Having a Journey Mindset as a Leader

by | Jul 30, 2025 | Coaching, Organizational Leadership, Personal Leadership | 0 comments

Introducing A Blog Series from Emily

When Marc and I began “dating,” we were both tangled in a web of well-meaning but toxic purity culture expectations. High achievers to the core, we were doing our best to follow all the right rules—but rarely checked in with our own wisdom, or even trusted the wisdom of those closest to us. Instead, we turned to books, experts, mentors (thankfully, some with more common sense than we had), and the ever-present pressure of doing things “the right way.”

We had both made a clear and serious decision: we were not dating. Especially not at that point in our academic journeys. We had far more important things to focus on than relationships.

But when we had our Relationship Defining Talk, we didn’t veer from that decision. Instead, we gave it a new name. We were “co-pilgrims on an unknown journey together, for an unspecified length of time.”

(Go ahead, I’ll wait while you wipe the coffee off your screen.)Emily and Marc in a pile of leaves

Marc, ever earnest, reported the new development to his roommates with great enthusiasm. I like to imagine the pause, the raised eyebrows, and finally someone saying, “So what the hell does that mean, Pitman? Are you dating or not?”

And yet—thirty years of marriage and business partnership later—we’re still co-pilgrims. That language has held up. We’ve learned that journeys, especially shared ones, can’t be measured only by milestones. They’re shaped by intention, discovery, and ongoing choice.

This morning, I was reminded of that when I came across this line in my journal:
“Coaching is all about a journey, and nothing about instruction or teaching.”
(Coaching for Performance)

Even back then, we were reaching toward the idea of a journey rather than a destination.

And that’s what this blog series is about: cultivating a Journey Mindset in leadership.

Agile, healthy leadership requires a mindset grounded in curiosity, flexibility, and presence. It’s not a formula. It’s a way of walking through uncertainty with integrity and courage. It’s available to all of us.

In the weeks ahead, I’ll share reflections on the patterns of journeys—

  • how they begin with Possibility,

  • how planning and preparation show up,

  • what happens in the phases of excitement, boredom, resolve, and completion,

  • and how we might respond to the inevitable interruptions and surprises along the way.

Because whether you’re leading a team, a business, or your own life, leadership is never a straight line. And that’s a good thing.

Let’s explore what it means to lead with a Journey Mindset.

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