life by design, alongside a business by design.
A workshop for entrepreneurs and leaders who want to think as intentionally about their lives as they do about their businesses.
Most entrepreneurs know exactly what they want their business to look like in five years, and almost nothing about what they want their life to look like. This is the session where they step back and get deliberate about the direction they want their life to take. It's the same framework I'm capturing in The HAPPY Entrepreneur, the book I'm writing now.
What is the happy work life MAP?
The happy work life MAP is an interactive workshop built around a simple, powerful idea: happiness is progress towards purpose. It gives entrepreneurs and leaders a structured way to reflect on where they are, where they want to go, and how to show up, in business and in life, in a way that's genuinely aligned with who they are.
This isn't a wellbeing tick-box. It's a real conversation, grounded in a proven framework, that leaves participants clearer, more energised, and more intentional about the life they're actually building.
HAPPY?
Highlights
The milestones, adventures, and accomplishments that pull you toward the future you want to live.
Identify the key life and business achievements you want to experience: the defining moments, big and small, that mark a life well lived. Your highlights aren't just things that have happened. They're the experiences you're building towards.
Appreciation
Appreciation grounds you, and reminds you of the strengths you've earned along the way.
Cultivate gratitude and recognise the value in the relationships, challenges, and moments that have shaped who you are. This isn't toxic positivity. It's a deliberate practice of seeing clearly what's already working and what you already have.
Progress
Real happiness comes from knowing you're moving forward.
Set measurable personal and business growth goals. This dimension is about building skills, forming habits, and taking meaningful steps toward a life that excites you. Not growth for growth's sake. Progress in the direction that actually matters to you.
People
The qualities you admire in others often reflect the potential waiting to be developed within yourself.
Strengthen the relationships that support, inspire, and challenge you to grow. Consider who energises you, who you want to invest more in, and who you want to become in the context of the people around you, in business, at home, and beyond.
Your Contribution
Define the impact you want to make, and then design a plan to bring it to life.
The lasting legacy you want to leave through your business, your community, and your personal actions. This goes beyond revenue and exits. It's about the difference you genuinely want to make in the world, and whether your daily life reflects that intention.
The workshop, step by step.
The session moves through four distinct phases: opening mindset, deep individual reflection, energised group sharing, and purposeful future planning. Dynamic, honest, and consistently surprising for people who expect a standard wellbeing talk.
Opening: Mindset, Means Goals & Why Happiness Is So Hard to Define
We start with the whole group. Before anyone puts pen to paper, we explore the ideas that make the rest of the session land properly: the difference between means goals (what we think we want) and end goals (what we actually want underneath them), why happiness is so slippery to define, and what we're really chasing when we chase it. We walk through the five HAPPY dimensions and what each one holds. This isn't a lecture. It's a conversation, and the room warms up fast.
Free Writing: 3 minutes per dimension. No editing, no filtering.
For each of the five HAPPY dimensions, participants write freely for three minutes. The timer is the point. Three minutes is long enough to move past the tired, easy answers, and short enough that your rational brain doesn't get a chance to say "that's not possible." What emerges in those three minutes tends to be truer than anything you'd write with more time to think.
Small Group Sharing: your top 2 or 3, dimension by dimension
After each writing round, participants share the two or three things that struck them most, in small breakout groups. Not to impress, not to perform: to spark and inspire. Hearing what actually matters to a peer you've known for years, and realising you had no idea, is one of the most reliably moving moments of the session. This is where the energy in the room builds.
The MAP: My Action Plan
Having surfaced what genuinely matters to them, participants identify the purposes they want to work towards across four horizons: this year, near term, medium term, and the long view, plus space for their own. The focus isn't to fill in every box. It's to be deliberate about the ones that matter.
Whole Room Takeaways, Insights & Energy
We bring everyone back together. No pressure to share anything personal, but the room is always ready to talk by this point. People leave feeling happier than when they walked in, and more connected to those around them.
A happier, more intentional room.
Their personal happy work life MAP
A clear visual snapshot of where they are, and where they want to grow, across all five dimensions of a fulfilling life.
One meaningful commitment
Not a wish list. A single, specific intention for the next 90 days, chosen by them, owned by them, grounded in what actually matters.
Renewed energy & focus
Not because problems are solved, but because clarity replaces fog. Participants know what they want, and why.
Permission to be intentional
Often the most powerful outcome: entrepreneurs feel seen, and given explicit permission to build a life that actually works for them, not just for the business.
An entrepreneur, facilitating for entrepreneurs.
- Deep understanding of entrepreneurial psychology
- Engaging, dynamic, discussion-led sessions
- Content designed specifically with entrepreneurs and leaders in mind
- Two decades leading learning and talent programmes internationally
- Trusted MC and facilitator for global conferences, summits and retreats
- Author-in-progress of The HAPPY Entrepreneur, the book behind this framework
I don't deliver generic corporate content. I facilitate structured conversations that continue long after the event ends.
Places I've spoken & worked
Delivering workshops, keynotes and strategy sessions to entrepreneurs and leaders around the globe.
What people say
Stephen did a phenomenal job. He brought the perfect mix of energy, presence, and timing. That's a craft, and he made it look effortless.
The clearest I've felt about my life and my business in years. Three hours in a room and I left with a plan I actually believe in.
Stephen creates the kind of space entrepreneurs almost never get to sit in. Honest, focused, and quietly transformational.
The workshop and the book.
The happy work life MAP isn't a one-off keynote framework. It's the same thinking captured in The HAPPY Entrepreneur, a book about building a life by design alongside a business by design.
Every dimension in this workshop, Highlights, Appreciation, Progress, People, Your Contribution, is a chapter in progress. The material has been tested live with entrepreneurs over hundreds of conversations, and it keeps improving each time we run it.
Designed to fit your event.
Half-day happy work life MAP workshop
The full experience: individual mapping, small group sharing, and 90-day commitments. Run as a standalone workshop, part of a leadership programme, or built into a conference, retreat or off-site. Flexible to your group's rhythm and agenda.
- 3 to 3.5 hours including reflection and sharing time
- Works well for 15 to 60 participants, no minimum required
- Open to entrepreneurs, leaders, teams and their families
- Small group exercises deliberately mix backgrounds, companies, and industries
- Each participant leaves with a completed personal happy work life MAP
- Facilitated by Stephen, no prep or pre-reading required
- Can be delivered in-person globally, or adapted for summits and retreats
let's design the session together.
Tell us about the group, the moment in the calendar, and what you want people to leave with. We'll shape the right version of the workshop for you.
Start a conversation