for us:

D: To work for yourself.
NR: To have others work for you.

This subtle difference of who does the work is a real mind bender for someone who works at the office. But let’s keep going.

D: To work when you want to.
NR: To prevent work for work’s sake, and to do the minimum necessary for maximum effect (“minimum effective load”).

One of my favorite quotes by Frederich Nietzsche says something that man uses work as a form of entertainment. You aren’t working because you are simply bored are you?

D: To retire early or young.
NR: To distribute recovery periods and adventures (mini-retirements) throughout life on a regular basis and recognize that inactivity is not the goal. Doing that which excites you is.

Have you ever considered breaking up your retirement years and distributing them across your whole life? This thought alone got me buying a one way ticket to Hawaii the first time I read it. The second time, I went to Barbados to compete in a grueling mountain terrain half-marathon called ‘To Hill and Back’, which happened to be one of my fondest memories. The third time I read it, I bought plane tickets to Mexico for a month long excursion with my family.

D: To buy all the things you want to have.
NR: To do all the things you want to do, and be all the things you want to be. If this includes
some tools and gadgets, so be it, but they are either means to an end or bonuses, not the focus.

Stuff really doesn’t make life better. Case and point: if my newborn son is more entertained by wrapping paper instead of the actual present, chances are that you and I are not all that much different.
D: To be the boss instead of the employee; to be in charge.
NR: To be neither the boss nor the employee, but the owner. To own the trains and have someone else ensure they run on time.

There really is nothing like being the boss. But I really enjoy paying the boss to do what he does best, being accountable to me for the results that I am looking for.

D: To make a ton of money.
NR: To make a ton of money with specific reasons and defined dreams to chase, timelines and steps included. What are you working for?

Money is entirely worthless if you aren’t giving it purpose for being in your life. And this is more than just giving your money a budget or putting it to work through investments. This is about understanding that there are experiences in your life that you want and trading money for those experiences is more important than simply having the money.

D: To have more.
NR: To have more quality and less clutter. To have huge financial reserves but recognize that most material wants are justifications for spending time on the things that don’t really matter, including buying things and preparing to buy things. You spent two weeks negotiating your new Infiniti with the dealership and got $10,000 off? That’s great. Does your life have a purpose? Are you contributing anything useful to this world, or just shuffling papers, banging on a keyboard, and coming home to a drunken existence on the weekends?

I hope you felt that mic drop moment too.

D: To reach the big pay-off, whether IPO, acquisition, retirement, or other pot of gold.
NR: To think big but ensure payday comes every day: cash flow first, big payday second.

I have fretted over this key distinction for a long time. We all want the big payday, but what we all really crave is to know that my income requirements are being taken care of by the cash I made today – and every single day after that.    

D: To have freedom from doing that which you dislike.
NR: To have freedom from doing that which you dislike, but also the freedom and resolve to pursue your dreams without reverting to work for work’s sake (W4W). After years of repetitive work, you will often need to dig hard to find your passions, redefine your dreams, and revive hobbies that you let atrophy to near extinction. The goal is not to simply eliminate the bad, which does nothing more than leave you with a vacuum, but to pursue and experience the best in the world.

The reason that the New Rich and Deferrers diverge so radically in terms of goals and objectives is that they value completely different things and they orient their activity around entirely different beliefs. Conveniently, Tim has has listed 10 beliefs that the New Rich have that differ from Deferrers, and it is these beliefs that will ultimately begin the process of jettisoning a person (you) out of the office:

  1. Retirement Is Worst-Case-Scenario Insurance.
  2. Interest and Energy Are Cyclical.
  3. Less Is Not Laziness.
  4. The Timing Is Never Right.
  5. Ask for Forgiveness, Not Permission.
  6. Emphasize Strengths, Don’t Fix Weaknesses.
  7. Things in Excess Become Their Opposite.
  8. Money Alone Is Not the Solution.
  9. Relative Income Is More Important Than Absolute Income.
  10. Distress Is Bad, Eustress Is Good.

While beliefs and orientations are important steps in Defining your own personal transformation, in the next post in this series we are going to continue to Define ourselves by exploring our fears and re-awakening the excitement that comes with pursuing our dreams.