Five Contemplations for Cultivating a Regenerative Livelihood

Aligning our work with our values and our aspirations for a more regenerative and equitable post-capitalist future.

By Della Duncan

Della is the co-designer and co-facilitator of the upcoming Cultivating Regenerative Livelihoods Course, a Right Livelihood Coach, and the co-host of the Upstream Podcast.

What would it look like to earn a living in a way that nourishes ourselves, our communities, and the living world?

For many of us, our livelihoods are a source of tension. We want our work to reflect our deepest values, contribute to a more beautiful world, and support the transition toward a more just and regenerative economy. Yet we are trying to do all of this within an economic system that often rewards extraction over regeneration, competition over cooperation, and profit over people and planet.

Cultivating a regenerative livelihood is about navigating these contradictions with intention, compassion, and creativity. It is about recognizing that our work can be more than a means of survival. It can also be an expression of our values, a contribution to collective liberation, and a way of prefiguring the world we wish to inhabit.

But what does this look like in practice?

Here are five contemplations I invite you to explore as you reflect on your own livelihood journey.

1. The Content of Your Work: What Are You Contributing to the World?

The work we do is never neutral. It can contribute to extraction, exploitation, and ecological harm, or it can help cultivate healthier, more equitable, and regenerative relationships and dynamics.

Whether we are educators, artists, organizers, entrepreneurs, caregivers, or working within larger institutions, we can ask ourselves: What is my work contributing to? Whose needs does it serve? What dynamics does it reinforce, and what possibilities does it help bring into being?

Aligning the content of our work with our values doesn't necessarily mean abandoning everything we are currently doing. Sometimes it means finding ways to redirect our skills, creativity, and energy toward work that feels more meaningful and life-affirming.

Contemplation: How does the content of your work contribute to a more beautiful world? What might greater alignment between your work and your values look like and feel like?

2. The Structure of Your Work: How Is Power Organized?

It's not just what we do that matters, but also how we organize ourselves to do it.

Conventional for-profit businesses are often structured hierarchically, concentrating ownership, decision-making power, and profits in the hands of a few. Even mission-driven nonprofits can reproduce top-down management, opaque decision-making, and inequitable distributions of power.

But there are alternatives.

Worker cooperatives, worker self-directed nonprofits, and other democratic organizational models offer opportunities to distribute power more equitably, share ownership and responsibility, and prioritize collective well-being over private profit.

These structures are not automatically free from the contradictions of capitalism, but they create opportunities to practice the democratic, cooperative, and regenerative relationships we want to see flourish in a post-capitalist economy.

Contemplation: Who holds power in your workplace? Who makes decisions, who benefits, and whose voices are heard? How might your work be structured more democratically and equitably?

3. The Culture of Your Work: Are You Practicing the Values You Believe In?

Even in the most mission-driven businesses and organizations, the dominant values of capitalism can quietly shape workplace culture.

Hustle, overwork, competition, urgency, perfectionism, and the norms of patriarchy and white supremacy can become so normalized that we reproduce them even while working toward liberation.

A regenerative livelihood invites us to pay attention not only to what we accomplish, but to how we treat ourselves and one another along the way.

Are we cultivating environments where people can bring their whole selves to work? Where rest, care, creativity, cooperation, and compassion are valued? Where conflict can be navigated with curiosity and accountability rather than domination and cancel-culture?

If we want to create a more equitable and compassionate world, our workplaces can become living laboratories for practicing those values today.

Contemplation: How does the culture of your work reflect the world you want to create? What values or practices might you need to unlearn, and what new ones are you ready to cultivate?

4. Systemic Change: How Is Your Work Contributing to Collective Liberation?

Cultivating a regenerative livelihood is not simply about finding personally fulfilling work or making more ethical individual choices. It is also about recognizing that our livelihoods are embedded within larger economic, political, social, and ecological systems.

We cannot build a truly regenerative future without confronting the systems that perpetuate exploitation, colonialism, imperialism, and ecological destruction.

This means asking how our work can contribute not only to making life more bearable within capitalism, but also to hospicing the systems that no longer serve life and helping to birth more just, democratic, and regenerative alternatives.

What would it mean for our livelihoods to contribute to an eco-socialist, anti-imperialist, Indigenous-wisdom-led, post-capitalist future?

None of us is doing this work alone. We are part of movements, communities, and lineages of resistance and regeneration that stretch across generations and around the world. Recognizing these connections can help us move beyond individual notions of purpose toward collective transformation.

Contemplation: What movements and lineages is your work part of? How do you practice solidarity with those resisting extraction, exploitation, imperialism, and colonialism? What role can you and your organization play in bringing about systemic change?

5. Your Attitude Toward Your Work: Does your work feel regenerative?

Sometimes, even when we know we are doing meaningful work, and even when others tell us we are good at what we do, something doesn't feel right.

We might experience resentment, boredom, listlessness, exhaustion, or burnout.

These feelings do not necessarily mean we have chosen the wrong path. Often, they are responses to structural conditions beyond our control, including the relentless demands and insecurities of capitalism.

But they may also carry important information about what we need and where we are feeling called.

Regenerative thinking reminds us that growth is not always about doing more. In healthy living systems, there are seasons of flourishing, rest, decay, and renewal. Pruning makes room for new growth. Composting transforms what is no longer serving life into nourishment for what comes next.

Perhaps there are aspects of our work, habits, expectations, commitments, or identities that we are ready to release. Perhaps we need more spaciousness, joy, play, connection, creativity, or rest.

Cultivating a regenerative livelihood means extending care and compassion to ourselves, recognizing that we, too, are part of the living world we seek to regenerate.

Contemplation: What aspects of your livelihood are nourishing you, and which are depleting you? What are you ready to prune or compost to make space for what comes next?

An Invitation to Cultivate Your Regenerative Livelihood

There is no single path toward a regenerative livelihood, and there is certainly no perfect way to work within an imperfect economic system.

For some, the journey might involve transforming an existing job, business, or organization. For others, it might mean starting a cooperative, shifting careers, embracing a different relationship to paid work, or finding new ways to contribute to movements for systemic change.

Whatever your path, you don't have to navigate it alone.

Each year, I teach a course I co-designed with Silvia Di Blasio called Cultivating a Regenerative Livelihood, creating a supportive space for people to reflect on their relationship with work, explore possibilities, and take meaningful steps toward greater alignment between their livelihoods and their values.

Together, we explore how to bring more regeneration, cooperation, equity, and purpose into our work while recognizing the larger systems we are seeking to transform. Through reflection, dialogue, and practical exploration, participants are invited to clarify where they are, envision where they want to go, and identify the next steps on their unique livelihood journeys.

This is not about finding the perfect job, becoming more productive, or placing the responsibility for systemic change on individuals. It is about cultivating livelihoods that nourish ourselves, one another, and the more-than-human world while contributing to the collective transformation of our economy.

If you are longing for greater alignment between your work and your values, navigating a livelihood transition, or seeking support in bringing your vision of a more regenerative and equitable future into practice, we would love to have you join us.

Let's cultivate livelihoods that not only sustain us, but help bring the world we long for into being.

Learn more and register for the Cultivating a Regenerative Livelihood course.

Photo by Gustavo Fring (Pexels).