Career Change at 40: How to Find a Better Work-Life Balance

There is a strange point that can arrive somewhere around your forties when you start looking at your life a little differently.

It isn't necessarily a crisis. Your life might actually look pretty good from the outside. You might have a decent career, a mortgage, savings, a relationship, a family, holidays booked and a reasonably comfortable existence. You might even be successful by almost every conventional measure.

And yet, somewhere underneath all of that, there is a quiet thought that keeps returning.

Is this really what I want to do for the rest of my life?

I know that feeling because I eventually had to ask myself the same question.

I spent around sixteen years working in the corporate world, most of that time with Superdry. I joined when the company was still a relatively small brand with just four stores. Over the years I worked my way through different roles, eventually helping run a UK retail operation that had grown to around 120 stores. I managed large teams, took on increasing responsibility and eventually spent time as acting Head of Retail.

On paper, it was a pretty good career.

And that was part of the problem.

When Success Stops Feeling Like Success

Leaving a career is one thing when you're miserable, being treated badly or desperately trying to escape.

It's much harder when you're actually good at what you do.

I had spent years building my career. I had worked hard for the promotions, the responsibility and the financial security. When the company floated after I'd been there for around ten years, I received shares through my employment and stayed for another six years.

I also became interested in property. At one point I owned five houses in the UK. They were all mortgaged, I rented four of them and lived in one. The rental income wasn't some magical passive-income machine; after mortgages and costs, there wasn't an enormous amount left over. But over time the properties increased in value.

Eventually I sold them, cleared the mortgages and bought a home outright.

By most people's standards, I was doing exactly what you were supposed to do.

Work hard. Build a career. Buy property. Create security. Keep going.

And I did keep going.

Until I started wondering where exactly I was supposed to be going.

After leaving Superdry, I bought an old cottage in the UK and spent about a year renovating it. I divided it into two, lived in one side and ran the other as an Airbnb. For years I was still building things, improving things and making sensible decisions.

Then my mum died of cancer.

My dad was also ill around the same period.

And something changed in me.

When people you love become seriously ill or die, all those distant plans about the future can suddenly feel very different. You start to realise that life isn't an unlimited resource that you can keep putting off until you've got everything sorted.

I remember thinking, in different ways, life is too short. What am I waiting for?

It sounds obvious.

But knowing something intellectually and actually feeling it are two very different things.

The Problem With Work-Life Balance

We talk endlessly about work-life balance.

Work less. Take more holidays. Don't answer emails at night. Spend more time with your family. Go for a walk. Put your phone down.

All of those things can be good advice.

But I eventually came to question something else.

What if the problem isn't the balance? What if the problem is the life you're trying to balance?

You can become very good at managing a life you don't particularly want.

You can organise your calendar beautifully, take your allocated holidays, exercise before work and make sure you're home for dinner, while still feeling that something isn't quite right.

Sometimes what we call work-life balance is really just an attempt to make an unwanted life more tolerable.

That doesn't mean everyone needs to quit their job. Far from it.

For some people, the answer really is better boundaries. For others, it might be changing their hours, moving into a different role, working remotely or simply making more space for the people and things they care about.

But sometimes the uncomfortable answer is bigger.

Sometimes you don't need to balance your life differently.

You need to ask whether you want to build a different life.

I Didn't Leave Because I Had Failed

My own transition wasn't some carefully constructed five-year plan.

I eventually left the corporate world and began experimenting with a completely different way of living.

Before Portugal, I'd already experienced what it was like to step outside the conventional path through property and running an Airbnb. But Portugal took it much further.

I moved to Portugal with savings, a car, a caravan and a tent and initially bought around a hectare of rural land. For a period, I lived with solar power and spring water and worked out the practical realities of creating a life with far fewer of the systems I'd previously taken for granted.

It wasn't glamorous.

There were plenty of moments when I wondered what the hell I was doing.

I eventually sold my remaining UK house and bought around fifteen hectares of rural land in central Portugal. There were three old buildings on it. They didn't have proper bathrooms, kitchens, running water or electricity, and two of the buildings were in extremely poor condition, including one with a collapsed roof.

I had gone from helping run a large corporate retail operation to figuring out how to rebuild old rural buildings and manage water, power, land and everything else that comes with living somewhere like that.

It was almost the complete opposite of my previous life.

And it taught me something important.

Changing your life doesn't necessarily make it easier.

Sometimes it makes it harder.

What changes is that the difficulty starts to feel like it belongs to you.

The Reality of Changing Direction at 40

There is a romantic version of career change that gets sold online.

You leave your job, follow your passion, move somewhere beautiful and suddenly wake up every morning feeling free.

Real life isn't like that.

There were things that broke. There were expensive mistakes. There were days when I missed the predictability of my old life. There were practical problems that couldn't be solved with positive thinking.

I had to learn about land, buildings, water systems, fire management, rural living and a whole collection of things that were never part of my corporate career.

But I also discovered something I hadn't expected.

I became much more aware of where my time was actually going.

I started spending more time outside. I became deeply connected to the land. I developed a retreat with a friend. I worked with people. I became more serious about photography, writing and personal development. I studied CBT and life coaching and continued exploring NLP and other approaches to understanding people.

