I was in Canada in September, standing on the balcony at my parents’ house when a school bus went by. September is when school starts. For fourteen years, it was also when I went back. And I felt something I hadn’t expected: relief. Pure, quiet relief. And then I felt surprised by the relief, because a few months earlier I would have been on my way in. Not literally on that route, but I would have been getting ready for my students to arrive. The bus going by was just a bus going by, and the fact that it was just a bus going by was telling me something I’d been trying to hear for a long time.

I’d been working in education for years, mostly as a technology coordinator. It was a good job, honestly (a job I’d wanted). And somewhere along the way I had started to dread going in. Hamster wheel. Same conversations, same outcomes with teachers week after week, and I could see what was coming before I was in it. Then there was the planning meeting where a colleague berated me. I felt attacked, deflated, at a loss for words (which is unusual for me). Her colleague apologised on her behalf. She never did. I was the one who smoothed it over. That was the beginning of the end. And underneath all of it was something I’d been avoiding: I was afraid of losing my identity as someone who was knowledgeable and good at her job. If not a teacher, then what? I didn’t have an answer. So I waited.

In this episode:

• The planning meeting and what was underneath it
• What a condition actually does
• What you practice when you wait
• The school bus in September
• What solo travel confirms that nothing else can
• The threshold sentence

“Every time you make a decision for yourself and follow through on it, you’re building evidence that you can be trusted with your own life. When you defer it, you’re building a different kind of evidence. And after a while, you have a lot of practice at one of those two things.” – Damianne

What does a condition actually tell you?

I had a condition before I left teaching. Actually, I had several, and they kept arriving, one after the other, each one feeling just as legitimate as the last. The timing wasn’t right, and then it was, and something else came up. Not enough savings, and then I had enough savings, and then the question became, “What if I couldn’t find a job in the next six months?” I had a plan for that, and then the next thing arrived.

What’s your condition right now? Not in general. The specific one. What needs to be true before you’ll book the trip you’ve been thinking about for longer than six months?

Here’s what I want you to notice: has a version of that condition been true before? Because if it has, and you still haven’t gone, then the condition isn’t really the condition. It’s practice. We tell ourselves we’re being practical. It looks like responsibility from the outside. But what we’re practising is putting ourselves last, and the longer we do it, the more natural it feels.

What are you practising when you wait?

This is the part I want to say plainly, because I think it often gets softened: waiting isn’t neutral.

You make decisions all day. Good ones, thoughtful ones, decisions other people rely on. You might have staff. Your family depends on you. It’s not that you can’t make decisions. It’s that you’re out of the habit of making them purely for yourself. A decision that requires something of you, that you might have to defend, that you choose anyway.

Every time you make that kind of decision and follow through, you’re building evidence that you can be trusted with your own life. Every time you defer it, you’re building a different kind of evidence. And after a while, you have a lot of practice at one of those two things. I had years of practice at deferring. I called it being responsible. But I was teaching myself that I couldn’t trust myself to choose.

What did the school bus in September confirm?

When I went to Canada to visit family that September, I wasn’t on a solo trip. It was an ordinary visit. But I was standing on the balcony when a school bus went by, and what I felt surprised me: relief. And I was surprised by it, because a few months earlier I would have been heading to the same place. That feeling was confirmation that the direction had been right. Even though I didn’t know my end goal, I was on my way.

The story of leaving often gets told as: she left, and then things got clearer. That’s not quite how it went for me. I consulted in education for a while because it felt familiar, then realised I was just playing it safe. I took courses: Laurie Santos on happiness, Barbara Oakley on learning how to learn. I was out of work for about nine months and tried many things that failed. But I kept moving, and what kept me going wasn’t a plan. It was that I’d already decided to keep going. Not because I was brave. I just wasn’t going to stop. I knew that I needed to move away from the thing that was making me dread Mondays, and toward figuring out what would make me feel alive and look forward to each week.

What does solo travel confirm that nothing else can?

Before I traveled solo, I knew logically I was capable. I’d been capable my whole career. But I didn’t have evidence of what I was like alone, in an unfamiliar situation, with no one to defer to, handling something I hadn’t planned for. And it turns out I was fine. I couldn’t have known that without going.

What changed when I came back wasn’t that I suddenly made all the right decisions. What changed was the quality of the doubt. Before, when I was uncertain about something, the question underneath it was: can I handle this? Now, when I’m uncertain, the question is just: what’s my next move? What’s my next action? One of those questions I can only answer by going and finding out. The other I can answer any day.

The trip doesn’t have to be long or expensive or far. What it needs to be is a decision you make and follow through on. Because that following through is what produces the kind of self-knowledge that changes how you make every decision after. You come back to yourself. And you start choosing the life you actually want.

A small invitation

Name the trip. The one that keeps coming back, the one you’ve been thinking about for longer than six months, that you think about and then talk yourself out of and then think about again. Write it down as a decision: I’m going to [place] in [month] [year]. Not someday. A specific month. A specific year.

That sentence is a threshold. On one side is the woman who wants to go. On the other is the woman who decided.

Join us in Skool

If you want help making that decision in a way you’ll actually trust (not because someone convinced you, but because you’ve worked through it and you know what you’re saying yes to), come find us in the Skool community.