Published by admin on November 6, 2015

Failing Faster: Not Your Mama’s Post on Failing

It sounds kinda funny, doesn’t it?

Fail? Who wants to fail?

But it’s the secret of a truly happy life, in my opinion.

So, let’s dissect it.


It sucks. I hate it.

And, yet, it’s the key.

Now, let’s be clear from the onset: I am not saying that failing is the key.

I am saying that failing faster is.

It’s inevitable that you will fail.

I will fail.

We will fail over and over.

But we can fail smarter.

We can fail faster.

We can choose to fail.

The goal: to get to the other side, of course.

Not the other side of the road like our friend, the chicken.

But to get to the next level.

To level up.

We never get to be comfortable for too long in this lifetime, it seems.

Most of us do everything we can to prevent failing.

Obviously, by now you understand that I am going to recommend the exact opposite.

Inviting failure.

Let’s take an easy example: sales.

You’re only going to get good–really good–at sales one way.

By sucking.

But sucking implies something else: that you’re actually out there trying. Participating. Playing. Learning.

Learning comes from experience.

But a lot of us are so scared to fail that we avoid playing; which means we avoid failing; which means we avoid learning; which means we avoid winning.

Name almost any field of life and point to a successful person, and I will show you someone who has first failed.

And often many, many times.

Remember Thomas Edison? He failed THOUSANDS of times trying to find a filament that would work to conduct electricity.

Imagine you knew him back in the day. He was probably a laughing-stock to many people.

What’s that crazy guy, Edison, up to? What a looney. 

The same thing with the Wright Bros.

Steve Jobs.




Fear is what keeps us from winning in any area of our life.

And what we fear is failing.



You can call it by many names, many labels.

But the feeling is always the same.


We loathe failing.

But champions teach us.

Champions like Michael Jordan.

I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.

They are willing to endure great failures.


Because failing is one of our best teachers.

Most poker players don’t remember the hand that won them the tournament as vividly as they do the one that lost it.

Most athletes remember their wins.

But nothing is seared into one’s memory as much as a bad loss.

And that pain.

That horrible, horrible pain…

leads to growth.

It leads to looking and seeing what was missing; what didn’t work; what can be improved.

Winners are always learning.

Always growing.

True champions study their wins–not just their losses.

They may be the greatest player of their sport, but they are driven to improve.

So, what does this have to do with me, you might ask?

I’m no NFL quarterback.

I’m no legendary salesperson.

I’m no best-selling author.


We are who we say we are.

And the simplest, fastest way to get there is to get over our fear of failing.

Many of you read my last blog where I talk about meeting a girl online who just blew me away. She could have been my soul-mate, I thought.

And then how I totally ruined a great opportunity with a flippantly perverse comment.

I could have stopped myself.

But I didn’t.

And I learned something powerful through that experience: that I’d rather lose the girl than pretend to be someone I’m not.

But my first reaction wasn’t so enlightened.



But I experimented. I played.

I just allowed what wanted to happen to happen.

And she followed her intuition, similarly.

And, hence, we danced.

In spirals moving away from each other.

And there’s beauty in that kind of dance, too.

There’s a beauty in finally letting go of that which doesn’t serve us.

For me, a lot of my life has been spent chasing the wrong women.

I failed. Often.

But I didn’t admit failure, even to myself.

And that’s another part of failing faster:

you gotta be willing to admit that you’re failing.

If you don’t admit it’s a failing, then you can’t grow from it.

So being honest about your failings is an important part of the process.

And this moves right into the archetype of the fool.

The wise fool.

The unwise fool is fronting like they’re not failing.

I used to be the unwise fool.

I wasn’t yet willing to look at where I was failing.

I wasn’t even willing to feel it.

I created a hard, impenetrable exterior which caused me not only to not allow others in, but it also caused me not to allow myself out.

I was a prisoner of my own making.

It wasn’t very fun.

And neither was I.

I was pretty much a miserable wretch of a person who thought he knew better than everyone, had an opinion about everything and who drew my sword at the speed of light against anyone who would dare challenge my way of life.

I remember one instance about six years ago in Australia. I was there for my lovely cousin’s wedding. It was my brother, my parents, my uncle and I on a ferry boat in Sydney Harbor, and one of them had just crossed the line–

they had asked me to smile for a picture.


Why must I smile for a picture.


That’s how I felt.

So, when my brother asked me to be in a picture with him, and then my mom told me to smile… and then he asked me to smile… I erupted.

