You can’t know if you’re succeeding until you know what you’re aiming for
Success—whether personal, organizational, or systemic—depends entirely on your aim.
You can’t measure progress without direction.
By definition, progress only exists toward something.
One of the most familiar examples is someone making a lot of money… and hating their work.
It’s not the money that’s the problem.
It’s hating the work.
Because if they loved the work, they’d be successful by a different standard.
So the real question is:
What game are you playing?
And who decided the rules?
The Goal Doesn’t Define Success
The reason behind the goal does.
This is why I think less in terms of “goals” and more in terms of infinite games—the kinds of games you would choose to play for the rest of your life, simply because they’re worth playing.
You don’t need a perfect answer today.
But over time, it’s worth crafting one.
Here’s mine:
Family and Health:
To spend as long as possible fully engaged with the people I love—full of energy, experiencing peak moments, dreams, vitality.
You-Centered Systems with Multi-Scale Design.
To explore, publish, and teach about human systems—through books, articles, events, and real-world application through consulting.
Finances and Mastery.
To grow the reach of my work and deepen my capability through the two long-term assets that matter most.
These aren’t “goals.”
They’re games I want to keep playing as long as I’m alive.
A book published, a newsletter posted, a habit solidified—those are milestones within the infinite game.
And with that clarity, I now have something I can measure against—personally, professionally, and across the opportunities I say yes or no to.
The Goal Isn’t the Success Metric
A goal is not a success measure.
A goal is a marker along the way.
The real success measure is this:
Does this goal serve the game I want to keep playing?
You can achieve many goals and still fail—if they pull you off course.
You can also hold onto identities that no longer serve your current or future aims.
There’s a name for this: the shadow career.
It’s what happens when your actions, roles, and milestones are impressive… but misaligned.
They succeed by one measure, and fail by another.
And if you’ve never defined the deeper aim, you’ll have no way to evaluate which is which.
Wrong Measures Lead to Wrong Optimizations
Success or failure is often a short-term judgment—a snapshot of a moment.
But what you need is a way to assess the trajectory.
Are you learning?
Adapting?
Heading in a direction that matters?
When leaders lose sight of this, they start zooming in too far.
They obsess over metrics and meetings, budgets and colour-coded status reports.
Are we on budget?
Did we hit the deliverable?
Can we turn this from red to yellow?
But those are just current events.
They say little about effectiveness—especially long-term.
Zoom out.
You-Centered Systems with Multi-Scale Design.
To explore, publish, and teach about human systems—through books, articles, events, and real-world application through consulting.
I used to evaluate my success by how much coaching and consulting I was doing.
Now I don’t.
Because that was the wrong game.
And you don’t measure a road trip by the number of speed bumps.
Zoom Out Further
For a long time, I thought “coaching” and “consulting” were goals.
But recently, I saw the trap: those are identity labels.
And I was clinging to a past identity—even as my future was trying to become something else.
I still coach and consult.
But those are delivery vehicles—not destinations.
They’re part of the system, not the aim.
The work I care most about is You-Centered Systems with Multi-Scale Design.
That’s a current representation of the infinite game I want to play (I’m slowly learning that each time I think I’ve found ‘the thing’ a new layer eventually unfolds.)
Knowing the current, contextual purpose within a broader infinite game allows everything else to realign.
Letting Go of the Labels
Sometimes, an identity must be released so something new can emerge.
That doesn’t mean everything from the past is wrong.
But it does mean you’re done using it to define your direction.
This is the “death of identity” I’ve been exploring in my next book (The Necessity of Destruction).
- Becoming a parent changes your identity.
- Shifting careers changes your identity.
- Retiring changes it again.
- Letting go of the things that used to define you is what makes room for what’s next.
This isn’t just personal.
It’s organizational, too.
Cultures shift. Missions evolve.
And unless you zoom out from current operations to ask what game you’re really playing, you risk optimizing for outcomes that don’t matter.
What Still Holds True?
Here’s a question I often ask when things feel unclear:
When you zoom all the way out—and lose sight of the current event—what still holds true?
That’s a hint about your infinite game.
In The Five Wishes, Gay Hendricks tells the story of how answering one vulnerable question reframed his entire life.
That one question surfaced his true aims.
And from that clarity, he could see what mattered—and what didn’t.
When you know the game, you know the measure.
When you don’t, everything looks like success… or failure.
So—Are You Succeeding?
Here’s how you might begin answering:
- What infinite game do you want to play?
- Are your current goals aligned with that game?
- Are your current identities supporting or obstructing it?
- What needs to be released?
- What would success look like—not just today, but in 10 or 20 years?
You don’t need a perfect answer.
But you do need a direction.
Because you can’t know if you’re succeeding
until you know what you’re aiming for.
– Gerrett
This was originally published on Substack in my Human Systems Playground. But I’ve decided to bring all my writing home here.
