Careering Off Course takes readers through a working life filled with unexpected detours, questionable choices, and enough entrepreneurial mishaps to make even the most optimistic business coach nervous. What prompted you to frame the book as a work of self-criticism rather than a traditional career or entrepreneurship guide? 

Simple really, I know friends have described me as a success, but I’ve never felt like that. I suppose I just didn’t feel qualified to write about entrepreneurship. I’d spent too much of my working life trying things, changing direction and making a mess of it to start handing out lessons. The more I looked back, the more I realised the story wasn’t really about a single dramatic failure. It was about all the small decisions that seemed sensible at the time: staying comfortable, putting things off, or convincing myself I’d try something properly later.

Writing it as a self-critique also let me be honest about my part in what happened. It’s easier to laugh at the mistakes when I’m the one making them. There’s also less chance of offending people. If readers recognise themselves in some of the choices, perhaps they’ll find a useful question or two in the book. But I’m not standing at the front of the room telling anyone what to do, I don’t think I even did that in my teaching days!

What originally attracted you to entrepreneurship, and how did your expectations compare with the reality of running a business?

I think the interest began with my dad, who ran a small vending business. I saw the practical side of it early on: buying and selling, solving problems, and working hard to make a living. Even as a kid, I liked the idea of earning money for myself. Washing cars, selling fruit and vegetables from the drive all made business feel exciting and full of possibility.  I just loved the freedom money gave you, not having to rely on mum and dad, being able to make financial decisions myself.

My expectations, if I’m honest, got rather ahead of the reality. I liked the idea of being an entrepreneur: the independence, the money, the freedom. I was less prepared for the patience, focus and ordinary hard work involved. I had plenty of ideas, but I was often tempted to jump to the next one before I’d given the current one a fair chance. I wanted the result more than I understood the process.

Looking back at your experiences across retail, sales, hospitality, customer service, marketing and teaching, what patterns do you recognise in the decisions that shaped your career?

The biggest pattern was drifting. I often made decisions to avoid discomfort rather than to move towards something I really wanted. I stayed in jobs because they were safe, hesitated to apply for roles to further myself, and sometimes when I did change job is was just a change in scenery instead of facing the underlying problem.

That pattern followed me into business too. I could get excited about an idea and explain how brilliantly it might work, but I wasn’t always as good at sticking with it, testing it properly or doing the less exciting work. For a long time, I was busy but was I making progress?  Not really!

Looking back, there were occasions where I manned up and got on with it, but I was very inconsistent and often got distracted. I can see that I was often chasing an idea of success I hadn’t examined very closely. It took me a while to understand that money and freedom matter, but so do time, family and feeling that the life you’re building actually suits you.

What can readers expect from the broader How to Get Things Badly Wrong series, and how do you envision the themes developing beyond this first volume?

How to Get Things Badly Wrong was originally intended to be one book, but I found I had far too much to say about my career, so I decided to split it into a series. The books will all share the same basic idea: we often understand things more clearly after we’ve got them wrong.

Careering Off Course explores work and entrepreneurship. Future books may look at parenting, teaching and education, family, and health. I’m still working through some family concerns about the parenting and family topics, so those may have to wait for now. Health is one subject I’m keen to explore. I’ve had a few health issues and struggles with alcohol, and I’d like to write about them as another cautionary tale.

When I get back to writing, I expect the approach to stay much the same: personal stories, honest reflection, and humour wherever I can find it. I want to show what our mistakes can reveal about us—and what readers might recognise in their own lives.