Planning for Prosperity Is Now a 5-Step Process
Everyone else was stepping back to reflect. Maybe I ought to as well?
A question landed in my inbox recently:
“Do you actually use that entire four-step planning process yourself — for your business or your life?”
It’s a fair question. Because we all know people who teach systems they don’t actually use or follow their own process and advice. But for me? Yes, completely; and ironically, using my own process this year is exactly why it changed.
For five years, Planning for Prosperity had four steps: Stepping Out, Stepping Up, Stepping In, and Stepping Through. That worked beautifully. Until this year, when my own planning process was unexpectedly influenced by those around me.
I Kept Bumping Into the Same Message: Reflect
During December and into January, I was working through my usual planning routine. Everywhere I turned — I mean everywhere — people were talking about spending more time reflecting. People I follow. My executive coach brother. Accounts I hadn’t paid attention to in a while. Even a workshop leader from one of my professional associations. All of them were emphasizing “Look back before you move forward.”
Now, I did have reflection in my process. But it lived inside what I called Stepping Out. It wasn’t the star of the show and shared space with the task of creating a bold vision that took one out of one’s comfort zone.
This year with so many people telling me that stepping back to reflect deserved more time and attention, I got curious. Instead of rushing past reflection so I could get to the “real” planning, I slowed down and gave it more room.
What I Noticed (And Didn’t Expect)
Let’s be honest — reflection is not always comfortable.
Looking at what didn’t work? Ugh.
Seeing where I played small? Also ugh.
Dreaming big enough to scare myself? Definitely out of my comfort zone.
But something shifted when I treated reflection as its own phase instead of a quick exercise to get through. My emotional reaction changed.
Instead of anxious, I felt curious.
>Instead of frustrated, I felt… surprisingly grateful.
>Instead of pressure, I felt grounded.
It stopped being “let’s review what went wrong” and became “ohhh… this is what I’m learning about myself.” Information learned from reflection on our past year informs our approach going forward. The process needs the energy of your attention to pull out all the information you can garner. That information feeds into the rest of the planning. What to do more, or less of? What needs a different approach? The reflection process needs strength and depth to support the other four steps with concrete information.
Step One Is Now “Stepping Back to Reflect”
Planning for Prosperity is now a five-step process, and it starts with Stepping Back. This step is about intentional reflection before planning forward. It creates awareness, emotional readiness, and clarity — not just a to-do list.
I was already using the exercise: What you wanted vs. what you got vs. how you contributed to that outcome. This is a powerful exercise that I love. It illuminates what was working and what wasn’t. The exercise spotlights one’s own behaviour – good back or indifferent – that contributed to that outcomes. It’s a fact-finding mission that produces insight and information.
With the reflection process taking the main stage in its own step, I added journaling prompts that took me deeper. For example:
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What am I ready to leave behind?
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What am I excited to carry forward?
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When did I do hard things?
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What actions actually moved the needle?
Those questions changed the tone of my planning. Instead of focusing on the gaps, I was looking at the gain. (Check out Dan Sullivan’s book The Gap and the Gain). I also started seeing evidence — resilience, growth, consistency, courage. From that place, visioning the year ahead felt energizing instead of forced. Once I had that clarity, the rest of the process felt more grounded and realistic.
Stepping Out — choosing goals that stretch me beyond what’s comfortable
Stepping Up — putting the real work, time, and money on the calendar, what is possible
Stepping In — managing the work by fine-tuning goals in focused 90-day blocks
Stepping Through — dealing with the fear, resistance, procrastination, and “gremlins” that always show up when we grow and evolve.
The structure is the same just better.
Why My Business Is Called Caldwell Evolution
As humans we are constantly evolving. That’s why my business is Caldwell Evolution – I’m here to support clients on their evolutionary journey. Our businesses evolve. Our tools should evolve too. This wasn’t a rebrand or a theory update. It came from sitting at my own desk, with my own plans, noticing what actually helped — and being willing to adjust.
Adding Stepping Back doesn’t slow the process down. It makes everything that follows more intentional, more sustainable, and honestly… a lot more helpful and therefore kinder.
And that’s a way better place to build a year from.
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