Defining Success in Life: the Dreamline Exercise

Without concrete goals you’ll never develop concrete plans to achieve them.

Above: One of my all-time dream destinations, Rapa Nui (Easter Island).

Last week Dan and Ian revisited a favorite topic: the Dreamline exercise. Despite having read the 4-hour Workweek at least 5 times, it was listening to the LBP#91 (Are you A Hustler or an Entrepreneur?) back in March that finally inspired me to sit down and go through the motions. (I wrote most of this post then, but this recent podcast inspired me to finish it).

Dreamlining can profoundly change your life. You just have to sit down and do the work.

Like a chess master, you want to see the end-game.

A chess master knows exactly what the end-game is and they’ve already thought through the next 20 moves to get there. When variables change they make small course adjustments, but ultimately check-mate is inevitable, if not in this game then in the next.

What’s surprising about my own life is how often I’ve been operating without a plan. A lot of us drift through life with general goals, like ‘get in better shape’ or ‘travel more’, but without more substance behind them these are just day-dreams.

One of the most effective ways I’ve found to define success in a concrete and action-oriented way is the Dreamlining exercise from the 4-hour Workweek.

dreamline worksheet

Dreamlining is just what it sounds like: thinking big (I mean, BIG) about what you want to do, determining the actual costs involved, and working on a plan to get there.

The purpose of the exercise is to define–without any kind of judgment (external/internal):

5 things you want,
5 things you want to be, and
5 things you want to be doing in 6 months or a year.

This an exercise in developing big, audacious goals, and it helps you determine the following:

What your highest aspirations are.
How much these goals will cost to achieve, in terms of money, time, and other resources.
Gives the guidelines for eliminating anything in your life that doesn’t move you closer to these goals.

While it sounds straight-forward, coming up with 15 things you want in life takes some work.

Realize that you have to go for it to get the most out of this: if you could do anything, if there was no chance of failure, if all social judgements go away, what would you want to do?

Or, the way I like to put this to people is: if you had $100 million in the bank, what would you do with yourself?

Here are the steps for working through the dreamline exercise:

Create two dreamlines (one 6-month, one 1-year) on a print-out or dreamline spreadsheet (see the TropicalMBA version here).
Sit down and meditate on what you would do if money were no longer an issue.
Write down 5 things you want to have, 5 things you want to do, and 5 things you want to be.
The key is to really write down what you want if there was no way you could fail. Money is no issue in this exercise and neither is capability. Don’t write down what social norms and conventions want you to write down either–this exercise is just for you.
Finish the worksheet by writing down the estimated monthly costs associated with each dream outcome and then a specific first step to get there.
Choose 4 things out of the 15 total that are most interesting/exciting to you.

And bam, if you really put your heart and soul into this you’ve just defined what you want and what it actually costs to do it, now you just have to make a plan for getting there.

How dreamlining currently works in my life

Once the dreamline is complete, I know what I’m working toward. I pull out a piece of paper (yes, paper), and write out these 4 goals in black magic marker (I’m a visual guy).

The next part is to work backward. What do I need to accomplish this month to get closer to the goal? I pull out another piece of paper and write out the big things that need to get done this month to move toward the goal. These are the monthly goals.

I do the same for the coming week: weekly goals.

Then I make a daily to-do list of no more than 2 major tasks off the week’s goals. What can I do today to make these things happen?

Then I start, right then, knocking out the tasks to make my dreams come true.

The key for me is the visual aspect. I need to see the high-level goals in front of me on a daily basis to remember what the most important things are (sometimes I feel like the lead character in Memento. Maybe I should consider tattoos…). I keep these pieces of paper on the counter*, and every morning I spend the first hour of the day evaluating the situation and figuring out what piece is next.

(*currently trying to figure out a way to do this on a computer. Best answer right now is the sticky note functionality on mac).

Eliminate the non-essentials / “minimizing monkey motion.”

If you’ve truly got your life’s primary goals in front of you, if these are the things that will really give you an activated, satisfying, and accomplished existence, then why would you work on anything else?

