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Rudy Massimo & Associates is proud to join forces with ALIVE Outdoors to offer true experiential development opportunities for students, families and organizations. ALIVE Outdoors is a Toronto based experiential education organization that has been working with Ontario and International Schools to engage students in meaningful outdoor, international and city-based character development programming for the last 21 years. We aim to empower participants to recognize and embrace their inner potential, helping people build enriching, respectful relationships with themselves, others and the environment in our local/global communities.

ALIVE Outdoors has designed and delivered character development, outdoor education and wilderness experiences - which have ultimately supported over 400,000 student program days of engaging meaningful experiences. 

We have all felt the unique challenges that 2020 and 2021 have presented. There is no doubt that new obstacles will continue to reveal themselves as we move forward.  Despite not being able to come together physically, we are still able to deliver many of the same important lessons that we have been dedicated to for two decades. More than ever we are seeing the importance of community, leadership, kindness, collaboration, listening, trust and the necessity of having a strong personal foundation to call upon to stay calm and grounded.

Since March 2020, ALIVE Outdoors has evolved its program delivery and successfully provided programs for 3,200 virtual participants

ALIVE Outdoors: About

ALIVE Leadership Team


Jalynn Bosley

Executive Director

Over the last few decades, as the owner of ALIVE Outdoors, Jalynn has had the privilege of nurturing strong relationships with many students, educators, administrators, parents and ALIVE instructors. She believes that your life is the result of your level of self-awareness, and if you are conscious enough you can feel when you are, or are not on a path that is right for you. She does not believe that there is only one path for each of us to follow. No doubt, we all have a series of possibilities, yet some are more authentic than others. One of the goals of ALIVE is to help people develop the confidence to truly be themselves and a sense of awareness to know when they are following a path that is healthy and will allow them to live a grounded, meaningful and intentional life. 

Jalynn uses her diverse skillset in experiential program development to help guide schools through their individualized process of building intentional, customized experiential programming that aligns with their own vision and strategic plan. She actively consults with schools on program development, risk management and scope and sequence planning both nationally and internationally. She has a B.Ed. and is a Certified Applied Positive Psychology practitioner through the Flourishing Center. The knowledge she gained through this Certification not only allowed her to enrich her own life, but has allowed her to expand the workshops that ALIVE offers and deepen her facilitation skills.


Sam Dear


From early experiences canoe tripping to becoming morally conflicted while travelling internationally, Sam’s career has been full of twists and turns.  For the past 10 years, Sam has returned to her roots of working in Outdoor and Experiential Education with ALIVE Outdoors, an environment that she believes to be the most powerful for developing a critical conscious, clarifying foundational values and developing a reverence for the natural world. A skilled lecturer and workshop facilitator, she acts as a consultant, is responsible for instructor hiring and the development of curricular scope and sequence programs both nationally and internationally. 

Sam earned an Honours Degree in Outdoor Recreation, Parks and Tourism and BA in Geography from Lakehead University in 2005. Following volunteer and travel experiences in Haiti, Southern China and Tibet she became increasingly interested and conflicted with the ethics related to international development and global education. To fuel this interest Sam returned to school to earn a post-graduate certificate in International Project Management from Humber College in Toronto in 2008 and a Master of Arts focusing on Exploring Issues of Reciprocity in International Service-Learning Programs in 2012. Through this decade in her life she realized that relationships based on honest (often hard) conversations and a relationship with the environment are at the root of real change.


Dr. Ryan Howard

Director of Research, Risk Management and Innovation

Throughout his career, Ryan has shown dedication to advancing the practices of outdoor education through both his field-based practices and his time conducting and disseminating research in experiential education. Ryan holds Bachelor Degrees in Outdoor Recreation and Geography from Lakehead University and a Master’s degree from Brock University which focused on commercial risk management and government regulations within the outdoor industry. He completed a Ph.D. in Applied Health Science, also from Brock University, and is currently completing the requirements for his Canadian Risk Management (CRM) designation through the Risk and Insurance Management Society (RIMS) and the Global Risk Management Institute (GRMI).

Ryan comes to ALIVE Outdoors after working in higher education for the past eight years, he has lectured at Brock University, was a faculty member at the University of Northern British Columbia, and most recently was a tenure track faculty member in the School of Outdoor Recreation, Parks and Tourism at Lakehead University. Ryan started in outdoor education as a canoe tripper, white water canoe, kayak, and raft guide, a swift water rescue instructor, and operations director with various companies in Ontario and Quebec.

Highlights from Ryan’s professional background in the fields of outdoor and experiential education includes: publishing research in numerous national and internationally recognized journals, and books; sharing research and workshops on risk management and experiential education at over 50 scholarly conferences and symposia; conducting government sponsored research with school boards; and consulting for Environment Canada on developing their risk management practices. He actively contributes to a number of outdoor and experiential education associations and continues to be a reviewer for numerous education and outdoor recreation journals.


Matt Peters

Program Manager

Matt exudes bottomless positive energy, a thoughtful understanding of self, and a commitment toward boosting the values found within experiential education programming. Each of these characteristics empowers Matt to make positive additions to all the programs he touches as a Program Manager at ALIVE Outdoors. Matt brings with him a depth of experience working in both regional and international experiential programming that stemmed from many of his early life experiences outdoors.

Matt earned his diploma in Outdoor Adventure and Business from Algonquin College which helped him to expand his understanding of the philosophy and practice of experiential education and outdoor business principles.

Most recently Matt has taken his practice internationally leading service learning and tourism trips in Kenya, Tanzania, and India. During this time, Matt focused on helping students build cross-cultural relationships and fostered the development of critical consciousness as a key priority within international service learning. In addition to these experiences, Matt has worked regionally with vulnerable student populations that have helped foster his interest in evaluating and measuring the longitudinal impacts of intentional outdoor programming.  Matt shares his dedication for creating progressive and relevant experiential programming that leverages both the power of the outdoors and the importance of positive community relationships.

ALIVE Outdoors: Team
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