This week I took a risk.

Instead of launching a book the traditional way, I decided to do something a little outside the proverbial box.

If people pre-order Do Over, I email them a digital copy of the book.

Not just a part of the book, the whole book.

Not just when it comes out on April 7, but right now.

Not if they pay extra, but for free.

Do-Over-3D-bookshot-with-spineI’ve never seen a publisher give away copies to everyone who orders a book months before it comes out.

It’s a risk. What if giving away all those digital copies hurts the sales of digital books? What if the process of delivering them to people doesn’t work? What if people read the book over a two month process instead of all at once in April and the momentum is divided?

These are risks, but I was willing to take them because I asked the three questions you should always ask before you take a risk.

1. What if?
Risks always start out the same way with someone asking the question, “What if?” Often they don’t use those exact words but instead say, “Wouldn’t it be crazy if we ______________?” Someone brave floats an idea into the room that is so crazy they preface it with a disclaimer. Once that question is out, it leads to the second one.

2. Why not?
Taking a risk doesn’t mean you make stupid decisions. Taking a risk is one part bravery and one bajillion parts intelligence. During the why not phase you lay out the risk on the table and really examine it. What is truly at stake? What could happen if you take this risk? What haven’t you thought of yet? What would happen if you don’t take the risk? Like a cop on Law Order SVU you place the risk under a bright light, interrogate it and see if it’s worth chasing. All that conversation leads to the third question.

3. How?
99% of people will stop at the first two questions because those are imagination questions. Question three is an action question and that’s a whole different beast. The first two questions focus on dreaming, the third focuses on doing. When you ask “how” you begin to look at the execution of the idea. You put systems in place and poke holes in the idea. You come up with strategies and the risk inevitably grows in complexity and scale. There are always more details than you anticipated. The risk was easy when it was just an idea, now it’s a real thing.

Those are the three questions you should always ask, but you should also keep things in perspective. A soldier on a plane taught me that unless people were shooting at me, the risk wasn’t as dangerous as I thought.

Here’s the experience we launched after we asked all those questions about risk.

There’s a chance the risk might not work.

If your risk is guaranteed to succeed you haven’t really taken one.

[Tweet “If your risk is guaranteed to succeed you haven’t really taken one.”]

I might fail. And I’m not going to sugarcoat that and give you some motivational nonsense about how failure doesn’t impact me because it’s such a wonderful learning lesson.

I can’t stand failure. I launched this risk with great waves of nervousness and anxiety, despite realizing I was not a heart surgeon with a patient on the table or a soldier with an enemy trying to shoot me.

I hate failure, but it stings a lot less if I know I tried my best.

[Tweet “I hate failure, but it stings a lot less if I know I tried my best.”]

And to try my best means I have to risk.

So do you.

Ask those three questions next time you do.