When people first reach out to me, they often report feeling “lost” or “stuck at a crossroads” in their journey. They know they can no longer continue with the work they’ve been doing, but they’re not quite sure where to go next. They will ask me, “Where do I even begin?”

My answer is always the same, “You begin with your beliefs.”

No matter who I work with and in what capacity, my first questio...

One of the most common doubts I encounter in those I work with is “What if what I have to offer the world is not enough?” Because folks seek me out in order to discover what work they want to create in the world, their deepest fear is that they will actually discover they have nothing of value to offer. Hidden within the dark recesses of their mind is shame around their own unworthiness, which pai...

Years ago, before I started this business, I was standing at a significant crossroads in my own work journey. I had been operating another business, which by external measures was deemed “successful”, however, it had come to the point where the work I was doing had lost all meaning to me and was devoid of any satisfaction or fulfillment. I knew I could no longer tolerate staying on the same path, ...

In Canada, where I live, this past Monday was the National Day for Truth and Reconciliation. It is marked as a day to acknowledge the harm perpetrated against the indigenous peoples of our nation and to honour the survivors. The intent is to begin the healing process from our painful history.

I don’t pretend to know the extent of suffering of those who endured the oppression at the hands of those...

I get bored easily. The thought of reading a book I’ve already read or watching a movie I’ve already seen is off-putting to me. It means I’ve missed out on the opportunity to have a new experience. I don’t even like cooking the same meal twice.

This is because one of my core values is adventure. I am internally driven to have new experiences. It doesn’t even matter if the experience is so-called ...

“I miss that part of myself,” I said to my then business client. My words hung awkwardly in the air, as if I had spoken a truth I wasn’t supposed to say. I’m sure my client wasn’t interested in hearing what I didn’t like about my work, but to me, my admission was like a siren piercing the silence of my own apathy. I couldn’t unhear my own words. It left me wondering what others parts of myself I w...

As a teenager, my friends nicknamed me “Dr. Kiley”. Whenever they were confused or depressed, or struggling with relationships, I was the one they sought out for advice. I think it was because I was willing to listen with curiosity and without judgement. Also, I didn’t say much back then, which was helpful because mostly they just wanted to feel seen and heard. Nowadays, people still seek me out f...

Many people who come to work with me identify as being “unconventional”. Regular-type jobs make them feel trapped. Old structures and systems stifle their adventurous spirit. They like to take the status quo, scrunch it up into a ball and throw it into the fire. They’ve spent much of their lives trying to reconcile the way they perceive the world with the way others proclaim it to be.

The unendin...

“They need to learn the value of money, but they don’t want to get a job.”

Because of what I do for work, some of my friends who are parents of teenagers vent to me about their “lazy” children. “I lined up a well-paying summer job for them and they refused to take it.”

My response is, “Good.” Usually followed by an awkward silence.

I ask, “What is it your children actually want to do?”

My frie...

I am genuinely surprised at how often people express guilt and shame around doing self-discovery work. I just welcomed a new cohort into the Vision Program and already this has come up in conversation. Some perceive themselves as being self-indulgent – irresponsible, even.

They question: Who am I to be sitting around figuring out what inspires me, especially when there is so much suffering in t...

When I used to operate my school as a physical entity, I would welcome people into the classroom and advise them that it was a space for “not knowing”. They would heave a sigh of relief and then ease into their chairs. They could finally relax.

If you are currently in a career transition, you might feel a tremendous amount of external pressure to know what’s next. Under the guise of caring, your ...

Every time I have occasion to visit my family doctor, I think about how much it would suck to have the job of a GP. All day, every day, they see humanity at their lowest. We go to them when we are sick, injured, or broken – literally. The primary tools they have available to help us include either referring us to another doctor or prescribing drugs. It must feel helpless. When my doctor enters the...