What makes someone skydive 704 times?

When I told the RedBalloon office that I was interviewing someone who’d been skydiving 704 times, questions started flying at me from all directions. Does he still get nervous? What’s it like doing a solo jump for the first time? Has he been skydiving at night? Is he insane?

I’m happy to confirm that Winston Taylor, or Win, is more sane than most people I’ve spoken to. He’s a security guard, has a very understanding wife and two beautiful girls aged 7 and 9. At RedBalloon we’re all about making the most out of life every single day, and this is one guy who takes life by the wheel (or parachute!) and steers.

Talk me through your first skydive, Winston. Where was it and how did it come about? I was actually given a RedBalloon gift voucher from a friend of mine. I did him a favour and he bought me the voucher to thank me. I’d always looked at skydiving and thought it looked pretty cool – it was something I’d been curious about but hadn’t gotten around to doing. Everyone’s nervous before their first jump and I was nervous alright! That first jump was in September 2007 in Wollongong.

Describe the feeling of freefalling for the first time? It’s a mixture of excitement, terror and anticipation…

Not sure if you were going to wet your pants? There are a lot of emotions going on when that door goes up for the first time.

So how do you go from one jump to 704? I’ve always been a speed freak, so I was blown away by how quickly we were moving and the speed we were going at. I thought that the first 10 seconds of the jump were awesome, and within those first few seconds I knew I was going to do more than one skydive... But I didn’t know I’d be past 700! After a few months I did another tandem jump down at Wollongong and then I started looking at where I could go to get my license.

solo skydive

Win on a solo jump

Was the first solo jump a different kind of adrenaline rush? Look it was definitely a lot scarier because on a tandem you’re just along for the ride – you’re a passenger and your instructor is the one controlling everything.  But when you do your first solo jump it’s very different. There are quite a few drills you’ve got to go through and once you’ve deployed your parachute you’re on your own – no instructor can help you if something goes wrong. So I’ve got to say that first jump I did was tough. You climb out of the plane, all the drills go through your mind and you just try to live to fight another day. 

Do you still get nervous? Being nervous and not being complacent is important. I do still definitely get nervous, but it can depend on whether I’ve had a bit of a break too. Sometimes I might go a month without jumping, other times I do 10 jumps in a weekend.

What do you think it is about skydiving that makes people want to do it again and again? For me it’s still very challenging. Even though 700 skydives might seem like a lot, there are guys at the drop zone who have done 15,000, so I’ve still got an awful lot to learn. It’s a challenge to get better but I also jump to have fun. There are lots of people at the drop zone who get in teams and do lots of serious training for competitions. I have to say I’ve been in some jumps where they’re a bit too serious and I’m like, “Come on guys I’ve come here to have fun”. I’m in it for the fun. I still like having a successful jump but it’s more about jumping out of a plane with your mates and having a good laugh. 

When I get old I want to have a goal that I can watch any James Bond movie that’s ever been invented and think, 'I’ve done everything there. I’ve done it all'.

celebrating 700 skydives

Win (on the left) celebrating 700 skydives

When will you stop? Do you have a goal? Will you end up being one of those guys who jumps 15,000 times? I don’t really know. I enjoy it when we do a jump with less experienced guys and I can try to teach them the stuff that I’ve learnt, so I’m looking forward to doing the instructor course and maybe I’ll be able to make a job out of it.

If you can make a job out of doing something you love, that’s the dream... Yeah that’s right!

So I’ve got to ask, because it’s the question everyone wants to know the answer to… Have you had any close calls? My worst jump was when I dislocated my shoulder as we left the plane. So that was probably my scariest moment. You need your right arm to actually deploy the parachute. At the time I didn’t know my arm was dislocated, I just knew I couldn’t actually find the handle to open my parachute. I ended up having to use my reserves which you activate with your left hand. So when I realised I couldn’t open my main chute I opened my reserve and then I had to try to land with one arm. You pull down on the handles to use the brakes when you’re landing so because I couldn’t really do that successfully with one hand I had to come in and hit the ground going full speed. So that was interesting...

And approximately what number skydive was that? Yeah good question, maybe about 400

So it didn’t stop you at all from going back? Nah

Well on the flip side, what’s been your most memorable jump? Look I don’t know if I could point one jump out and say that was the best jump. They’re all fun. I suppose lately I’ve been doing a lot of the big formations where you jump out with 10, 15 or 20 other people. So at the moment I am enjoying jumping with lots of people and being able to build formations. 

solo skydive

Win and 14 others on a group jump

Before my first jump, I was so scared. But it’s a refreshing feeling when you can look at your fear and conquer it.

Have you ever skydived at night? I did three night jumps last year. It’s definitely a new feeling just diving out into darkness. They had a row of about 20 cars all lined up with their headlights on illuminating a bit of a runway. But the trick is you’ve actually got to hit the runway. If you miss it you’re landing in darkness and that can be tricky. Lucky I managed to hit the runway.

Have you done anything that gives you more of an adrenaline rush than skydiving? I’ve done a few base jumps. They were pretty cool. And since taking up skydiving I’ve started to learn how to ride motorbikes. I’ve got some fast motorbikes that I like racing on the track.

You’ve ticked a lot off most people’s bucket lists. Is there anything you want to try next? I don’t know what’s left! I suppose I would like to go overseas and do wingsuit base jumping one day. It's mega dangerous and my daughters need a dad right now so maybe a bit later in life. I think my biggest fear in life is being old and tied up in a nursing home thinking, “I wish I’d done this but now I’m too old to do it”.  When I get old I want to have a goal that I can watch any James Bond movie that’s ever been invented and think, “I’ve done everything there. I’ve done it all”.

What would your advice be to someone who is afraid of heights, but really wants to give skydiving a go? I would say that no matter what people say, everyone is nervous. I’m not going to try to act as if I’m some tough guy. Before my first jump, I was so scared. But it’s a refreshing feeling when you can look at your fear and conquer it. When most people are afraid of something they don't go anywhere near it, but I see it as a sign of weakness and I think to myself, “I can conquer that fear and beat it”.  

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