Eventually, the property was filmed for New Lives in the Wild with Ben Fogle, I continued developing my photography and writing, and the life that had initially seemed like a crazy detour gradually became my actual life.

I wasn't simply escaping something anymore.

I was building something.

You Don't Have to Throw Your Life Away

This is probably the most important thing I would say to anyone considering a career change at 40.

You don't have to become me.

You don't have to sell your house.

You don't have to move to Portugal.

You don't have to live in a caravan.

You don't have to buy fifteen hectares of land.

And you definitely don't have to hand in your resignation tomorrow morning because you've read an inspirational article on the internet.

The point isn't to copy somebody else's life.

The point is to start paying attention to your own.

Maybe you genuinely love your career but need to change the way you work.

Maybe you need to start a business on the side.

Maybe you want to move somewhere quieter.

Maybe you want to spend more time with your children.

Maybe you've spent twenty years climbing a ladder and have suddenly realised it is leaning against the wrong wall.

Maybe you don't know what you want yet.

That's okay too.

One of the biggest mistakes we can make is believing that we need to know the entire destination before we're allowed to change direction.

You don't.

Sometimes the first step is simply admitting that something isn't working anymore.

The Fear of Starting Again

One of the reasons career change becomes harder as we get older is that we have more to lose.

At 20, starting again can feel exciting.

At 40, you might have a mortgage, children, responsibilities, savings, a reputation and a career you've spent half your adult life building.

You may also have an identity wrapped around your work.

That was something I understood personally.

When you've spent sixteen years becoming good at something, walking away isn't just a financial decision.

Part of you has to ask:

Who am I if I'm not that person anymore?

That's an uncomfortable question.

But it can also be liberating.

Because eventually you realise that your job is something you do.

It isn't necessarily who you are.

I became a manager. Then a senior manager. Then someone involved in running a large organisation. I became a property owner, landlord, renovator, Airbnb host, photographer, retreat host, writer and coach.

None of those things completely define me.

They're simply different chapters.

And perhaps that's something we forget.

We don't actually have to live one continuous life.

We can live several.

What If Work-Life Balance Means Something Completely Different?

For years, I thought freedom meant having enough money that I didn't have to worry.

There is some truth in that.

Financial security matters.

But I've discovered that freedom is also about having some ownership over your time, your attention and the direction of your life.

You can earn a lot of money and have very little freedom.

You can earn less and have far more control over your days.

Neither is automatically better. It depends on what you value.

That's why I don't particularly like telling people what they should do.

The life that makes me happy might make somebody else miserable.

Some people thrive in cities. Some need rural life. Some love corporate careers. Some want to build businesses. Some want stability. Some want adventure.

There isn't one correct answer.

The real question is:

What does your answer look like?

You Might Not Need a Career Change at All

This is something I think is worth saying because the phrase "career change at 40" can make it sound as though the only solution is a dramatic reinvention.

It isn't.

You might need a conversation with your employer.

You might need to work four days instead of five.

You might need to stop taking work home.

You might need to move into a different department.

You might need to start something alongside your existing career.

You might need to take six months to work out what you actually want.

Or you might discover that you really do want to leave.

The important thing is not to confuse action with progress.

Quitting your job without knowing why you're leaving isn't necessarily freedom.

Moving to another country because you're unhappy isn't necessarily the answer either.

You take yourself with you.

I learned that one too.

The purpose of changing your circumstances isn't to run away from yourself. It's to create enough space to actually hear yourself.

So How Do You Know When It's Time?

I don't think there is a magic age or a checklist that can answer that question.

But I do think there are questions worth sitting with.

If money wasn't the deciding factor, how would you spend your time?

If nobody else could judge your decision, what would you choose?

What parts of your current life give you energy, and which ones quietly drain it?

Are you genuinely happy with your career, or are you simply comfortable enough not to leave?

If nothing changed, would you be happy living essentially the same life in ten years?

And perhaps the hardest question of all:

If you could step outside your own life for an hour and look at it as a complete stranger, would you choose to live it?

You don't have to know the answer immediately.

But if the answer is no, don't automatically treat that as failure.

It might simply be information.

Maybe a Different Life Starts With a Different Question

Looking back, I don't think the biggest change in my life happened when I moved to Portugal.

It happened earlier.

It happened when I stopped asking:

"How do I make the life I've got work?"

and started asking:

"What would a life that actually feels like mine look like?"

Those are very different questions.

One keeps you inside the existing structure, trying to improve it.

The other opens the door.

I have no idea what your version of a different life looks like.

Maybe it involves Portugal. Maybe it doesn't.

Maybe it involves changing careers at 40. Maybe it means staying exactly where you are but changing how you spend your time.

Maybe it means leaving a job, starting a business, moving to the countryside, travelling, making art, spending more time outside, repairing a relationship, simplifying your life or finally doing something you've been telling yourself you'll do "one day".

You don't need to have it all worked out.

You just need to become honest enough to admit when the life you've built no longer feels like yours.

Because life really is too short to spend all of it waiting for someday.

And if there really is another way to live, perhaps the first step isn't finding the answer.

Perhaps it's finally allowing yourself to ask the question.

What would my life look like if I stopped living according to someone else's definition of success?

That is the question at the heart of Wylde Roots.

Not how should you live?

But what kind of life is actually yours?