Getting Comfortable Being Uncomfortable: A Leadership Practice

124 hours on sea anchor. Gale-force winds, seven to eight metre swell, thrown around the cabin through the night with no way to make the boat move in the direction we needed. On the Atlantic, discomfort wasn’t an event — it was the baseline. You don’t get to wait for conditions to improve before you keep going. You get comfortable being uncomfortable, or you don’t get across.

Modern leaders are asked to do a version of the same thing far more often than they’d like: stretch beyond their comfort zone, make calls with incomplete information, hold steady while a plan falls apart around them. Most of us try to prepare our way out of that discomfort — more research, more contingency plans, more certainty before we act. It rarely works, because the discomfort was never really about the plan. It’s about tolerance.

Three things I learned at sea that apply directly in the boardroom:

Discomfort is data, not a warning sign

When the storm hit, the instinct was to treat the fear and disorientation as a signal that something had gone wrong. It hadn’t — it was just what a storm feels like from inside a rowing boat. Leaders often mistake the discomfort of a hard decision for evidence the decision is wrong. Usually it’s just evidence the decision is hard.

You can only control the next two hours

We rowed in two-on, two-off shifts. Thinking about the full crossing while pinned on sea anchor would have been paralysing. The only useful unit of time was the next shift. Leading through uncertainty works the same way — the plan that matters is the one for this week, not the one for the next three years.

Morale is a decision, not a mood

After the storm broke, the boat felt like a different place — not because anything material had changed, but because we chose to treat catching two fish as a win worth celebrating. Teams take their cue from how their leader frames the moment, especially the bad ones.

None of this makes discomfort pleasant. It just makes it survivable, and eventually, useful.