That is a question I have asked myself many times since I graduated with an English degree in 1988.
And here I am a 44-year-old mother of four about to begin a PGCE at the fourth attempt.
When I first graduated I began working as a journalist for a local newspaper.
It was a dream job for me and I loved writing stories, meeting people and seeing my name in print.
But after three years there were aspects of the job I could never come to terms with such as the "death knocks" in which a reporter is sent to the home of bereaved relatives in the event of a sudden death such as road accident, fire or murder.
It was around this time that I started visiting schools to talk about my work and I started to experience the classroom from a different angle.
So in the early 1990s I applied for a PGCE at Liverpool University and was offered a place.
Just before I took up my place I was offered a job at The Liverpool Echo - a massive step up from a weekly newspaper- so I declined the PGCE place.
As the years passed and the death knocks increased my family circumstances changed.
I was now a mum and loved spending time with my baby son and watching him learn.
Inevitably, my thoughts turned to teaching again and I applied a second time for a PGCE.
It was 1994 and I was all ready to start the course when I discovered I was pregnant with my second child.
Life as a mother of two was hectic and I was able to step down to part-time work which gave me time to help out in the classroom at my sons' school.
I loved the balance of my work and was able to accommodate a third child in 1997 and in 1998 I secured a much coveted place on the Features Desk - so much more creative than the newsroom where I had worked for 10 years.
By 2003 I was juggling a part-time job as a features writer with my role at home as a mum of four (my fourth child was born in March 2000) but it was tough.
So tough that I decided to leave and become a freelance writer.
This proved to be the perfect solution.
I won commissions to write for local, regional and national magazines and set up my own small PR company. I never missed a school assembly or sports day and even had time to help out in the classroom again.
As my older children grew I became interested with the way English was taught in High Schools.
I started to read many of the texts they were studying and felt myself drawn to teaching again.
In January 2007 I was offered a place on the Flexible PGCE course which meant I could combine my roles as writer and teacher.
But in May 2007 I saw a job advert in The Guardian for a "writer in residence" at a men's prison not too far away.
I couldn't resist. I applied and was successful.
And this proved to be the perfect transition role.
I mentored the magazine team, organised author events and taught creative writing for up to nine hours a week.
I loved the challenge of creating interesting workshops and tweaking classes to engage all participants.
Although the recession meant my freelance journalism was dwindling I didn't mind as by this time I was also an accredited Creative Practitioner and I was creating and delivering writing projects in schools across Merseyside and Lancashire.
The turning point came in August 2008 on the day I was told I had won a travel writing competition in The Guardian.
That very same day I also heard that one of the prisoners I had helped write a play won first prize in The Koestler Awards.
I got more pleasure from the prisoner's succes than my own achievement and it was then I knew.
My contract was renewed for another two years but I had already made my mind up.
In October 2009 I appplied for a fourth time for the PGCE and here I am just days away from finally taking up my place.
On Thursday September 2nd I will teach my final class in the prison and on Friday September 3rd I will enrol on the PGCE.
I feel exactly the same as I did the day I walked into the prison - excited and terrified.
