My Planning Process for Achieving Unrealistic Goals

Over the last 6 years, I have deliberately put myself in "no retreat" situations. 

I have moved to a new city, I have set a hard deadline, or signed up to do something out of my comfort zone. Whenever I'm becoming a big fish in a small pond with my personal development, I jump into a bigger pond – even if I'm not ready.

I've done this so often, in fact, that I developed a process that helps me achieve the "unrealistic" goals necessary to make it in the "bigger pond."

Right now, I have yet another unrealistic goal. So here is how I planned to achieve it:

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 milestone that “sealed the deal,” then ask yourself,

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

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


Step 3: Next Steps

Now, that we 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 will complete those steps and hit the first milestone.

Repeat this process for each milestone on your path.

Step 4: How Did It All 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. 

Step 5: Break It Into Daily Goals


One of the most effective life strategies I've used is "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.

That's why I've been developing this method 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!