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Startup 101: do a skydive

Yes, you heard me correctly

· Entrepreneurship,skydiving,face your fears

This article was originally published on my blog Wantrepreneur on 31 August, 2016

In July 2015, I did something I thought I would never do.

Six months previously, I had signed up to do a skydive for charity. I knew it was one of my greatest fears and I knew I would be terrified. However, having done a few things in the previous few months that felt pretty scary, and feeling that I needed to do something I was proud of, I threw myself headlong into this challenge.

Do one thing every day that scares you. - Mary Schmich

I first heard this quote in my formative teenage years courtesy of Baz Luhrman's Everybody's Free to Wear Sunscreen. Regardless of how I felt about the song, it had quite an impact on me at the time, and consciously or not, I’ve carried this phrase with me ever since.

I was very nervous as a teenager and into my twenties, and a lot of things scared me. Conversations were terrifying, conflict petrifying and confrontations unbearable. Failure wasn’t an option, as the humiliation in front of my peers and parents was too great to bear, so it wasn’t hard to find several things in a day that scared me, whether it was a casual conversation, or a chat with a work colleague, or sometimes simply crossing the road (I’m not joking – I found navigating life that hard!).

So without having to try very hard, I lived by the motto of doing at least one thing every day that scared me. Even if I hadn’t heard that phrase, I would still have had to deal with difficult situations, so acknowledging this fear helped me to push through and understand why I was hesitating.

Over time (we're talking 10 years or more), I gradually became less afraid, and I arrived in the surprising position of finding it hard to find something I was scared of every day. So I started engineering artificial situations that I knew would push me out of my comfort zone, just so I could feel that sense of achievement at the end of the day. My approach to risk changed, perhaps imperceptibly at first.

This eventually morphed into chasing slightly bigger and more ambitious fears; ones that required some planning and deliberate forethought. Over the next few years, I tried working abroad, scuba diving, abseiling, rock climbing, asking for promotions at work, volunteering for projects, asking out that really special someone, going to trampolining classes, learning Italian in Germany and Spain, driving in America, running long distances, a triathlon, quitting my job, changing industry.

This all came to a head in January 2014. I had moved to London (something that I had resisted doing for the past 10 years), found myself in a job I wasn’t much enjoying, and living a life that I felt wasn’t quite mine. It certainly wasn’t the one I would have designed for myself. Whether I realised it at the time or not, I needed to do something dramatic to shake down my way of thinking and put me on a path that suited me better.

So why the hell a skydive?

Quite simply, I couldn’t think of anything that I was more afraid of than this.

However, the part of me that wanted to do it was curious to see what effect it would have on my confidence. If I could face this and win, if I could actually put myself in a position where I would actually go through with it, I could pretty much do anything.

I had talked about this with a girl I knew not-that-well about skydiving being my greatest fear. She was in agreement, it would be one of her biggest fears too. One evening after a couple of glasses of wine, we agreed by text that we would do a skydive together.

This text exchange is where it all started.

Now my friend’s influence here is interesting. At the time we agreed to do the skydive, I didn’t know her that well. We were just becoming friends, but she was someone I admired a lot. I liked that she was ambitious, conscientious and keen to push herself in all areas of her life, and reflecting on it now, she had a lot to do with my change of mindset around doing a skydive. She wasn’t pushy; she showed me the possibilities and that they were there for the taking, rather than showing me the way. There aren’t many people who could have inspired me to voluntarily do a skydive, but whatever we said to one another that day, had some kind of impact!

Even then, it was a good few months after those messages that I finally built up enough courage to actually sign up, and nearly 9 months before I would actually leap out of a plane at 13,000 feet.

An aside here only because people are bound to ask why we didn’t jump together in the end: my lovely friend would clearly have been up for jumping with me, but between our agreement to jump and my signing up to actually do it, she found out she was a mum-to-be. So her skydive plans were on hold, for a little while ;-).

Facing the fear

The day I made the decision to sign up for the skydive, I didn’t confer with anyone else. I didn’t tell anyone I was thinking of doing it. I knew that if I did, I might talk myself out of it, or allow myself to be talked out of it.

In the days and weeks leading up to the skydive, at first I simply pushed the skydive out of my mind and pretended it wasn’t happening. For a few weeks, I was more worried about being able to collect enough sponsorship money, and the embarrassment of not being able to do so, than the dive itself (like I said, I was in denial.) I’d never asked people for real sponsorship money before, what if I couldn’t meet the target? This fear was quashed reasonably quickly, though, and in the end I was proud to say I had nearly doubled the sponsorship target.

