These Three Questions Drive Every Decision We Make

Running a business can feel like a never-ending exercise in looking ahead. You’re always planning for the next promotion, the next ad campaign, the next product.

It’s like how they say that sharks have to always keep swimming or else they’ll die, right? If you don’t keep moving, you’re done for!

Here’s the thing, though:

Sharks don’t ACTUALLY have to keep swimming nonstop.

(Not all of them, anyway.)

Plenty of sharks are able to just stop, sink on down to the ocean floor, and chill out for a while. Doesn’t make ‘em any less, you know, shark-y.


That’s the kind of shark you want to be. Not the kind that’s always zipping along full speed ahead, sniffing out its next meal, but the kind that can sit still sometimes and just breathe.

It’s only when you take the time to stop and assess what’s going on that you can make sure you’re planning ahead effectively. Every now and then, you just have to take stock of what you’re doing!

Once a week, we set aside time to ask ourselves three big questions. (Literally. We write down our answers and everything.) It gives us the insight we need for planning whatever comes next – and asking these questions of yourself can do the same for you.

So, what ARE the three questions you can ask yourself weekly to make sure you’re planning effectively?

#1 – What went well?

This is a good one to ask first – and not just because it does wonders for your ego.

(Even though it does.)

If you ever worry about not being good enough at what you do, or about everything you’ve built falling out from under you – pay attention.

It’s perfectly normal to feel like you’re just not enough, whether that’s good enough, smart enough, or successful enough. It’s normal to look at the other people in your industry and want to compare yourself to them – especially when it seems like they’re lightyears ahead of where you are.

It’s actually so normal to worry about this stuff that it’s weirder if you DON’T. Even the ridiculously successful have a way of convincing themselves that they’ve only gotten as far as they have by sheer dumb luck, and that they’re one goof away from blowing everything! It’s actually a sign that you set high goals for yourself – which you totally should.

This is a big reason why you should make it a point to recognize your successes.

What did you do in the past week that went well? What did you really just get right?

(It doesn’t have to be huge, either, so don’t get all self-critical and say “nothing.”)

Maybe you worked out a really good system for assigning tasks to a VA, or for giving feedback to the people you work with. Maybe you came up with an awesome idea for your next project, or you dealt with a customer service crisis like a pro. Heck, maybe you just installed a browser plugin that’s making your life easier.

Wow, you did it!

Whatever you did, make a point to acknowledge it, so that you can recognize the cause-and-effect relationship between what you do and your own success. It’s the things you’ve done that got you where you are – and don’t you forget it!

But like we said, identifying your successes is about a lot more than your ego.

The better you are about recognizing the things you do right, the easier it is to do those things again and again. It’s hard to repeat your successes if you don’t identify what those successes are!

Using sports metaphors in business is super lame, we know, but this is one of the reasons athletes watch film of their previous games. If you’re going to do what works and ditch what doesn’t, you need to know what those things are.

And speaking of that second thing…

#2 – What could have gone better?

This question isn’t as fun to answer as that first one, but it’s still important.

When you make a mistake, your brain recognizes it almost immediately – it’s an instinctive way of teaching you not to do that thing again.


Unfortunately, our brains are also really good at rationalization and denial. We ignore things that make us feel uncomfortable, like the memories of mistakes and failures, and that makes us more likely to repeat them.

The more you confront the things that could’ve gone better, the easier it gets – and the more helpful it becomes.

Normalize the idea that things are going to go wrong. Make it less a question of if there’s something you’d like to improve, and more a question of what you’d like to improve.

Whether a certain task took longer than you’d hoped, a project didn’t turn out quite the way you wanted, or a deal you’d been hoping to land fell through, you need to recognize what could have gone better so you can identify how to improve in the future.

Which actually leads into the most important thing you need to ask yourself on a weekly basis:

#3 – How can you improve?

Chin up – there’s no point in dwelling too long on the things that haven’t exactly gone your way.

You’re much better off shifting your focus toward what you could have done differently – in fact, that may make you realize that the things you thought were big deals didn’t have to be in the first place!

For example, we frequently realize that the thing we should have done differently was ask for help sooner. Somebody got stuck trying to figure out a piece of code or a plugin all alone, instead of asking someone else to step in. Somebody hit a creative wall on a blog post or an email, and instead of getting someone else’s feedback, they stared at the blinking cursor and fretted.

When you point out what you could have done differently, it makes you realize that you don’t have to be afraid of that bad thing getting in your way again. Because if it does, you know what to do!

Going back to that example, we often find that we do our best work when we collaborate – and recognizing what happens when we don’t is encouraging, in its own way. It shows us that there is, in fact, a right way and a wrong way to handle a less-than-ideal situation, and when we run into that situation again in the future, we’ll know what to do.

Make the things that haven’t gone well into teachable moments, so that you don’t have to worry about running into them again – it’s like taking that whole “hindsight is 20/20” thing and actually making it work to your advantage!

(Hint: This is especially useful for learning how to deal with situations in which something went wrong and it wasn’t your fault.)

Sometimes the mistakes we make aren’t very dramatic or conspicuous – in the moment, they might not even feel very much like things we did wrong! But if you set aside time on a regular basis to look back at what you could have done even better – and how you could have done it – you might find more room for improvement than you realized was even there.

Getting started

Remember – you don’t ALWAYS have to keep pushing forward in your business! It’s okay to stop and reflect sometimes, instead of charging full speed ahead.

Set aside regular time for looking back at the your recent wins, your recent setbacks, and the things you could’ve done differently, and you’ll be able to move forward more prepared and more confident than ever.