Life After Headship: Setting Up Your Own Business with Confidence

For many former school leaders, the transition from headship to running your own business is both exhilarating and daunting. After years of navigating budgets, staffing, and school improvement plans, the idea of being your own boss can feel liberating, until reality hits. No guaranteed salary. No HR department. No IT team to reset your passwords.

With the right mindset, strategy, and support, moving beyond headship and into business ownership can be one of the most rewarding journeys of your career.

Here’s what you need to know if you’re considering the leap.

1. Create a Financial Roadmap Before Leaving Headship

One of the biggest adjustments when moving from headship to business ownership is the loss of a steady salary. Preparing financially before you take the leap is essential. This is a huge psychological adjustment, and it’s essential to approach it with a clear plan rather than blind optimism.

Know Your Numbers – Determine how much income you need to cover your living expenses and what level of revenue would allow you to thrive.
Build a Financial Cushion – Aim for 3–6 months’ worth of savings to ease the transition.
Start Lean – Keep initial costs low. You don’t need an expensive website or office space from day one.

2. Find Your Business Sweet Spot with the Hedgehog Concept

Jim Collins’ Hedgehog Concept is a powerful tool to help you clarify the direction of your business. It asks you to focus on the intersection of three key areas:

What you’re deeply passionate about – What do you love doing? What energises you?
What you can be the best at – What skills, expertise, or experiences set you apart?
What drives your economic engine – How can you turn this into a profitable business?

When these three align, you have a business that is not only sustainable but also deeply fulfilling. In the Beyond Headship Programme, we help you work through this process so you can launch a business with clarity and confidence.

3. Ditch the Shoebox and Go Digital with Your Finances

If you’ve ever found yourself with a pile of crumpled receipts at the end of the tax year, it’s time for an upgrade. Really. Using a digital accounting platform like FreeAgent can save you hours of admin and give you real-time insight into your business finances. You won’t need training! It’s so easy to use and the help/support team are good!

Easily track income and expenses

Automatically generate invoices

Connect to your business bank account for seamless reconciliation

Trust me, this is one of those small decisions that makes a big difference. Do it early on and keep it up to date!

4. Make Sure You Get Paid (On Time!)

One of the biggest frustrations for new business owners? Chasing late payments. Schools and local authorities, in particular, are notorious for lengthy payment cycles. You will probably have to accept their 30 day payment terms, but you don’t have to accept late payments; the law is on your side. Include this link https://www.gov.uk/late-commercial-payments-interest-debt-recovery

Set clear payment terms upfront

Use invoicing software with automated reminders

Charge for late payments, yes, it’s allowed!

Check out the UK Government’s Late Payment Guidance to know your rights.

5. Get Help: A Virtual PA Can Be a Game-Changer

Running your own business doesn’t mean doing everything yourself. A Virtual Personal Assistant (VPA) can take care of admin, emails, scheduling, and invoicing, so you can focus on what you do best.

Be clear about what you want, or look around at what’s on offer so you can start gathering your ideas. A good VPA will be keen to tell you in a discovery call what they can do to support you.

6. Enjoy the Journey - It’s Full of Learning

Running your own business after headship is not just about financial independence, it’s about designing a life and career on your terms. Yes, there will be challenges, but there will also be incredible moments of growth, freedom, and joy.

The Beyond Headship programme is here to guide you through every step—from financial planning to business strategy—so you can make this transition with confidence and clarity.

Ready to Make the Leap?

If you’re serious about setting up your business after headship, Beyond Headship will give you the strategy, support, and community you need to succeed.

Join Beyond Headship today and build a business that works for you.