In the two weeks leading up to the jump itself, I started reading lots of skydiving stories online, talking to people who had done skydives, and watching videos on YouTube of skydives, so that I could mentally prepare for the process, and for the sensations. Visualisation can be a very powerful tool with preparation, and I wanted to know that I would understand all the safety measures, all the signals, everything that would happen during the jump. Whenever I felt nervous about it, I would squash those moments of panic and focus on something that I could more easily do something about, like deadlines at work.

The jump itself

On the day of the jump, the waiting was agony. We got there super early, and ended up waiting for 5 hours before we actually got to do the jump. I was with two friends, and they were both called on planes before me. I would be the last to jump, having seen them both jump first.

Getting into the plane was fine, then I looked around me. The setup on the plane was 2 long, wooden benches, like the ones you got in PE in primary school. That was it, there were no individual seats, no seatbelts, no armrests, and, most alarmingly of all, no door to the plane. What there was resembled a shower curtain. Plus, we were facing backwards. I didn’t feel very safe as we were taking off, and the plane was going up at an angle. If we fell against that shower curtain when we were lower than 800ft, no parachute would save us. The plane felt very rickety and old, and was the smallest plane I’d ever been in. As soon as we started taxiing on the grass runway, I realised that the sooner I could get out of the plane, the better. Now that was a weird thought!

My skydive instructor was amazing. He was bossy, direct, and took 100% control of the situation. I had no choice in anything I did from the moment I stepped into the plane. He was so confident and assured; he did everything for me; I literally just had to sit there.

I had a momentary wobble as we were told we could move into position to leave the plane. I was nearest the door so would be the first one out, and all of a sudden, despite all the mental preparation and regardless of how determined I was to complete this challenge, I didn’t feel ready, I wasn’t ready, I couldn’t go. The task ahead suddenly seemed so incredibly frightening and insurmountable.

Thankfully, though, my brilliant tandem skydive instructor, Ralph Mitchell, took no notice of my feeble doubts and manhandled me to the edge of the plane (I learnt after the event that Ralph had been one of the first people to tandem skydive onto Mount Everest and held the world record for highest skydive landing – good hands if ever there were!). Every beginner skydiver had been told the drill for getting out the door of the plane. The instructor (the person at the back of the tandem) sits on the edge of the plane, with the student suspended over the side of the plane in front and below them. We were told to bend our legs around the outside of the plane, towards the belly of the plane, with our arms crossed on our chest. The instructor would rock forward three times, and on ‘three’ we would launch ourselves into the sky.

The most frightening moment of my entire life was when I was hanging out of the plane waiting to jump. Despite being attached to my instructor, I felt completely alone and vulnerable, and even though I trusted this person as much as I could trust anyone in this situation, it was all I could do to control my panic and follow the instructions to ensure my survival. I felt so exposed as the wind was rushing past me and there was nothing in front of me but air, cloud, and patches of ground.

I had no idea what the freefall would feel like, and this was the thing I was most afraid of. I had been on rides like the Tower of Terror at Disneyland, and they made me feel quite sick, although I knew that ride only lasted 10 seconds. During my skydive, I knew we would be freefalling for 30 seconds or more, and was worried that it would feel like the Tower of Terror. I wasn’t sure I could handle that sensation for 30 seconds. Would it hurt? Would I be a screaming mess for the whole time? Would it make me feel sick? I couldn’t wait for the parachute to open and to be gently drifting to earth, the freefall part of the jump over.

I love this shot of me and Ralph leaving the plane (see what I mean about no door?).
Yes, my eyes are shut. No, I'm not proud of that.

As we fell away from the plane, I closed my eyes to try to calm myself. I waited for my senses to be bombarded, for us to be upside down and falling at 100 miles per hour.

Almost in disbelief, I very quickly realised that the freefall part wasn’t nearly as scary or dramatic as I had imagined. In fact, bizarrely, it was really quite beautiful! It’s hard to say it was ‘peaceful’ when there’s air rushing past and buffeting your body at 120 mph, but there was a serenity to the situation. Rather than feeling like I was falling to my death, it felt as though I was lying on a pocket of air that was blasting up from the earth, keeping me afloat. It wasn’t the extreme sensation that I had imagined, and as each second passed, I realised it wasn’t making me sick, and I wasn’t uncomfortable.

That realization probably took about 2 seconds. After that, I concentrated on being in the moment as much as I could, and in trying to remember every detail. The weirdest thing was being able to see the cameraman I’d hired to take a video falling opposite us, capturing every expression on my face for the few seconds we were falling. He was wonderful, funny and making faces at me even whilst we were falling. I must have looked like a deer in headlights, and whilst the fear was fading and I was realising I probably wasn’t going to die, I even managed a weak smile.

