The Fastest Route to Your Goal Is a Crooked Line
We’re taught—implicitly and explicitly—that progress should be linear.
Set the goal. Create the plan. Execute harder. Repeat.
But in high-performance environments—whether in sport, leadership, or life—that approach often breaks down. The tighter someone grips the outcome, the more rigid their thinking becomes. And rigidity is rarely what produces breakthrough performance.
In my work with athletes and executives, I’ve come to believe something counterintuitive but deeply practical:
The fastest route to your goal is often not a straight line.
It’s a playful one.
When Chasing the Outcome Becomes the Problem
I see this pattern constantly.
An athlete becomes consumed with hitting a specific time, ranking, or performance metric. Training tightens. Races feel heavy. Confidence wavers—not because they aren’t prepared, but because they’re over-attached to how success must look.
The same thing happens with executives and founders. Revenue targets, KPIs, or career milestones become the singular focus. Decision-making narrows. Creativity drops. Teams feel the pressure. Ironically, the very effort to control the outcome reduces the likelihood of achieving it.
In both cases, the issue isn’t lack of motivation or discipline.
It’s outcome attachment.
Why Play Is Serious Work
From a psychological perspective, play is not the opposite of discipline—it’s a different mode of engagement.
Psychoanalyst Donald Winnicott described play as happening in a “potential space”—a psychological middle ground between inner experience and external reality. In this space, we’re not paralyzed by consequences or self-judgment. We’re free to experiment, explore, and discover.
Modern psychology supports this. Positive emotional states like curiosity, interest, and enjoyment broaden our thinking and expand the range of actions we can perceive. Over time, this broader mindset builds durable resources—confidence, adaptability, creativity, and resilience.
In other words:
- Play loosens fear
- Loosened fear expands options
- Expanded options improve performance
Play isn’t a distraction from excellence.
It’s one of the most reliable pathways to it.
Why Great Outcomes Are Often Side Effects
Innovation research reinforces this idea.
In Why Greatness Cannot Be Planned, researchers Kenneth Stanley and Joel Lehman argue that ambitious goals often cannot be reached directly. The path is too complex, too uncertain, or too novel. Instead, progress happens through what they call “stepping stones”—useful discoveries that don’t look like progress at first, but later become essential.
When we fixate on a narrow objective, we often miss these stepping stones entirely.
When we allow exploration—curiosity without immediate payoff—we collect experiences, insights, and skills that eventually converge into meaningful outcomes.
This is just as true in performance psychology as it is in innovation science.
Personal bests, leadership breakthroughs, and creative solutions often arrive as byproducts, not direct targets.
Improvisation: Training for the Unknown
This is where my background in improvisation—both in acting and music in Los Angeles—deeply informs my work.
Improv trains a very specific mindset:
- Act without certainty
- Stay present
- Build on what’s available
- Let go of “getting it right”
There’s no script. No guaranteed outcome. And yet, when it works, it works because of that openness—not despite it.
In performance terms, improv develops:
- Divergent thinking (generating multiple options)
- Tolerance for uncertainty
- Trust in process over control
These are exactly the skills athletes need when a race doesn’t go to plan, and executives need when markets, teams, or strategies shift unexpectedly.
The ability to say—internally—“Let’s see what emerges” is a performance advantage.
Beyond Win/Lose: A Non-Dual Way of Performing
Much of performance anxiety comes from binary thinking:
- Confident or not
- Winning or failing
- In control or falling apart
But elite performance rarely lives at the extremes.
A more effective approach is non-dual performance—the ability to hold multiple experiences at once without being ruled by them. Confidence and nerves. Effort and ease. Structure and spontaneity.
From this perspective, the question shifts from:
“Am I succeeding or failing?”
to:
“What’s available to me right now?”
Play naturally invites this wider field of awareness. It reduces self-monitoring and increases responsiveness. You’re no longer performing for the outcome—you’re performing with the moment.
Try This: 5 Playful Interventions This Week
You don’t need to abandon goals to work this way. You just need to relate to them differently.
Here are a few simple practices I use with athletes and executives:
1. Loosen the Goal (Temporarily)
Name the goal—then intentionally release it for a session or meeting.
Shift the focus to learning, feedback, or exploration.
2. Add a Playful Constraint
Instead of “perform better,” try:
- “Run with quieter feet.”
- “Lead this meeting asking only questions.”
- “See how relaxed I can stay under pressure.”
Constraints invite creativity.
3. Collect Stepping Stones
Afterward, ask:
- What did I notice?
- What surprised me?
- What worked indirectly?
Not everything valuable looks like progress at first.
4. Practice “Yes, And”
When something doesn’t go as planned, resist shutting it down mentally.
Build on it. Adapt. Continue.
5. Zoom Out
Notice where you’re trapped in win/lose thinking.
Widen the frame. Performance lives in the gray.
Final Thought: Let Outcomes Chase You
Goals matter. Structure matters. Discipline matters.
But when we hold them too tightly, they stop working.
Play creates movement where force creates friction.
Exploration reveals paths that planning alone cannot.
So loosen your grip—just enough.
Collect stepping stones.
Let curiosity lead.
Outcomes tend to follow.
