Design Your Own Retreat

Retreats, like people, come in all shapes and sizes – from corporate board retreats with colleagues to vacation getaways with good friends to silent meditations in the woods. While there are usually some common elements to what we want out of a retreat (e.g. feeling rested, clear-headed, transformed, refueled), there are an infinite number of ways to create this kind of an experience.

What I want to share with you all in this post is a set of questions to guide you in creating a retreat experience for yourself. While it can be wonderful to work with someone to design a retreat just for you (imagine: no work! just show up for the experience!), it is a great gift to be able to give yourself whenever the spirit moves you.

There are some elements that are pretty intuitive and often talked about related to a creating a retreat. It is great to be able to get away to a beautiful setting, to integrate movement, to take care of your whole self (mind, yes, but also your body, your heart, your spirit). This is all great advice. AND I believe you don’t have to go away and schedule a massage and hire a gourmet chef to make your retreat experience amazing. (Though if you have the time, interest, and means, go for it!) My promise to you: You can create a meaningful, impactful retreat experience simply by giving yourself the space to look inward. You can do that from wherever you are, even with just an hour or two.

Alright, let’s jump into the questions!


What theme best describes your ideal retreat?

As you set out to design your own retreat, a great starting point is getting clear on your focus. Perhaps you have a question you want to explore (e.g. How do I take my business to the next level? What do I really want in my life? How do I prepare for this impending (fill in the blank) life transition?). Perhaps you have a clear objective that you want to pursue (e.g. When I went away recently for my annual Entrepreneur’s Getaway, I knew that I wanted to walk away with an editorial calendar that took me through maternity leave and beyond). A great way to clarify and simplify your focus is to pick a theme. This can be a single word or a simple phrase. It doesn’t matter if it makes sense to other people – just make sure it sparks in you the feeling and focus that will serve you during your retreat. (Our focus at this year’s Entrepreneur’s Getaway? Direction and Mindset.

What kind of experience do you want?

You’ve heard me say already that there are many different types of retreats out there. The question for you is what kind of retreat lights you up right now? Don’t try and design a retreat for your future self. Really consider what’s needed now and plan from there.

To get your juices flowing, here are some broad retreat categories to steward your thinking about what might be a good fit for you:

Types of Retreats

Personal Exploration – Maybe what you really want is time to yourself. Those of us drawn to personal exploration retreats tend to be pretty good at structuring time for ourselves, but struggle to actually find the time to sit with our own thoughts. A personal exploration retreat might borrow its structure from a single question or theme you are pondering (e.g. journaling in the morning and collaging in the afternoon) or it might follow the cues of a book or online course. I recently signed up for Paul Jarvis’ Grow Your Audience course and I am carving out time for a series of mini retreats to take in this virtual content and work through the reflections and actions it inspires.

(Psst, for those of you wanting to set and activate your vision, that’s what I designed the Go Beyond Coloring + Activity book to offer.)

Guided Learning – If the idea of structuring your own retreat feels daunting or you find yourself getting lost or stuck in your own thoughts, a guided learning experience could be a great help. Whether you hire someone to customize your retreat experience or join a community offering depends on what feels like the right fit for you. Trust your gut.

This kind of retreat will often integrate skill development, free space for personal reflection and movement, and an inspiring setting. You might choose to travel to the coast of Mexico for a yoga and surfing retreat that’s organized by your local studio. You may venture offsite with the board you volunteer on to have a facilitator guide you through the development of your strategic plan. You might spend the day working with an executive coach to get really clear on what it is that you want and then begin to map out how you can realize that vision. You may decide to work with someone who inspires you to customize a retreat just for you. The possibilities here really are endless.

Play Space – Sometimes the key priority for your retreat will be fun and free play and adventure. One of the first group retreats I ever designed was a Summer Camp for adults. While there were some community building moments woven into the week (communal meals, an evening bonfire, an optional hike in the Adirondacks), most of the days were open by design. It seems that the older we get the more rigid our schedules can become. A play space offers a nice counterbalance to that trend.