The deer grinning into the headlights. My hands read 'Hello Mum', in case you're wondering. (I didn't tell her I was doing this!)

Then, in no time at all, Ralph and the cameraman were making some very decisive hand gestures to one another and I knew it was time to open the parachute. The cameraman moved away from us in the air and I braced myself for the sudden braking when the parachute opened. Again, it was nowhere near as bad or as unpleasant as I had imagined, and we continued our vertical journey to earth at a more sedate pace.

For the first few moments, I did enjoy the scenery. However, pretty soon, we started doing super tight turns, which threw us up to 90 degrees with the land. This made me feel completely and utterly travel sick in about 5 seconds. The G force was more powerful on those turns than any other part of the descent, and I pretty much felt sick as a dog for the rest of the trip down. It lasted about 4 minutes. Needless to say, I didn’t fully get to appreciate the scenery, as I was concentrating quite hard on not throwing up, and listening and complying with my instructor’s commands.

We landed uneventfully in a field. The adventure was over, and I felt sick for the rest of the day. :-s Unfortunately, this took the edge off the sense of achievement for me, and actually made the day slightly anti-climactic, so it took a few days for the pride of the event to really kick in.

However, I’ve surfed this wave of pride for over a year now, and still can’t quite believe how easy the skydive was in hindsight. If I were to do this again, I wouldn’t be nearly as afraid, and I’d be more mentally prepared to be able to cope with the travel sickness of the parachuting part of the descent.

Doing the skydive instilled in me a deep sense of pride, accomplishment, and gave me an unshakable confidence in my own abilities. If I can do a skydive, the thing I thought I was most afraid of in life, and something I never thought I would conquer, I can pretty much do anything.

I've been chasing fears all my life

It took a while for the effect of facing this particular fear to sink in for me, but it was undoubtedly the beginning of a new cycle of thought that have meant I’ve made some massive changes to my life.

Since the skydive, I’ve quit my job (again), moved away from the city to a foreign country (again), started freelancing, started a blog (you’re here!), started doing more on social media, and have even fulfilled a dream of starting my own business – all these things required me to be brave, and have pushed me out of my comfort zone. There’s no question in my mind that doing a skydive contributed to this sequence of events and what I’m doing now.

I class the skydive as a pivotal moment for me. Whether it was the decision to do the skydive in the first place, or the skydive itself is kind of irrelevant; it marked a change in the way that I was thinking, my approach to risk, and the way I lived my life. I stopped feeling so constrained by society and other people, and started doing things for myself.

My whole life, I’d simply accepted that doing a skydive was not something available to me. It was something that other people did. It felt really good to flip that on its head.

The legacy of the skydive

Now, you may not think that the stuff here sounds particularly brave or transformational, and of course the things you fear may be different. You may be someone who loves meeting new people and who can walk into a room and immediately feel at home with complete strangers. You may not think twice about falling from a plane at 13,000 feet. The thing I want to you to take from this is that, in order to fast-track your personal development, you need to find the things that you’re afraid of, and run towards them. For some people, that might be a skydive or scuba diving or skiing or snowboarding; for others, it might be taking on a challenge that stretches you to the limits of your physical endurance like doing an ironman or a marathon or learning how to do a handstand; for others, it may be accepting yourself for how you are and beginning to live life on your terms.

Of course, there are loads of things that I’m afraid of that I haven’t yet confronted. Right now, a few I can think of are tarantulas, bungee jumps, posting this blog post, and linking to my skydive video on YouTube. Some things I’m totally not OK with, and doubt I’ll ever be OK with, are public humiliation and, although I wish it weren't the case, public speaking.

However, sometimes I feel afraid of simply picking up the phone to have a conversation about something I don’t fully understand. I’m afraid of going to the gym because it might hurt. I’m afraid of speaking in public because people will think I’m an idiot. There’s still plenty of stuff to work on.

So what next?

So, although the title of this post is ‘do a skydive’, I don’t mean that everyone reading this post who is dreaming about setting up their own business should go out and do a skydive. I do mean that, in order to prepare yourself well for the life of being an entrepreneur, you have to be OK with doing things that scare you and that push you to the limit of what you think you're capable of. For me, I’ve chosen some of the things that scare me most and run towards them head on. I think you should be doing the same. The magic only happens outside of your comfort zone, so get used to stepping as far outside of your comfort zone as you can, because in doing so, you will expand your horizons, and your perception of failure will change.

Now, go chase your fears.

If you like this post, you can see more of what I write right here on Wantrepreneur2entrepreneur. The articles here document my journey from corporate escapee to wannabe entrepreneur: all the highs, all the lows, and everything in between. It's a work in progress and I'd love to hear what you think, so drop me a line at, or on Facebook or Twitter.

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