Expanding Perception. Changing what becomes possible.

I advise founders and CEOs on business development, commercial strategy, and high-stakes negotiations. I also write and speak about work, ambition, perspective, and living well.

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A white mug with steam rising from hot coffee or tea, placed on a table next to an open book in front of a window with sunlight.
ALIVENESS IS STRATEGY

Writer · Speaker · Strategic Advisor

Brian Jackson & Shai Littlejohn on Owl Have You Know Podcast
Audio Reflection
An Apple iMac desktop computer on a wooden table surrounded by lush green plants in an indoor space with a framed picture on the wall.

The future belongs to organizations that still feel human.

The most successful organizations don't choose between commercial performance and human flourishing. They understand that businesses exist to serve people, customers, employees, partners, and communities and that long-term success is built by creating value for all of them.

I've spent my career advising founders, CEOs, and executive teams on the decisions that matter most: growth, commercial strategy, negotiations, partnerships, corporate social responsibility, risk, reputation, and transformation. Now I help leaders make better decisions because I’ve learned to see those challenges through multiple business perspectives.

I'm Looking for Signs of Life

In businesses. In leaders. In careers.

The biggest opportunities often begin with a different perspective. I help founders, CEOs, and ambitious professionals uncover new possibilities through business strategy, commercial leadership, high-stakes negotiations, and thoughtful leadership.

  • I advise founders and executive teams on growth, commercial strategy, and high-stakes business decisions.

  • Build stronger leadership teams and healthier organizational cultures where people and performance thrive together.

  • Create more meaningful customer and employee experiences that strengthen trust, loyalty, and long-term value.

  • Provide one-on-one thought partnership for founders and senior leaders navigating growth, difficult decisions, leadership challenges, and organizational change.

  • Keynotes, fireside chats, executive retreats, panels & moderation.

How I Help Founders & Executive Teams:

How I Help Professionals:

  • I help professionals navigate career transitions with confidence and perspective.

  • Redefine success without sacrificing ambition.

  • Build a more meaningful life and career.

  • Discover practical ideas for living well through essays and video.

The Journal

The Conversation That Changed My Life
Featured Shai Littlejohn Featured Shai Littlejohn

The Conversation That Changed My Life

After my mom was diagnosed with brain cancer, I flew to visit her at least monthly. I was General Counsel of the DC Sports and Entertainment Commission during that time, so having a flexible leave policy and the ability to work remotely from Houston was the only way I made it through.

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How to Make Sure Your Cup Is Full
Featured Shai Littlejohn Featured Shai Littlejohn

How to Make Sure Your Cup Is Full

The farmer who wants to produce a high quality harvest to sell to the market at premium prices must execute a strategy that fuels her intention to produce a quality bean. She must exercise patience, and craft, to allow the tree to time produce. It can take 3 to 4 years of cultivating a coffee tree before it ever produces fruit. There are routine steps that all farmers must take, but if she can tend to the trees under just the right conditions, the cherries will ripen right on time.

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