Lessons from Now Teach about your second career

Teaching is a rewarding second career. The co-founder of Now Teach shares insights about switching tracks

In 2016 FT columnist Lucy Kellaway and I co-founded Now Teach. We did not do this in the conventional way with business plans and market research. We plotted most of it in my kitchen holding a newborn each (I’d just had twins) and talking faster and faster as we persuaded ourselves it was a good idea.

The straightforward idea behind Now Teach

The idea was simple. We wanted to help people who’d had successful careers to start all over again as teachers. People, in fact, like Lucy. Lucy had had, by anyone’s reckoning, a successful career. She was an acclaimed journalist who enjoyed her job, but felt she’d stopped learning or getting better. She was 57 and had years of life and career ahead of her; plenty of time to retrain. We were sure she couldn’t be the only person in her position.

And we were right. We have been overwhelmed by how many brilliant people have joined us as Now Teachers.

The issue: No path to teaching

We all know that we are living longer and that we are moving towards the idea of a multistage career. What is not always clear is how one should move from one stage to the other. There has never, technically, been anything to stop older people retraining as teachers. But not many have retrained; and many of those who started dropped out. By September 2021, around 500 older people will have become Now Teachers.

How to change career to start teaching 

So, what have we learned about what people need to change career?

A push

We can’t control this, but we can encourage people to listen to their instincts. Many Now Teachers come to us at a time of personal change or challenge: the children moving out / parents dying / a divorce. Conventional wisdom might say not to make rash decisions at these moments, but our experience would say the reverse. There is often a moment of clarity at these times. 

A pull

It is crucial that we, all of us, make sure that we are not ageist in our assumptions about who should be doing which job at what stage and age. Now Teach works simply because it celebrates and encourages – and normalises – people doing something which is generally considered the territory of people in their early twenties.

More conversations

We’ve recently produced a podcast with the great Jenni Murray in which she is pondering her next steps at the age of 71. “Maybe all of us should think of teaching as we grow older,” she says. “We have so much knowledge and wisdom to pass on and it’s high time the generations paid each other more attention.” One of the guests was Andrew Scott, author of The 100 Year Life, who spoke about the importance of planning for a multistage career. Whatever our age we should assume that our careers will not be linear and we should plan for that.

Career change coaches

Now Teach does celebrate and encourage people into teaching. But it also provides personalised support and recruitment coaching. In 2020 our research showed that 43% of those over 50 who were considering a career change wanted career coaching or guidance in order to do so. We need to get better at thinking about career support and education at all stages of life.

Ongoing support and research

Career trajectories look different at different stages. Many Now Teachers don’t want to rise up the traditional school hierarchy. This doesn’t mean they don’t want to learn and develop as teachers – or contribute to the wider school system – but the way in which they do it may be different. We need to help both career changers and their organisations reimagine what success looks like.


Most of us won’t want to work part-time for most of the time; but most of us will want to work part-time at some point in our lives. One of those times is likely to be as we get older. Those sectors which best support flexible work will be the ones who find they hold on to talented women when they have babies – and talented and experienced people as they get older.

Now Teach’s top tips for your midlife career change interview:

  • Don’t worry about spending money or lots of time on what you’re wearing. A lot of early-stage recruitment is online, and even when interviews to return to being in person, a good employer is far more interested in what you say than what you wear.
  • Expect the interview to be a different format from previous more senior roles where you might have been headhunted. Instead of a one-on-one, possibly over lunch, you’re likely to be talking to a panel of people in a graduate style interview. Remember to engage with everyone, rather than focussing solely on the person asking the questions.
  • Make your peace with the idea of being more junior. You’re starting afresh and there’s no shame in that. The great thing about starting over is that you’re not expected to be a finished product. You can be honest about not knowing any answers, as long as you demonstrate your willingness to learn.
  • Starting in a new field doesn’t mean that all your previous work experience is erased. Before your interview spend some time assessing how aspects of your previous career might pertain to this role.
  • Don’t be afraid to cite parenting experience if you’ve spent a significant portion of your life looking after your children. After all, the logistical skills honed through childcare are much the same as they would be in a paid administrative role, and you wouldn’t have any qualms about discussing having worked as a nanny or PA.

To hear more about career change, longer working lives and all things education, you can tune in to Now Teach’s podcast Now I’m Grown Up, hosted by Dame Jenni Murray.

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