Why Doubt And A Willingness To Fail Is Crucial


Doubt is important.  Failure is critical.  I never let either one of them stop me.

Today I wanted to do something different and really pull open the blinds on how I feel about myself sometimes.  A big problem with any form of social media, whether it’s a blog, Instagram, Twitter, Facebook, or whatever else, is that sometimes people get the wrong impression on what a person’s life is really like (read: whether they are really that happy all the time).  Instagram is the biggest culprit here, creating a whole generation of insecure people who believe that their lives don’t stack up to the lives they see on the internet.

The thing is, most social sharing methods are a way to share the highlights of someone’s life.  For every picture on Instagram there is an entire day of mundane activities leading up to it – struggling to wake up early, eating regular food, traveling in a beat-up car, sitting on a cramped airplane, missing connections, experiencing delays, failures, etc.  But because these things aren’t shown, we all assume that the people we follow have these amazing lives.

For me personally, the biggest thing I hide on social media is a healthy amount of self-doubt.  People who know me in real life know that I carry a lot of confidence with me everywhere I go, but the truth is that underneath everything else lie myriad doubts about my skill, my work ethic, my prospects as a writer, myself in general.

Herein lies the second problem, which is that a lot people people might see that statement as some bombshell revelation, a moment of vulnerability that shows everyone how unhappy I actually am with life.

It’s not!  **Throws hands up in air** Of course I have doubts!  If I didn’t have any doubts I would be a robot, and I told you already that I’m not ready to reveal that secret to the world just yet.  Please just continue reading this blog post quietly, fellow humans (a species to which I, too, belong, obviously).

Everyone in the world has doubts.  You doubt.  He doubts.  She doubts.  They doubt.  We all doubt.  You get a doubt!  And you get a doubt!  Everybody gets a doubt!  


Doubt is an important feeling to have.  Every single one of your awesome, heroic characters doubts themselves at some point.  Aren’t we all awesome, heroic characters in some way?

When it comes to glossing over the boring and showing just the highlights, the internet isn’t the only culprit.  Even books are their own form of Instagram.  I mean, sure, we all want to be Harry Potter and do magic, but do you remember how many times he spent hours in the Common Room writing essays by quill?!  Yeah, ain’t nobody wanna do that.  (Seriously, what was up with that, by the way?).  But the book happily skips over Harry’s homework and goes straight to the next Defense Against the Dark Arts lesson, just like skipping to the next Instagram story.

Now, I know I’m no Instagram supermodel posting pictures of my butt, but I do tend to write mostly happy/upbeat posts about my life and my connections with the people around me.  None of that is fake, not even close – I really am a happy and upbeat person.  BUT that doesn’t mean that I don’t struggle, that I don’t doubt myself, that I don’t worry, that I don’t fail.  Trust me, I fail a lot.  I fell at the gym like 3 hours ago while failing to do a 4 foot box jump – I have the bruise on my knee to prove it, just like any other normal human would, right guys?  And just like any other normal human I did a quick look around the gym to see if anybody else saw me fall.  They didn’t.  Nice.

It took me a long time to learn to overcome my doubt and embrace failures.  It’s embarrassing to admit how long I rebelled against anything of the sort – how long I chose not to share any of my writing with anyone, or how long it took me to write something true about myself on the blog.  Failing at writing is now one of the most important parts of my life, because it’s only by failing at creating a 3-dimensional character, or a compelling plot, or a tense scene that I can realize what I’m doing wrong and get it right the next time.

It’s unfortunate that our doubts often lead us to avoid failure at all costs – that can be disastrous, because the truest way to avoid failure is not to try, not to give something our all, not to put ourselves out there.  And by following this path we lose all of our opportunities to learn.

There’s a reason why we so often hear of the bestselling author who collected 200 rejection slips before being published as opposed to the one who got published on their first try.  It’s because that’s what it takes.  The bestselling author was willing to fail 199 extra times before giving up, to take 199 extra chances to learn from those failures, to get better 199 times, and that’s why he/she made it.

All of this is so important, in fact, that I want to share a couple of my biggest struggles, doubts, and failures, in the hope of making them a little less scary by putting them into words.

