Failing Well – Overcoming That Constant Feeling of Not-Good-Enough

The Monstrous Self-Imposed Bar of Success

Failure is inevitable.

It happens to everyone.

It’s as sure to occur as rain and breathing, and stopping it is sort of like stopping clouds from moving or crushing coal into diamonds with your bare hands.

For the last few mornings I’ve felt its weight. You see, I made a habit — a good habit. I wake up every day at 5am, head to a local coffee shop and write or edit for two hours before work. Things were going swimmingly, and I got a lot done for the first two months, but a little over a week ago I finished the project that was consuming me for the last two years. And now for two weeks, ten sessions and fourty cups of coffee, I’ve written maybe twelve words.

I can’t decide how to move forward, and I can’t help but feeling like a failure every single time I go through the motions of waking up, heading to the coffee shop, and staring at a screen for two hours. It’s not like its my job. Writing is something I do because I like it, one of my outlets for artistic creativity. And yet I’m falling short of my meaningless self-imposed bar of excellence.

Like Dr. Frankenstien, I’ve created a monster, and that monster is me.





Hi, My Name Is Brian – And I Am A ______

Fill in the blank. I know you’ve got one too.

Ball Dropper. Over-Promiser. Self-Criticizer. Poor Executer.

My personal favorite is the last one. I do it all the time. Establish a cool idea, something big and exciting, and then get the machine running. I hype up my audience, get my team put together, maybe even have an initial meeting… and then – BANG. I look up at the enormous mountain of work ahead, and I recalculate the data.

“Fourteen miles at a seventy degree incline… and I didn’t even bring shoes… This is NOT a mountain I want to climb. Anyone up for carrying me?”

This is a classic poor-executer. And I wish I could tell you I did it all the time. It’d be easier that way, to always and consistently run from mountains. But no. Instead I succeed at executing a plan MOST of the time. In fact, I almost always reach the peak, which makes all those times when I don’t execute the plan that much more soul-crushing.

No matter what I do to better position myself – trying to only take on what I can handle – to only create plans for things that are humanly possible – it still happens. I still fail once in a while.

We all have our cross to bear.

But any good Catholic (or Christian in general for that matter) can tell you a thing or two about what happens next. There’s a confessional, an opportunity to be forgiven and to accept the forgiveness yourself, and then you end up rinsing and repeating. Over and over.

Fail. Confess. Forgive. Try Better. Fail. Confess. Forgive.

But the point of this process is not failure and redemption. As I mentioned above, failure is inevitable. The point of this process is learning how to fail well.

That’s right.

Because there is a difference between failing and failing well.



How to Fail Well


I love playing games with my nephews.

I’ve got a boatload of them, being the youngest of four with three older sisters, with a 10 year gap. Apparently after none of us killed one another growing up, we all decided big families were cool.

I remember what it felt like to be the youngest.

If I’m honest, I wasn’t good at it. I hated being left out and would generally get angry and go do my own thing instead. But one of my nephews, the youngest one, he was cut from a different cloth.

He’s three years old, four inches tall and maybe ten pounds soaking wet. I’ve caught fish bigger than my three year old nephew.

So it should come as no surprise that when I brought the 5 year old, the 7 year old and the 8 year old into the basement to play some “tackle” football, I was hesitant to let my 3 year old nephew participate. Nonetheless, when he insisted, I put him on my team.

He got creamed at first. I tossed him the ball, he stood there wide eyed as the posse of older cousins came running, and he took about two steps before being dragged to the floor. He bumped his head, shed a tear, and to my surprise got back up to try again.

He played along for a while longer, timidly, not wanting me to pass the ball to him. I tied up the game by passing to myself and walking to the endzone, fully expecting to allow my nephews to win. They scored again as expected, and I was about to call the game when my 3 year old nephew told me he wanted to run it again. He wasn’t afraid anymore. He wasn’t done trying yet. I told everyone we were going to play one more down.

I tossed my 3 year old nephew the ball , and with a gutteral roar he ran as hard and fast as he could towards the other end of the basement. His cousins were unsure how to react to this little lion screaming and swinging his free arm while he sprinted full-boar down the hallway. They snapped out of it when he got closer, and all jumped on him but he just wouldn’t stop, barbarically forcing his way forward with an incredible force until he fell to the floor, a half inch from the touchdown line. He didn’t win the game, but he stood up and smiled like it didn’t matter.

My 3 year old nephew knows how to fail well.

Failure is inevitable.

But how we react when we fail is up to us.

We can let it crush us. We can let it stop us or control us. We can grow tired or timid or afraid and make excuses for ourselves. Or we can adjust the bar. Because maybe winning the game all of the time isn’t what matters most. Maybe getting close counts for something. Maybe waking up at 5am to go to a coffee shop and write 4 words in two hours is still worthy of a pat on the back.

It’s a starting point. It’s a position — ahead of where I was before, but behind where I want to be.

It’s a step in the right direction.

Because failing well doesn’t mean avoiding failure – it means reacting better to it. It means stepping, redefining where we are and being honest with how much further we have to go. It’s a process that doesn’t stop, never stops, can’t stop and won’t stop.

Failure is like the rain. It happens. But we can still choose to fail well.

And that’s what I aim to do.



3 thoughts on “Failing Well – Overcoming That Constant Feeling of Not-Good-Enough

  1. You finished a project that’s taken two years – are you talking in your post about starting something new? If so, allow me to butt in with my opinion. 🙂

    Take a break. Sometimes, especially after two years of hard and heavy writing, you need it. Sometimes a few degrees of separation, just to think about things (and make notes if something stellar hits you upside the head) is all it takes to stoke the furnace. I don’t know how many completed projects you have. I don’t know your writing work habits, etc., but that was the first thing that came to mind when reading your post. Writing four words is, IMO, perfectly fine/normal. It’s four words you didn’t have when you started – if you keep them, and if you don’t, so what.

    This stagnant period isn’t failing. To me it’s simply finding the new story.

    • You’re probably right. I should probably take a break and read ten books, but I keep coming back to this article –

      And it keeps making me realize that the writing muscle, like any muscle, needs to be worked out and flexed. The whole “books aren’t written, they’re rewritten” comment really stuck with me. Honestly I feel like I need to be more willing to write some garbage and toss it out. I feel like every time I write a short, I want to make it a book, but most ideas aren’t really worthy of the long format and the work that would be needed to put it in.

      What I need is a graveyard of garbage writing to dig through from time to time, and I think the way to get that might be writing prompts. Or just writing random stuff. Just to write. Just to unload the well and force it to be refilled.

      The other quote that hit me hard was Hemmingway’s. About breaking his writers block by always stopping writing when it’s the most exciting so that he is really looking forward to coming back to it!

      I don’t know. What are your thoughts? Does this article make you feel guilty too? 🙂

  2. This piece you said about writing “just to unload the well, and force it to be filled…” is fine b/c everyone has their way. And if you needed to write something every single day, that’s okay – I guess you just have to be aware some days it will be good, and some days it will crap. Like running. Not every run is a good run – and I’ve been doing that for about 25 yrs. When I have a bad run, I just finish it and know it’s going to be better next time around.

    I read the article, (and bookmarked the site b/c that was actually a GREAT tidbit of info) Funny, it didn’t make me feel guilty, you know why? Because I think this is what they do when they are into a project. I don’t think they write those volumes unless they are working on a new book. That was my take on it. One that stuck out was Susan Wittig Albert, I don’t know that I’ve heard of her, but she indicated she writes 8-9 months out of the year, 1,500 a day. And that’s partly why I think these are simply word counts during a project. I do read every day – that’s one thing I don’t take a break from! 🙂

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