From the Vault: Feeling Ready When You Take The Solo Trip

I'm bringing this one back from the vault. I recorded it in April, before this month took me through Nigeria, Ghana, and Rwanda, and before I missed an episode for the first time because I didn't have reliable internet. It still holds up. The next two episodes are going to get specific about this trip, the Nigerian visa that almost didn't come through in time, and what I learned about connecting with strangers.

I left a fourteen-year teaching career without knowing what would come next. I remember standing on a balcony in Canada that September, watching a school bus go by, and feeling relief instead of grief. That relief was the confirmation, not a plan. Since then I've spent three months living as a digital nomad in Southeast Asia and built a life I would not have believed was available to me back then. None of it started with feeling ready. It started with one decision I was willing to name.

In this episode:

- The planning meeting that broke something
- Watching the school bus go by
- The conditions that kept multiplying
- Clarity comes in the decision
- Three months as a digital nomad
- Naming the trip as a decision

This episode is for you if:

• you keep waiting for one more condition to be met before you'll book the trip
• you're a woman over 40 who left something certain for something you couldn't yet imagine
• you think clarity has to arrive before the decision instead of inside it
• you've been telling people about a trip for longer than six months and still haven't named a date
• you've caught yourself treating "someday" as a real plan instead of a way of avoiding one

Resources mentioned:

• Laurie Santos's course The Science of Wellbeint
• Barbara Oakley's Learning How to Learn
  
  

