How to Know When You’re Ready to Book a Trip
Making sense of uncertainty before you commit
The pause before the journey
There is a rush you get when you think about going somewhere new. Or going somewhere you have been before, but want to see more deeply. That first sense of “Could this actually happen?” is incredibly exciting. Then the wobble shows up. Am I really doing this? Maybe it is a jam band in Riviera Maya. Maybe it is Machu Picchu. Maybe it is New York City and you have never been before. I remember the first time I went to Jazz Fest in New Orleans. I was thrilled just to be there, completely wowed by the food, the music everywhere, and that strange feeling of being somewhere familiar and foreign at the same time. It was one of those trips that lived in my head for a long time before it ever became real.
That excitement shifts once you slow down and start thinking about what it will take. The conversations with a partner, or the decision to go alone. A girls’ trip, a trip with friends, or something you have never done before. You start researching, looking at dates and costs, and doubt creeps in. Can I get the time off. Can I afford this. Is this realistic. You end up in that in-between space where you want the trip to exist, but you are not yet sure you can pull it off. That back and forth is normal. It is the same wobble that shows up when you try to build anything meaningful in your life. Planning a trip works the same way. You do not need certainty. You need readiness. You hold the idea, make small course corrections as you go, and trust that the next step will reveal itself. More thoughts on pre-planning and how to orient your planning in January’s Blueprint.
Readiness Is Not Certainty (and It Never Has Been)
The best trips have a balance. You have enough going on to keep your mind engaged, and enough relaxation and downtime, without every decision being made for you, to really enjoy being away from home. Getting from idea to reality means accepting uncertainty and embracing readiness. There is a subtle place where readiness begins to outweigh the need for certainty. You are open and willing, even though not everything is under control. You can move forward, even if your confidence is not fully settled. You are just about ready to begin planning.
Having some healthy hesitation and recognizing it as different from fear-based stalling is half the battle. There is a common misconception that you need to have everything figured out before you start serious planning. In reality, planning is the bridge between something that exists only as an idea and something that actually comes to fruition. Try trip planners to ease any anxiety.
Moving toward ready. Photo by Wendy Stieg
Three Kinds of Readiness: Emotional, Practical, and Self-trust
Being able to recognize what readiness looks like, and what kind of readiness you are in, helps you know when you are ready to start planning. It may sound like splitting hairs, but when you get this part right, you usually get the trip right. I used to hate planning. Part of me still does. What I have learned is that I can either underplan, overplan, or plan somewhere in between. This trust, along with the old idea that the more time you spend sitting with uncertainty, the better your decisions tend to be, is where my best plans emerge. Staying in uncertainty, without rushing it, leads to emotional readiness, practical readiness, and self-trust readiness.
Emotional readiness comes from allowing the in-between stage to do its work. You let doubts and excitement surface without judging them. You still feel some anxiety about the trip, but you know it is manageable. You are more curious than fearful. Practical readiness shows up when you have a rough sense of when and where you want to go, and you have looked at airfare or lodging enough to understand the general range of costs. You know the shape of the trip, even if the details are not fully decided. Self-trust readiness is there when you trust yourself enough to adapt. You know things may go wrong, but you also know you can handle them when they do.
At the ready
What Actually Needs to Be Decided Before You Book
At this point, the question is not whether you have everything figured out. It is whether you have enough to take the next step.
Start by choosing a general destination or region. Not every stop. Not a perfect route. Just the place you are saying yes to.
Then choose a realistic time window. A few possible dates that work with your life as it actually is, not as you wish it were.
From there, pause and check one more thing. Does this trip make sense for you right now? Financially, emotionally, and practically?
If those pieces are in place, the next thing to do is simple. Look at flights. Not to buy yet, but to understand what is possible.
When you can see the shape of the trip, the costs, and the timing, you are no longer guessing. You are planning. This is usually the point when things begin to click into place.
Tower at Silves Castle, Algarve, Portugal Photo by Wendy Stieg
Spending time in uncertainty is often the best way to begin planning. You do not need every dot connected to take the first step, and it is fine to leave space for revision along the way. Hold onto the idea of course correction and make a simple commitment to stay with the process. Every trip I have ever taken has included moments when I thought it might not happen. Allowing those moments to exist, while still trusting that you can pull it off, is part of what makes travel both exciting and meaningful.
