About 18 months before I left a ‘proper job’ I asked myself, ‘If I’m going to leave employment to be a freelancer what would I need to be successful?’

I decided that the most important things were that people needed to know;

· Who I was

I also knew that I needed to build a financial buffer so that I could survive for three months without earning a single penny. (I picked three months as long enough to test if my business could make money balanced with an achievable amount of money to squirrel away. It was uncomfortable but if I had gone for a longer time frame I’d still be commuting in and out of an office every day)

In order to work my way through the above list I started to put myself forward to speak at conferences. Terrifying.

I started to blog. Terrifying — but in a different way.

I started to side-hustle by doing odd bits of training and consultancy before and after work or taking holidays to do it and asking for testimonials and recommendations.

It was exhausting. But it paid off.

After about a year people wanted me to work on larger projects with them, but I couldn’t because I still had a full time job. In order to really seize the opportunities that I had created I needed to leave the day job.

I felt like I was standing on the edge of a cliff looking down into the sea below. My potential clients were all in lifeboats, shouting and waving, ‘jump, we’ll catch you’ But I had to jump in order to be caught.

I procrastinated. Listened to friends and family who mostly thought it was too risky. Got the fear. Talked myself out of it. Felt ashamed for not being brave enough. Talked myself back into it. I asked myself ‘What was the worst that could happen?’ The worst that could happen was that it didn’t work and I could get another job.

Then in February 2012 I was invited to speak at a conference on the Gold Coast in Australia.

That was one almighty nudge. It doesn’t get better than that. I decided to hand in my notice and get myself to Australia.

I remember the day. 5 October 2011.

I was really anxious about quitting. It was the only day my manager was in the office so I had to do it that day. I think it was the normal anxiety of leaving a job, feeling that you are letting the remaining employees down in some way, compounded with the inner critic that tells you that its ludicrous that you could do something different and that it would never work anyway (we all have that voice — my learning is that the people who get stuff done are the ones that can better manage that voice).

On 5 October 2011 I woke up and turned on my TV. The main news story was that Steve Jobs had died. I turned on my Macbook and the screensaver was Jobs face. I looked at my Twitter stream and it was mostly about Steve Jobs’ death.

I had a little cry.

I know this sounds ridiculous, but for me it felt like a sign. I thought about what Steve Jobs would have done. He’d have quit (he’d have probably quit ages ago). It helped me turn the inner critic down voice and I went into work and handed in my notice.

I’m not suggesting that you wait for an inspirational icon to die to make the leap, but it’s an important part of my story.

You can listen to more of my story at the Good Leaders podcast.

I’ve now been a freelancer and building my own business for five years. I’m proud to be unemployable in a conventional sense. I love what I do. Ironically as far as my business is concerned, the worst thing that could happen now would be to get another conventional day job.

You will have your own story and there is by no means one right way to embark on a freelance lifestyle. But if you are considering it (and even if you are not) ask yourself the question, If I want to be