Assume You’ll Succeed When You’re Planning

Do you think you’ll fail when you try something new?

Despite what we tell others, deep down many of us think we’ll fail when we try something new. One of the places the assumption of our failure pops up is in the way we think about planning our goals. I’ve seen it over and over again: people automatically assume that they’re going to fail, and most of their plans revolve around preventing failure.

Instead of going that route, assume you’ll succeed and then figure out how you’re going to do it. While this reframe has a heavily linguistic component to it, it also has an important practical component to it — it makes success the primary consideration.

When success is at the forefront of your plans, it makes you think about what success looks like.

Sadly, many of us know what failure looks like, but we rarely take a second to think about what success looks like. Not knowing what success looks like is like starting a trip knowing all the places you don’t want to go but having no idea where you do want to go.

Once you know what success looks like, you can identify all the parts of the plan that will make success less likely — I call these parts drag points because of the way I think about planning. Imagine that your plans are like airplanes; they’re designed to get you somewhere. The smoother and more aerodynamic a plane is, the less energy it requires to keep moving. But if it has a lot of places that increase drag, it has to fight against those drag points the whole time.

It’s a known phenomenon that airplanes have to fight drag, and engineers design planes based around the fact that there is drag. Likewise, many of our plans have their drag points — if we’re honest, we know where we’re likely to go wrong and what types of things are likely to mess us up.

For instance, if you’re wanting to write an ebook but know you have trouble organizing your ideas, you need to come up with a plan that addresses that drag point. Note here that you’re still not assuming failure: you’re assuming you can write the ebook, but to write the ebook, you’ll need to do something to overcome the natural drag you’ll face.

When assessing drag points, it’s critical that you’re honest with yourself. If you really don’t like doing something or you’re not very good at it, put that on the board as a drag point. This lets you have an action plan for those points: you can either make a plan for improving your competence or you can figure out ways to minimize the actions you don’t want to do. But ignoring the fact that it’s there is an invitation for disaster, because, should you succeed, those drag points will become even harder to deal with. The faster you’re going, the more you have to fight against drag.

When we start from the assumption that we’ll fail, it’s hard to figure out where to start — after all, whatever we do is not likely to work anyway. But when we start from the assumption that we’ll succeed, we can identify what we need to do to get moving and what will drag us down. The assumption of success gives motivation, and identifying what needs to happen gives clarity and actionable steps.

Think about your plans. What would be different if you just pretended you would be successful? What is preventing your success, and what can you do about it?


Charlie Gilkey is an author, business advisor, and podcaster who teaches people how to start finishing what matters most. Click here to get more tools that’ll help you be a productive, flourishing co-creator of a better tomorrow.