Why you never end up taking that solo trip

You’ve thought about it. Maybe you’ve spent hours looking at flights, saved hotels on Instagram, created a Pinterest board, and even told your friends: “I think I’m going to travel on my own this year.” You can almost picture yourself there. Having a coffee somewhere beautiful. Waking up with nowhere to be. Meeting people from all over the world. Finally doing the things you’ve been putting off.

And yet… you still haven’t booked the flight. You keep telling yourself you’ll do it when you have more time, when work calms down, when you’ve saved a little more money, when you feel more confident, when you find the right destination. And somehow, weeks turn into months. I’ve seen this happen with women I’ve spoken to about solo travel, and I completely understand why. Wanting to travel alone and actually committing to the trip are two very different things. Sometimes, the biggest obstacle isn't the destination, the money or even safety. It’s everything that happens in your head between “I’d love to do this” and “I’ve booked my flight.”

1. You are waiting to feel confident before you go

This is probably one of the biggest traps. You think: “Once I feel more confident, I'll book it.” But confidence rarely arrives first. You usually become confident because you did something that initially scared you. I know this from my own travels. Even after numerous solo trip, it still get the jitters a few days before going and wondering “what the hell am I doing ?”

And if it’s your first solo trip, your brain can suddenly produce an impressive list of things that could go wrong. What if I hate it? What if I get lonely?What if I don't meet anyone? What if I get sick/something bad happens ? What if I make a stupid decision because there's nobody with me? Who will I share my memories with ?

You don't need to eliminate every one of those thoughts before you leave. You need to learn how to make decisions despite them. Instead of asking: “Do I feel confident enough to travel alone?” Ask: “What would make me feel confident enough to take the first step?”

Maybe that's choosing a destination with easy transport. Maybe it's booking your first few nights somewhere you feel comfortable. Maybe it's having a rough itinerary rather than travelling completely spontaneously. Maybe it's knowing exactly how you're going to get from the airport to your accommodation. Confidence often comes from reducing uncertainty, rather than trying to eliminate fear.

2. There are simply too many choices or you’re worried you’ll make the wrong choice

You start researching your trip and suddenly there are 47 tabs open. Bali or Thailand? Japan or Vietnam? Hotel or boutique guesthouse? Should you travel for a few days or two weeks? Should you book everything in advance? Should you leave it spontaneous? …

And suddenly your exciting solo trip has become a research project. And one of the things nobody tells you about solo travel is how exhausting constant decision-making can become. When you're travelling alone, every little decision is yours. Where to eat. Where to stay. Whether to take the bus or a taxi. Whether to move on or stay another week. Sometimes freedom feels amazing. Sometimes you just want someone else to say: “This is the hotel. This is how we're getting there. Let's go.”

But you don't need to find the objectively best destination, you just need to find the destination that works for you. Your budget, personality, travel experience, interests and comfort level should all influence the decision. The best destination for a confident backpacker who loves spontaneity might be completely wrong for someone taking her first solo trip at 35 and wanting a calm and introspective trip.

3. You're scared of being lonely

This is one I hear all the time. And interestingly, I don't think loneliness is necessarily the biggest problem. It's not knowing when you'll next have company. If you travel with a partner or friend, you have a guaranteed person to share the tiny moments with. When you travel solo, you can have an incredible day and still have a moment at 8pm where you think: “I wish I had someone to tell this to.”

And that can feel surprisingly emotional. But there is a big difference between travelling alone and being socially isolated. You can build your trip around opportunities to meet people without staying in a hostel. Yoga studios, diving, surfing, pottery classes, Pilates clubs, coworking spaces, language exchanges and small group experiences can all create natural opportunities for connection.

I've actually written a whole guide about 10 activities to meet other solo travellers without staying in a hostel because this is something I think is hugely underestimated.

4. You're imagining solo travel as one giant leap

Another reason women don't take their first solo trip is that they're imagining the entire experience at once. But your first solo trip doesn't have to mean backpacking around five countries for three months.

It could be:

• five days in one city

• a week-long yoga retreat

• a diving trip

• a wellness holiday

• a long weekend somewhere in Europe

• two weeks in Southeast Asia with your first few nights planned

• a trip you start with a friend and then extend for a few days on your own

You don't have to prove anything. The goal isn't to become the most adventurous traveller you know. The goal is to experience what solo travel feels like for you.

5. You're afraid of being with yourself

This is the part people don't talk about enough. Sometimes you're not just afraid of being alone. You're afraid of what you'll discover when you are. When you don't have your usual routine, your partner, your friends, your job and all the small distractions of everyday life, there is suddenly a lot more space to think and that can be uncomfortable.

But that’s actually one of the most beautiful things about travelling alone. Solo travel is one of the best form of introspection you can come across. You will hear your thoughts, your internal monologue, your beliefs but also how much other people’s thoughts are occupying space in your life. You might realise that you want something different from your life. You might discover that you actually love your own company. You might realise you are much more capable than you thought. Or you might simply come home knowing yourself a little better.

You won’t just discover a new country. You're discovering what you are like when nobody else is making the decisions for you.

So, how do you actually stop overthinking and book the trip? Start with these five questions:

1. What am I actually looking for from this trip? Adventure? Rest? Meeting people? A reset? Independence? A challenge?

2. What scares me most? Safety? Loneliness? Getting lost? Making decisions? Being bored?

3. What would make me feel safer? A particular destination, organised activities, a good hotel, airport transfer, travel insurance, having someone at home who knows your itinerary?

4. What kind of solo travel actually suits my personality? Hostels and party ? Yoga retreat ? Sporty and spontaneous ?

5. What is the smallest version of this trip I could realistically book? Maybe that's your first week or simply booking the flight.

And If you still feel you need a bit of help to book that trip, I created The Go Solo pan. A personalised 1:1 planning experience. We'll talk through what you want from the trip, what's making you hesitate, what type of travel actually suits you, where you could go, how long you should travel for, how to meet people, how to make the logistics feel manageable and what you can do to feel more confident before you leave.