Why Good Decisions Still Feel So Hard

In the first two reflections, we’ve named something many leaders quietly experience in seasons of change.

First, the recognition: you’re not stuck — you’re in transition.
Then, the impact: transition rarely touches just one part of life.

But there’s another layer beneath both of those.

Even when a path forward seems wise, something inside can still feel unsettled. Even when a decision aligns on paper, tension lingers.

Why? Because transition doesn’t just disrupt circumstances. It surfaces fear.

The Tensions Beneath the Surface

One of the frameworks I use when walking with leaders through change is what I call the Core Tensions Framework. It highlights three areas where fear commonly rises during transition: identity and calling, family and relationships, and community and belonging.

These are not problems to eliminate. They are tensions to manage, to steward.

When transition touches identity, the questions often become deeply personal: Who am I if this role shifts? What does faithfulness look like in this new season? Am I stepping toward or away from my calling?

Family and relationships introduce another layer. No decision is made in isolation. We often carry not only our own uncertainty but the weight of how change will affect those closest to us. Even a wise move can feel costly when others are involved.

And then there is belonging. Transition frequently disrupts community expectations. Where will I fit now? What assumptions will others make? Am I stepping outside the story people thought I was living?

These tensions do not necessarily signal that something is wrong. They often reveal what we most want to value and embrace.

Tension Is Not the Enemy

When someone in transition says, “I feel torn,” our instinct — especially if we care about them — is to help resolve that tension quickly. But discernment is not the elimination of fear. It is the patient naming of it.

Often the more helpful question is not, “What should you do?” but, “What feels most at risk here?”

When fear is named honestly — identity, responsibility, belonging — clarity begins to deepen. Not because the tension disappears, but because it is no longer hidden.

A Reflection for You

If you are personally navigating change, which of these tensions feels most alive right now? And if you regularly walk alongside others in transition, where do you most often see the struggle emerge — identity, relationships, or belonging?

Naming tension does not rush resolution. It creates space for wisdom.

Walking With Others Through the Tension

On May 19th at 12 PM MST, I’ll be hosting the next Walking with People in Transition webinar.

This session is designed primarily for those who accompany others through seasons of change — coaches, pastors, leaders, and mentors. We’ll explore frameworks like the Transition Curve, the Impact Assessment, and the Core Tensions Framework — not as scripts to follow, but as lenses that help you listen more deeply and ask wiser questions.

If you regularly sit with people who feel torn between identity, responsibility, and belonging, this space may give structure and language to what you’re already sensing. And if you find yourself in transition personally, you’re welcome as well. Details are available on the site, and I’ll share more as we get closer.

Transitions stretch us not because we are weak, but because they touch the deepest parts of who we are. Identity. Relationship. Belonging.

Those are worth tending carefully.

— Tim

P.S.
If you feel the urge to relieve someone’s tension quickly this week — or your own — consider slowing down instead. Could it be that wisdom wants to grow in the space between fear and decision?