When you’re planning for something—like a project, an event, or even just your day—it’s easy to hope for the best and expect things to go smoothly. But good planners know that things don’t always go as expected. Instead of guessing what will happen, try to picture a few different ways things could turn out. This helps you get ready for surprises and make better choices.

A simple way to do this is to think about three possible outcomes:

• Best case: Everything goes really well.
• Likely case: Things go about as you expect, with a few small bumps.
• Worst case: Some things go wrong, but it’s still realistic.

Here’s how this might sound in a real conversation:

• Victoria: I’m excited about our road trip next month, but I want to make sure we’re prepared. What do you think the best case looks like?
• Chris: Best case? We hit the road on time, find great places to stop, and come back with awesome memories and money left over.
• Victoria: And worst case?
• Chris: Car trouble leaves us stuck somewhere, we spend too much, and we end up stressed instead of relaxed.
• Victoria: Okay, that would be uncomfortable, but survivable. What's the likely case?
• Chris: Probably running into a few hiccups, but we'll most likely have a great time regardless of those bumps in the road!

Notice how Victoria and Chris talk through the best, worst, and likely cases together. By doing this, they turn a vague worry into clear, specific possibilities. This makes the trip feel less uncertain and helps them feel ready for whatever might happen. Imagining different outcomes gives them a plan, instead of just hoping for the best.

Once you’ve pictured a few possible outcomes, it’s smart to ask yourself, “If things don’t work out, what might have caused the problem?” This is called doing a pre-mortem. It just means you imagine that your plan has already failed, and you try to figure out why.

To do this, say to yourself: “Let’s pretend this plan didn’t work. What went wrong?” Write down any ideas that come to mind, even if they seem small.

For example, if you’re planning a community picnic, here’s how a pre-mortem might look:

Thinking about these possible problems ahead of time helps you make backup plans and avoid surprises. The pre-mortem works because it gives you permission to think negatively without being accused of pessimism. You're not saying the plan will fail—you're exploring what could go wrong so you can prevent it.

After you’ve thought about what could go wrong, it helps to know what signs to look for that tell you things might not be going as planned. These are called early warning signs. They help you notice problems early, so you can fix them before they get bigger. Think of early warning signs as your dashboard indicators. If you're driving and the fuel light comes on, you know to find a gas station soon.

For each outcome you imagined (best, likely, worst), try to think of one thing you could watch for. For example, if you’re organizing a bake sale:

• Best case sign: You get lots of sign-ups from volunteers in the first week.
• Likely case sign: You have enough volunteers, but a few spots are still open.
• Worst case sign: Almost no one signs up after a few days.

The key is to identify these signs in advance, before you're in the middle of the situation. That way, you're not caught off guard because you're already watching for the signals that tell you whether to celebrate, stay the course, or pivot quickly.

By imagining different outcomes, thinking about what could go wrong, and watching for early warning signs, you’ll be ready for whatever happens. These habits make planning less stressful and help you handle surprises with confidence. Next, you’ll get a chance to practice these skills by working through some real-life scenarios and planning for different outcomes yourself.