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The Story of My Transition

Updated: Oct 21, 2022

This article offers a first glimpse into my spiritual journey since leaving my corporate job at Yahoo! over 10 years ago. I explain the stresses I experienced in the corporate world and some of the insights I gained since. In particular, the importance of kindness along the spiritual path.

A photo from Guatemala, right after I left Yahoo! in 2007.


It was the fall of 2006 and I was exhausted. I had recently come back from a trip to Australia. My intention was to spend time with a good friend and rejuvenate. The spending time with a good friend part was great. The rejuvenation part didn’t last long.

My vacation buzz quickly wore off and before long I was back at work. I felt the weight of the world on my shoulders. Later, I would realize that I was actually the one putting it there.

Because of my past experiences launching high-profile products at Yahoo!, I was asked to be on a newly formed team where that was part of our mission. Given the heavily matrixed organization we were in and the size of the projects we were given, it started to feel like trying to move entire mountains with a pinky. My team had experienced these challenges before, only this time I was getting burned out after years of trying to ‘move the needle’ and putting everything I had into high priority projects at the company.

I found myself dreaming about my next vacation. Peru, Iceland, India…where to go next? Only I wasn’t there. I was here, smack dab in the middle of the matrix working harder than ever before. I was working on the newest of the new projects and simply pushing on through to the next vacation. Wash, rinse, repeat.

The feeling in my gut was screaming: "Are you nuts?" But I wouldn’t listen. I was too scared to make a change. And if I did, I wouldn’t know what to do next anyways. It was just too fuzzy of a plan.

One night I woke up around 3am and felt the walls closing in on me. I had to rush to my patio to catch my breath. I sat there and started to breathe deeply. I knew right then that this was the beginning of the end for me in this kind of life. My body was telling me it was time for a change or it would shut down. I decided to listen for the first time in a very long time to see what it had to say.

After a few minutes some images came to me. I envisioned what it would be like in five years – working in the same company and with the same two hour round trip commute. Only this time I imagined being in some of the roles I had always been striving for. That claustrophobic feeling immediately started to come back. And there it was.

The path I was headed down (which was much better suited for others and their unique path & talents vs. for me) made me feel more compressed, less fully alive, and, frankly, physically ill. And the funny part about all of it was this: I created this world for myself. Not because I had to, but because I thought I would be happy and fulfilled. I felt that if I just pushed a little bit more, I’d be totally secure and free of all financial worries.

Practically speaking, of course, staying on with my company was somewhat of a known quantity. And, if not there, then another similar company. Another few years and it's likely I would have been making even more money and in charge of an even larger team. I imagined what that felt like and observed the sensations in my body.

First, the nausea (judgement towards myself), then the claustrophobia (feeling trapped on a path that wasn’t for me), and finally a feeling of sadness and helplessness (my anger at myself turned inwards that I wasn’t owning my freedom to choose).

On the other hand, leaving Yahoo! and finding a new job, or even career, was a complete unknown and scary but again I observed what was happening inside of me -- lightness (a freedom to be more of who I am) and a subtle knowingness (there was another journey for me to go on, even though I didn't understand what it was yet).

That was enough for me. A week later I handed in my resignation and went on an extended trip through Latin America to step outside of my old beliefs and patterns for a while and experiment with a new way of seeing life. Many of these experiences, I captured in my travel blog.

And it was from that day onward, that I started a 12 year journey into the unknown. Travels through remote lands, ‘successes’ and ‘failures’ of new businesses and relationships, universal mysteries revealed, even more questions and mysteries surfaced, moments of complete confusion and fear, times of absolute clarity and peace.

Would I trade any of it? Never. The most challenging years of my life were the ones during which I felt most fully alive.

Anyone who goes through a process of breaking free of their own version of the matrix may have a different set of circumstances but the emotional experience is often similar. Right before it starts and the portal of opportunity opens, there's a sense of something more and a feeling of longing for something that we just can’t put our finger on. There may be a fear of the unknown and questions about how we're going to manage without all of the answers laid out right in front of us. There's exhilaration at the thought of freedom -- the freedom to be who we really are and to live that fully whatever that may be.

It's that step into the unknown that led me to an extraordinary journey that continues to this day. Yes, when I returned, I took adventurous leaps into new businesses and relationships, but the biggest jump was inward. And with that came a process of remembering who I really am.

‘Remembrance’ was not just a set of words anymore but a deep feeling of who I am as a soul in this body. Of what I’m here to do and be. Of how I’m here for others. And a new and completely unexpected version of that continues to unfold.

This kind of path is a different one than before. Although there’s a time for intention-setting and planning, there’s a different quality to the experience. A recognition that no matter how many goals we set, or plans we make, there’s still a grand mystery to it all.

I've come to see that it's more about how we respond and awaken to the mysteries that unfold right in front of us rather than to the actual content or outcome that we originally expected.

In essence, it's about the type of people we become along the way and how we treat others under the most trying of circumstances. And, of course, how we treat ourselves even with all of the mistakes we make, the shame or guilt we feel, the broken promises we’ve made along the way.

How much love and kindness can we show ourselves in the midst of it all?

From that place of compassion, we become more and more open to life expressing itself through us. It's the very art of surrendering and then allowing that brings forth our new creations into the world.

I used to have a painting in my house that said: “Sometimes your only available transportation is a leap of faith.” As people on a spiritual path, we are all on a sacred journey that takes an extra-ordinary amount of faith and trust in something bigger than ourselves. We are on a personal journey of healing and through our presence we create a space for the healing of those all around us. For our partners, our clients, our friends, our families, and our communities.

Whatever our path may be, creating change through personal transformation takes patience, commitment, and immense kindness towards ourselves to explore the truth behind who we really are.

Our work does not come with a rule book or a set of predefined answers but simply with the presence of our hearts and the support of others to help us move forward.

I want to thank you for doing what you do and for the very presence that you bring into the world.

I wish you many blessings on your journey,

Ryan Rigoli

Spiritual Guidance | Executive & Life Coaching | Healing Music


Ryan's Bio

As a Spiritual Guide and Executive & Life Coach, I help business leaders, entrepreneurs, & truth seekers access their intuitive guidance & follow their purpose, at work & beyond. I am also a Meditation Teacher, Improvisational Classical Pianist, & a Professed Monk and use my business, creative, and spiritual backgrounds to support people in living with greater purpose, presence, and peace.

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