Losing Sight of Shore: The Leadership Move Most People Avoid

Transformation demands drift. You can’t discover new waters by hugging the dock. Here’s why leadership means letting go - of safety, of clarity, and of who you were yesterday.

“You cannot swim for new horizons until you have courage to lose sight of the shore.” – William Faulkner

Beautiful quote. Very poetic. Also: deeply uncomfortable.

Because here’s the part people don’t talk about.

Swimming toward new horizons sounds great.

But actually losing sight of shore?

That’s the part that makes your stomach drop.


Let’s Translate This into Leadership-Speak

You don’t get new outcomes with the same safe inputs.

You don’t transform teams by tweaking one meeting.

At some point, you have to leave the dock entirely:

  • Cut the old reporting structure that’s slowing you down
  • Step away from the tool everyone hates but no one questions
  • Kill the pet project you’ve been defending since 2022 because “it’s too far along to stop now”

Every Agile transformation hits this moment.

So does every career leap.

So does every culture change worth doing.

The hardest part isn’t doing something new.

It’s stopping something old.


The Shore Is Comfortable. That’s the Problem.

The shore is:

  • The status update meetings no one questions
  • The passive-aggressive email chains that substitute for real conflict
  • The PowerPoint decks we make to avoid making a decision

But here’s the truth:

You can’t reach new ground while dragging your anchor.

Real change doesn’t happen until you choose discomfort over familiarity.

That moment when you stop clinging to what sort of works

and instead bet on something better—even if it’s unproven, unpolished, and a little terrifying.


How This Shows Up in Work

  • A manager says they want cross-functional teams but won’t stop assigning work from the top.
  • A leader says they want innovation but vetoes anything not in the Q4 roadmap.
  • A team says they want autonomy but refuses to stop asking permission.

We say we want agility, ownership, growth.

But we also want to keep the life jacket on.

Can’t have both.


The Faulkner Test

If you’re serious about leading change, try this:

  1. Name one thing you’re holding onto that you know is outdated.
  2. Ask what it would take to let go of it—completely.
  3. Commit to one uncomfortable step this week.

If you never feel like you’re drifting a bit too far from shore,

you’re probably not swimming toward anything new.


Final Thought

Faulkner had it right.

But he also left something out.

Yes, you need the courage to leave the shore.

But you also need the conviction to keep going when the horizon still looks like a blurry rumor.

The payoff?

You stop managing the shoreline.

And you start building something new.

No lifeboat required.


Want to push this further? Try this with your team:

Ask everyone what “shore” they’re still clinging to—and what might be waiting if they finally let go.

Let’s get uncomfortable. That’s where the good stuff is.