Sitting With Ambiguity

Why this practice matters

The leaders who navigate complexity well aren't the ones with the best frameworks or the fastest instincts. They're the ones who have built the internal capacity to stay - to remain present with tensions that don't yet have answers, to resist the pull toward premature closure, and to make decisions into uncertainty rather than out of it.

That capacity a developmental achievement, which, like any muscle, is built through deliberate, repeated practice.

This blueprint gives you a structure for that practice. Use it however serves you: as journaling prompts, as walking meditations, as questions for a therapist or trusted friend, or as material for a coaching conversation. What matters is not the format but the willingness to stay with the questions longer than feels comfortable.

How to use this guide

Set aside 30-45 minutes. Choose one current tension you're sitting with - something genuinely unresolved in your leadership life right now. Not something you've already decided and are seeking validation for. Something that's still alive.

Move through the four steps below. Resist the urge to rush. If a question doesn't land, sit with why it doesn't land - that's often where the work is.

Step 1

Naming What's Actually Here

Before you can hold a tension, you have to see it clearly. Most leaders skip this step and try to resolve a tension they haven't actually named.

  • What is the situation I'm sitting with right now that I haven't been able to resolve?
  • If I had to name the two (or more) poles pulling at me, what are they? Can I name each one in its own language, on its own terms?
  • Which pole am I more comfortable articulating? Which one do I find myself minimizing or arguing against?
  • What would each pole say if it had a full voice at the table?
  • Whose interests, values, or concerns does each pole represent - including parts of myself?
Step 1

Step 2

Noticing Your Relationship to the Tension

The tension itself isn't the only thing worth examining. Your response to the tension carries crucial information.

  • Where do I feel this tension in my body? What does the discomfort actually feel like?
  • What am I telling myself I need to do to make this feeling go away?
  • If I'm honest, which pole am I quietly hoping will win so I can stop holding both?
  • What would it cost me - internally, relationally, professionally - to fully acknowledge the legitimacy of the pole I'm resisting?
  • When in my history have I felt something like this before? What did I do then? Is that pattern serving me now?
Step 2

Step 3

Examining the Pull Toward Closure

Premature closure is the great enemy of leading well in complexity. This movement is about surfacing the forces pushing you to decide before the situation has shown itself.

  • What is the actual deadline here, versus the deadline I'm imposing on myself?
  • Who am I performing decisiveness for? What do I think will happen if I'm seen as not yet knowing?
  • What would become possible if I gave this one more day, one more week, one more conversation before deciding?
  • What information am I missing that I could actually go get? Whose perspective haven't I sought because I'm afraid of what they might say?
  • If I decided right now, what would the version of me six months from now wish I had paid attention to?
Step 3

Step 4

Staying Long Enough for Something to Emerge

This is the heart of the practice. Not resolving the tension. Not flowing past it. Staying with it long enough that something true can surface.

  • What does this situation seem to be asking of me that I haven't wanted to hear?
  • If both poles are legitimate and neither can be eliminated, what becomes possible? What kind of decision would honor both?
  • What would I do if I trusted that staying in this question a little longer would yield something better than deciding right now?
  • What is the trace of what I'll exclude when I do decide? How will I stay in relationship with what I didn't choose?
  • What is the smallest, most honest next step I could take - not to resolve the tension, but to learn more about what it actually is?
Step 4

Step 5

Building the Muscle: A Weekly Rhythm

A single reflection session won't build the capacity. The work is in the repetition. Consider a rhythm like this:

Weekly: Choose one current tension and move through the four movements. Thirty to forty-five minutes. Same day each week if possible.

Daily: A two-minute check-in. What tension am I carrying today? Am I trying to resolve it prematurely? That's it. The point is not to solve anything - it's to develop the habit of noticing.

In the moment: When you feel the urge to collapse a tension quickly, pause and ask yourself one question: What would it cost me to wait one more beat? Then wait that beat. Over time, the beat extends naturally.

Step 5

Step 6

Practicing With Others

Some of this work is solitary. But some of it requires another person - someone who can hold the tension with you without rushing you toward resolution, and who can ask you the questions you can't quite ask yourself.

That person might be a therapist, a coach (like me!), a trusted peer, or a friend with the right kind of attention. What matters is that they don't need you to decide quickly in order to manage their own discomfort. The right thinking partner is someone who can stay in the question with you - not someone who will solve it for you.

If you're not sure you have that person in your life right now, that's worth noticing too. Building the capacity to sit with ambiguity is harder alone than it needs to be.

Step 6

Conclusion

The Benefits of This Work

The leaders who do this work change in ways that are visible to everyone around them. They become harder to rattle. They make better decisions because their decisions are made into reality as it is, not as their discomfort wishes it to be. They give their teams permission to think clearly because they're no longer demanding false coherence to manage their own anxiety.

That is the developmental work of leadership in complex times. And it begins with a willingness to stay in one question, just a little longer than feels comfortable.

Conclusion