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Personal reflection

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Leadership

The power of a courageous question

Unatributed
May 21, 2025
In an era where old playbooks no longer hold, leadership demands a different kind of courage. Speaking at the Fortune Most Powerful Women International Summit, SYPartners CEO Jessica Orkin explores how bold questions—rather than fast answers—help leaders navigate uncertainty, unlock innovation, and design organizations for both performance and humanity.
2025-05-21
Leadership
Decision-making
Leadership behaviors
Mindset shifts
Strategy activation
Personal reflection
Creativity

The beauty of an unspoiled mind: 4 creative benefits of practicing not being an expert in your field

Unatributed
November 16, 2021
In a world built on best practices and proven frameworks, creativity can narrow under the weight of expertise. Original thinking requires the discipline to question assumptions, trust intuition and resist defaulting to what is already known. Protecting an unspoiled mind creates space for courage, imagination and new ways of seeing.
2021-11-16
Creativity
Imagination
Mindset shifts
Personal reflection
Purpose

Reflecting on flourishing

Unatributed
June 1, 2022
As conversations about work, purpose and well-being evolve, flourishing has emerged as a critical lens for navigating ongoing disruption. Drawing from recent convenings and lived experience at SYPartners, this reflection explores what flourishing really means, how it shows up at different levels, and why it requires both systemic support and individual intention.
2022-06-01
Purpose
Human systems
Personal reflection
Leadership behaviors
Creativity

Between image and reality: How we all perceive the world

Unatributed
December 20, 2016
In an era shaped by images, narratives and belief, the line between truth and fiction has grown increasingly unstable. This article explores how perception, imagination and design shape what we accept as real—and why restoring clarity and responsibility in communication is essential to understanding the world we share.
2016-12-20
Creativity
Imagination
Design
Personal reflection
Leadership

What tennis can teach us about ambiguity

Unatributed
June 22, 2016
Ambiguity can make even experienced teams freeze or rush ahead too soon. Drawing on an unexpected lesson from the tennis court, this article explores how timing, awareness, and pattern recognition help leaders and teams navigate uncertainty with greater confidence and clarity at work.
2016-06-22
Leadership
Decision-making
Mindset shifts
Personal reflection
Purpose

Heartbreak and the in-between

Unatributed
January 19, 2021
The events of 2020 left many leaders suspended between loss and possibility. In this deeply reflective essay, the author explores heartbreak, transitoriness, and the discipline of holding creative tension. It is a meditation on resilience, leadership, and learning how to stay present in the in-between.
2021-01-19
Purpose
Personal reflection
Emotional intelligence
Resilience
Leadership

Great leaders redesign their roles

Unatributed
December 21, 2021
There is no single right way to be a CEO or senior leader. What matters is designing your role around where you add the most value. This article explores why redefining leadership roles around individual strengths helps leaders guide change, build stronger teams, and focus on what truly moves the business forward.
2021-12-21
Leadership
Leadership behaviors
Personal reflection
Capability-building
Leadership

How to do the harder, necessary DEI work in your company

Unatributed
July 26, 2022
Embedding diversity, equity, and inclusion into company systems matters. But real progress depends just as much on the quieter, more personal work leaders do every day. This article explores why individual DEI leadership, personal accountability, and reflective practice are essential to building a truly inclusive workplace culture.
2022-07-26
Leadership
Inclusion
Leadership behaviors
Emotional intelligence
Personal reflection
Leadership

The pull back. The call forward

Unatributed
November 7, 2022
As work and life resettle after the pandemic, many leaders feel a quiet tension between old habits and new possibilities. This essay explores the pull back to familiar ways of working—and the call forward to more human, sustainable leadership. It offers a reflective lens on the future of work, behavior change, and purposeful transformation.
2022-11-07
Leadership
Personal reflection
Leadership behaviors
Mindset shifts
Resilience
Creativity

The creativity conflict

Unatributed
June 25, 2024
Creativity is celebrated, but rarely protected, especially in professional life. As efficiency, digital tools and AI reward speed and certainty, imagination often gets sidelined. This article explores the tension between productivity and creativity, and offers practical ways individuals can reclaim space for discovery and new ideas.
2024-06-25
Creativity
Personal reflection
Imagination
Innovation practices
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