Updated 2026
Caroline Ulmer's observation cuts right to the heart of the travel decision: 'You are young, you are free, what holds you back?'
It's a provocative question because the answer is usually not a real obstacle - it's psychological.
Your assumption is that the perfect time arrives naturally. You'll finish school, establish your career, save enough money, and then travel will fit into the plan. But travel doesn't fit into plans. It disrupts them. That's the point.
Caroline's timing was strategic. She planned her trip 'about two years before the end of her studies.' This is crucial. She didn't wait until graduation to start planning. She made the decision early and built her entire post-academic timeline around it. She saved money specifically for this. She structured her life to make it possible.
Most people do the opposite. They say 'after graduation' or 'when I have a better job' or 'once I save $X.' These are shifting goalposts. Your career will always have another advancement to pursue. Your savings will never feel fully adequate. There's always a reason to wait.
Here's what actually holds you back:
Fear disguised as practicality. You tell yourself you can't afford it or don't have time, but the real fear is that you'll fail. You'll run out of money. You'll get lonely. You'll regret it. You'll miss important opportunities back home. These fears are valid, but they're not reasons - they're obstacles to work through.
Social obligation. Your peers are following a conventional timeline. You're supposed to be establishing a career, building credentials, moving into adult life. Taking a year off looks like falling behind, even though you're actually running a different race.
The sunk cost fallacy. You've invested in a degree or job or relationship in your home city. Leaving feels like wasting that investment, even though continued investment in something wrong is bigger waste.
Momentum. You got into a track. You keep moving on that track because the alternative requires conscious decision-making and courage. Staying is passive; leaving requires action.
What holds you back isn't external. It's your own beliefs about what you should do, when you should do it, and what people expect of you.
Caroline's advantage wasn't exceptional wealth or luck. It was clarity. She decided that experiencing the world before settling into career life was a priority. That clarity made everything else a logistics problem, not an obstacle.
Most people approach it backwards. They wait for the perfect moment and the obstacles to clear. But the perfect moment doesn't arrive. Obstacles are constant. Clarity about what you want comes first. Then you build life around it.
Here's the reality: the best time to travel long-term is when you're young and unencumbered by mortgage, kids, and career advancement. Traveling at 65 is possible and valuable. But it's different. The energy is different. The risk tolerance is different.
If you're 20-35 and have been thinking about RTW travel, stop waiting. Start planning. Not 'someday.' Specifically. When will you apply for visas? When will you book your first flight? What's the exact timeline?
Caroline planned two years before departure. That's enough time to save money, arrange visas, finish your current commitments, and mentally prepare. It's also aggressive enough to be real - a vague 'I'll do it someday' is not a plan.
What holds you back is the decision itself. Everything after that is logistics. Make the decision. Then logistics becomes solvable.
You have more freedom than you think. You just have to claim it.