Becoming a More Confident Traveller

Safe & Sound

Having just arrived home from a two-week trip to Holland, I can’t help but think back to when I set myself the goal of becoming a more confident traveller. I dreamed of exploring new places but found myself overwhelmed by all that I didn’t know or understand. How does the airport work? What about security? What should I pack? What can I bring on a plane? How do I get from the airport to the hotel? Should I stay in a hotel? How do I choose one? How do I do manage if I don’t speak the language? How do you even begin to find your way?

I started with setting an intention.

The moment I said, “I want to become a more confident traveller,” my world began to change.

Opportunities started to show up, like assisting Jennifer Louden at the Kripalu Centre or an invitation to visit my sister Suzie on the East Coast. There were things I wanted to do like go to the World Domination Summit in Portland and travel to Paris for my 10-year wedding anniversary. And so I started to say yes and I started to learn.

Being willing to learn is the beginning of everything.

I didn’t try to take everything in at once but instead I let each trip be a focal point for learning. In my creative life, I do this too, allowing each project to give me focus and direction as well as motivation to gain useful, practical knowledge that will serve me in the current project but also in many projects to come.

With traveling, first I learned to buy my own airline ticket online. I must have checked the order a thousand times before finally hitting “submit” but I did it. Then, because I was flying Air Canada, I focused on what their website told me about what I could pack, how early I should arrive, how to get a boarding pass, that kind of thing. Little by little, I was learning.

Trip by trip, I started to build my knowledge, to gain experience and my confidence started to grow. With each trip I stretched a little bit further. I travelled by myself. I travelled to a different country. I travelled on public transport. I travelled between two places in one trip. I travelled to a place where the language wasn’t English.

Now I can say I have travelled to Portsmouth, Portland, Halifax, Vancouver, Sedona, San Francisco, Paris, Avignon, Nice, Amsterdam, Brussels and more!

My confidence has grown exponentially and there is still much to learn. I remain afraid of flying, especially over the ocean, and though I may never be at ease with that aspect of the journey, I have strategies that support me. Most recently, thanks to a great suggestion from John Austin (thank you, John!) I brought my sketchbook and doodled on the plane. Filling up the pages with colour and line gave my body and mind a way to channel my anxious energy. I felt calmer as I worked on my Safe and Sound page both on the way to Amsterdam and back to Toronto. Another great tool in my confident traveller’s toolkit.

To gain confidence, eventually you must do the thing that you wish to gain confidence in.

I am a huge fan of preparation, even over-preparation! I know it calms my nerves when I have researched to the nth degree, when I have made and checked off every list (twice), when I have double (or triple) checked reservations, confirmations and what’s in my suitcase.

I am big believer in doing everything you can do to make it easier on yourself, especially by working with the truth of who you are. If calling makes you anxious, email. If arriving four hours early calms your nerves, do it. Give yourself all the understanding and loving support available as you cross over that thrilling, terrifying, glorious threshold of new learning.

Do everything you can to prepare and then go.

This is one thing I learned in the theatre, both as an actor and as a director. Do everything within your power to support success, work wholeheartedly, with passion and commitment, and when opening night arrives, let it go.Live it. Breathe it. Experience it. Do it. This is what you have been preparing for.

Let your preparation ground you. Trust yourself. And know that you can always ask for help.

As a highly sensitive person and a Canadian, I have a tendency to sit back quietly suffering while I try and figure things out for myself. On this trip I saw my much more direct Dutch father-in-law over and over again ask people how to get places, what was worth seeing and even, with great interest and curiosity, what they were doing. (“So, is this your boat?” “It’s lovely how you sit out here. Is this a restaurant or your own home?”) Over and over again he was met with helpful, interesting and friendly replies.

Learning to trust your ability to handle what comes up is the greatest confidence builder of all.

As the plane was descending on the way home, I watched a show I’d never seen before called “Staycation.” A New York couple hopped on the subway and went across town for an overnight adventure in Brooklyn. They stopped in eclectic little shops and restaurants and grabbed drinks in a local bar. As they sat alone in a neon-lit dive, laughing while enjoying the drink special of the day, I realized that one of the things that made their staycation an adventure was the risks they were willing to take. They risked that the food would be bad, that the bar was a bit seedy, that the shopkeeper would be unfriendly. They didn’t check Yelp or worry about whether it was the right place, the best place or the coolest place. They just risked it and had the experience.

This trip to Holland has been amazing and I am so proud of how much confidence I have gained as a traveller. Always looking to the next horizon, I see that for me there is a growing edge around loosening up, around asking for help and around allowing myself to get it wrong. It’s amazing how the lessons that show up in one thing tend to be the lessons that show up in all things. There’s always more to learn.

What adventure(s) do you want to go on? How might you make a start and build your confidence?

Over the next little while I will be sharing my Holland adventures, including a few Confident Traveller Tips that I hope you’ll find helpful. I hope you’ll enjoy coming on the journey with me.

Holland Sky


  1. Hi Jamie, I discovered your studio just before you went on your trip and I could so identify with your apprehension! I’m very happy to read that all went well, and I find your confident traveller tips very helpful! While you were away, I listened to several of your podcasts while working in my studio and found them to be so inspirational! So glad to have discovered you and your studio on the web! What a gift you are to the creative souls out there – including me!

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