There is a “business conference like no other” created every May out in Big Bear, California that tops my list of play spaces (with lots of guided learning opportunities built in) that I’d like to attend. I won’t be showing up with a newborn there this year, but perhaps in 2018…

Work-treat – I love this term; thanks for coining it at our recent Getaway, Catherine Orr! =) Work-treats are about going away to a relaxing setting to get (ahem) stuff done. It’s usually not so much about checking off tasks that you are already doing in your daily routine, but for digging into those projects that you keep pushing off. A work-treat tends to balance holding a strategic focus with time and space for execution. At our Getaway last week, we spent a lot of sitting on beautiful old leather seating, laptops and tea mugs strewn around us, just digging in to key questions we had prioritized for the weekend. It wasn’t uncommon that we were up and working by 8:30 or 9am and we were usually not powering down until dinner time. And we may have pushed our 7:30 dinner reservation back an hour one night, just so we could have extra time to work. (You caught us!)

One note on sustainability for this kind of retreat: Even a work-treat needs breaks. Especially ones that bring in movement and creative thinking. Most of us don’t tend to have our best ideas or discover new solutions in the 10th hour of sitting at our desk in front of a computer. The way to monitor whether your work-treat is moving towards breakthrough versus burnout is to check in with your energy. If doing the work is creating positive energy for you and you want to keep going – do so. But be weary if you start feeling drained. We all need breaks, even on a work-treat. (Maybe especially then!)

What will be different at the retreat’s conclusion?

I love this question, because it really helps to bring your theme back into focus. But instead of looking out to where you imagine spending your time during the retreat, you actually step into the post-retreat future and determine what’s changed. What accomplishments are you celebrating? What do you notice is different about how you feel? What is possible now that wasn’t possible before?

What activities will support you in moving towards your objectives?

Journaling, collaging, brainstorming, coloring, planning, writing, emailing, walking, running, hiking, eating, sleeping…and the list goes on. For all the things you imagine yourself focused on and all the goals you see yourself achieving, there is only one route forward. You must take action. To that end, you are wise to consider what types of activities will serve you best as you work towards your retreat objectives. I’d also suggest you get clear on what activities you won’t be doing.

What environment feels most conducive to your retreat goals?

Location, location, location isn’t just a real estate mantra. Your retreat setting will influence your mindset. Consider what kinds of settings feel inspiring to you. Which end of the spectrum do you feel will best steward your retreat goals into fruition?

  • city versus country
  • resort versus apartment
  • indoors versus outdoors
  • familiar versus new

I know for myself that I am most often drawn to rural settings for my group retreats. Spending most of my days in Washington, D.C., I appreciate the chance to leave the traffic and fast pace behind and slow things down. I want to look out of my window and see undisrupted nature. That said, when I’ve created a personal exploration retreat for myself (e.g. I went on a Writer’s Retreat in December 2015), I am usually drawn to NYC. There is an electric buzz that I get from being there that makes me feel less alone, which I appreciate when I’m flying solo for several days. The energy that I get from being there allows me to stay focused inward on my retreat goals. I’ve spent a lot of time in New York so it’s familiar, but still feels fresh. I love my hometown of DC, but know that if I’m close to home my mind will move towards home projects that need doing or laundry that needs folding and a plethora of other distractions. For me to really step into a retreat mindset, I like to get away.

All that said, you don’t have to leave home to create a retreat for yourself. When resources – whether time or money or priorities – keep you close to or at home, fear not. You can create you own retreat from wherever you are. To do this, consider: What boundaries you will set to serve your retreat objectives (e.g. phone away/no answering the front door, hide out in a new local coffee shop for the morning)? What might you do to make staying home feel fresh and new (e.g. buy a new candle and a fresh bouquet to heighten your senses in your everyday workspace)?

What kinds of interactions (if any) do you envision having with other people?

As you’ve been wending your way through these questions, perhaps you’ve already clearly seen who is with you on your retreat. Are you spending all or most of your retreat on your own? Are you surrounded by your inner circle? Are you a stranger in a crowd of people drawn together by similar interests? A retreat often takes us to a place of deep personal reflection. Consider who you want around you to support this exploration. What’s the balance of time spent on your own versus in community with others? Do you want to go on retreat with people you know or use this time to make new connections? There is no right or wrong way to do it, but it is important to be clear about what you want.

My wish for all of you is that these questions empower you and your businesses to bring the spirit of pause and freedom and gratitude that pervade any retreat into your everyday lives. I would love to hear what kinds of retreats this inspires you to dream up. Happy retreating!