Designing a business around what matters now

Carlos Saba has spent over a decade supporting people who walk away from conventional business paths. At the Happy Startup School, he and his team run a variety of programs designed to support purpose-driven entrepreneurs. These include in-person retreats in nature, an annual community festival that blends business and wellbeing, and the Vision 2020 group coaching program: a structured, yet personal approach to building businesses that align with who you are. 

Their offerings blend personal development with business thinking, always grounded in real relationships and shared values. Through the Happy Startup School, which he co-founded, Carlos helps professionals at a crossroads, often in midlife, shift from burnout or boredom toward something more purposeful. Instead of focusing on rapid growth or exit strategies, the Happy Startup School promotes a slower, values-led model that reflects its founders’ own journey.

This article is part of the Business Insights Series, where we explore what it really takes to build a business that feels aligned. We’re not chasing big headlines or billion-dollar valuations. We’re more interested in the everyday realities: What drives people to change direction? How do they build something meaningful and financially sustainable? And what happens when you try to build a business that feels good, not just looks good on paper?

In this piece, we look at how the Happy Startup School has become a home for what Carlos calls “restartups”: entrepreneurs leaving behind the first mountain of traditional success in search of something more grounded, more human, and more fulfilling.

What a startup looks like the second time around

Carlos doesn’t work with the kind of startups that chase venture capital and scale fast. Instead, he calls his clients “restartups”: people in midlife, often coming from corporate or traditional business environments, who want to build something that aligns with who they are now, not who they were when they started out. Many of them are stepping away from careers that once seemed successful but no longer feel fulfilling. What many are looking for is a new kind of fulfillment: something that brings meaning, supports autonomy, and fosters connection.

“Most of these people are entrepreneurs and professionals on a midlife pivot… moving away from business plans and corporate structures to something more driven by freedom, meaning, purpose.”

The Happy Startup School provides a landing space for these shifts. Rather than pushing a fixed path, it offers a framework for exploring what business could look like when built from the inside out. The format is flexible: a mix of online courses, in-person retreats, live events, and peer-led coaching. Instead of following a set of instructions, participants are encouraged to reflect, experiment, and explore: what would you create if you let go of the expectations?

The heart of their approach is through community. The School doesn’t position itself as an authority with all the answers. Instead, it facilitates relationships between people asking similar questions, each trying to build something more honest. This community-focused approach aligns with research showing that community-based business models can create sustainable value through shared resources, peer collaboration, and mutual support. Perfection isn’t the focus. The work is guided by alignment, making sure what you’re building feels honest and right for where you are now.

Business as a personal journey

Carlos sees entrepreneurship as both a way to serve others and an opportunity to better understand yourself. Starting a business becomes a way to face the things many people spend their lives avoiding: limiting beliefs, old habits, inherited expectations. That kind of work isn’t always visible in traditional business metrics, yet it often determines whether a venture becomes sustainable or collapses under hidden pressure.

“It’s a journey of personal growth. What often comes up are questions around money, self-worth, purpose, and what truly matters to the individual.”

His clients often arrive at a point where something in their work no longer fits. They’ve followed the steps: education, promotions, success; but it no longer feels like theirs. They’re not necessarily inexperienced. What’s new is the desire to create something with personal meaning, something that resonates beyond what’s expected in traditional business logic.

The School uses a framework based on four quadrants of success: happy money, intentional time, authentic connection, and effortless impact. These function as reflective prompts that invite individuals to explore what truly resonates with their current values and aspirations. Happy money might mean financial simplicity that reduces stress. Intentional time could mean choosing how to spend each day with more agency. Authentic connection recognises the value of being seen and understood, relationships that go beyond networking and support a sense of belonging. Effortless impact might be the quiet ripple effect of doing work that truly resonates. Together, these areas invite people to approach work with clarity, consistency, and a deeper awareness of how their choices shape their experience.

The shift from agency to community

Carlos didn’t start out this way. His early path followed the blueprint many professionals are told to pursue: get the grades, gain expertise, move up the ladder. With a PhD in physics and years spent leading a digital agency, he ticked the traditional boxes of success. But somewhere along the way, the excitement faded.

“More headcount meant more salaries. More salaries meant more cashflow pressure. And then you’re stuck doing things you don’t enjoy just to feed the beast.”

Despite running a respected agency, the work began to feel mechanical, focused more on maintaining momentum than creating value that felt meaningful. At the same time, Carlos and his co-founder began to notice a pattern in the clients they served. Many wanted to launch digital products but had rigid expectations and limited openness to experimentation.

This tension sparked a shift. They began to question what it really means to build something worthwhile: how people build, why they choose to build, and what kind of work feels truly fulfilling. That led to the creation of a manifesto they called the “happifesto”, a call to rethink the role of business in our lives.

Thousands of people signed up. It didn’t follow a typical business plan format. Instead, it acted as a signal that something in their message resonated deeply with others. There were others out there who felt the same. That validation gave Carlos and his co-founder the courage to close a successful agency and pour their energy into something far less certain, but far more aligned: the Happy Startup School.

What people actually want from work

The Happy Startup School has hosted thousands of participants through retreats, festivals, and coaching programs since its founding. These events are carefully designed experiences that invite people to pause, reflect, and reconnect with what they actually want from their work and life. They avoid a standardised approach, allowing space for personal exploration and realignment. 

Each year, the School runs key events that have become pillars in its ecosystem: the Summercamp in September, which combines fireside chats with practical workshops; the Alptitude Retreat in June, focused on deeper, more personal reflection; and the Vision 20/20 coaching program, now in its fifth year, which brings small groups together for shared growth over time.

