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Questions to Consider Before Embarking on a Meditation Retreat

It seems as though everybody and their mother is talking about meditation right now, operative word being talking.

Including every successful entrepreneur, CEOs of enterprise businesses and of course all the yogis. Self-help extraordinaires consistently include meditation in their list of ingredients to becoming “successful”. It’s become quite the popular catch-all cure for many of life’s ailments; a seemingly simple cure that is already within you while simultaneously being somehow just out of reach.


From my very limited experience, I can tell you that meditation is none of the above, while simultaneously being all of it. Your relationship with meditation and whatever you manage to make of it will be a wholly different experience than anyone else’s. Though an avid yogi, I’m very much a novice in the mediation department. Through my experiences I’ve been taught that yoga is a lifelong mental preparation for stillness. While I understand this, I am far, far from mastering it. I was lucky to have had the opportunity to explore this further in a 7-day silent meditation retreat in Koh Samui, Thailand. If you’ve read some of the hype about mediation and have been intrigued, or have dabbled a bit with it on your own and want an extended amount of time to fully immerse yourself, a meditation retreat can seem like a favourable option. There are so many positive reasons to commit to a retreat but there are also some important questions to ask yourself before you do. Surprisingly, one of the least important questions is if you’ve ever meditated before. I had not before completing mine and I still managed to make it through, but more importantly I was still able to highly benefit from the experience. It’s much more important to understand your why. If you’ve been considering a retreat, below are some questions to ask yourself before you set out.

Why do you want to sit in silence listening to your thoughts for an extended amount of time?
Understanding your why will serve as a pillar you can lean on when your wandering mind gets overwhelmed, or if you want to give up. There will undoubtedly be challenges during this experience, one of which might just be extreme boredom. I highly suggest you find a monastery that offers the retreat for free. By eliminating the concept of tying a monetary value to the experience up front, it will leave you space to figure out exactly why you want to do this. Even if you do pay (maybe not for the retreat but if you invest time in a flight to get there, for instance) the fact that you spent money won’t be enough to keep you committed if you find this experience challenging . Wanting to understand your mind, or why you always seem to default to negative thoughts, might. If you’re concerned about wanting to show appreciation to the monastery, don’t worry, they offer the opportunity to donate to them once the program is complete to show your gratitude.

How much time do you have?
Time is a funny concept. I did the retreat during a 6 month period in my life when I was funemployed. With months of unscheduled time stretching out ahead of me 7 days seemed like a drop in the bucket. Now that I have three weeks off a year, it’s a serious time commitment to consider going on a retreat for a third of that time. Consider how much time you are willing to dedicate to this, including possible travel times. Where you do your retreat will undoubtedly have a large impact on your experience. There are 10-day silent retreats, 7 day, 1 day even. You can find them in Canada, or you can travel abroad to a country where meditation is more part of the daily regimen.

What type of retreat are you after?
Note: These are highly simplified explanations of some basic types of meditation, to learn more check out this insightful post outlining dozens of different meditation methods.

Vipassana: Focuses on training the mind to “see things as they really are”. When the mind wanders, you are trained to consistently bring it back to the present by methods such as mentally scanning your limbs or focusing your attention on your breathing. By focusing on seeing things as they are, you can begin to accept them without judgment or constantly wanting to change them. Also referred to as Mindfulness meditation, which can also be applied as a blanket term to the act whereas Vipassana is a Buddhist meditation technique.

Transcendental: uses a mantra as the foundation. The guide will give you small sentences to repeat in your mind to continuously return to. The goal is to “transcend” present thoughts and states of being.

Loving Kindness: You begin by thinking thoughts of literal love and kindness towards yourself, slowly expanding your thoughts to include friends, family, enemies, and eventually encircling the world in the soft glow of your loving thoughts. (It’s impossible not to feel a little bit warm and fuzzy after this one)

Taoist “emptiness”: is a mental exercise where you attempt to completely empty your mind of all thoughts, like take clothes out of a drawer. You allow thoughts and feelings to rise and pass without becoming actively engaged in them.

A retreat geared towards beginners will most likely offer a combination of different techniques so you can figure out what works best for your mind.

What are you expecting to take away?
Acknowledge what you expect the outcome to be from the answer to the first question posed here, your why. Do you expect to walk away an enlightened, buoyant being, full of light and fresh perspective? Squash all expectations now. Be completely open to whatever comes up for you during your retreat and whatever state of mind you have when you leave, (even if you leave early). By opening up your mind to infinite possibility you’ll be more likely to withstand staying when the experience is assuredly not what you were expecting.

I highly encourage those interested to attend a meditation retreat. It’s been more than a year since my retreat; do I meditate on a regular basis? Nope. But I consider the understanding of my mind that I garnered in those seven days priceless. The experience has given me invaluable insight into how I handle everyday stress, and has served as a foundation for the times I do manage to steal a few minutes from my day to find stillness. It’s a vulnerable thing to want to understand the inner workings of your mind better, and by considering some of these questions before you embark you’ll be better equipped to fully embrace the experience, whatever that may be for you.

Carla Bragagnolo

Carla is in constant pursuit of the extraordinary; she is based out of Toronto due to its proximity to great food, its diverse music scene, and because it allows her to catch a flight to pretty much anywhere. Follow her adventures at @carlabrags.