Sure, you currently have obligations that get in the way, like a job. The dreamline is the first step in evaluating the status quo: does the job get you any closer to your real dreams and aspirations? If not, it’s probably time to plan an exit strategy.

Having an explicit set of goals gives you the framework for decision-making: will this thing/activity/event bring me closer to my goals? No? Then forget it! Whenever I have too many things to do, it’s usually the result of not prioritizing correctly based on this framework or I’m adding filler that I don’t need. This is easy to write about, but it took me a long time to really get it.

The most productive and satisfying time I’m spending now are days spent when I literally do nothing that isn’t on this goal-oriented action list.

No email. No phone calls. No checking Facebook. No reading the news. Nothing. Suddenly I have a ton of free time. Suddenly I find myself moving toward my goals at a deliberate and astonishingly fast pace.

Focus and elimination of filler means more free time and less busywork. This is making me happier and a lot more productive. Beyond Tim’s examples of ‘work expanding to fill the time available’ there’s a growing body of research to support the work less get more done line of thinking. It’s almost scary how quickly you start moving in the direction you want your life to go in.

This part is key for lifestyle-business entrepreneurs: I use the same process here for goals in work. Once you have the goals laid out and the to-do list you’ve also given yourself a guilt-free way to stop working (the hardest part about working for yourself I’ve found). You now can stop working when you’re finished, whether it takes 10 minutes or 18 hours. This is a profound psychological tool.

How to automate for success

Many times in my life I’ve outlined the goal and the steps telling me what to do to get there, but I’ve failed to define “the cadence with which I check in on progress toward that goal.”*

Basically, without this piece your efforts are largely wasted. I’ve seen this many times in business too, where even when the cadence is initially defined (“let’s check back on this on Friday”), it isn’t codified/scheduled and the wheels fall of the cart after a week or two.

Don’t do this. Once you have the goals in place, write down exactly when you’re going to review progress and schedule a reminder. This is probably the most important thing you can do, because even if you didn’t have a goal in place you’ve already set aside the time to come to that realization and re-define success.

A weekly check is a great way to do it, but here’s one better: win the first hour and you win the day.

My worst and most unproductive days come when I jump right into work. It’s far better to relax and ponder for the first hour than start mindlessly answering emails.

My new routine is to wake up, grab my BulletProof Coffee, and stare at my pieces of paper that live on the counter/sticky notes. I spend the first hour thinking about the goals, my progress, and the next piece. Then I deliberately make a to-do list with the most important things. I don’t do anything that isn’t on the list.

And I’ve never been so effective, productive, and had more free time in my life.

* Thanks for that one Dan.

An Example of How Dreamlining changed my life in 2013

So although I’ve filled out this Dreamline worksheet before, I decided to take it a little more seriously after listening to LBP #91 back in March.

The interesting thing about the results of my first real Dreamline was that none of my 4 initial goals cost any money. They were all related to things I want to develop as a person, not material goods, which means every hour I spend making money is not necessarily going to get me any closer to them.

So for example, from my 6-month dreamline with the first action item:

Become a real lifestyle-business entrepreneur => Listen to the Lifestyle Business Podcast daily.
Fix previous injuries and get back in shape => Go through the MobilityWOD project from day 1. And wow, here’s where that took me.
Become a travel blogger => 2 hours writing each Friday, post x1 per week.

And so on.

When you have a flywheel like the dreamline spreadsheet and a schedule for working toward your dreams, things snowball and success becomes inevitable. It’s also naturally habit-forming: the positive feedback from doing things that are exciting can keep you going indefinitely.

If you haven’t completed the Dreamline exercise before I would recommend you take an hour this week and fill it out. Definition is always the first step to get anywhere and there’s no time like the present.

Props to Tim for developing the first Dreamline exercise (and to David Schwartz for what I believe is the original inspiration), as well as Dan and Ian for actually motivating me to do it.

Resources: Check out the TMBA #40 for more resources on this, and make sure to listen to the episode.

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