The Five-Star Trap: Why Optimism (Not Perfection) Builds Better Plans
100% feels nice, but it won't get you anywhere worthwhile.
“Given these numbers, there’s no way we can set the target that high.”
Almost every planning cycle has a moment like this. Someone points to a line in a spreadsheet and says this with total confidence. It lands with a certain authority: the data has spoken, the limits are clear, and anything beyond that range feels irresponsible.
Scary even.
People nod because the argument sounds rational. Careful. Serious. Pessimism — especially when wrapped in numbers — has a strange way of sounding more rigorous than optimism ever does.
But that instinct, if you follow it unquestioningly, leads teams into a quieter danger: the urge to design goals that are safe, predictable, and perfectly achievable. The kind of goals that make everyone look competent… and keep the company exactly where it is.
And beneath that instinct lives an even deeper one: the pressure to keep a perfect record.
We’re all living in a five-star world now.
Uber drivers need five stars.
Airbnb hosts need five stars.
Most people want performance reviews that border on immaculate.
Inside companies, the same psychology kicks in: give me a target I know I can hit, so no one questions my abilities.
It’s deeply human. But it’s also the fastest way to build a plan that’s too small.
When Pessimism Sounds Like Rigor
What looks like pessimism almost never introduces itself that way. Nobody says, “I’m scared this might not work.”
Instead, it arrives wearing a suit and carrying a spreadsheet.
Someone pulls up a tab, taps a cell, and delivers their verdict with the calm certainty of a surgeon announcing a prognosis. The chart points down, the comps looks rough, the conversion rate “just won’t support it.”
Technically true, but misleading.
Because under all that sober logic is the same human reflex that once told our ancestors: rustle in grass = probably a tiger. Better run!
The modern version is more subtle: ambition = danger. So… lower the target!
And it’s amazing how often “being realistic” is just code for “I don’t want to stick my neck out.”
The mistake isn’t using data. The mistake is treating data like a ceiling instead of a floor — as if the past is the full map of the future rather than just a starting point.
The Five-Star Trap
Once you notice it, you can’t unsee it: the obsession with hitting 100% of goals is just the five-star rating system sneaking its way into planning.
Teams sandbag not out of laziness, but out of self-protection. A perfect hit rate implies competence. A miss — even on a stretch — feels like exposure.
But perfection in planning is almost always a sign that the targets were too low.
That imagination was too constrained.
Or that the culture quietly punishes ambition.
Any team hitting 100% of its goals is either cheating, under-reaching, or both. I’ve never once seen a group hit every “stretch” OKR without the goals being more padded than my toddler’s bike helmet. Perfect scores don’t mean “high performance”; they mean “we played it safe.”
Indeed, OKRs were originally built to prevent this. Hitting ~70% of an ambitious target was considered healthy. Missing was expected.
The problem is, over time, teams tend to drift back toward the siren’s song of perfect scores, turning goal-setting into performance theater rather than a tool for meaningful progress.
How to Build Plans That Don’t Retreat Into Safety
Here’s the tricky part: you can’t fix conservative planning by announcing… drumroll…
“Let’s be more ambitious.”
People will nod politely and then design goals that keep them batting one thousand.
You have to change the conditions around planning so ambition feels safe and workable, not reckless.
In my experience, three things matter more than anything else.
1. Make “ambitious but missable” genuinely safe
Teams only stretch when they know that missing the top of the range won’t get them punished or quietly downgraded.
And you can’t just say that misses are acceptable — you have to prove it when it happens.
When a team falls short of a stretch and everyone looks at you, your reaction sets the culture:
If you’re steady: “Awesome. We learned something. Keep going.”
If you tense up: “Err… uhh… we need to talk.”
People absorb that instantly.
And when it comes time for performance reviews and comp, you need to celebrate an 85% win. Which means you need to truly believe in that impact so you can go to bat for it.
That single act often breaks the five-star psychology more than any slogan about “embracing learning.”
2. Set the stretch — then define the value at 70% or 80%
You don’t need a multi-target system to cushion the blow of sub-100%. But you do need to make the stretch legible.
The way I’ve done it:
Set the ambitious target — the thing worth chasing.
Then explicitly outline what 70% or 80% would mean. Spell it out.
“If we hit 80%, it means X. That would be a strong outcome.”
“If we hit 70%, it still moves the business meaningfully.”
When you show people how the “partial win” still creates real value, the fear drops. Suddenly the conversation shifts from “What if we miss?” to “What would make this achievable?”
It reframes ambition as something with multiple successful outcomes, not one cliff edge.
3. Make the path unmistakably clear — metrics, sequencing, and visibility
Most fear around stretch goals doesn’t come from the goal itself. It comes from the fog and uncertainty between here and there.
That is, people often don’t mind aiming high. They mind aiming high with no way to tell if they’re on pace until Q4.
So your job is to burn off the fog:
Clear, observable metrics that update frequently enough to allow real calibration. When people can see the feedback in real time, they stop treating stretch targets like lottery tickets.
Crisp sequencing with the first handful of steps laid out clearly… not a giant hairball of parallel workstreams. When people understand how the goal will be built, it feels attainable rather than abstract.
This part isn’t about reducing the “cost of being wrong.” This is about reducing the ambiguity that makes people hesitant in the first place.
Ambition thrives in environments where the work is visible, trackable, and adjustable, not just pie-in-the-sky dreams.
The Real Goal of Planning
Planning isn’t about guessing the future correctly. (Good luck with that).
It’s about designing a path that forces progress — and making it clear enough that people can actually walk it.
If you create safety around misses, define the value in the middle of the range, and make the execution unmistakably visible, teams stop planning around simply looking good on paper.
They start planning for real impact.
And the moment that shift happens, the five-star trap loses its grip — because the culture is no longer judging people on perfection, but on meaningful forward motion towards goals worth hitting.