How to start to go from a steady job to being your own boss.

Two years ago, I left my headteacher role and the security of a regular salary. In truth, I never intended to leave the profession but when it came to applying for another school leadership role, I just couldn’t stomach the thought. Four months later, I founded my own business and entered the world of being an entrepreneur.

Thinking of doing the same? Unsure where to start? Let me share some of my tips and lessons I have learned along the way.

The unknown is scary.

Tip – Face the fear.

What is the worst thing that can happen? Now put together a contingency plan. Once you do this, your biggest fear is not the unknown anymore. You have two plans – one being the journey you want to take; one being what you will do if it starts to go wrong.

You will not go from being okay to being in dire straits overnight, so fear of running out of money to pay your household bills is a real fear but not a sudden ‘out of the blue’ scenario. I had a bail out figure in mind when I set up my business – the point in which to implement my plan B. At any given moment, I could judge how much further I could go until my business gained traction and became successful.

It doesn’t have to be all or nothing.

Tip – Make a plan that works for you.

Some people are more risk adverse than others. That is okay. You are running your own race; what others do is not what you have to do. Stop comparing. If you are not comfortable with the idea of walking away from a steady income to become your own boss, why not start to think about how you can set up your business as a side line and have a more flexible transition? When I started my business, I had zero social media presence and it took me around 4 months to ‘get out there’ in any real sense – 4 months of not earning a penny. What can you do NOW whilst you are in your steady role and how can you scale later when you have the foundations in place?

Is the journey to entrepreneurship worth it?

Setting up a business can be stressful but it is also one of the most stimulating things you can do in your career. Over the past 2 years, I have developed new skills and achieved a life that would not have been possible if I had not taken a risk and trusted in myself. The journey was not all plain sailing… I’ve yet to find an entrepreneur who has not faced huge challenges to overcome. I came within one month of not being able to pay my mortgage – the point where I had a bail-out plan – but I have pushed beyond the limits. I now enjoy a flexible working life that fits my life, I have time with my family and friends, I am accountable only to myself (bliss!) and whilst I do not have a “steady” monthly salary, I earn more than I ever did as a contracted primary school headteacher. Best of all, I LOVE my job!!

I am a leadership, life and career coach. I help people who are lost or stuck at a crossroads find their right path so they can have the courage to live a life they’ll love.

Curious about starting your journey?

Message me to learn more about how my coaching can support you.



I first worked with Will whilst I was a junior member of a teaching team. I worked closely with him for around three years and he became a true mentor to me. During this time Will helped encourage me to discover my own leadership style and he mapped out what it takes to be successful. I highly recommend Will for life and career coaching.

Will is a professional, natural leader who manages to make you feel at ease. He manages to be both emphatic and encouraging, whilst also managing to challenge you to find your own answers. Will’s approach is totally non-judgmental and the sessions are really focused on you and on what you want to achieve. Working with Will has allowed me to address challenges I was facing and he brought a wealth of resources and practical tools to help me set goals, clarify my values, and explore avenues right away. Even though I left teaching 5 years ago, I still seek out Will for his help and guidance and I appreciate his versatility as a thought partner, ally, and coach. Our sessions are always productive and efficiently run, which is perfect for someone who is juggling many priorities! Will brings great communication, professionalism and quality to his work and I highly recommend him as a life/business coach.
- Jamie T (Leadership Coaching)

Highly recommended

I am so glad I found Mapleleaf Vision! Will has been super supportive and understood exactly what I needed to help me to redirect my focus. I now have fresh enthusiasm for what lies ahead.
- Greg M (Life Coaching)


Will at Mapleleaf vision fitted me in for a last minute decision-making session that I needed to make ASAP re. a job offer / career change. He was friendly, professional, and really knew his stuff! He unpicked things that I could never have done on my own. I’m so grateful to him & will be highly recommending him to everyone! Where there is a ‘Will’, there’s a way! Thank you, Will. You truly have a gift.
- Cat K (Career Coaching)