Adding Method to Madness — The Planning Process I Use to Achieve Unrealistic Goals

At the age of 15, I burned my first boat…and I haven’t stopped burning them since then.

I’m not talking about real boats, of course, I'm talking about putting myself in a position where I have “no retreat.”

Whenever I’m becoming a big fish in a small pond, I know it’s time to jump into a bigger pond — even if I’m not ready.

I have moved to new cities…

I have set near impossible deadlines…

Or I signed up for events, competitions, speeches, etc. that force me out of my comfort zone.

I do this so often, in fact, that I’ve built a process to achieve the “unrealistic.”

Think of it as a road map for those who believe they have what it takes to make it in the “bigger pond.” It won't provide a shortcut to being a big fish in that pond, but it will provide clarity on what it takes to get there.

I’m currently in the middle of yet another unrealistic goal, so I provided my step-by-step planning process with examples.

Step 1: How Did I Get There?

Visualize yourself having achieved your goal, but instead of the power of positive thinking method, don’t just visualize how great you feel.

Instead, ask yourself:

  1. What have you accomplished?
  2. What challenges did you overcome?
  3. Who helped you along the way?

This simulation will help you identify the key points along the path from where you are to where you want to be.

  • For help, this checklist provides all questions to ask yourself at this stage.

Step 2: Identify Milestones

Working backward, identify the key milestones you reached between now and then.

Start with the one you achieved that “sealed the deal,” then ask,

What major obstacle or challenge did I conquer in order for me to reach that milestone?

Then repeat for as many key obstacles that occur from where you are today to your goal.

Step 3: Next Steps

Now, that you have an outline, it’s time to connect the dots.

This round, you want to go more detailed and simulate each step you took to get the milestones.

Because it’s more detailed this time, you want to Think about each step you took from where you are to the first milestone.

Then you can give an estimate of when you can complete those steps and hit the first milestone.

Repeat for each milestone.

Step 4: How Did It ll Go Wrong?

Now, it’s time to identify all the things that could go wrong.

This isn’t to make you feel bad about yourself, it’s to identify everything that you need to be mindful of going forward.

As an optimist, this is always the crucial step for me.

It’s far better to confront your weaknesses with calm, cool-headed planning, than when you’re tired and stressed from pushing your comfort zone.

Get my Goals Checklist


One of the most effective life strategies I’ve used is leaving “burning my boats” and forcing myself into difficult situations. Left with no retreat, your brain will switch from thinking about excuses, to thinking about solutions.

I haven’t always been able to rise to the occasion, and failing in those situations hurts even worse than normal. That’s why I’ve been developing a method to my madness to help me learn, grow, and increase my chances of success.

If you ever decide to jump into a “bigger pond” I hope it helps you do the same!