When Trying Something New Doesn’t Work Out

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Trying something new can sound really exciting. We always encourage someone to take the chance, try something different, or go somewhere you’ve never been. There’s something energizing about the idea of stepping outside what you already know and seeing what might happen.

Now, actually doing it can feel very different because trying something new means giving up at least a little bit of certainty. There’s some comfort in the familiar, even when you’re ready for something different. The new thing comes with possibilities, but none of them are guaranteed. You can prepare and think it through as much as you possibly can. You can make what seems like a really good decision and still, have no idea how it’s going to turn out.

That can be hard enough on its own, but we tend to pile more on top of it. Once something doesn’t work out, hindsight has a way of making the decision look incredibly stupid. Suddenly all the uncertainty you accepted beforehand starts looking like evidence that you should have known better. You can look back and remember things being safer or better than they actually were. You can convince yourself that there were signs you should have noticed, even though they may not have meant much at the time because you didn’t know how things would turn out.

Once you know the ending, it’s surprisingly easy to rewrite everything that came before it. Something that seemed like a small possibility starts feeling like an obvious outcome. You remember the reasons not to do it much more clearly than the reasons you decided it was worth trying in the first place. From where you’re standing now, it can feel like the version of you who made that choice was looking at all the same information and somehow failed to see what was right in front of them.

But you didn’t know any of this then.

None of us gets to make decisions with information from the future. We make them from wherever we are, with what we know at the time. We get some decisions right and others wrong. We can also make a perfectly reasonable choice only for something outside our control to knock the whole thing sideways anyway. What happens afterward doesn’t automatically rewrite what was true when you made the choice.

We’re often much kinder to ourselves about trying when the story ends well. If you take a risk and it works, you are brave. You trusted yourself and took a chance on something better. If you take the same kind of risk and it blows up in your face, suddenly you were reckless.

But those decisions may have looked exactly the same when you made them. The only difference is that now you know how one of them turned out.

Maybe there are things you would do differently knowing what you know now. There probably will be sometimes. Trying something new doesn’t mean every choice you make along the way was a good one, and giving yourself grace doesn’t mean refusing to admit when you screwed up. You can recognize a red flag you ignored or a mistake you made without turning that into I never should have tried at all. Those are two very different conclusions.

And before you decide you failed, it’s worth asking whether what you did even had a pass or fail attached to it. Sometimes you try something and discover you don’t like it. What you want can change once you actually experience something instead of imagining it. You can decide not to continue without that meaning you failed.

But sometimes you try and you do actually fail. And that’s ok.

I don’t think we have to rescue ourselves from that word every time. We don’t need to turn every failure into something positive just to make ourselves feel better about it. Sometimes you wanted to accomplish something, you tried to make it work, and you just couldn’t, no matter how hard you tried. That sounds a lot like failing to me.

But “I failed at that” is still very different from “I’m a failure”. They are not interchangeable. One describes something that happened. The other takes what happened and turns it into something about who you are.

It doesn’t take much to make that jump. One thing doesn’t work, and suddenly your brain starts dragging up every other time something went wrong. Before long, you’re not just thinking about this one thing anymore. You’re wondering if maybe this is what you do. Maybe you make bad decisions. Maybe you aren’t as capable as you thought you were, and trying again is just going to give you another chance to screw something up. One failure has somehow turned into evidence against you.

And maybe, right now, you do consider what happened a failure. Someone else might look at the same experience and see it differently, and you might eventually see it differently too. Failure is partly a matter of perspective. Something that feels like an enormous failure while you’re standing in the middle of it may look different when you have some distance from it.

That doesn’t mean you need to go looking for the better perspective immediately. If something you were excited about just fell apart, you’re allowed to be upset about it. You don’t have to immediately start looking for the lesson or listing everything you supposedly gained from the experience while you’re still trying to deal with what you lost. Sometimes the first thing you need to do is admit that this really sucks.

You can be disappointed, angry about what happened, or wish you had made a different choice. You can have absolutely no idea what you’re supposed to do next. Giving yourself space for all of that isn’t the same as deciding you’re going to stay there forever.

Eventually, though, you have to look at where you actually are.

Sometimes that means dealing with very practical problems before you have the luxury of finding some deeper meaning in what happened. Perspective is useful, but it doesn’t pay a bill or fix the thing that just broke. There may be something in front of you that needs your attention today, and it’s okay if figuring that out comes before figuring out what the experience taught you. You can come back to the rest when you have a little more room to think about it.

Maybe then you realize you know something you didn’t know before. You might understand something about yourself that you couldn’t have known without actually trying. The experience may even have changed what you want next. None of that means you have to decide everything happens for a reason or turn a bad experience into something that was secretly good for you.

Sometimes something just turns out bad. I don’t think there always has to be a bigger reason for it, but that doesn’t mean nothing can come from it either. Maybe you learned something or gained experience. Maybe all you know is what you don’t want to do again. That’s still information you didn’t have before, and none of it requires you to pretend you’re glad things turned out the way they did.

You may also look back and realize that what happened wasn’t entirely your fault. We tend to call something our failure simply because it happened to us, even when circumstances outside of our control played a pretty significant role in how things turned out. There’s a difference between taking responsibility for the choices you made and blaming yourself for everything that happened afterward.

Maybe you made a bad call. Maybe you genuinely failed. Or maybe you did everything reasonably well and it still didn’t work.

Giving ourselves permission to try has to include giving ourselves permission for the thing not to work. Otherwise, we haven’t really given ourselves permission to try at all. We’ve only given ourselves permission to succeed, and that can start getting tangled up with how we see ourselves. If part of you already worries that you aren’t good enough, that you make bad decisions, or that other people will see you as a failure, succeeding can start to feel like proof that those things aren’t true. Which means failing can feel like proof that they are.

That can put a lot more pressure on trying something new than we realize. Now you aren’t only hoping something works because you want it to work. You need it to work because of what you’re afraid it might mean about you if it doesn’t.

But there’s no way to try something new and guarantee yourself a good outcome. There will always be some risk in doing something you haven’t done before. You can make thoughtful choices and still regret some of them. You can prepare and still get caught off guard. You can do your absolute best and still end up somewhere you never intended to be.

And if that happens, the experience may take something from you. It might cost you time, money, or confidence. It may change plans you were excited about. But it doesn’t need to cost your willingness to try again.

Trying something new was never a promise that it would work. It was a willingness to find out. Sometimes you find out that you love something you never expected to love. Sometimes you discover that you’re capable of something you weren’t sure you could do. And sometimes you find out that this particular thing isn’t going to work.

When something doesn’t work, you don’t have to turn it into a success story before you’re allowed to move forward. You don’t have to be grateful it happened. You just have to eventually let one thing that didn’t work be one thing that didn’t work, instead of turning it into evidence that you should never take another chance on yourself.

And then, when you’re ready, you get to decide what you want to try next.


✦ Closing Glimmer

Something not working out doesn’t mean you were wrong to try. You can be disappointed by how something turned out without regretting that you gave it a chance.

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