Here they are, a few of my doubts:

  1. I’m a middling writer.
    • Man, what a BUMMER that would be.  Before getting published I can entertain the possibility that my writing will be a lightning strike to the world.  But what if it’s published, and it’s just… ‘Fine’?  I mean, sure, nothing is wrong with that, some people like it, some don’t, and I might be able to make a living.  But if I’m being totally honest in this post, I have to say that I would be hugely disappointed.  This is one of the biggest doubts I have – I doubt that I’m good enough to stand out from the pack.  I hope I will.  Every once in a while I’m able to visualize it and it makes me so excited I can’t sit still.  But every once in a while I think, ‘This book is good, but that’s all.  It’s just good.’  I’ll never know until I get there, though, and I still have hope that I will be the kind of storyteller I’ve always wanted to be.  I just have to work and wait and see!
  2. Piggybacking off the above – Leaving my day job was a mistake.
    • Talk about another big doubt.  I left a great job with a lot of flexibility, colleagues I really liked, and a lot of room to grow.  So… what if this jump doesn’t work out?  What if I have to go back and I never find anything as good?  To say that this doubt doesn’t pop up once every couple of weeks would be the biggest lie of all – who in the world would take this kind of risk and not think about it?  But as I said above – if you don’t put yourself in a position to fail, you don’t put yourself in a position to succeed either.  I’ll learn from this no matter what, and I’m beyond happy I did it.
  3. I failed to get a big promotion at the job I had before I started writing full-time (the first time I went up for it), a promotion that I was put up for early by my managers.
    • Wow, this failure really hurt.  I was upset for days and days about it.  I was doing really well in my role and was put up for a promotion early.  I was well-prepared.  Then halfway through the case study my brain completely shut off and I crashed and burned.  I learned from the experience, though, and came back up for it 3 months later.  Knocked it out of the park, and it felt even better than it would have the first time.
  4. The first book I wrote is the single worst piece of literature ever created in the history of all time, ever, out of all books written, ever.
    • Oh boy, all of my early writings were pretty terrible.  Like really, really bad.  Like drinking Gatorade after you just brushed your teeth bad (Ew).  I made my Mom struggle through my first book, Forza Academy, which was the worst copy of Harry Potter ever created.  I was 16 when I wrote it, and my mother (bless her) told me that it was amazing.  When I re-read it 3 years later I wanted to laugh/cry/throw-up.  Upon confrontation, my Mom admitted that it was awful and that she hadn’t wanted to discourage me from writing more so she lied.  Later on, in college, I wrote the first few chapters of a book and was excited about it (I still think the premise is cool) – it had just become known around my fraternity that I was writing books, and a few people offered to read it.  I sent it to 5 people.  Only 1 ever got back to me (thank Doug!) and the rest either didn’t read it or found it so awful they couldn’t get past the first page (if you’re reading this, guys, you know who you are).  I was too embarrassed to follow up with them.  But the experience did make me critically re-read what I’d written and figure out where I went wrong.  Another good learning experience.

In conclusion: Failure is good.  It’s great, even.  Once we conquer our fear of failure, more possibilities open up in life than we ever knew existed.  This doesn’t mean we should set out trying to fail, but we can’t be afraid to fail either. 

Most importantly, if you fail, you have to learn from it.  To take a teaching from the business world, Ray Dalio has said that one of his main principles is to always create an environment in which it is okay to fail, but unacceptable not to learn from it.  Trust him, he’s a billionaire (lol).

What about you?  If you’re willing to share, what are some of the things you struggle most with, some of your biggest doubts, biggest failures?

9 comments on “Why Doubt And A Willingness To Fail Is Crucial”

  1. The trick is to know when to pick yourself up and try again or call it done and walk away.
    I tried tap dancing, golf, and took a flight lesson once. Not for me. I quit.
    I got a lot of things wrong in my first book, but I’m still writing, still learning.
    When do you take a breath, figure out where you went wrong, learn from your mistakes?
    When it’s something you really want 🙂

  2. Sometimes it’s about how you define success/failure. Is the post a success if you’re proud of it and it says exactly what you wanted it to say? Or does it take X amount of likes to make it a success? We all have doubts and insecurities, but we do get to choose how to frame things in our minds. And, the older I get, the more I realize that most things don’t matter that much. Do what you have to do. Do your best when you can. Prioritize the people you love, because life is short!

  3. This was a great post to read and I can definitely relate to thinking that my writing is not that good and having a hard time letting others read what I have written. I am often surprised by how many people read my blogs, but just going for it feels really good. Making this year my consistent year in writing! I felt encouraged by your blog. Thank you!

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