WHEN?
For so much of life, we’re waiting for when . . .
When I’ve got that job.
When we’ve bought the house.
When we have kids.
When the kids finally leave home.
When our parents pass.
When we retire.
And so it goes – yes, we’re living, but often only after we’ve ticked off everyone else’s milestones, or the expected milestones, before our own.
And while we’re waiting, we’re also compromising. Handing over our time, our energy, our weekends – doing what it takes to keep the peace, and keep everyone happy. Even holidays end up belonging to someone else.
At first, it feels fine – a shared goal with partners, family or friends. But before you know it, you’re juggling, balancing, keeping all the balls in the air, and your own wants are quietly parked in the corner. Sometimes they’re parked for so long you forget they even exist. Or worse still, you’ve never really stopped to consider what you want for yourself.
WHEN Do We Say Yes – To Ourselves?
Too often, our yes goes everywhere else. Yes, to make life easier. Yes, to avoid judgement. Yes, when we really mean not really (which is just a polite no in disguise).
But here’s the thing – every time we say yes to someone else, we’re quietly saying no to ourselves.
So the real question becomes: When will I finally say yes to me? Yes to the trip I’ve been dreaming of. Yes to the pace that suits me. Yes to the little indulgence that makes me smile.
Because saying yes to yourself isn’t selfish – it’s a way of finally giving yourself permission to live.
WHEN Does the Budget Stop Running the Show?
It’s not just people we bend to – it’s money too. How many times have you made a choice because it was the cheaper option, not the one you really wanted? I’ve lost count.
I grew up in a household shaped by scarcity, my mum, a war baby, raised when everything was rationed. Decades later, my childhood was still about stretching, saving, and making do. It’s a skill worth having, don’t get me wrong, but at some point you have to ask: When will I stop letting the budget decide my happiness?
Because joy doesn’t always come with the cheapest price tag – and sometimes joy is worth every cent.
WHEN Do We Choose Ourselves?
Case in point: I recently needed a new car. Now, I’m not a ‘car person’, the only thing I cared about was that it came in this beautiful shade of green I’d seen on other cars.
So off I went to the dealer and after looking around I said, ‘I’ll just have the small car’. All that was left was to choose the extras: mats, window tint, and colour. The saleswoman shook her head and said, ‘Sorry, that green only comes in the larger model.’
For decades, I would’ve sighed, thought of the budget, and settled for the cheaper car in a colour I didn’t love. But this time? I surprised myself. I thought, stuff it. I ALWAYS compromise. I want that colour green. So I went for the slightly bigger car, and it felt liberating.
When I told a friend about it, she confessed she bought her car because it had a crystal gear knob. Crystal gear knob! Proof that sometimes it’s the little things that make us happiest.
WHEN Do We Stop Waiting?
We often hear from people (especially solo travellers) who have, once too often, handed their holidays over to other people’s plans. Their must-see museum. Their pace. Their location choice. Meanwhile, the thing they wanted most quietly got shelved.
Because our groups cater to solos*, couples and friends, we’re increasingly hearing from people who’ve finally reached their ‘when’. They’ve stopped waiting for permission, stopped deferring to other people’s expectations, stopped bargain-hunting at the cost of joy.
They realised the answer wasn’t later, or someday. It was now.
And you know what? That’s not selfish. It’s freeing. And it’s not just them who benefits – their happiness ripples outward. When you’re content, energised, and joyful, everyone around you feels it too.
*Solo travellers aren’t always single. Many are married or in long-term relationships, but their partner simply isn’t keen to do the same thing at the same time. Instead of shelving their own dreams, they choose to go anyway. And here’s the beauty of it – the partner who stays home doesn’t miss out either. They get to do what they love, while the travelling partner returns refreshed, fulfilled, and often with a spark that strengthens the relationship.
WHEN Do We Finally Live?
Think back. Your parents, your grandparents – whole generations who never got the chance to do something purely for themselves. It wasn’t the done thing. They waited their whole lives for ‘when’, and often, it never came.
So here’s the question: when will you stop waiting?
Maybe it’s not a big leap at first. Maybe it’s ordering the dessert you actually want, not the cheapest one. Taking a Saturday just for yourself. Choosing the hike, the hotel, or the holiday that lights you up inside.
Because ‘when’ can stretch on forever – unless you decide that your time is now.
WHEN Becomes Now: Permission Granted
So, what’s your ‘when’? What’s the trip, the adventure, the little or big indulgence that you’re going to say yes to – not because it’s cheapest, or easiest, or expected, but because it’s yours?
Go on. Permission granted.
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