Should I quit my job and travel? This is a question many people sit with for years. It can feel like a battle between craving freedom and fearing you’re making the biggest mistake of your life. I’ve been on both sides of this decision. Clarity comes from understanding the costs, the trade-offs, and which kind of regret you’re more willing to live with.
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Why this is such a big decision
Deciding whether to quit your job and travel can take a long time because it feels impossible to resolve with the advice that’s out there.
Half the internet tells you to ‘follow your dreams’ as if courage is the only missing ingredient. Meanwhile, the other half warns against career gaps and financial ruin. So you’re stuck in a loop of researching, planning and asking around.
The decision feels high-stakes because you’re not just choosing a holiday. You’re questioning the structure of your life. The security of your routine, your professional identity, and the version of yourself you’ve worked hard to become all come into question.
What makes this so difficult is that quitting your job to travel feels irreversible – even when it isn’t.
The real question
People tend to get stuck by treating this as a binary, permanent decision. The question isn’t whether extended travel is valid – it’s whether this timing, under these conditions, is right for you. You’re not deciding who you are. You’re deciding how to use the next few months of your life.
When you consider quitting your job to travel, you’re weighing time pressure against financial pressure. You’re weighing the risk of disruption against the cost of deferral. Every option has a cost – including staying.
The real question is which version of uncertainty and discomfort you’re more willing to live with.
Weighing the costs
If you quit your job to travel, there are costs. Career momentum often slows. Re-entry can mean starting at a different level or pivoting sideways. This isn’t catastrophic – but it’s real.
Financial certainty disappears once your pay cheque stops. You start counting down your savings and assessing the affordability of everything. Meaningful experiences don’t remove that pressure.
While you’re gone, life continues back home. You miss weddings, births, and the small moments that quietly hold friendships together.
If you stay, there are costs too. Staying means remaining within a familiar version of yourself. Over time, commitments accumulate: mortgages, partnerships, children, family, health. The logistics of travel and the rationale for leaving often get harder.
This can lead to quiet regret that surfaces years later. Even in a satisfying career, there’s a cost to permanently closing a door you once wanted to walk through.
When this tends to work — and when it doesn’t
If you’ve been thinking about quitting your job to travel for years, that persistence matters. It suggests a long-standing pull rather than a temporary reaction to a specific moment.
Financial margin also makes a difference. Travelling with minimal savings and no emergency buffer often creates constant background stress, which can shape the experience more than people expect.
Expectations matter too. Travel won’t erase grief, restore motivation, or deliver a new identity. When a trip is expected to fix something or justify itself through transformation, that pressure can undermine it.
For some people, the steadier choice is to go. For others, the calmer choice is not yet — not because travel isn’t valid, but because the conditions aren’t right.
What this looked like in practice
I left my job after a long-term relationship ended and years of high-functioning work burnout. I’d been thinking about long-term travel since university, but it took those circumstances to finally push me to book my round the world trip. Here’s what I misjudged.
During my first few days in India, I committed to publishing my blog regularly, took on a 30-day art challenge and added other projects. I was so focused on proving my trip was ‘worthwhile’ that I started missing the more spontaneous parts of travel. Letting go of productivity created space for what I’d actually left my job to do.
One practical thing I did get right was creating a buffer. Before leaving, I secured a working holiday visa for New Zealand. Knowing I had a legal way to earn money if I needed it relieved a lot of my anxiety.
When I returned home, the career gap in my CV mattered less than I expected. I’d built it up as a big obstacle in my head, but it rarely came up during interviews – and when it did, it was easy to explain.
Quitting your job to travel isn’t a test of courage or a measure of how much you want freedom. It’s a decision about timing, conditions and which trade-offs you prefer to carry.
If you’ve thought honestly about the costs on both sides and know which version of regret would sit harder with you, whatever you choose will be grounded and valid.
The goal isn’t to eliminate uncertainty. It’s choosing the uncertainty you can live with – and stopping the loop.
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