Communication. Connection. Resilience.

Transformative Growth for Leaders.

Journeys. Sabbaticals. Wayfinding.

Trilogy Design Works provides high-value experiences, travel, and intentional sabbaticals that present leaders the opportunity for personal and professional transformative growth. 

For Profit. For Good.

Designed as a sustainable business that makes a profit and integrates social impact, we are committed to programs for underserved students that strengthen their agency muscles and confidence.

Curious? This work is for and with people, let's chat.

Personal & Professional Wayfinder




Travel isn’t always pretty. 
It isn’t always comfortable. 
Sometimes it hurts, it even breaks your heart. 
But that’s okay. 
The journey changes you- it should change you. 
It leaves marks on your memory, on your consciousness, on your heart, and on your body. 
You take something with you… 
Hopefully, you leave something good behind.
– Anthony Bourdain


Friends and Fellow Travelers...

What Do You Want?
What Matters to You?

Hello, I am Annette Mason, a Leadership Guide and founder of Trilogy Design Works. 

We help Leaders grow their communication and connection skills through innovative, creative journeys. These are high-value experiences that present leaders the opportunity for personal and professional transformative growth.

Our Three Pillars
Compass: Our unique combination internal value drivers.
Maps: Where we’ve been (and what it means), where we are, and where we are going.
Constellations: Our community and our wayfinders.

Our evolving business model, designed as a sustainable business that makes a profit and also has social impact at its core.

The social impact is to offer underserved students a life skills curriculum that puts them in the driver seat of their lives, to build their agency muscles and confidence.

As I deepen my relationships - I continue to invest time and service with like-hearted, globally recognized thought leaders and their communities.

Come journey with me.

I am grateful wife and mom to two amazing global citizens.
Kind Words from Remarkable People

Travis Scott

Author • RevOps • Marketing Operations • HubSpot • The Winding Road Careers Podcast

Before I worked with Annette, I couldn't see what was really getting in my way. She was able to expose the self-limiting thoughts I had that were holding me back from doing great things. 

She made the space and showed up when I needed it most.

Cecilia Persson-Ramos

Diversity, Equity & Inclusion Leader @ Intuit I Global ERG Management I Culture, Engagement & Belonging

Annette Mason is an extraordinary coach and mentor.  When we worked together, she helped me organize my experience, thoughts and abilities. She made me realize that everything is inside me. 

As a result, I walked confidently into an interview where I not only landed the role, but the scope was also expanded based on what I shared. 

Wayfinding with Intent

Work directly with Annette, creating your Personal Transformation Map that charts the course for what matters most. 

Here we create a Compass and a Map, leading your forward toward your desired future. 

This is a quick, agile method.

Travel is never a matter of money but of courage.
– Paolo Coelho
The same can be said about Sabbaticals.

We work with individuals or groups to design successful sabbaticals – time that we set aside from our work and our regular life. By creating space (in both time and sometimes place) we begin to see our self and our life through a new lens. 

Three essentials for a successful sabbatical are Courage, Intention, and Co-design

Intentional Sabbaticals are designed with constraints in mind.  Time, money, people, and places are not insurmountable barriers. Working together we create Sojourns with Intention and Impact. 

Kind Words from Remarkable People

Melanie Hagerty

Sr Director IT, Engineering Applications

Annette provided the “ground rules” for my exploration journey via weekly reflection questions AND helpful exercises with clear templates, and shared specific and relatable examples from her remarkable life and career that then helped me organize my past experiences to inform my future choices as well as prioritize my goals for more effective decision making. 


Let's have a conversation

Sabbaticals are available to all of us. Let's work together to craft one that works for you.


A short journey or trip, especially one engaged in as a leisure activity.

Also a deviation from a regular pattern, path, or level of operation.

The orientation is to provoke some new, fresh thinking in context of current and future  circumstances.

The promise is some cultural learning through creative means.


A journey or voyage undertaken by a group of people with a particular purpose, especially that of exploration, research, and quest for growth and insights.

The orientation is that of a quest, finding it is not promised.

Learning and Adventure is promised and leadership growth is inevitable.

Curated travel as an ultimate lifetime learning experience

Travel has the power to inform our worldview as we discuss social issues, election choices, and how we make a difference whether in business and career  or making choices of what we buy and how we dispose of things.

At Trilogy Design Works we co-create travel experiences with our client and our partners around the world, delivering something far beyond the traditional tourism model. 

We may use the words Excursion or Expedition to explain this work better. However we describe it, the intent is learning and transformation. 

Curated to Return Insights and Impact with Your Investment. Venturing while adding value personally, locally & globally.

I believe in The Power & Gift of Travel as a way forward to raise the tide for all of us.


Let's have a conversation


An Evolving Manifesto

While I believe that profit is an engine for choice,

I believe it requires appropriate context 


This insight is inspired by Hubert Joly’s point of view on profit:

“I now see shareholder primacy as the root cause of the problems that my children and I were talking about around the dinner table. Although making money is of course vital and a natural outcome of good management (as we discuss in chapter 5), considering profit as the sole purpose of business is wrong for four fundamental reasons: 

(1) profit is not a good measure of economic performance; 

(2) an exclusive focus on it is dangerous; 

(3) this singular focus antagonizes customers and employees; and 

(4) it is not good for the soul.”

— The Heart of Business: Leadership Principles for the Next Era of Capitalism by Hubert Joly

Drawing by Ayse Birsel