It merely failed

How planning for failure will make us happier and more successful

The future is a mystery to us all.

And that means the greatest risk is in assuming it isn’t. In assuming our plans are perfect and won’t need adjustment.

But as John Kenneth Galbraith once wrote, “very specific and personal misfortune awaits those who presume to believe that the future is revealed to them.”

Great strategies, then, don’t seek to avoid all possibility of failure. In fact, the opposite is true.

Great strategies plan for failure.

Indeed, “by planning ahead,” as Annie Duke wrote in Thinking in Bets, “we can devise a plan to respond to a negative outcome instead of just reacting to it.”

Planning ahead will, of course, better prepare us to adjust or optimize our efforts before outright failure.

But even more than that, Duke continues, “we can also familiarize ourselves with the likelihood of a negative outcome and how it will feel.”

Because much of our fear of failure is actually our fear of feeling failure.

But if we assume it will happen and we prepare ourselves emotionally, we’ll be much better positioned to seize new opportunities or make necessary adjustments, before it’s too late—or even too soon.

Some of our plans will not work out. Some of our marketing messages will not succeed. And some of our best advertising efforts will provide no returns. We need to be ready for that.

This requires us, though, to have carefully considered what failure really looks like, ahead of time. We need to know why to change, when to change, and how to change if things take a bad turn.

In doing so, we won’t have to grapple with the embarrassment or shame that comes with failure—because it was always part of our plan.

And by knowing ahead of time what we will consider a true failure—what would cause us to stop working on an initiative or marketing effort—we’ll also know when not to stop.

We’ll know whether we simply need to stay on course and land long because we’re getting close, because we know what close looks like and what we were truly working toward.

Failure isn’t just inevitable, it’s necessary. As former Pixar president Ed Catmull wrote, “if you aren’t experiencing failure, then you are making a far worse mistake: You are being driven by the desire to avoid it.”

And that robs us of the creatively, boldness, and commitment that successful strategy requires. Because a strategy with no risk for failure has no hope of success.

So, to succeed, we need to spend time thinking about failure.

When you embark on anything new, take the necessary time to think about how and why it could fail. Consider what element of it is mostly likely to disappoint. And then think carefully about how you’ll feel and what you’ll do if it happens.

If you’re launching a new marketing position, strategy, campaign, messaging—or any significant change to your life or business—ask yourself these questions:

What would cause me to pause these new efforts, and why?

How will I feel if this doesn’t go the way I hope?

What would make me change course or try something new?

When would it be time to give up, and up to what threshold would I keep pushing?

How will I know I’ve succeeded, and how long am I willing to wait for that success?

This isn’t simply risk planning, making scenarios of likely problems and generating ideas for avoiding or mitigating them. Risk planning is about avoiding failure.

But planning to fail is about accepting the inevitability of some form of failure.

It’s about accepting that, no matter how much risk planning we do, something will elude or disappoint us. And it’s about realizing that, even when something fails us, we have not failed.

Because we planned for it.

Which means planning for failure is not pessimistic or negative—it is actually a form of optimism. 

“Optimists aren’t idiots,” Margaret Heffernan wrote in Uncharted. “They do better in life—live longer, healthier, more successful lives.”

How? “For the simple reason that they don’t ignore problems or give up easily.”

Indeed, optimists plan for failure so they can keep making progress even when failure strikes. Because they’re not surprised, disappointed, or embarrassed when it happens, and they feel no compulsion to ignore it or delude themselves into thinking nothing went wrong.

Because it was always just part of the plan.

They’re able to analyze, learn, adjust, and keep moving forward—because they’d prepared themselves for the inevitable.

To borrow from Fitzgerald, disappointing results or unexpected outcomes don’t mean our work has been “proven a failure.”

No, “it merely failed.”

And so we prepare.

We learn.

We adjust.

And we keep moving forward.


What would you like discussed in an upcoming edition of The Strategy You Want? Reply to this email or contact me at joel@familyknife.com to let me know!