Transcript

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I missed putting out an episode last week. I was traveling through Ghana without reliable internet, and by the time I got back online, I figured I'd just wait for this week and bring back an episode from the world rather than leave it. I recorded this one back in April, and recent events have reminded me how much this still holds up. The next two episodes are going to get specific about the trip I'm currently on, about the Nigerian visit that almost didn't come through, and conversations I've been having with people on this trip and what they taught me about connecting with strangers. This connects really well with the interview that I had with Christine recently. Before I get into either of those two episodes though, I am bringing back this one from the vault because it's irrelevant to both of those two episodes. You really don't feel ready. I don't feel ready before I go on the trip often. Usually what I feel is curiosity or excitement. And at some point during the trip, I realized, oh, I'm doing the thing. I was ready. I figured it out. Whether you're new here or you just need this reminder, here's the episode for you. That September, instead of going back to school, I was in Canada. And so as I watched the school bus go by, I felt something that I hadn't really expected to feel. I felt relief. And I was surprised by the relief because a few months earlier, I would have been on that route. Okay, maybe not literally on that route, but I would have been on my way to school. Or I would have been at school getting ready for my students to arrive. Most women think solo travel is about being brave or fearless. But it's really about letting go of the expectations holding you in place. This show is about what happens when you stop waiting and take yourself seriously, starting with intentional travel. I'm Debian, and this is Freedom Looks Like This. Let's get started. I'd been working in education for years, mostly as a technology coordinator. And it was a good job, honestly. It was a job that I dreamt of as a child. Well, actually, I dreamt of being a math teacher, but that morphed into me being a technology coordinator. And somewhere along the way, I had started to dread going in. It felt like Hunster Wheel, where I was having the same conversations and the same outcomes with teachers week after week. And I could see what was coming next before I was actually in it. And that was getting quite boring. And then there was the planning meeting where a colleague berated me. I felt attacked, deflated. Really, I was at a loss for words, which is unusual for me. And even her colleague apologized on her behalf. You know what? She never apologized. And I was the one who ended up smoothing things over. I think that was really the beginning of the end. Underneath all of that, there was something that I was avoiding looking at. I was afraid of losing my identity as someone who was knowledgeable and good at her job. People trusted me. People came to me when they needed help. I knew how things work. And maybe you felt a similar tension. Maybe you've been sitting with a change that you haven't made. And it could be part of what's underneath that indecision, the whole idea of accomplishment and what is your identity. I had been a teacher for 14 years. So if not a teacher, what else could I do? What else could I do well? I didn't have an immediate answer for that. And so it was rather scary. I knew that I wanted to do work that I loved, but I didn't know what that meant. And I was kind of struggling with the idea of why leave something that is certain, something that is good, for something I couldn't even imagine at the time that I had no idea about. If you're anything like me, you probably have a condition before you'll make a change. There is something that you think needs to be true before you'll move, before you take some action. I certainly had conditions. I didn't just have one. And they kept arriving one after the other. And each condition felt just as legitimate as the last one. So something would come up, I would resolve it, and then a new condition or question would come up. Maybe the timing wasn't right. I could wait another year because then I would have more savings. I resolved that. And then the next thing was, well, what if I couldn't find a job in the next six months? I had a plan for that. There was always something. So what's your condition right now? And I don't mean in general, but I mean the specific condition that you're waiting for before you'll do whatever it is that thing that you've been putting off, that trip that you've been wanting to take? What needs to be true before you'll book the trip? So here's what I want you to notice. Has there been a version of you in the past where this condition has been true? Because if that's the case, if the conditions have been met and you still haven't done the thing, then what's even the point of having the condition? You're just setting yourself up for practice for inaction. So you might think that you're waiting for clarity, but you're not waiting for clarity. And the reason that I know that is because I've been there. We think that clarity comes before we make a decision. But really, clarity comes in the decision. You can't see the path from where you're standing. It only emerges and you start to see it as you start walking. The key is to start taking action. And you might be waiting for permission from someone outside of you to do that. But guess what? If you've been waiting for a while, it's not coming. And the reason for that is because permission doesn't actually come from outside of you, it comes from inside of you. You get to decide. The thing is that waiting, it's not neutral. Every time you defer an opportunity, you're practicing putting your dreams aside. You're getting better at putting yourself last. And the longer you do that, the more natural it feels, the easier it is for you to continue. So you need to do something different. I know you've been working hard, and sometimes you feel that means that you don't have time for breaks. What would happen at the company if you took a holiday? You've got so much on your plate that it feels like things will fall apart if you're not around. But is that really how you want to live? Do you want to live in such a situation where there's always more for you to do and never any help, never any support? Never a chance for you to just breathe and take a holiday and reset when you need that? A lot of us call that being successful, but I don't think that's what success is all about. I don't think success means that we need to be busy every moment with other people's priorities, whether it's your children or your parents or your boss or the company that you work for. Every part of our lives asks something of us. And those asks are relentless. Where's your ask? Where are you in all of this? Is there room for your true self to show up? For her to get her needs met, for her to explore her desires? When is the last time that you made a decision that was entirely for you? And you didn't feel the need to even justify it. I know. You make decisions all day. You make decisions at work, you make decisions for your family, you make decisions with your friends. Some of them are good, some of them are thoughtful. They are decisions that other people rely on. You might have a team at work even. You might have staff. Your children or your parents might depend on you. So it's not that you can't make decisions. It's that you're out of the habit of making them purely for yourself, putting yourself first. I mean a decision that requires you to show up, that asks something