At one point, I thought I was doing well.
Not rich, not where I wanted to be, but at least moving in the right direction.
Businesses running, bills paid, building something. By most measures, I was ahead of where I started. That felt like enough.
Then I sat down one day and actually tried to answer an honest question: Am I really achieving prosperity, or am I just comfortable?
I didn’t have a clean answer. And that bothered me more than I expected.
The two things feel similar from the inside. Comfortable means your life isn’t falling apart today. Prosperous means your life is genuinely expanding. Your options are growing, your capability is compounding, and the version of you five years from now is meaningfully better than the one sitting here right now.
I wanted to know which one I was actually living. So I built a tool to find out, for myself first, and now I’m sharing it in the hope it’s useful for someone else.
The Problem With How We Measure “Doing Well”
Most of us are working with an incomplete scorecard, especially if you’re an entrepreneur.
The one we’ve been handed has one column: money.
Net worth, income, the size of the investment account. And look — money matters.
I’m not going to pretend otherwise. But I’ve learned that money is a lagging indicator.
It tells you where you’ve been, not whether you’re equipped to get where you want to go.
You can have money and zero control over your time.
You can have money and skills that are quietly becoming obsolete.
You can have money and a body that’s running on fumes, relationships that are slowly eroding, and no real sense of where you’re heading.
Technically successful. Not actually prosperous.
The gap between those two things is what I wanted to measure.
The Individual Prosperity Index
After some research and testing out a few factors, I landed on five pillars that I referred to as the Individual Prosperity Index.
It explores the conditions that I believe determine whether your life is expanding or contracting.
Not your account balance. Not your title. The stuff underneath both of those things.
🧭 Agency — Are you steering your life, or just reacting to it?
This is control. Real control, not the illusion of it.
Do you choose how you spend your time, or does your week just happen to you? Can you make a significant decision without months of paralysis?
Low agency looks like a calendar that belongs to everyone else. High agency looks like a life you can actually recognise as yours.
🛡️ Security — If something goes wrong, how protected are you?
How fragile are you, honestly?
If your income stopped tomorrow, how long before the panic sets in? Do you have single points of failure: one client, one income stream, one skill set, the market could devalue overnight?
Security isn’t about being risk-free. It’s about not being one bad event away from crisis.
⚡ Capability — Can you reliably turn your intentions into outcomes?
Skills, yes, but also health, energy, focus, and the systems that let you execute consistently. Are your abilities increasing in value year on year, or quietly depreciating?
A lot of smart people are operating well below their actual capacity because the fundamentals like sleep, movement, and routines are quietly wrecked. They think they have a strategy problem. They have a capability problem.
🌿 Wellbeing — Is your life actually sustaining you?
This isn’t soft. This is your fuel. Chronic stress, isolation, and physical depletion don’t just feel bad; they destroy decision-making, kill execution, and make everything harder than it needs to be.
Are your relationships strengthening or slowly eroding? Is your body supporting your ambition, or quietly working against it?
📈 Trajectory — Are your options expanding or shrinking over time?
Not where you are but where you’re heading. Are you measurably better off than you were 12 months ago? Are you building assets: skills, capital, systems, relationships, reputation that compound over time?
This is the pillar that separates people who are progressing from people who are just busy.
Where You Actually Stand
Here’s the thing about these five pillars: most people have a rough sense of one or two of them. They know their finances are shaky, or they know they’re burned out. But they haven’t looked at all five together, and that’s where it gets interesting.
Because the pillars affect each other.
A low Security score makes your Agency feel worse than it is.
A low Capability score quietly kills your Trajectory.
The place where you’re weakest is often the thing silently limiting everything else.
I didn’t know which one was holding me back until I measured honestly across all five.
If you want to find out where you actually stand, not where you hope you are, not where you’d like to be, the IPI Scorecard walks you through it.
Ten questions.
Specific behavioural anchors for each score, so you’re not just guessing.
A guided reflection on each pillar to help you understand not just your score, but why it is what it is. And a structured space to commit to one 90-day action on your biggest bottleneck.
It takes about 15–20 minutes. Most people find it uncomfortable in the right way.
Download the IPI Scorecard & Reflection Worksheet → Link here