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who i am

Andrew

I’m a designer, founder, and educator drawn to helping people navigate meaningful transitions. Through building Mission Critical, teaching university level design studios, and decades of nature-based practice, I’ve learned that clarity often comes from a shift in perspective. Tending the Trail is the practice I offer to hold space to slow down, see more clearly, and explore what’s next, together.

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Mission

To create a space for perspective, where people can slow down, see clearly, and move forward with intention.

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Vision

People living and leading from alignment, connected to purpose, community, and what’s naturally emerging.

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background

Much of my work has grown from a simple observation: clarity often comes not from pushing harder, but from learning how to listen more carefully, to ourselves, to others, and to what’s already unfolding.

Friends often describe me as a guide. Not because I know the way, but because I help people explore what isn’t fully known yet, mapping the terrain of their own life and finding a way through it with more clarity and ease.

I studied Environmental Design at the University of Colorado Boulder, and later returned to teach studio courses in Product Design and Landscape Architecture. In those studios, I worked closely with students navigating ambiguity- teaching them to trust their instincts, refine ideas, and bring thoughtful work into form. That experience shaped my appreciation for how people grow when they're supported with both structure and space.

Alongside teaching, I spent years designing and building products with a strong focus on purpose and connection. I founded Mission Critical, a consumer products brand created to help dads connect more deeply with their kids. Our flagship product, a modular baby carrier designed specifically for fathers, grew from the belief that thoughtful design can shape relationships and create meaningful experiences. Through this work, I saw how even accomplished people can reach moments where the next step isn’t obvious, not because they lack direction, but because they’re standing at the edge of something new.

Over more than two decades, I’ve also been deeply engaged in nature-based learning and connection practices. These experiences shaped how I approach this work today, with patience, attention, and respect for how things naturally emerge.

A big part of this work is language. Not in a technical sense, but in how we make sense of our own experience. Often, something real is happening, but it hasn’t fully been put into words yet. When that shifts, when you’re able to name what’s actually there, perspective tends to open up.

That’s where I tend to work.

I listen closely, reflect what I’m hearing, and help bring language to what may already be present but not fully formed. As that becomes clearer, direction often follows, not forced, but recognized.

Tending the Trail brings these threads together.
I don’t offer formulas or fixed answers. I walk alongside you, helping you step back, see more clearly, and move into what’s next with intention.

This is simply a space to tend the trail together.

business

As founder, CEO and lead designer, I built a consumer product company from early concept through growth and eventual exit. My work began with hands-on prototyping and product development, and extended into material sourcing, factory partnerships, quality control, regulatory compliance, and international importation.

Over time, my role expanded to include hiring and mentoring team members, shaping the brand, designing the website, and guiding marketing and creative direction. I oversaw fulfillment across both direct-to-consumer and Amazon channels, while also leading business strategy, financial planning, and fundraising. Through this work, our products helped connect more than 55,000 dads with their kids, a mission that grounded the business in meaningful, real-world impact.

This experience gave me a practical, end-to-end understanding of how ideas take shape in the real world, and what it means to navigate uncertainty, growth, and transition while leading a business.

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Ceremony

Sometimes the next chapter doesn’t come from pushing forward, it comes from taking time to look back and notice what’s already been forming.

This eight-phase directional process is a guided reflection through your experiences, decisions, relationships, and turning points. Together, we move slowly and intentionally, uncovering patterns, clarifying what matters, and identifying the seeds you want to carry forward. This is typically a weekly process, unfolding over the course of two to three months, allowing insights to emerge gradually and integrate into your day-to-day life.

For business owners, this often includes stepping back from day-to-day operations to look at the broader arc of your work, how your business has evolved, where your energy is drawn, and what the next chapter of leadership, direction, or impact might look like. We can also explore the real elements of your business, strategy, structure, finances, branding, and creative direction, through a more reflective and integrated lens.

It’s a way to step off the main path for a moment, to listen more closely, reconnect with your gifts, and return with a clearer sense of direction.

Walking this stretch of trail together often opens a broader landscape for what comes next. 

training

My approach is also shaped by years of immersive training in nature-based leadership and regenerative design. I studied at the Regenerative Design Institute, completing programs in the Ecology of Leadership and earning a Permaculture Design Certificate.

 

I’ve also participated in extensive mentoring and Nature connection-based training through programs such as 8 Shields, Art of Mentoring, Mind of Mentoring, Native Eyes, Designing with Natural Cycles, Harmonizing with Nature, Discovering the Emergent Mind with Nature, all centered on deep listening, awareness, and working with natural patterns.

More recently, I’ve complemented this experiential foundation with formal coaching training, including Ikigai Coach Certification and Neuroscience-based Coach Certification.

 

Together, these experiences inform a grounded, integrative approach that blends intuitive awareness with practical insight, supporting people as they navigate transitions and step into what’s next.

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Contact

Andrew Wollenberg

Andrew@TendingTheTrail.com

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© 2026 Tending The Trail & Andrew Wollenberg

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