About Red Sky Life
I work primarily in 1:1 coaching relationships, supporting clients as they move from stability into depth, from recovery into fulfillment, and from survival into a life that feels genuinely worth living.
My approach blends:
Mental wellness and emotional resilience
Recovery-informed guidance (non-clinical)
Values-based decision-making
Purpose and identity exploration
Practical navigation through life’s challenges
Applied Philosophy
I am a guide — not a clinician — and I work alongside, not in place of, medical or therapeutic care when present.
13
100+
Lives impacted
Years experience
About the Founder
Josh Fass is the Founder and Head Coach at RED SKY, LLC. Before beginning the RED SKY Recovery and Life Coaching journey, Josh spent his 25 career in the Enterprise Technology/ Software Industry, spanning CPG and Healthcare verticals.
There is an epidemic of people who are living a life that is fractured; both successful and wounded. Where there is little interpersonal connection, and a deep sense of isolation due to alcohol, drugs, or other addictions. I have lived through this exact state of being, and have come out the other side; more balanced, more joyful, and far more peaceful. RED SKY was founded on the principles of restoring harmony across the three fundamental domains (or relationships): Relationship to Self; Others; and Universal. I've been blessed to witness life restorations take root, and lives transformed... and this is my higher calling."
Josh lives with his wife in Westport, Connecticut. An active family with three children, and two bulldogs (Stella and Luna). When he is not working with clients, Josh is learning life lessons while sailing, playing golf, and simply enjoying "Being"...
Voices
What clients say about RED SKY
Working with Josh has shifted my mindset in ways I didn’t expect. His steady guidance and thoughtful questions helped me uncover strengths I’d overlooked. I feel clearer and more in control of my direction with his help over the years.
Rob S
I met Josh and it was immediately clear that he approaches this work with both heart and strategy. He is always thinking about how to shape his offerings in a way that truly serves people. What stands out most is Josh’s clarity of vision around who he can help most and how to support them in a way that creates real impact.
Melissa S
Denver CO
★★★★★
★★★★★
★★★★★
“I am grateful to work with Josh because he gives me the space to say all the crazy things in my brain. He listens without judgement, with spiritual generosity. And when I’ve aired it all out, he responds with understanding and respectful compassion. This level of openness, and our deep relationship is essential to my journey.”
Matt D
Westport CT
Fairfield CT
★★★★★
"Josh helped me clarify my life goals and identified the tasks required to attained them. For the first time in my life, I feel like I have a plan."
Robert S
Fairfield CT
