Fail Forward: Failure is a door, not a brick wall

Fail forward is a term I first heard in tabletop roleplaying. It means that when you fail, something interesting should happen that moves the story forward. In life, we should look at our ‘failures’ as opportunities, not the end of the road. Failure is a door, not a brick wall. It gives options and clarity, even it’s not what we would have hoped for.

In this article, I’ll share some examples and lessons around failing forward, including an embarrassing story of my own that turned out great!

In many traditional roleplaying games, failure can often look like this:

Game Master (GM): “You’re attacked by an ogre with a club!”
Player: “Aaah! I attack it with my axe! I rolled… 5…”
GM: “Okay, you miss and it attacks you… rolling a 2. It misses. Your go!”
Player: “Come on, dice! Ugh! I got a 6. Not enough, right?”
GM: “Yeah, you miss. It attacks… and misses too! Your turn again.”

Critical Miss

In a game like Dungeon World, failure might look more like this:

Game Master (GM): “You’re attacked by an ogre with a club!”
Player: “Aaah! I attack it with my axe! I rolled… 5…”
GM: “You swing your mighty axe but the ogre brings up its club just in time. Your axe smacks into the massive club and lodges there. The ogre swings the club back over its shoulder. You can hang onto your axe and go for a ride, or let it go. What do you do?”
Player: “Woah! Uh… okay, I’m going to hold on. Or try to!”
GM: “Okay, roll to defy danger. Strength, I think.”
Player: “Ugh, 8. So, partial success.”
GM: “Okay, you manage to hold on as the ogre swings the club, the axe and you over its shoulder, but your grip is slipping. You can keep all your weight on the axe and dislodge it as you and it fall from above the ogre’s shoulder to the ground. Or you can let go and leave your axe there, but land on the ogre’s back. What do you do?”
Player: “Yeah! I let the axe go and drop onto its back, daggers drawn!”
GM: “Awesome! Roll for it!”

See the difference? In the second example, the failures and partial successes lead to new and exciting options. None of them are exactly welcome, but they’re something.

I admit, lots of traditional RPGs have more colour than the first example, but some do devolve into that sort of boring exchange of non-blows. Nothing happens. No options open up.

Don’t let real life feel like this. If you fail, fail forward.

Here’s how I recently failed forward

I accidentally skipped out on the bill at a coffee shop. Whoops!

I had gotten there first and ordered, then the person I was meeting with – who had said they’d shout me a coffee – arrived and ordered. I assumed they paid for mine, they assumed I’d already paid for mine.

I only realised after I left. I checked and yes, they had not paid.

E) Steal Coffee mug
E) Steal
Coffee mug

So, I felt terrible, but it was an honest mistake so I called up the coffee shop. I explained, apologised and said I’d be back in a few days and could pay then. They asked me details, then they actually thanked me.

They actually thanked me.

A few days later when I arrived to pay, the manager was there and she must have thanked me three or four times in our conversation. They had even mislaid the receipt, so they had no record of me not paying. I told them what I ordered and paid for it.

She told me how she had done the same thing in an important business meeting with someone who has helping her start up her shop. We got talking, as small business owners, and even discovered we both did work for the same place some time ago. It was a great conversation and I feel I made a new connection there.

I made a new connection there.

After one last sorry and one last thank you, I went and sat down to wait for my client. After a few minutes a waiter came up to me with the drink I had ordered and not paid for last time I was here. “Sir, this is on the house” he said. I thanked him and couldn’t stop smiling as I sipped my drink and mused on the way this had all turned out.

I couldn’t stop smiling as I sipped on my drink and mused on the way this had all turned out.

If things had gone to plan, my drink and pastry would’ve been paid for by someone else the first time around. Instead, I failed forward – I failed, in that I had done something wrong and did have to pay my own money for it – but I made a new connection and actually got another drink out of.

Who would’ve thought my failure would lead to this?

What’s the lesson?

As I mentioned, failure is a door, not a brick wall.

In my story, it could’ve gone differently. I could’ve not owned up to it pretended like it didn’t happen, hoping not to get found out. I could’ve had that stress on my conscience. But what do I gain? Everything stays the same, or gets worse.

Instead, I took the failure and got an unexpected benefit.

These lessons were reinforced for me:

  • Don’t let mistakes or failure stop a good thing
  • Be brave: own your mistakes
  • Don’t make failure a bigger issue than it is
  • Fix what you can, learn and move on

Don’t let mistakes or failure stop a good thing. Another way I could’ve reacted is to avoid that coffee shop forever. But it’s perfect for all my meetings and in a great spot. Don’t let failure stop a good thing. Find a way to keep the good thing going, even if that means harder options. At least consider it.

This approach leads us into…

Be brave: own your mistakes. Admit you stuffed up and deal with the consequences. If you’re frozen by fear of what may happen, you’ll never find out what will actually happen. There’s always the infinite ‘what ifs’ but there’s only one ‘what is’. Go make it happen for you, with agency, instead of waiting for it to happen to you.

There’s the infinite ‘what ifs’ but only one ‘what is’.

Make it happen for you, instead of waiting for it to happen to you.

On this note…

Don’t make failure a bigger issue than it is. I could’ve blubbered or freaked out when I called the coffee shop – or spent hours crafting the perfect thing to say. I mean, technically I stole from them!

There’s no sense crying over every mistake.

But instead, I considered the reality of the situation and treated it like it wasn’t a big deal. Because it wasn’t! I stuffed up, I would make up for it.

I know that my attitude on the phone influenced how the coffee shop treated me. They knew I hadn’t done it on purpose and I had taken steps to fix things as best I could.

I know, though, that sometimes it doesn’t work out so well, or you can’t just go back and do what you forgot to do.


Fix what you can, learn and move on. Sometimes, you can’t unburn that bridge. Sometimes failure means you’ve lost something permanently – an opportunity, a contact, reputation. You could dwell on that and never move on, or you could fail forward. Make something interesting happen. Continue the story. Find an opportunity in the failure and act on it. Even if that opportunity is just learning from it, that’s something.

Make something interesting happen. Continue the story. Find an opportunity in the failure and act on it.

If you fail, fail forward

So, next time something doesn’t work out as you had planned, see how you can make it work for you. What can you salvage? Where can you fix things? What can you learn? What opportunities await thanks to this result not being the one you expected?

Perhaps you could think of this as not even a failure at all, just a result. But that’s another article for another day.

For now, know that failure’s not the end. It’s not a brick wall, but a door.

Open it.

Open Chat

When have you failed forward? What’s some mortifying thing you’ve done that somehow turned out well? What other wisdom is there around the idea of failing forward? Feel free to add your comments below.


When Jarrod's not writing about personal development through pop-culture, he's helping people like you reach their goals through fun, empowering coaching.

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