Curse words. Yelling. In front of 100 unsuspecting tourists.


I ceremoniously then kicked my brother–hard–and left.

It was a full-blown tantrum.

And I was 35.

When we got off the boat, I walked alone to the hotel.

In my mind, I was already out of there. I had dreamed of spending a full month exploring Australia, and I was going to end the trip early and head back to the States.

Fuck this, I thought. I’m gone.

But then something awesome happened.

(And I will assert that awesome things often happen right after huge failings.)

I opened up. I talked to my parents about leaving. I admitted to being depressed. And they were very cool. They told me that if I wanted to leave that it was no problem. I should do whatever I felt like I needed to do. My brother had to leave early, so that would mean it would be just the four of us. I ended up staying. We went down southern tip of Australia and rented a cabin for a few nights. I hiked a lot by myself during the day, and we all played poker and ate and drank at night.

They allowed me to be as I was.

It was just what I had wanted when that picture was being taken–

to be myself, as I was.

However, I now realize something that I couldn’t at the time:

my walls prevented them from knowing what was really going on with me, so they couldn’t relate to me as I was.

Taking down my walls allowed them to understand me better.

To relate to me better.

My vulnerability did.

And here’s the ultimate kicker: it wasn’t them that changed; it was me.

My change precipitated theirs–not vice-versa.

Now, that shit ain’t easy.

One of the strongest, most courageous things that I can imagine doing is being vulnerable.

And it’s also one of the absolute toughest.

For me, it was equally embarrassing.

But even running water–given enough time–can wear down rock.

Our protective layers, our defenses that once solidly defended us from our aggressors, one day becomes our prisons.


How the hell did we get here, and what does any of this have to do with failing?

I believe, again, it’s surrender.

Surrendering to looking like a chump; looking bad; looking like an idiot; being an actual idiot; telling a joke and nobody laughing; singing a song and not hitting the right notes; not keeping time; making a shitty meal; speaking a foreign language–badly; hosting a party and no one coming; asking a girl to dance and having her just walk away; asking a girl out and getting rejected.

The list goes on and on.

And that’s just my list! We all have our own lists.

And each failing is a good excuse not to try that again.


It’s November the 5th, which makes me think of V for Vendetta: “364 days. 364 failures!”

We avoid failing at all costs.

And that’s our main problem.

On the other side of failing is the life that we want.

On the other side of sucking is the life that we want.

On the other side of looking like a fool is the life that we want.

I remember being in a thrift shop in Little5Points in Atlanta a few years ago, and I walked across that invisible line.

Which one, you ask?

The one separating the women’s section from the men’s section.

Now, before you get all crazy on me,

I’m not a cross-dresser.

Not that there’s anything wrong with that…

But when I committed (surrendered to the dark side?), something magical happened.

I found AMAZING CLOTHES that didn’t exist on the men’s side.

All kinds of magical clothes and colors that ended up being part of my party/festival wardrobe.

Like an amazing purple, puffy, velvet coat.

It was tough to cross that line, feeling the eyes of women (at least in my imagination) following me, thinking, that boy is out of his element. He better stay away from that belt.

I kid.

Anyways, surrender.

Failing is our friend.

But the object isn’t just to fail.

It’s to win. To succeed.

And failing is the pathway to get there.

And it’s non-negotiable.

You gotta play the fool at some point.

But you can do it willingly and win much sooner,

or you can do so kicking and screaming–

and throwing a tantrum off the back of a ferry.

Your choice.

Women are way better at this than most men.

Surrender comes way more easily to them.

Men… we are retards when it comes to surrendering.

As in actual retards.


The definition via google: less advanced in mental, physical, or social development than is usual for one’s age.

And the faster we admit it, the better off we’ll be.

I think my work is done here.

I hope my openness with my own failings gives you permission to be more open with yours.

I promise it’s a lot more fun than the alternative.

#charlie sheen#depression#failing#failure#family vacation#happiness#jordan#success#surrender#tantrum#winners#winning


  1. Lynette Spring
    November 6, 2015 - 4:01 am

    I am going to share this one! Once it’s published, of course. Perhaps some new followers await…

    Your quiet, humble SuperFan,

    Lynette the Brunette (lest you forget)

    • skyxander
      November 6, 2015 - 4:38 am

      Go to You always see the first, uncut version. I hit publish, and then I go back and edit. This one just streamed out of me for two straight hours. I didn’t have to edit much. Share away! And miss you!!! I’ll let you know when I’m in your neck of the woods next. 🙂

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