I was at the riverbank in Okazaki in March, there to see the cherry blossoms in the evening. It was raining, and the area was lit up for the first day of the festival. From a distance, it was genuinely beautiful. But when I got closer, I realized most of the buds were still closed and nowhere near the full bloom that was all over social media. And I felt this wave of disappointment.

What’s strange is that nothing actually changed. The blossoms were the same from up close as they were from far away. What changed was me, and more specifically, I started measuring. Suddenly I was running a calculation. “Is this actually worth what I was expecting?” I had gone from being in the experience to evaluating it.

I think about that moment a lot, because it’s the same thing that keeps a lot of women from booking a trip at all. It’s not logistics but all the niggling questions that come up. And there’s one questin in particular that I have beef with: “why should I …?” That question, it turns out, is designed to keep us asking.

What does “why should I go” actually do?

The “why should I” question is reasonable. We ask it before most decisions because we want a good reason for our actions. But here’s what I’ve noticed about it: it has a moving answer. When the money’s there, the timing’s not right. When the timing’s right, something comes up at work. When that resolves, there’s a new concern about the destination. Answer one, and another appears. The question doesn’t close; it generates more of itself, especially if the why doesn’t have something we can clearly measure on a scale or in a matrix.

The same thing happens on a trip. “How do I make this count?” doesn’t close either. You could always stay longer at the market, eat at one more restaurant, ask the guide better questions. So you end up on a trip you worked hard to take, running a calculation about whether you’re doing it right.

I’ve been thinking about a different question instead. I’ve used it for years. I made a presentation about it at work in 2018, and I really do think it’s shaped the life I have now. It’s two words: why not?

What does “why not” do differently?

Why not doesn’t require a perfect reason. It just requires the absence of a real blocker. And a real blocker is something specific. You can look at it directly and either solve it or accept it as something you can’t change. The mindset and perspective is focused on finding and overcoming challenges.

“I don’t feel ready” isn’t a specific blocker. Neither is “the timing could theoretically be better” or “I haven’t researched enough yet.” Those are conditions, and conditions can always multiply as we’ve seen. A real blocker is concrete. You can name it, look at it, and do something about it.

When I was in Sapa in March, my guide offered to take me off the main path and walk through the rice terraces. The answer was so clear to me. I wanted that. But I had a hesitation, and the fastest way to get to it was to ask: why not? What came up was my fear of heights. I wasn’t sure I could manage some of the inclines on an unpaved path. That was real and specific. So I asked the guide: what’s the path like? How much climbing is there? And she told me. And I remembered that on a previous hike, all the guide had to do was hold my hand, and I’d been fine. One why not question, a few minutes, and I felt confident to go.

We walked off the path for three hours with almost no one else around. I experienced walking in rice fields, a stone for a picnic table, an umbrella for shade, a banh mi my guide made from scratch. At some point I had to remind myself how lucky I was. And later, reflecting on it, I realized it had been one of my best days on the whole trip.

What happened in Tirana (and in Prague)?

I went to Albania in March, directly from Prague. In Prague it was still early spring, so I packed accordingly. What I was not prepared for was late March in Tirana. The sun was directly overhead as I walked around the city, and I had no water. I had no agenda, no itinerary, no research on the city. I’d gone because I wanted an adventure, because I’d been curious about Albania, and because when I asked myself “why not?”, the only real concern was a class I’d been taking. Once I’d confirmed I could afford to miss one session, there were no more obstacles.

I found a pyramid in the south of the city. A strange concrete structure built as a monument to a communist-era dictator, with odd, off-kilter elements around it. I climbed it, standing at the top looking out at a city I knew almost nothing about, hot and thirsty and completely unprepared. Not a glamorous moment. But I was there. And I ended up having a lovely weekend, featuring a tasting menu, a visit with some Baha’is who invited me for dinner, long walks through a green space that felt like early summer.

Moving to Prague was a bigger version of the same question. I moved there in 2013 without ever having visited. I knew almost nothing about it but people told me there was good beer, and when I said I didn’t drink alcohol, they said there was good bread. But I had no strong reasons not to move here. So I applied and took a job in Prague.

I realized recently that Prague is about to become the place I’ve lived the longest in my entire life. Thirteen years. The only other place that came close was where I grew up. And I got here with a why not.

What are your why nots?

Here’s the thing about that question. It asks you to look honestly at what’s stopping you, specifically, not vaguely. When women tell me they can’t travel solo because of safety, I ask them to go further. What does that mean, exactly? Not knowing the rules in a new place? Worry about getting into a situation with no way out? A fear of flying? A medical condition requiring specific healthcare access? Those are all different things, and most of them are solvable.

The “why not?” question also builds something over time. Every time you ask it honestly and deal with what you find, you’re building evidence that you can be trusted with your own decisions. The trip matters. But so does the act of deciding because that’s what compounds. This episode goes deeper on how the small decisions you make while traveling teach you something about yourself.

A small invitation

So here’s the invitation this week. Name the trip you’ve been circling, a specific city or country. Maybe you already did this last week. But if you’re stuck on that part, this episode on destination indecision is for that.

Now, this is the extension: write down every “why not” you can think of, real and imagined. And then for each one, think, Is this solvable? If it is, solve it. Some of them you can handle in the next ten minutes. And if you’re ready to level up, open your calendar and pick a window for your trip.

If something in this episode landed for you and you want to work through it with a group, learn about my next free workshop at https://freedomlookslikethis.com/training.

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.

Freedom Looks Like This podcast with Damianne President, episode about the why not question for solo travel decisions