Strategy Loves Options (Fear Hates Them)

Unexpected events have a way of arriving like a rogue wave: no warning, lots of spray, and suddenly everyone is shouting at the wind.

Over my career, I’ve watched organizations get blindsided and immediately panic, not because the situation is unsolvable, but because they have no options on the table. When you haven’t thought through alternatives ahead of time, it feels like there are no alternatives. That’s when fear takes the wheel.

And fear is a terrible strategist.

The “No Options” Trap

When things go wrong and you’re unprepared, the brain does a very human thing: it narrows. Decisions get reactive. Messaging collapses into frantic blurts:

“We’ve got to do something! Anything! Make more money! Cut costs! Pivot! Now!”

In that state, you’re not making thoughtful choices. You’re flailing. And flailing burns time, credibility, and morale.

Options change the psychological terrain. When you’ve already discussed a set of alternatives, you’re not inventing a solution under stress. You’re selecting from a menu you prepared while you were calm, clear-eyed, and capable of judgment.

Sailing Is a Master Class in Options

Sailing taught me this lesson in a way that business never managed to, at least not at first. At the start of a race, there’s always an ideal plan. Maybe it’s the perfect spot on the line. Clean air. A small advantage over the fleet. The crew is dialed in. Everything looks crisp.

And then reality strolls in with the muddy boots.

You’re late to the spot. Someone fouls you. A line snags. The timing slips. The “perfect start” evaporates. If you only have one plan, you’re now in pure reaction mode. Strategy disappears. You’re just trying to stay in the game.

But if you have options, the moment doesn’t own you.

In sailing, we’ll often say something like:

• Plan A: Start here, on this part of the line, for a tactical advantage.

• Plan B: If we’re not set up in time, tack away and reset for a cleaner lane.

• Plan C: If the reset fails, follow a specific group of boats and hunt for an opportunity later on the course.

  
  

The magic isn’t that we predicted the future. It’s that we rehearsed our response.

Saying those alternatives out loud gives the whole crew shared expectations. When Plan A starts to unravel, I don’t have to narrate every move. Everyone can see what’s happening. They can help execute the shift to Plan B or Plan C without panic, without drama, and without wasting precious seconds arguing about what reality “means.”

Why This Is Rare in Business

What’s wild is how uncommon this is in organizations.

In business, many teams operate on a single primary plan with no meaningful backup. No alternatives. No option set. No agreed-upon “if this happens, we do that.”

And it’s easy to dismiss this idea at first. “Options? There are always options.”

Not really.

When the business starts to go sideways, people don’t talk about options. They talk about survival. They talk about urgency. They talk about doing something immediately, which often translates into doing the first thing that reduces discomfort, not the right thing that improves outcomes.

Options don’t magically appear in the moment you need them most. That’s the point.

A Portfolio Isn’t Just What You Plan to Do

This is where “portfolio thinking” becomes practical.

A good portfolio isn’t only a list of initiatives and big bets. It’s a list of alternatives. It’s the set of credible paths you can take when conditions change. You can think of each option as a controlled experiment: a way to limit exposure, reduce all-or-nothing risk, and keep the organization coordinated.

The goal isn’t to over-plan every scenario. The goal is to avoid being trapped by a single story.

The Real Power Move: Triggers

Options are only useful if you know when to switch.

In sailing, triggers are often obvious and time-bound:

“If we aren’t in position by this moment, Plan A is dead.”

In business, triggers can be equally concrete, especially for products and services:

“If we don’t have X customers, Y revenue, or Z retention by this date, we shift.”

The specific metrics depend on what you’re trying to accomplish, but the principle is stable: Define what success looks like. Define what failure looks like. Agree on what you’ll do next.

That’s how you stay strategic under pressure.

If You Want More Options, Build Them on Purpose

If you want a practical way to uncover and shape options for your organization (or for your own career), that’s exactly what my Business Agility Assessment is designed to do.

It helps you surface viable alternatives, clarify what you’re really betting on, and identify meaningful triggers so you can act decisively instead of reactively.

Because when the wind shifts, you don’t want to be inventing the race plan. You want to be executing it.