You made a plan. A good one. The kind you thought through carefully, maybe even color-coded. And then something shifted — a staffing issue, a budget cut, a mandate from above — and suddenly that plan doesn’t fit anymore.
For most of us in medicine, that moment feels like failure. We were trained in straight lines. Med school, match, residency, fellowship, attending, chief. The path had steps. You followed them and it worked.
But leadership and real careers don’t work like that. And if you’ve been holding fast to your plan, trying to steer a straight course through genuinely uncertain conditions, you are exhausting yourself for nothing.
On today’s episode, we’ll talk about what sailing — yes, actual sailing — taught me about leading when the weather changes. And it has changed how I coach my clients through some of their hardest decisions.
Physician Leadership and the Illusion of the Straight-Line Path
When I became chief, a mentor said something to me that has really stuck: “Your path may not lead you in a straight line to the final destination. There are likely to be many curves along the way.”
I didn’t know how to interpret that at the time. My whole career trajectory had been linear. You study, you pass, you match, you train. The system rewards the person who stays on track. So when she said that, I nodded politely and filed it away without fully understanding it.
Years later, I finally get it. The straight-line path was the training path. Leadership is more like a sailing trip. The destination matters. How you get there is negotiable.
You may even have a destination that changes mid journey.
When we are in training, the goal is to follow the course correctly. When we are in leadership, the goal is to enjoy the journey — and you use whatever life gives you to get there. Some days that’s a straight shot. Most days it isn’t.
A Sailing Story: When Scrapping the Plan Was the Best Decision
My family has been sailing together for a few years now. I’ll be honest — at first it felt like camping on a boat. But it has seriously grown on me, specifically because of what it demands of you. A letting go that we don’t often get in real life.
You can’t rigidly plan a sailing trip. The weather won’t allow it. So you loosely sketch the route, you dream through the possibilities, and then each morning you wake up and read the conditions. What’s the wind doing? What’s coming in the afternoon? What does that mean for today’s plan?
One morning off the coast of Croatia, we woke up with a plan to set sail. Blue skies. The kind of morning that looks like nothing could go wrong. But there was big weather rolling in by afternoon, and we knew every other boat would be racing to find a dock. We already had one. The obvious call — for a sailor — was to stay put.
For someone like me — a planner, a mover — it felt uncomfortable. We had a plan. We were supposed to move.
Logic of course won out and we stayed put. We built a new plan from scratch. And what followed was one of the best days of the entire trip. We toured a family winery tucked into the hills. We got caught in a downpour and ended up hanging out in a local’s pub. We ate food we never would have found if we’d kept to the original route. Later that day, we heard a boat had capsized in the gusts.
That discomfort of abandoning the plan? I’ve learned to roll with it and embrace the uncertainty. Because on the other side of it is almost always something better than what I originally imagined.
A Framework for Women Physician Leaders Navigating Uncertainty
In leadership, we face the same choice when circumstances and demands change. Do you stay on the original tack, or do you change course? The problem is that most of us were never taught to think like this at work. We were taught to follow the plan.
One of my clients was facing exactly this recently. She needed to let someone on her team go. Intellectually she knew it was the right call. Emotionally, it felt terrible. So she kept putting it off. And the longer she stayed in the status quo, the worse it got.
Here’s what I offered her — and what I’d offer you.
First, name both paths honestly. Be honest with yourself about what each choice will bring you and your team. For this example, keeping this person most certainly leads to a culture problem. Letting them go opens something unknown, yes, but it also frees the team. And sets the path forward with more alignment.
Second, check for what you’re ignoring. Sometimes we don’t change course because we genuinely believe the storm will pass. And sometimes we just don’t want to see the weather report. Be honest about which one is happening for you.
Third, run it through your values. Not “what should I do?” Not “what would look best?” Ask: what does this decision say about the kind of leader I’m choosing to be? Which path actually aligns with your purpose?
She made the call. Difficult and uncomfortable, yes. But she also told me afterward that the team exhaled. The culture shifted in a positive direction. She could feel the changes within a week.
Next Steps for Women Physician Leaders Ready to Lead Through Uncertainty
The most skilled sailors aren’t the ones with the best original plan. They’re the ones who read the conditions clearly and adapt without losing sight of where they’re going.
That is leadership. That is what your team needs from you — not certainty, but clarity. Not the original plan, but the willingness to flex and make a new one.
If you’re sitting with a decision right now that feels like you have to choose between a comfortable bad option and an uncomfortable good one — I’d love to chat. That’s exactly the kind of work I do with my clients.
You can apply to work with me at womenmdleaders.com/work-with-stephanie. And if you’re not ready for that yet, start with my values journal — it’s free, and it’s the exact tool I use with every client at the beginning of our work together. You’ll find it at womenmdleaders.com/valuesguide.
Thank you for listening today. Protect your peace.