How to Turn “I Should” Into “I Did”. Optimists' blind spots, premortem and coaching process.

Too optimistic for your own good?

“You know, my blind spot might be being too optimistic,” a client, an accomplished business owner, told me recently.
“And I’m not sure it’s always working out well for me.”

"Should I invite more critical feedback from my team? Ask them to voice doubts more often?

Maybe.

Actually, something else might work better,

A premortem.

“A premortem is a risk management practice where a team imagines a project has already failed and then works backward to identify the reasons for that failure. This proactive approach helps teams surface hidden risks and develop strategies to avoid them, saving the business from potential big losses”

Not postmortem. Pre.

A client was happy and was ready to move on with the insight.

But insight isn’t action. Many people get all the insights and ... nothing changes in the way their life or business go.

As a coach, I’ve seen this before, insight without a system to follow through: no cue, no clear process, no reflection loop - nothing changes.

I always remind myself, when staring at multiple to-do items to work on to make progress towards complex goals – resistance is often a lack of clarity.

This is the process I use now, incorporating different coaching, habit and behavioral psychology schools of thought - to ensure our aspirations become our better futures.

From “I should” to “I did”

The 8-Step Practice Loop

  1. Define the behavior that’s not working anymore (Not just I want to be less optimistic, how does it look? If I were to videotape it, what would I see?).

  2. Define the starting point and your winning state.

  3. Identify the system that’s currently producing the problem (Every system is optimized to get the results it's getting now).

  4. Choose the practice that bridges the gap between now and the win.

  5. Design systems that support the practice, and block what’s not working.

  6. Set up a way to track whether it’s working.

  7. Schedule regular reflection and adjustment.

  8. Win🏆

Clarity crushes procrastination.

When I find myself staring at a pile of “messy work” delaying action - proposals, strategy, outlines - it’s not laziness. It’s lack of clarity.

Once I reset my North Star (why this matters), define the next step, and choose how to proceed today step-by-step, motivation replaces inaction.

So yes, I’ll hand over a premortem process draft to my client soon.
But more importantly, we’ll build the system to turn insight into our future.

Now over to you.

Think of one area of personal growth, one habit, one attribute, are you using a process like this?
And what’s one adjustment you can make this week to improve it?

PS Would love to hear your thoughts if you have them. Comment below.