“I want you to help me find the shortest path to becoming an extraordinary leader,” my client said, setting down his coffee cup.

“That’s great,” I said. “What do you want to lead?”

“I don’t know.”

“Then you’re not on a path,” I said. “You’re on a quest.”

Paths and quests

All we ever really do as coaches is help our clients get from A to B. As I wrote in my previous post about how I help clients dream in the first session, their dream — their B — can be aspirational or a diminished version of what they really want to create.

B can be anything: clarification of their essence or purpose; a change in feeling, mindset, or behavior; the solution to a problem; or the creation of a billion-dollar business (I work with a lot of entrepreneurs and CEOs).

When you have some clarity about what they’re trying to create it can be helpful to know if they need to be on a path or a quest to get there. Here’s the difference:

If you know clearly what B is and where it is and you know where A is, you’re on a path. You’re really looking for the shortest distance between two points. It’s a project management challenge. If I’m working with an executive and it’s a business challenge, I’ll suggest that they delegate the project to a pathfinder — a manager — because if you know what you want and how to get it, getting it isn’t very strategic. (If B is personal, then they’ll have to be their own pathfinder and I’ll help them think through their plan and act on it.)

If you don’t know exactly what you’re trying to create (and maybe not even where you actually are), you’re on a quest. If you try to figure it out step by step, you’ll probably end up somewhere you don’t want to be. As Yogi Berra said, “If you don’t know where you’re going, you’ll probably end up somewhere else.” (We actually want them to end up somewhere else, but somewhere better than they can imagine when they set out from A.)

Everyone is always on a path somewhere in their life (or business) and on a quest somewhere in their life (or business). Our job is to help them understand the difference.

Everyone is always on a path somewhere in their life (or business) and on a quest somewhere in their life (or business). Our job is to help them understand the difference.

Every good quest starts with a quest(ion)

Let me give you two examples of what I mean:

Elon Musk never intended to start SpaceX (entrepreneurs love this example). He started with a question. His question was: “Why haven’t we sent people to Mars?”

He thought it was a problem of will. He went to Russia to try to buy a rocket from the Russians so he could send it — and a mouse or some plants — to Mars. Then he could say there was life on Mars. That ought to get people motivated. The Russians laughed at him (this often happens to entrepreneurs who try to do the impossible; it’s our job not to laugh).

What Elon found was that it wasn’t a problem of will, but rather a problem of way. The problem was single-use rockets were prohibitively expensive. He started SpaceX to build multi-use rockets and change the economics of space exploration.

Let me give you a personal example:

At the end of 2014, I experienced a heartbreak that sent me into a dark passage. I experienced not only emotional heartbreak but physical heartbreak, too. In 2016 I had two heart operations for atrial fibrillation. Almost every day for two years, I would wake in the morning and ask myself, “How did this get to be my life?” I had somehow managed to create the exact opposite of everything I thought I wanted.

One day I had an epiphany: I was half-hearted everywhere in my life. I had one foot in and one foot out of my relationship. No wonder it imploded. I was a hired gun in my work, showing up and doing only what I was paid for. My work was very transactional, I wasn’t building relationships. It was the same with my friends and family. It was a harsh awakening.

So I went on a quest. My question was, “How can I be wholehearted?”

I was intentional about showing up, as much as I was able, with my whole heart. I made new friends (and I was astonished that they would be friends with me because I was in a very dark place — I didn’t even want to be around me — something for which I am eternally grateful). I completely reinvented the way I work as a coach (which has become what I call Coaching From Essence), focused on creating relationships with my clients and doing deep personal as well as professional work. When I was ready, I started dating again, showing up as my wholehearted, imperfect self.

The results were better than B (what I call B-prime, but that’s another post). I met an extraordinary beloved in 2017 and we married a year later. My coaching practice is full of clients I love. Last year I made more money than ever (multiple six-figures) and a full practice is only about a dozen clients (and a third of those are pro bono because I love working with early-stage founders and entrepreneurs).

How to quest

If you’re on a quest, you need to be a leader. A leader is someone who knows how to journey. They aren’t afraid of the unknown. While a path is predictable or easily discoverable and repeatable, a quest is unpredictable (once it has been discovered and it becomes repeatable, it’s a path).

It’s hard to know where to start when you’re on a quest. As Joseph Campbell wrote, “You enter the forest at the darkest point, where there is no path. Where there is a way or path, it is someone else’s path.”

As coaches, we are allies on the quest. We have to help our clients find their own path.

I always start by helping my clients articulate their Quest(ion). What is it that’s missing? What are they longing for? What is the life that is trying to be lived through them? What are their tropisms? (Tropisms are what they naturally turn towards; plants are tropistic to light.)

The next step is to help them become comfortable with the unknown, to embrace uncertainty. They have to have the mindset that they are embarking on an adventure. They are putting themselves in the way of serendipity (I often talk about the ways of optimizing for serendipity with my clients), of unforeseen possibilities. Now we are creating from the future, where dreams and possibilities are not dictated by what was possible in the past.

I can think of no better advice, once a client has clarified their Quest(ion), than this quote from Lewis Carroll: “If you don’t know where you are going, any road will get you there.” I encourage them to take any road.

I can think of no better advice, once a client has clarified their Quest(ion), than this quote from Lewis Carroll: “If you don’t know where you are going, any road will get you there.” I encourage them to take any road.

When you take a road, you don’t have to go down it very far to know whether or not it is leading you in the direction of your longing. If it gives you life, it’s easy to see it. When I work with clients who have begun a quest and are headed in the right direction, it’s always visible on their faces. You can feel energetically that they have found a thread. A road that lights you up may become a path — or lead to another road that does.

I emphasize to my clients that there is no failure. It’s not possible. You either got your B — something you were after — or something else equally satisfying, or you got B-prime (something better than you could have imagined when you set out from A; we are always helping the client optimize for this), or you got a lesson. It’s impossible to fail if you are paying attention.

If the road doesn’t light them up, they learned something. We can also help them to get the lesson (and the light) by helping them notice what the journey is bringing them.

Especially in my first several sessions, I will often open the session by asking the client, “What’s different? What’s different since the last session? What’s different since we first started working together?” What we pay attention to grows and what goes unnoticed withers. If they can notice some positive change, however small, we can amplify it. That’s food for the journey.

So. What’s your Quest(ion)? And what road are you taking?

Photo by Lê Tân on Unsplash