⚡️TIWIKE: How to Build Habit Systems to Achieve Anything in 5 Years

Hello Dear Friend,

Welcome to the Sunday edition of the Things I Wish I Knew Earlier (TIWIKE) Newsletter!

Here is a four-step framework for building a habit system to achieve anything in 5 years.


TIWIKE #1: Write out the biggest possible vision for your life in 5 years

For the past week, I’ve been interviewing beta participants of the Big Bad Plan Challenge, and one thing has become abundantly clear.

​Henry Thoreau famously said that most people live lives of “quiet desperation.”​ This is as true today as it was 150 years ago. The reason is that people never take the first, and most basic, step toward a different kind of life.

Most people don’t take the time to write out clearly what they want their life to be like in the future.

I have been asking participants to give me words or phrases that describe their experience in the challenge.

Words like inspiring, thought-provoking, deep, profound, vulnerable, and enlightening have cropped up over and over. My follow-up question has been whether they have ever done anything like this before. Every single one of them said no.

Isn’t it insane that most people never ask themselves seriously what they want out of life?

That means life is happening to them rather than them happening to life.

No wonder why they are so quietly desperate! I want to help create a world where every person willing to do the work can escape this desperation and build a life filled with abundance, love, and meaning. The process of developing this challenge curriculum and then following up with participants has helped me crystallize a framework that anyone can follow to do precisely that.

If you are feeling that quiet desperation, then I have a simple message for you: you need a bad plan.

Since you want to do something you’ve never done before, how would it be possible for you to develop a good plan?

You simply don’t know enough about the murky, uncertain future to make anything better than a bad plan. The key is mustering the courage to make a bad, written plan, and then directing that courage toward implementing the plan. Feedback from the real world shows you all the holes in your plan, which allows you to fill them in and set in motion a process of increasing plan proficiency that inevitably leads to better and better outcomes.

All you need is the Bad Plan Framework, which has four components:

  • Vision for the future you want to create
  • Goals that would make this vision true were they to be completed
  • Projects that would complete these goals were they completed
  • Habit systems that consistently move you toward your vision, including time set aside to work on projects

The first step is to write out the biggest possible vision for your life in 5 years.

TIWIKE #2: Break the vision into specific goals

The opening paragraph of my own professional vision looks like this:

I envision a world where entrepreneurship is accessible to anyone bold enough to begin, where creativity meets discipline, and where imperfect action is celebrated as the foundation of success. Through my work, I aim to inspire, educate, and connect lifestyle entrepreneurs—creators who build businesses not to scale and sell, but to live fully and make an enduring impact on their communities and the world.

But a vision alone isn’t enough.

What are the specific milestones you need to reach to manifest that vision in reality? Don’t confuse goals with projects. Goals are quantifiable milestones. Projects are the groups of tasks that must be completed in order to reach those milestones.

One of my big projects to make this vision a reality is to build Bad Plan Academy, an online educational community for aspiring entrepreneurs at all levels.

A few of my goals for bringing my vision into the present:

As you read over your vision, ask yourself what specific milestones would signal progress toward that vision.

Brain dump as many goals as possible to create this list. Then separate the list into 1, 5, and 10-year goals. Then sequence the goals inside of each of those categories from most to least pressing.

The second step of the Bad Plan Framework is to break the vision into specific goals.

TIWIKE #3: Break goals into a set of sequenced projects

But goals alone are not enough.

What tasks need to be completed for you to accomplish those goals? Undertake the same exercise at this stage as the last stage. As you peruse your newly-crafted goal list, brain dump as many tasks you can think of into a single list.

Then group the tasks on that list into primary projects.

It will quickly become obvious which tasks should be subordinated under which other tasks.

Remember, projects are bundles of tasks that must be completed in order to reach your goals. Once all tasks are consolidated under particular projects, sequence the list of projects, with the most impactful projects first. Then establish a deadline for when all those projects will be completed.

I am busting ass right now to set the stage to launch the academy and the content ecosystem that will fill it up in the first week of February.

My wife and I are going to Thailand at the end of December to celebrate her graduation from nurse practitioner school (proud of you, Lee!).

I want to come back from that trip refreshed, then throw the full extent of my effort behind growing that business. My project pipeline looks like this:

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Inside each of those projects is the list of tasks I need to complete to conclude that particular project.

This is what it looks like inside the first project:

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The third step of the Bad Plan Framework is to break goals into a set of sequenced projects.

TIWIKE #4: Install project work into goal-aligned habit systems

What you do today determines where you will be in five years.

The best way to increase your chances of ending up in your ideal future is to do the things you need to do today to bring about that future. The only way I know how to do that is to build habit systems that are in alignment with your vision.

Projects and habits connect vision of the future to the present.

Articulate the vision.

Break it down into goals. Break those down into projects. Design the habit systems that contain all the tasks you need to do consistently to get there. Make completing projects essential to your habit system.

Then focus on executing the habit system and projects in your pipeline every work day.

​“Decide the type of person you want to be. Prove it to yourself with small wins.” James Clear​

This whole endeavor is about taking the necessary actions today to create the IDENTITY you want to have in your future vision.

This is an identity issue. Clear says every action you take today is a vote cast for a particular identity. What we want to accomplish with this Bad Plan Framework is the development of a written system (plan), that when completed ushers you on the most direct path toward your ideal future.

My daily habit system currently looks like this (it is ever-evolving, like the entire system):

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I have a corresponding weekly, monthly, and yearly habit system as well, but this gives you the idea.

It is made of the things I need to do every day to take me toward my ideal professional, familial, financial, and health-related goals, most importantly including project work time.

The fourth, and final, step of the Bad Plan Framework is to install project work into goal-aligned habit systems.

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