Canoeing the Mountains by Tod Boslinger

There’s a confronting insight at the heart of Canoeing the Mountains: sometimes the issue isn’t effort or sincerity—it’s that the terrain has shifted, and we’re still reaching for tools shaped for a different task.

Lewis and Clark prepared to canoe in central USA in the early 1800s. What they found were mountains. More paddling skill wasn’t the answer. 

Bolsinger frames this through technical and adaptive challenges. Some problems are technical—clear issue, known solution, better execution. But many of the challenges we face are adaptive. The situation is unclear, the way forward uncertain, and the work involves learning, change, and even loss.

That’s why the line from Chapter 10 lands so strongly: “your system is perfectly designed to get the results you are getting.” If a church is plateaued, stuck in conflict, or increasingly disconnected from its community, it’s not accidental. It reflects the systems, habits, and instincts that have been formed over time. What once served well may no longer fit the moment.

The instinct is to reach for technical fixes—adjust programs, tweak structures, work harder. Sometimes that helps. But often it just reinforces the existing pattern. The deeper work is more demanding: culture shifts, and so the way we minister in and to that culture must adjust. Not a new gospel, but a freshly embodied one.

This is where leadership becomes costly. Drawing on Ronald Heifetz, Bolsinger describes leadership as disappointing people at a rate they can absorb. Move too fast, and people lose their bearings. Move too slowly, and you lose relevance. The tension must be held.

You see this in Paul the Apostle. He refuses to change the gospel, but he adapts its expression—becoming “all things to all people” without surrendering its core. And in John Wesley, who stepped outside inherited structures to reach people the church had missed.

The enduring gift of this book is its clarity. Faithfulness in a changing world is not about clinging to familiar methods, nor chasing novelty. It is about holding firmly to the gospel while learning, patiently and courageously, how to carry it over the mountains.