How Optimism Can Get in the Way of Effective Coaching

George Bernard Shaw's quote, "The optimist invents the airplane; the pessimist, the parachute," is a useful metaphor for coaching.

Optimism matters. Coaches need to believe clients can change. But optimism can also lead us to help clients imagine change only under ideal conditions, when they're rested, motivated, supported, and everything goes right.

But real life rarely works that way.

The more useful coaching question is not only, "How will you do that?" but also, "What happens when it gets hard, when the…"

Craving hits.

Pain flares.

Schedule falls apart.

Old unworkable patterns show up again.

Pessimism doesn't mean doubting the client. It means helping the client discover how they can succeed when real life shows up.

The optimist may invent the airplane.

But the coach who remembers the parachute may be the one who helps the client land.

The great Irish playwright, critic, and social commentator George Bernard Shaw is credited with the quote, "Both optimists and pessimists contribute to our society. The optimist invents the airplane, the pessimist, the parachute."

As a coach, which are you?

We tend to think the best coaches are the encouraging ones. The ones who radiate confidence that the client will get there. Optimists, basically.

But there's something the optimistic coach consistently misses. And it's a miss they don't see.

When a client says, "In my better future, I'd be able to stop at two drinks" or "I'd stop at two scoops of ice cream," the optimistic coach hears a solution and moves on, saying, "Great, so how would you do that?"

The pessimistic coach thinks: "yeah, but what about when you want the third one?"

Here's what the pessimist actually doubts: not the client. The plan. Most solutions get built for the days when everything goes right, when you're rested, you're not stressed, and nobody brought donuts to the meeting. Those plans work fine. Until there's a bump in the road, a departure from the routine.

And they believe, completely, that their client can handle the bumps and departures, but only if those are part of the plan.

And so they ask:

That's not the same conversation. One builds a plan for the easy days. The other builds the capacity to get through the hard ones. One produces intention. The other produces coping.

This is the question that develops a client's ability to handle what actually shows up: the craving, the stressful week, the alarm that didn't go off. Not by avoiding those things, but by having already imagined navigating them successfully. The pessimistic coach gets there because they can't help asking "but what if it doesn't go that way?" and then immediately following it with, "and you handled it anyway. What would you have done? What would that look like?"

This matters even more when the obstacle isn't a craving that might pass, but a condition that won't. Take a patient managing arthritis. The optimistic coach might orient entirely around better days: less pain, more mobility, getting back to what they love. Meaningful goals. But incomplete ones.

The pessimistic coach asks:

That question doesn't ignore the pain. It builds around it. It helps the client develop the capacity to live well inside their actual circumstances, not just on the days when circumstances cooperate. That's what sustainability looks like for someone whose obstacle is permanent, not a plan for when things get better, but a way of navigating that holds even when they don't.

The research on goal pursuit arrived at exactly the same place from a different direction. Decades of studies show that pure positive visualization, just imagining the desired outcome, consistently underperforms compared to imagining the outcome and then immediately confronting the obstacle. Dreamers without a back-up plan, it turns out, are often not doers.

The coach who anticipates what will get in the way isn't introducing doubt. They're doing the work pure optimism skips: building the client's capacity to stay in their preferred future even when real life pushes back.

So if your instinct is to ask but what if the craving hits anyway or the condition doesn't get better, that's not a liability. That's the most important question you could ask.

And the saying goes, "I'm not a pessimist. I'm just an optimist with experience."