How to Retreat

For the first six years of my entrepreneurial career, I did not take a break or vacation. Working six to seven days a week, I was all-in, all the time. Despite me being in my twenties and feeling invincible, I was in reality not. 

The first vacation I took turned out to be the best thing I could do for my struggling business. Initially, I was scared that things would fall apart and we’d have set backs. In reality, taking the time away allowed me to see more clearly one of the most important insights as a leader: I’m not as important as I think I am.

The process of stepping back from my day-to-day allowed me to see the business more objectively, including what was working and what was not working. It was only by stepping away could I stop fooling myself into thinking something was working just fine only to find out that the moment I looked away, it fell down. As a leader, my job was not to do everything myself, but to make everything work without myself having to be involved.

The regular retreats became a measuring stick for me on how good of a job I was doing as a leader. A necessary part of the process.

I would go on to take at least one week away from the business, each quarter, for the next ten years. And time away meant to fully disconnect and unplug. It became a constant reminder that I’m not as important as I think I am.

Taking time away to retreat away from my daily life on a regular basis has helped me in countless ways personally.

I once asked a meditation teacher about her routine. She explained it back to me in such a simple way that has stuck with me to this day.

“On a daily basis, I sit alone for ten to twenty minutes, and that’s the equivalent to taking out the trash. If I don’t take out the trash after a few days, the place starts to get a bit stinky”. I’ve learned that it’s best to take out the trash every day.

“On a weekly basis, I will do a longer meditation or a group meditation, which is the equivalent to tidying up the apartment or house”. This keeps the place looking clean and avoids things from building up.

On a quarterly basis, I go on a retreat of some sorts. Be it a structured and guided retreat or a self-retreat. This is the equivalent of a deep scrubbing of the place”. Keeping up with the daily and weekly cleaning, I can get the more difficult to reach places during retreat.

This is what retreats are for. Cleaning out the corners of my mind, that have been quietly accumulating dust. When I come back from retreat, I feel fresh and ready to give more of myself to my life and my world.

“We liked it better now that you live in New York”, my mom had commented to me once while I was visiting them in Toronto, not long after I had moved away. 

Previously when we were living in the same city, although I would see my parents pretty much every weekend, our time together became routine, unfocused and distracted. The proximity of a twenty minute drive away meant I took seeing them for granted, and I believe they did as well.

Once I was living in a different city, when I would come home to visit, despite it being far less frequent, the attention and quality of our time together was significantly different and better than before. The scarcity of interaction made it more valuable.

Now I primarily see my parents when we are all traveling, as I’ve noticed that the quality of their attention is even greater once they are removed from their natural setting. A forced retreat of sorts.

At home, although we may be spending time together, they are in their natural rhythm and flow of errands, chores and to-do lists. While physically away, they mentally also step away from their daily lives and can focus their energy and presence on me.

My recent trip to Delhi was timed for when my parents were also visiting India. We had dinner one night, just the three of us, at a restaurant and I enjoyed a higher quality of attention than I usually get from them over a meal. The conversation went deeper and wasn’t stuck in the mundane of our daily lives.

Taking a step out of my normal place and pace helps me to detach from all of the unconscious associations and patterns in my mind, making more space to discover new associations and patterns consciously.

Adding a dose of nature to a retreat takes it to the next level. 

The beautiful thing about being in nature, be it hiking a mountain, enjoying a view of the ocean, or seeing an open landscape, is that it is expansive. In the process of looking outwards at something so large, I start to feel small. In that process of feeling small, my worries and anxieties also start to feel small. Nature helps put my life into perspective. I can’t get that perspective while in it. I have to momentarily step outside of it.

Nature is also calm. Trees, water, grass, rocks and more all are quiet, still and at peace. It is often said that the world is a mirror. When I stand in nature and see it at peace, I am looking at a mirror and am reminded that I am at peace as well.

And this is how I learned to retreat.