My Skate Of Mind

Feb 23, 2013 • 8.11111111111111min read

It took me 12 hours to skateboard 85km from Sydney to Wollongong.

The way down

Where the idea came from

Years ago I was sitting at work and found Al Humphreys website. He cycled around the world in 3 years. This caught my attention but what held on to that attention was his ongoing lifestyle. He didn’t just do this one big trip but he continues to do a lot of smaller ones too which he calls Microadventures. One that comes to mind is his walking home for Christmas. These Microadventures stirred inside me because they are all about having an adventure filled life without having to drop everything for 3 years like he did.

That day I almost instantly knew i wanted to skateboard from Sydney to Wollongong. I looked up how far it was and made a twitter account @myskateofmind.

But then I started comparing myself to people like Al. You try and do something new and different and someone has done it already, or something even better.

So that is how this idea came about but because of my negative thinking I continued to put it off almost feeling embarrased if I were to do it. Because I was be comparing myself to people who have done greater things.

Reasons not to do it this time

I had some serious problems to deal with on this attempt and they were more legimite excuses than I had ever been presented with before:

  • Weather. The forecast was for 60km winds and heavy rain, all day. My wheels. My board has small wheels which means I would be slower and the rattling on the gravel would hurt my legs more. Ideally I needed to buy and put bigger wheels on first.
  • Indoor paintball. The night before I left i just happened to have indoor paintball booked. Now if you have done any type of skermish paintball before, you can understand how sore you are the next day. No backpack. I had no suitable backpack to use, for bottles of water and food.
  • 2 hours sleep. After a night of paintball and friends, my 3am start time was only 4 hours away. After tossing-and-turning in bed for 2 hours, I got a broken 2 hours sleep before 3am struck.

I had calculated that it would take between 12 - 15 hours to complete (without stopping); so it felt like everything needed to be perfect.

I had so many reasons to put it off.

Two past attempts

There have actually been two times before where I was packed and ready to go. One time I actually started but got nervous, scared and embarrased so took a turn and skateboarded 35km to Cronulla and back instead. I thought next time i’ll do the real thing, but before that chance came around, my skateboard was stolen. I was almost happy to be able to use that as excuse to put it off for another year.

Why I actually did it this time

I was tired of thinking about the possibility of skateboarding to Wollongong, tired of coming up with excuses, tired of worrying what people will think, tired of whether anyone will care.

I was warm in bed at 2:58am and I really didn’t want to go.

But this was it, this time was different. I didn’t even think about it. More like the past regrets and should haves, took over my actions.

I just got up and started pushing my skateboard.

If you want to get somewhere in life, no one is going to do the pushing for you. You have to push yourself.

I did not feel physically prepared but I did feel mentally prepared. And based on experiences I have had with some other projects like this one in the past, I knew the mental side was key.

Early thoughts

Instantly I knew I needed to stay focused on what was immediately in front of me. Thoughts about being pulled up by cops on the M1 would pop into my mind, being hit by a car going 110km/h, or the pure distance between me and my destination.

I was very quick to stop these thoughts. I was going to do it this time. No more negative thoughts.

Dark, and scared

It was so dark. Cloud cover made it darker than night. I found myself 3 hours into the push when i was greeted with the mouth of the M1. It was pitch black. I could not see a thing. I hadn’t thought about freeways not having street lights. This is a car coming from behind me:

The darkness of the highway

This was my first scare. I turned around and thought man that is too dangerous, i’m invisible. But just a few seconds later I forced myself back around and onto my skateboard and just went. No more thinking, I thought.

If it excites you and scares the crap out of you at the same time, it probably means you should do it. - Unknown

The weather

It rained heavily, and often. You know those big rain drops that cloud your vision and you can actually feel the weight of each one as they hit your head? The type that makes you wish your car had an even faster mode for its windscreen wipers? Yeah, that kind of rain.

Wet weather

Only in shorts and a T-shirt (because I wanted the least amount of weight as possibile) I was quite cold most the time but i think less weight was worth it in the end.


Convinced the Police would spot me on the highway and it would be all over, I cherished every moment.

Looking down the highway

Feeling silly

I must admit at times I felt quite silly. When it was heavy rain and I was in the middle of a highway pushing my skateboard with another 52km ahead of me… I just had to laugh. What am I doing? What am I trying to prove?

Camera equipment

One of the saddest things for me was that the rain was going to make it difficult to take photos and video. This was the thing that almost stopped me. But in the end, I was doing this for myself and peace of mind.

Sometimes the rain was just so heavy I honestly thought my iPhone was going to be ruined for ever. It rained for hours and hours.

I had imagine myself placing the camera on a post on the side of the road and timing a photo of me skateboarding down the highway. This just wasn’t a good idea in the torrential rain. But to be honest, most of the time I just kept pushing my skateboard trying to soak in the moment and became content with the idea that I was finally skateboarding from Sydney to Wollongong.

My board

For those interested - this is the board I used.

The skateboard I used

The handshake

Cycling to Wollongong is a common practice and that means I saw, despite the weather, quite a few cyclists pass me.

In the last 5km between Bulli and Wollongong, two guys in cyclist gear walking the opposite direction stopped to ask me if it had been me early riding down bald hill. I said yes most probably (I don’t know what bald hill is) but I doubt there were many other skateboarders going down steep hills wearing bright blue shorts and a bright orange shirt.

“Why do you want to skateboard to Wollongong?”

“I don’t know. I’ve wanted to for years. I decided last week that today would be the day. Then the weather turned out like this but I just said screw it, i’m doing it anyway. I left at 3am from Sydney this morning. I’ve been riding for 11 hours.”

“Good on ya! That’s impressive.” the other guy said as he shook my hand.

That handshake meant a lot. They went out of their way to talk to me and shared their thoughts with me. It was very encouraging and very helpful for the remaining kilometres.

The finish

I was in so much pain.

My pushing ankle was in too much pain to use. I had swapped to pushing with my left foot and by now that was on the verge of being unusable as well.

A huge smile was on my face when I rolled into Wollongong. I had just removed a big burden from my shoulders. It was no longer a possibility.

It happened. I’ve done it.

And I’m never doing it again.

Update: if you read this far, you might like to watch the video.