of you, and you might even have to defend it with other people. And then you get to choose it anyway. The fun thing here is that once you start making decisions for yourself, they accumulate. Because every time you make a decision for yourself and you follow through on it, you're building evidence with yourself, evidence that's really important that shows you that you can be trusted with your own life. When you do the opposite and you defer it, you're building a different kind of evidence. And after a while, you have a lot of practice of one of those two things. Either of making decisions for yourself and following through, showing yourself that you really do care, or deferring decisions for yourself and showing yourself that you don't really matter that much. At least not as much as everybody else in your life. And I want to be clear that I'm not saying that to judge your experience. I've had years of practice myself deferring. And I still do it sometimes. Because every time I defer a decision, it feels like I'm being responsible. And that's what it looks like also to people from the outside. But the woman that I am becoming, the one that I am being, when I defer a decision, it's the woman that doesn't trust herself to choose. And that compounds. When you do something just for yourself without guilt, there is an opportunity for such pleasure. Of course, you can get pleasure from doing things for other people, but that pleasure of just putting yourself first and exploring your desires. It feels like meeting a really good friend. That is something that can always be available to you. That's what makes it so important. And this is really where a solo trip can be a game changer. It's not because travel is magic, but because it puts you in a situation where there is no one else for you to defer to. There's no one for you to check in with or consult. It's just you making decisions in real time, figuring out what is it that you actually want, and also finding out what is it that you do when things don't go according to the plan. That's information that you can't get any other way. Of course, you could think about yourself and journal. You could be very self-aware, but none of that produces the same information as actually doing something. The doing is where you find out. If you think about your past experiences, you will notice that you learn so much from actually taking action, from actually doing the thing. And this is part of why I keep coming back to taking a solo trip. It's one of the best ways to take action that I know of. And I found out all about that, about the importance of action after I left teaching. It wasn't on a solo trip, but it was September, and I decided to do something different. To take some action that was different from what I would typically be doing in September. So I visited family in Canada. I was on the balcony when I watched a school bus go by. Of course, September is when school starts. And so there is a rhythm of when you're used to doing something, right? Like you know what I mean, if you're used to sending your children off to school in September and all of a sudden they no longer live at home, or they're now in university, or if you've moved and you no longer are able to join the family dinner on Sundays. There are lots of examples like that we can come up with, right? So that September, instead of going back to school, I was in Canada. And so as I watched the school bus go by, I felt something that I hadn't really expected to feel. I felt relief. And I was surprised by the relief. A few months earlier, I would have been on that route. Okay, maybe not literally on that route, but I would have been on my way to school. Or I would have been at school getting ready for my students to arrive. And so that feeling of relief was telling me something that I needed to pay attention to. It was a confirmation for me that I had made the right decision. And so really that decision started to feel like freedom. So even if I didn't know what I was going to do next, I knew that the direction I was moving in was right. I didn't need to see where I was going yet. Just the fact that I was taking action away from something I didn't want and figuring out what it is that I wanted next was significant. Now, often the story of living sounds like she left and then she found herself and she found this great career and lived happily ever after. And that's not quite how the story went. At first, I started consulting in education because that felt familiar. I knew that I was really good at it. But when I reflected, I realized, oh Damian, you're just playing insane. This is actually not what you want, but you're afraid. You're afraid that you can't figure out a new career. And so I decided to take a step back to give myself some space. I took a course from Laurie Santos on happiness. And I took another course on learning how to learn by Barbara Oakley. Because I figured that if I was going to change my career, if I was going to change my life, I would need to learn a whole bunch of stuff. So I tried a number of things that didn't work out. I did some temp work, but the thing is that I kept moving. I applied for jobs, I had interviews, I had rejections, but I kept going. And what kept me going wasn't a plan. Because I have to be honest, I didn't have a plan yet. But I know that I needed to move. And even before I gave myself this sabbatical, one of my constraints was, oh, you're not just gonna hang out and relax. Like this is about getting in touch with yourself. This is about figuring out what it is that you want morals. And it's about finding the pivot from teaching and education to something different. So I knew that I wasn't going to stop. I'd already decided that. So it wasn't really about bravery, but it was that I had made a decision to keep going. Sometimes we hear a story about how somebody made a decision and they find their path pretty quickly. And that's really not my story. I was out of work for about nine months. Well, I was doing some temp work here and there trying to figure things out. But it was the first time in my life where I didn't leave a job, already having another job. I knew that I needed to move away from the thing that was making me dread Mondays. That's really what it came down to. I needed to move towards figuring out what was that thing that would make me feel alive, that would make me feel excited and look forward to each week. To be honest, at that time, even very small successes were a big deal to me. So I remember I had an interview with Amazon and I didn't get the job, that I got really good feedback and suggestions from the interviewer, and that felt like a positive experience for me. But even before that, before the job interviews, before me taking all those courses and figuring things out, I gave myself a break. So I took the summer off, I reset, I rested, and then I went to Canada to visit family. And the woman who came back from Canada was not the same woman who left teaching. I was somebody at that point who had chosen. I hadn't chosen a place or a career. I didn't really know where I was going yet or where I would land, but I had chosen myself. And that is something that's available to you on the other side of making a decision. It's not about having a perfect plan, but it's about having the knowledge that you can move and trusting yourself to figure out what comes next. Because the truth is that the version of View moves through the world on her own terms, it only stays in the realm of possibility until you go. It's only when you take that action that you confirm yourself. And I think you know the difference between those two things. You know what it's like to