Welcome back, Jack here.
This is Modern Monastery: your guide to contemplative practice. We connect you to traditions we trust and create spaces to practice together.

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I was in Tassie last week for one of my best mates’ weddings. Nine of us lived and worked together for a week.

It was like a mini retreat!

The other day we started chatting about taking extended breaks.

Most of us have 4 weeks per year of annual leave. And often we're so exhausted from work, that all we want to do is relax. It is an enormous privilege to be able to take a holiday, and I’ve made a tonne of memories abroad. However, I often find myself getting stuck overseas in a cycle of endless consumption and indulgence. And that consumption doesn’t always leave me feeling full when I get home.

So over the past couple of years, I've explored a few different ways of taking a break. Here are three that have stuck with me.

In the last few years I’ve been lucky enough to explore so much of what I love. Yes, monasteries are a big part of this, but I also love electronic music, modern art, listening rooms.

Instead of picking a destination and filling it with activities, I try to start with what I'm deeply curious about, and find the place in the world that does that best.

Here are some of the highlights from the past few years.

These experiences have opened my eyes to new possibilities. Different ways of working, creating, living. The best inspiration has rarely come from what everyone else sees online. It has come from that random book in the library that no one has read. The corners of the world that no one has explored. The spontaneous conversations with strangers.

And the more I've explored, the clearer I have become in what I want. To the point where now it feels easier to just create it myself. Not being able to find what we want can feel frustrating, but it also presents an opportunity. An opportunity to apply our taste and skills to create something that only we can envision.

Who else is going to build a monastery with a dance floor?

The next type of break I am obsessing over is time away purely to create.

Taking time off to create can be as restorative as a holiday, maybe even more so. It doesn't need to make money, or turn into a career. Because creating something is deeply satisfying in itself. Not only can it can nourish you, but it can give you an opportunity to offer something meaningful to others.

There are a few popular formats out there, here are the ones I am exploring.

Artist Residencies

There are places around the world that host artists to focus on their work. Some of these are fully funded!

The idea behind these residencies is to give artists a beautiful setting with like-minded creatives to do their best work.

Founder Residencies

These are similar to artist residencies, but focus on building businesses. It looks like they are less about creating in solitude and more focussed on connecting with other founders. It’s a space to work together and learn from each other.

I found another one last year called The Residency. They offer a 3 month, all-expenses-paid residency in San Fransisco. Meaning they pay for you to fly to SF, give you a room in their campus and a space to work on your idea. These opportunities don’t even sound real.

There are many more examples of these, but they roughly boil down into three main categories:

Want me to find more of these for you? Reply and let me know.

For me, contemplation is the foundation for everything else. Modern Monastery is the result of a lot of introspection and contemplation. Whenever I go on retreat, all ideas fade away except this one.

Coming back into the real world, it feels as though everything is trying to kill the idea. But I find solace knowing that if I step back into silence, it will be there waiting for me.

Working on something I care this deeply about has given me more confidence, energy and courage than ever before. I never thought I’d be wanting to speak in front of an audience, but the desire to create beautiful experiences for people is overriding any fear that arises.

Here are my some of the contemplative retreats I’ve been exploring.

Meditation

Exploring the nature of mind, consciousness and reality - experientially.

Yoga

I did my first yoga retreat last December, it was great. The main benefit was that I got to skip being really bad. Now I have a daily practice that flows easily and I can enjoy downward dog, no worries.

Journalling

One day I randomly decided that I was going to book a 3 star hotel for a couple of nights so I could journal for an entire weekend. This was before I knew that meditation retreats existed. My family thought I was a bit crazy, as they should. But it ended up being amazing! So much creativity comes from deep boredom. I ended up envisioning a beer brand that I never launched properly.

Think Weeks

Popularised by Bill Gates, a Think Week is a week set aside to do nothing but read and think about the future. Gates used to do this twice a year in a cabin in the woods, and claimed it led to some of his most important decisions.

I haven’t done this one yet, but I can understand the value. Especially in times like these, it feels important to understand the state of the world and what the future holds, in order to make the right decisions in the present.

Contemplative breaks have been the most important by far. I will continue to revisit them regularly. The only way I can know what to do next is if I can see things clearly.

A final note before I close.

I wanted to call out that taking an extended break is a huge privilege. If you have kids, financial obligations, or a job with no flexibility, that’s a real barrier. But I'd argue that more people can do this than they think. More companies will grant extended leave if you simply ask. More grants and free fellowships exist than you'd be led to believe. And you’d be surprised by the opportunities that can come out of taking a break.

I’m building a database beyond mindfulness, that expands to creative residencies, co-living experiences and more.

Want early access? Reply and let me know.

3 Day Silent Retreat (TBC)

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If you got this far, I love you.

See you soon.

Jack