Why retirement is less like a destination, and more like Race across the World

If you watched the latest series of Race Across the World, you’ll know it’s not really a travel show. It’s a life lesson disguised as an adventure. If you haven’t seen it, the show follows pairs of travellers racing thousands of miles across unfamiliar countries, without smartphones or credit cards. No access to the internet, just maps, the cash equivalent of the airfare, intuition, and the kindness of strangers.

These couples were all heading to the same place, but how they got there was entirely up to them, subject to checkpoints along the way. They need innovative ways to manage their budget and conduct their journey. Would you choose to stick to the big cities, betting on better transport connections? Or perhaps the scenic route, even if it means fewer buses and longer waits. Do you splash your cash? after all, there’s no point in getting to the end of the race with money in the bank, but you risk running out of money, and you’re out of the game? Who’s your ideal partner for the journey?

They all face delays, disappointments, and wrong turns. But nine thousand miles and fifty-one days later, they all arrive at the final checkpoint within three hours of each other - and nobody’s talking about who won. They’re talking about what they learned, what they overcame. How they changed. The journey.

Which is all, as it turns out, a pretty good way to think about retirement.

We may all have similar goals - enough money to enjoy life without worries and grind; a bit of security, a chunk of fun - but how we travel is deeply personal. There’s no one-size-fits-all path - it’s not a linear “start here, end there” process.

What matters most isn’t necessarily when you arrive at your final destination or how fast you go. It’s what you learn about yourself along the way.

Retirement: a new kind of journey

I’ve had a few people recently ask if I’ve retired - but I’m becoming used to being the youngest person in the room, at 58. I used to bristle at the question. Now I quite like it.

Because retirement isn’t the end of the road. It’s not about winding down or becoming invisible. It’s a whole new phase where, for once, you get to choose your pace. You can be adventurous. You can take it slow. You can try something new or just sit and watch the ocean with a bag of chips and not apologise for it. (Milford-on-Sea, if you’re asking.) A time to thrive.

Until recently, life for many was a pipeline. School. Work. Marriage. Kids. Retire. Fade out. But that’s not the deal anymore. We live longer. We work differently. We want meaning, and experience, and space to figure things out.

And that freedom is brilliant – but it also requires intention, conscious decision-making. In other words, it’s over to you. When there’s no default route, you have to start asking the big questions. Not just “When do I retire?” but “How do I retire and what do I actually want next?” Otherwise, it’s an opportunity missed – an opportunity to be you.

The wisdom we almost ignored

It’s funny how, when we’re younger, we dismiss all the advice our parents and grandparents tried to pass on. I used to know every word of The Hitchhiker’s Guide to the Galaxy off by heart. Not a wasted youth. There’s a brilliant line in it where Arthur Dent says, “It’s times like these I wish I’d listened to what my mother used to say,” and Zaphod Beeblebrox replies, “Why, what did she say?” And, frustrated, he retorts, “I don’t know, I wasn’t listening!”

That’s how a lot of us treat wisdom. We roll our eyes at things like “look after the pennies and the pounds will look after themselves,” or “there’s no such thing as a free lunch”. But those old sayings have lasted because they’re true. We just need to grow into them.

Financial planning is a bit like that. It starts as a problem you want to solve, it feels like a maths problem, numbers. But there’s so much more to it than that.

And realisation dawns. It’s about working out where you are going with your life, helping you navigate your journey, with all the obstacles, unexpected detours and surprises there might be along the way. Making sure you don’t run out of money before you get to the end but also don’t leave it all in the bank. Putting life into your money.

A journey only makes sense in hindsight

In my youth, I was taught there’s a perfect way to do things – right and wrong, ticks and crosses, the smartest path, the shortest route. Science over Art. You just need to discover the secret, the hack. Starting with the perfect morning routine. But with time (and maybe a few missed trains), you realise it’s not all about optimisation and evidence. Life is more nuanced. It’s also about awareness. Growth. Enjoyment. Forgiveness. And knowing you’ll get there, even if you’re not quite sure how.

That’s why retirement - and planning for it - is about shaping something that fits us, now. And being open to reshaping it again down the line.

Like all good adventures, we won't always know what's ahead. But with the right guide, some time-tested wisdom, and a bit of curiosity, we can find our way.

Helping you find what you really want

If there’s one thing I hope clients take away from working with me, it’s that I help them figure out and do what they really want to do, not just what they think they should do. An empowerment that comes from financial security with the confidence and liberation for life that comes from being in control of your own financial destiny.

Like the travellers in Race Across the World, everyone starts with a rough idea of where they’re heading. But it’s only when you’re in it - when you’re making decisions, facing forks in the road, or missing a bus and having to rethink - that you really start to understand what matters.

Retirement is like that. It’s a journey you get to shape. And the best journeys rarely go exactly to plan. But they teach us who we are - and remind us that how we get there matters just as much as where we end up.