Leaving the Corporate World, Finding Freedom Work

Leaving the corporate world in your 50s to start and online business isn’t just a career move — it’s a life gamble.

Imagine you have a job you love, great colleagues, and the kind of professional reputation that took decades to build. Most people would hang on into their 60s. After all, it’s unlikely you will find another employer. I knew that when I walked away — and I did it anyway.

The Leap into the Unknown

I found meaning in carrying out a job I was good at. But something deeper kept stirring — a quiet knowing that there was more to life. 

Someone close to me said, “You keep talking about living abroad and creating your philosophy thing — why not just do it?”

That was the push. But there was something else as well. My dad passed away at 46. The realisation that this life can be short had a lasting impact. 

Within months, I’d handed in my notice. No grand plan, no spreadsheet.

It wasn’t a rational decision. It was a calling. For others, this leap needs to be a meticulous 10-page spreadsheet. But for me, it was a conviction that it was time.

Freedom — and the Shock That Follows

At first, it felt exhilarating to be fully committed to my own projects. I’d promised the world 20 years ago, I would create a philosophy channel and website to help people.

I’d imagined I’d transfer my 30 years of skills into building Undullify Media, and shaping a new creative life.

But the reality was different. Once I tasted freedom, I didn’t want to work as hard. I enjoyed more time with friends, I wanted to relax. To play golf and pool. To wander with my camera. To create, write and design things purely because I enjoyed making them — not because of a deliverable.

And here’s the surprising part: I didn’t miss the corporate earnings like I thought I would. Losing the company car, not buying things, spending less — it didn’t feel like a loss. I embraced having less and it brought even more appreciation for what I did have.

The Mindset Shift: Navigating the Identity Void

Still, I hadn’t anticipated the vacuum leaving a job creates. 

For decades, I have been conditioned to do a 9 to 5. Work has given my life structure, achievement, and a sense of momentum. Suddenly, the days stretched more open — quiet, unstructured, calm. It was exactly what I wanted… and yet something felt missing.

It’s what I call the vacuum.

That space between who you were and who you’re becoming. It’s similar to what people experience in deep meditation — space, silence, stillness — but then comes the question: What do you fill it with?

Some days, I felt flat or disoriented. The buzz of constant responsibility was gone. No one needed me to do something, to lead, to deliver. That might sound like paradise, but humans don’t deal well with drastic change.

The "identity void" is a much trickier stage to navigate than most people think, and it's the part of the journey we need to talk about more.

Corporate life can give you a constant sense of importance and progress. When that disappears, you have to redefine both. 

Not Retiring — Redefining

I never resonated with the word retirement. I didn’t leave to stop working — I left to start working differently. As a creative person, I’d always assumed I’d be working, creating something for ever. But I wanted to create things from my own vision without a brief. Philosophical, soulful, expressive — unhindered by corporate systems.

Once I launched the philosophy project, something unexpected happened: I thought I would return to more business style projects. But I didn’t want to chase clients. I only wanted to make work that felt 100% aligned and inspiring — joyful creation.

That shift brought guilt at first. When you’ve spent your life building skills and working hard, doing what you want feels almost wasted. Lazy, even. The truth is at this point I‘m still open to all types of projects if I enjoy them. I’m finding my way. Finding full alignment.

I’ve learned that once you find this freedom the only way to become productive again is to  focus on work you truly love. 

And the good news is there is a place for someone like me, the creator. Modern social media and AI offer endless opportunities.

A Different Kind of Structure

Freedom without purpose can blur into drift. So I learned to build just enough structure — creative projects, and curious travel — to keep me grounded, but not trapped. Work, for me now, isn’t about earning or status; it’s about rhythm and expression.

The irony is that, after decades of structure, you have to learn freedom as a new skill. It takes time to find your pace again. But once you do, it’s profoundly rewarding.

The Relocation Opportunity

I had figured out the 'why' of my new life, but the 'how' was still uncertain. How do you sustain a life of joyful creation without the corporate salary? The answer came in Thailand.

When I found myself enjoying the temples and beach something really hit home. I met an Australian who was working from Chiang Mai. When he outlined his business he was only working two days a week. I asked him why not make more money but living in Thailand meant he didn't need to. He had decided to spend more time doing other things because of the low cost of living.

The beginning of all wisdom is wonder
- Aristotle

A major advantage of not working for a company is you can potentially live in a more beautiful but cheaper country. This takes the pressure off how much you need to earn. It also frees you up to work on what you really want to. Or take a risk building something. Both of these have the potential to be successful because you're doing what you love.

The Risk Was Real — And Worth It

Walking away from a well-paid, respected role in your 50s is terrifying. There’s no guarantee you’ll ever be employed again. I still took this major action later in life when I had good foundations: financial stability and a strong skillset. I’m not advising anyone to go completely crazy.

If you can afford to do it, here’s what I’ve discovered: the risk of staying — of not living fully, of never finding out who you are beyond your job title — is far greater.

Freedom is not a comfort zone. It’s a process. A leap not a stroll. It strips away the familiar and hands you back yourself — raw, uncertain, alive. And on the other side of that discomfort, life opens up in a way no career ever could.

I’m still figuring it out. But I know this: leaving my job was less about losing something, and finally moving towards who I really am.

Taylor

Thank you for being here!