There’s No “Right Time” to Change Careers, Only the Time You Choose

I often hear people ask: ‘But is now the right time?’, or ‘What if now isn’t the right time? How will I know when it’s time?’ 

One of the biggest myths about career change is that it should happen at the perfect moment, when you have total clarity, a foolproof plan, and a smooth path ahead. Life and work are rarely like that. A job I’d been waiting to apply for was advertised when my baby was 4 weeks old. I applied, borrowed some clothes from a friend for the interview, interviewed in between breastfeeds and landed the job. I was thrilled, loved the role and stayed for five years.  

For headteachers considering a move away from school leadership, this belief that there is a right time and a right path can be especially paralyzing. You’ve dedicated years to education, built an identity around leadership, and now the idea of stepping into something new can feel overwhelming.

But change is messy, and career change is rarely a straight, predictable path.

Shifting the Question: From “Is this the right time?” to “What could be my first small step?’’ or making a commitment to do one small thing towards a new career everyday are different approaches to help ease the transition. 

Rather than waiting for certainty, it’s more useful to take a structured approach to exploring change. Gerard Egan’s Skilled Helper Model offers a powerful framework for navigating career transitions:

Stage 1: What’s Going On? Gaining clarity on why you want to leave headship. Is it burnout? A desire for new challenges? A pull toward something else? This stage is about honest reflection about what’s really going on for you right now. 

Stage 2: What Does a Better Future Look Like? This is about exploring possibilities. If you think about the future you’d like: Where would you be? Who would you be working with? What kinds of conversations would you be having? What would you be doing and how would it fulfill you? What is it you care deeply about that you want to be part of your working life?

Stage 3: How Do I Get There? Turning insights into action. This is a 3 step process:Firstly Identifying all and any possible actions to help you get to your goal, even the outlandish! Try and get at least 25 possible actions down, challenge yourself.

Second, identify the actions which are most likely to help you get to your goal. Third step, from those actions, what are you going to do within the next 7 days to get you started? 

The Illusion of the “Right Path”

Many headteachers fear stepping away because they don’t have a clear alternative mapped out. But most successful career pivots don’t start with certainty, they start with curiosity and small experiments.

Instead of looking for a single “right path,” consider career change as a series of steps into new territory. Each move teaches you something. Each decision opens new possibilities.

As David Whyte says, “Often to make a living we have to risk ourselves on the world.” Career change is that risk, but it’s also the beginning of something new.

If you’re a headteacher considering a career move, what’s one small step you could take today? Drop your thoughts below.