Carlos references The Second Mountain by David Brooks as a helpful metaphor for what many of these participants are navigating. The first mountain is about career achievement, status, and proving yourself. The second is about meaning, contribution, and alignment.

“People get to the top of that first mountain and realise something’s still missing. We work with the people in the valley, between the mountains.”

Brooks’ framework has particular relevance in today’s business environment. As described in research on his work, the second mountain is characterised by commitment and community, where individuals shift from ego-obsessed, individualist culture to lives defined by deeper relationships and service to others. This transition often involves what Brooks calls moving from asking “What do I want from my life?” to “What is life asking of me?“

This “valley” is a space where ambition shifts from external validation to internal clarity. Participants often come from industries where burnout is common: tech, finance, marketing, and arrive feeling disconnected from their work. Some have taken sabbaticals. 

Others are in the midst of a career change. The Happy Startup School gives them language, tools, and community to reframe their careers. The goal is to create businesses that evolve alongside their founders, ventures that are informed by lived experience, personal growth, and a changing sense of purpose.

Evolving from values into practice

Turning ideas into something real took time. Carlos and his team began with a shared set of values and a strong desire to connect with like-minded people. Their direction emerged gradually through real conversations, honest feedback, and the willingness to explore new ways of building together. What came next was shaped by listening, experimenting, and staying close to what felt right.

“We started with what mattered to us: values like connection, creativity, and integrity. Over time, we shaped offerings around those principles that people were genuinely excited to be part of.”

Their early gatherings focused on small retreats that invited honest conversation, fresh thinking, and deep human connection. These moments became the heart of the Happy Startup School. From there, they developed group coaching programs, including the Vision 20/20 initiative, a collaborative journey that supports entrepreneurs in building something aligned with their lives.

Another standout event is their annual Summercamp, what they affectionately call a “business hippie festival”. Rather than centring on big-name speakers or rigid agendas, these gatherings prioritise connection, reflection, and learning in a way that feels alive and genuinely human.

Their approach has continued to evolve in thoughtful ways. Rather than chasing visibility or volume, the team prioritises presence, community, and shared intention. This helps the work remain meaningful, not just to their participants, but to themselves.

Philosophy over pressure

Carlos distinguishes between what he calls the “material” and “spiritual” approaches to business. The material path is grounded in striving: chasing metrics, expanding for the sake of it, and measuring success by what others can see. It’s a mindset shaped by performance, productivity, and comparison. The spiritual path, by contrast, asks different questions: What do I want? What feels true? What would it look like to work with life instead of against it?

“We respond without trying to fight it, and that’s how we actually find, like water, the least effortful way forward.”

This philosophy challenges the dominant business narrative that equates struggle with virtue. For Carlos, clarity in direction and values is what helps move the work forward. When you’re clear about your values, your needs, and your direction, the next steps often become obvious. That doesn’t mean things are easy, but the energy is different. You’re no longer pushing against something, but flowing with it.

He sees entrepreneurship not as a race to win or a puzzle to solve, but as an evolving relationship: with yourself, your work, and the people you serve. That shift, from effort to ease, from external pressure to internal focus, is what keeps him and his team motivated. It’s also what makes their work resonant for others who are tired of pushing and ready to listen instead.

It’s still hard but it’s better

Running a purpose-driven business doesn’t remove the everyday complexities, it reshapes how they’re experienced. The Happy Startup School still navigates shifting trends, evolving technologies, and the logistics of staying operational. But underneath the daily effort is something steadier: a sense of clarity about why the work matters.

“We’re still in the grind. It’s just less suffering within the grind.”

This distinction is crucial. Research on workplace wellbeing shows that when employees feel connected to purpose and meaning in their work, they experience significantly lower levels of stress and burnout, even when facing similar workloads. The study mentioned found that five key elements drive wellbeing: mental and emotional support, sense of purpose, personal support, financial health, and strong workplace relationships.

Could it be that challenge, when chosen, feels different from struggle? What if the friction we feel at work isn’t always a sign to quit, but an invitation to realign?

Rather than rushing to meet external expectations, the team at the Happy Startup School leans into focus and intentional pace. Decisions are made with presence instead of pressure. When uncertainty shows up (as it inevitably does) they return to the foundations: rapport, curiosity, and care. How does this next step feel? Does it support what we want to grow?

This rhythm has helped them sustain momentum without burning out. Their work isn’t defined by urgency but by honesty. And that honesty resonates. People who are asking similar questions: about purpose, meaning, and alignment; are drawn to that energy. The way challenges are approached makes a difference: when they’re acknowledged with confidence and intention, they can feel more manageable and meaningful.

Entrepreneurship here involves staying connected to what matters, while applying practical thinking to bring those values to life. It’s a space where showing up consistently, through change, doubt, and growth, becomes its own form of progress, grounded in awareness and perseverance.

What if your business was built to feel good?

Carlos’s story reflects the reality many entrepreneurs face, recognising when something isn’t working and choosing to explore what might be possible instead. Along the way, we’ve learned that growth doesn’t always follow a straight line, and success can take many forms.

Entrepreneurship often invites deeper questions: What does fulfilment look like now? How can work reflect personal values without sacrificing stability? Is it possible to build something meaningful that also works in the long term? The experience at the Happy Startup School suggests it is and that community, patience, and reflection are key parts of that process.

The journey of building a business can be uncertain, but it doesn’t need to be isolating. When people are supported to listen inward, connect outward, and act with awareness, the path ahead can feel less rigid and more alive.

If you’re exploring what a different kind of work might look like, this could be a supportive place to begin.