Coaching Asks the Big Questions

In coaching, a single question, uttered out loud, can lead to powerful places. This is a core part of my job as a coach: to ask what needs to be asked.

What needs to be asked is not always what wants to be asked - or answered. The questions we need to hear can often feel confrontational: they can push us into sticky places in ourselves that simultaneously desire and resist growth.

Because, as I will always and forever normalize, change is hard.

The things we know - the familiar paths, habits, routines, and ways of being - carry a certain amount of safety and comfort. Even if these ways of being are actively keeping us stuck, the place beyond is unknown.

And the unknown is scary as hell for most of us.

I know, because I have been on the other side of change: gulping for air as my fear screamed caution. And I have eventually taken the leap: allowing myself to believe less in my fear and more in what could be.

Part of what propelled me into coaching work was my own experience navigating change and challenges. I was in a time of life where there were many questions just beneath the surface that I was trying desperately to ignore.

To nobody's surprise, as I pushed the questions aside and tried to silence them, they worked together to get louder.

The questions rallied together and shouted at me: What’s stopping you from changing your life?

The changes I wanted were tangible:

  • I wanted to step away from an established career where I had gained respect and success, yet felt miserable.

  • I wanted to try living in other places in order to embrace my love of adventure and new experiences, even if I eventually returned to where I’d started from.

  • I wanted to do something radically unconventional to heal from burnout and give myself permission to take a break; I wanted to build an inspired, creative sabbatical.

  • I wanted to actively write the story of my life with intention and purpose.

What was stopping me?

  • Fear. Was I capable of changes so big?

  • Self-doubt. Who was I without all the career and life identifiers I wanted to step away from?

  • Worry. What would people think? Would quitting a bunch of stuff that felt draining and misaligned make people think less of me?

Fear, self-doubt, and worry were effective blockers. The first time the question What’s stopping you? screamed at me, I stayed the course, pushed it out of my head, and didn’t make any changes.

The question had to surface again and again, each time helping me get more clear on what was moving me - slowly - towards change.

The question had to haunt me a bit. It had to haunt me so I could really explore what these changes would mean for me. Why they were not just worth it, but necessary. And what I would lose by staying the same.

I still remember the ordinary, not-at-all-special day that something shifted. I went to my 9-to-5 job, sped across town to an appointment after work, drove home in irritating traffic, parked while sighing audibly, opened my front door, and without even a hello, said to my then-partner, “I’m ready.

Within a few months I’d sold my house, stored, sold, or given away all my worldly possessions, given notice at work*, and planned a cross-country road trip sabbatical. I didn’t yet know where all of this was leading me. I only knew what it was leading me away from: a life that was misaligned in purpose and missing a sense of adventure I needed to thrive.

As I build my coaching practice, I think of this story that ultimately led me to become a coach. I think of the bravery that clients bring to every session in which they face what is haunting them. Every session that they tune in to the questions surfacing. Especially those pesky questions that are waving wildly to get their attention.

As I watch brave human after brave human turn to face the big, life-changing questions, I hold my breath with them, wondering where this could lead. I marvel at another human who only knows that they must let go of what is familiar to make space for what is possible.

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