Lots of the most worthwhile things in life carry a high risk of failure.

Will your direct action succeed? What’s the boss going to say when you ask for the raise? Is this campaign going to work? Will this fundraising plan reveal you as a leader, or make you look silly?

To make ourselves vulnerable to failure requires courage. Courage is one of those weasel words that can mean something very different to different people. It’s often understood as a mysterious thing that comes out in moments of great drama, and that can certainly be true. It’s been usefully described as “not action without fear, but action despite it.” But what if we approached courage from a slightly different angle?

What if, for the sake of argument, we thought of courage as a muscle that can be developed? How might that notion change the way we approach moments of fear and vulnerability, big decisions that we may very well get wrong? And what habits and thought processes might we adopt to do a thing like develop courage?

If we take courage to mean decisive action in the face of uncertainty, we might begin to think about the steps we could follow to feel more confident in the decisions we make. Steps like these:

1. Ask yourself: what does success look like?

Imagine the ideal outcome for your decision dilemma. Then, ask yourself what, from that ideal picture, you’d be willing to sacrifice and still remain satisfied. You’ve now got something like a goal window–an ideal state to aim for, and a set of realistic acceptable tradeoffs that will still allow you to achieve a win.

When I was Interactive Director of The Parley a few years ago, we wound up taking a risk I didn’t feel ready to take. The Creative Director and I had discussed putting together a locally-focused TED-style event that was designed to bring together activists, technology & knowledge workers, and artists. I loved the idea and thought “I can’t wait to start planning this, with a couple of months lead time we could put on a great event.”

I arrived home after our meeting to discover that the excited Creative Director had sent out an e-mail to some of our most impressive contacts announcing we were doing this event in 3 weeks, asking if they’d like to participate. I was immediately horrified. Three weeks? Surely he was crazy. This was going to be a disaster.

But he seemed sure of himself. I sent him a gently inquiring e-mail asking him just what he thought we could pull together in 3 weeks, and his answer was short, and assured: he laid out the contours of the event as he imagined it, and said “this is totally doable.”

A failure here would be embarassing for us, but I trusted him. Before I had wrapped my mind around it, he already understood what success looked like.

2. Determine the Importance of Your Goal

How important is achieving this end-state to you? Is this a question of deeply held values, or would you just *rather* have a certain outcome? Figuring out how important this goal is to you will help you determine how hard to fight for it.

The Creative Director and I had a long set of discussions about what this event could mean if it was a success. I hadn’t fully wrapped my head around it, because I couldn’t banish mental images of the Hindenburg. The CD laid it out: making this happen would be a splashy entrance into the world we were hoping to break into. If we succeeded, it would be by pursuing something that was at the heart of what we were about as an organization–connecting people across boundaries to make cool ideas into reality. A success here would be huge for us. And we had 3 weeks to do it. I suddenly understood: we had to get moving, fear of failure be damned.

3. Weigh Costs & Benefits

What will you have to sacrifice to pursue this goal? You don’t have an infinite number of hours, and to take on new goals you’ll need to make room for the work of pursuing the goal.

Before I’d come home to see the announcement e-mail there were a half dozen other ideas I was interested in pursuing, but they were all going to have to be set aside in the single-minded pursuit of making this thing real (now we only had 2 weeks!). Still, the meaning of pulling this off successfully wasn’t lost on either one of us–and the meaning of pulling it off at the speed we were doing it definitely wasn’t lost on me. The CD pushed us, because he knew the cost was worth the benefit.

4. Is this the right time?

Why pursue this now? Is your interest in this uncertain project something that aligns with your longer-term goals? Are there obstacles in place now that might disappear if you wait?

This sure as hell didn’t seem like the right time to me, at least not at first. We had two days to go before this event was happening, tickets were on sale and moving at a quick clip, and I was still scrambling to get us intermission entertainment and to confirm the last few prominent speakers for the event. From where I stood it seemed like the decision to put this together was impulsive, and that if we’d had more time to plan we could ensure a success.

The CD understood something I didn’t: even if this event wasn’t perfect, we could use it as a foundation–it would be a learning experience for all of us that we could use when we tried it a second, third, fourth time. As he knew, and as I’ve learned, there are benefits to just starting.

5. Backup Planning

Your ‘oh shit’ moment could be the most important part of your planning: what happens if despite all your planning and foresight, it turns out you’ve made the wrong decision? What will you do?

In our case, our contingency plan was “do it again, but better.”

That’s probably not the best Plan B you’ve ever heard of, but we were young and full of belief in what we were doing.

—

As it happened, the event was a huge success. The thing I didn’t think was realistic to do in the time frame we’d allotted, the event I’d feared would make us look like fools when it fell apart, went off without a hitch. We got press coverage, we watched people from different worlds shake hands and plan to collaborate on future projects, and we walked away with a higher profile than we’d had to date.

Oh, and I DJ’d a minimal house music set as DJ of last resort.

This all came together because we worked hard, but none of it would have happened without our Creative Director having the courage to throw together an ambitious event with prominent guests on a short timeline. He had that courage because he had already made the calculations–this was a risk, but it was one worth taking.

Know what you’re aiming for, decide how hard you’ll fight for it, make sure you’re ready to make sacrifices, make the time to act, and have a backup plan. When you know the contours of success and the costs of failure thoroughly, courage can be easier to find. And if it’s easier to find today, it’ll be easier still to find tomorrow.