Okay, it’s happening. Like, for real happening.
For months, this career break was this grand, exciting idea we talked about with our family, friends and colleagues. But now, we’re less than a week away from the first leg of our trip. Suddenly, all those little “what ifs” that used to feel distant are screaming in my ear.
I’ve been doing the rounds, saying my goodbyes to friends and colleagues. It’s been a weird mix of emotions. I’m excited for what’s next. But there’s also this unexpected tint of sadness too, realizing I’m stepping away from routines and faces I’ve seen so regularly. I’m especially grateful for the valuable opportunities and support my different bosses have given me over the years and that’s not something I will ever take for granted. Saying thanks, sharing those last laughs, and getting well wishes – it all feels so final, yet so hopeful.
And the common questions hit differently now: “Are you sure you’ll have enough money?” “What if it doesn’t work out?” “You’re so daring to let go of such a stable job and career!” At first, I could brush them off, easy. “Don’t worry, we’ve thought it all through.” But as the date looms – today’s my last working day – those external doubts are feeling a lot like my own internal panic.
What’s the Worst That Can Happen?
But here’s the thing that brings me back from the edge of that panic attack. The ultimate question I keep asking myself: What’s the worst that can happen if we actually do this?
Worst case? We come back to Singapore. We come back to the corporate world, back to the grind. It’s a safe default. We would just pick up where we left off.
But on the other hand, what’s the worst that can happen if we don’t actually take this leap?
That’s the never-ending “what if.” The constant wondering of what could have been. The missed adventures, the unexplored paths, the simple act of trading money for time. This whole concept of a “micro-retirement” – stepping out now, while we have the energy and curiosity, instead of waiting until we’re older and perhaps less able to truly experience slow travel. To me, that unlived possibility, that regret of not trying, is a far more terrifying prospect than any financial wobble or a trip that doesn’t go according to plan.
So yup, the fear is very, very real. But the regret of not trying? That’s an even bigger monster. And that’s what keeps us going.