imagine a version of yourself and what it's like to really embody it. And now I have a job where I can work remotely. To be honest, I can't imagine the life that I lived before. It's not funny how quickly we can kind of forget. And last month I spent three months digital nomading in Southeast Asia. What that actually looked like was balancing my responsibilities and work with the ability to be flexible and to sightsee and to really experience living in different places, the cultures and the sites. But this is something that would have never been possible for me when I was a teacher. Yes, teachers get lots of time off, but we never get to choose when we're having time off. And so this opportunity to take three months and go somewhere, choose where I want to go, go there and work from them, none of that was available to me when I had all of that time off that people like to point out for teachers. The life I have now is a life that I have been able to create and curate because I made a decision. And the specific thing about solo travel is that solo travel confirmed for me that I can't handle things. Things do not go perfectly when you're solo traveling. You might lose your luggage, you might end up somewhere and your reservation is not confirmed. You end up in Laos and you thought you were getting a private taxi, but really it was a group taxi. I don't always know what to do in the situations that come up, but I trust myself to figure it out. And I trust that I'm going to be fine. This is what I mean about meeting yourself and learning about yourself. Because before I was a solo traveler, before I had all of these different experiences, I knew logically that I was capable. I've been capable my whole career. But I didn't have evidence of what it's like when I'm alone in an unfamiliar situation with no one else to consult with or defer to. And it turns out that I was fine. The only way that I could know precisely what the experience will be like for me in reality is by going on the trip, by doing the thing. And of course, when I come back from a trip, it doesn't suddenly become easy to make all the right decisions. But what changed was the quality of the doubt. I don't really ask myself, can I handle this? When I'm uncertain, instead the question becomes what's the next thing that I can do here? What's my next action? That's a very different question. And it's one that I can figure out. And sometimes it is to ask somebody else for help. But I'm confident that I can figure that out. So really, when you ask yourself that first question, can I handle it? The only way you can really know is by taking action, by doing the thing. That's how you find out. When you don't take a trip, you may not actually feel its absence. Or it might be that you're so used to talking about the dream that you had and how you've never been able to go that it becomes even more elusive. Then you never have the opportunity to find out what it's like when you're no longer needed. When everything can go on without you being around, and when you can be in a new situation that is unfamiliar. You don't get to find out what is it that you can handle entirely alone, and when is it that you really need help. And you don't get those opportunities to ask for help when you really need it. Going on a solo trip lets you meet the version of you who can find her way through an unfamiliar place. Entirely alone, make decisions in real time and come out on the other side. Okay. And then you get to carry that into your regular everyday life. And the only way you can access that is by doing the thing. For example, going on that solo trip. Now, the trip doesn't have to be long or expensive. It doesn't even have to be far for it to be significant for you. Really, what it needs to be is a decision that you made and then you followed through. Because that following through is what produces the kind of self-knowledge that changes how you make decisions after. You come back to yourself. Or even better, I could say you step into yourself even more fully. And you can start to choose what is it that you want more of, what is it that you want less of. Because you get to know yourself really well. And that lets you build a life that you actually want. I wish I could tell you something different, but really you're not going to feel ready before you book the trip. You're going to feel what I felt watching that school bus on the other side of the decision after you've taken action. That's the order. The other is action and then confidence. So I want you to name the trip. You know the trip. It's the one that you've been telling people about, and then you've been saying how your husband or your friend stood you up or didn't go with you. It's that trip that you've been thinking about for longer than six months. You thought about it so much that you've talked yourself out of it actually. I want you to pull up that thought and write it down. Because writing something down makes it more real than when it's just in your head. And I even want you to write it as a decision. I want you to write, I'm going to, and then write the name of the place. The month and the year. We want to get out of Sunday because someday is often never. We want to get into a specific month and a specific year. That sentence you just wrote, that sentence is a threshold. On one side is the woman who wants to go. And on the other side is the woman who has decided. And crossing it doesn't just happen when you book the flight. It happens now with that sentence. It happens with the actual decision. What does it feel like for you to write, I'm going to with a real place and a real date? What does it feel like in your body? I want you to focus on the positive. What are the helpful emotions that come up, like excitement and curiosity? This is what we're going to use to help you take the next action. So have you got it? That's not just the beginning of a plan. That's the beginning of you choosing yourself. If you're ready to stop waiting and you want help making this decision in a way you actually can trust, not because somebody convinced you that is the right thing for you, but because you have decided, then come join us in school. You can find the link in the show notes. And I'm always happy to talk to you. Reach me at contact at freedomlookslike this.com. Make sure you're subscribed to this podcast because I am going to be offering a workshop. I'm just putting it together right now. And this workshop will help you figure out the person that you're stepping into for the solo trip you're going to take. And in case you're like me, because I needed to borrow a little bit of confidence when I was going from teaching and changing my career. I needed to borrow a little bit of confidence to know that it was possible before I had actually stepped into it. And so if you need to hear this, I want you to know that you are more ready than you've been letting yourself be. You are more ready than you think you are. Given my reflections on this current trip, here's what I'd add. Readiness doesn't even really need to fully arrive. What we get is information. We realize what are the things that we can actually handle, which are the situations in which we're comfortable, which one stretches, and who are we when things get hard. And often things are hard before they get interesting. So if there is a trip you've been putting off, you do not need to feel ready to book it. You need a decision that you're willing to stand behind. And if you want the simplest place to start, come join My School Community. It's a place where we talk about the things that come up and we are able to support you within community. The link is in the show notes.