Last week I embarked on a solo adventure to renew my soul and solve some “big picture” issues I was facing in my life. It was successful in every way I needed it to be; I left with more clarity and direction than perhaps any other retreat in my life.

The planning and process of this retreat was something I forged myself, though I took from many inspirational sources, which we will discuss below.

What is a personal retreat?

A personal retreat can be defined in a variety of different ways, and subsequently can be named different things, too. Throughout history, people have taken retreats that give them the space they need to develop thoughts that can be life-changing, both on a personal and global level. Let’s take a look at some examples.

Bill Gates frequently had “Think Weeks” where he went off-grid to think and read.

Greg McKeown conducts what he calls “Quarterly Offsites” which are fundamentally important to his development. As the author of Essentialism and Effortless, this was the person who made me realize these concepts were essential to a meaningful life.

Ed Catmull, the author of Creativity Inc talks about how he and his team frequently have offsite retreats. They help them solve big issues that can’t be cracked in everyday life.

Step 1: Decide on The Boring Stuff

The first thing you’ll need to do is figure out the logistics of your trip. I call this The Boring Stuff, because it is…you guessed it, BORING. But it’s absolutely necessary to figure out in order to have a successful retreat. 

Most of the articles I found when searching “how to plan a personal retreat” focused 90% of the content on The Boring Stuff, so for our sake, this version will be abbreviated.

Location

First, you need to figure out where to go. I cannot overstate the value of getting away from the routine scenes and places you’re used to. You will think in new thought patterns when you’re in a new environment, so I think it is imperative to leave your current town/city and be somewhere that can inspire new thoughts and ideas.

In all of my research for my retreat, I could not find a solid example of a location. They all said things like “go to a cabin in the mountains” or “try a secluded beach” but nothing about specifics, unless they were promoting their own business that leads you through a structured program. If that is helpful to you, that is great! But for me, I wanted something less structured so I could do this retreat my way, but still get solid ideas on what people have found in the past.

The place I decided on for my getaway was this Airbnb called Sanctuary. It was absolutely perfect. Located 3.5hrs away from Washington DC, I enjoyed the drive down and felt removed enough from the hustle and bustle of everyday life. It was also secluded with gorgeous views of the mountains, and crucially for me, no wifi access. I highly recommend a location like this.

How long should a personal retreat be?

After location, the next thing on our Boring List is duration. How long will you stay? Obviously, this will vary wildly depending on your schedule and what is available to you. 

It might come as a surprise though, that I would not recommend a retreat longer than 7 days. The point is to give yourself space to think and breathe, but not so much space that you become complacent.

I have also seen retreats done in as little as just a couple hours, like in this post. If circumstances of life make it so that fully removing yourself is not possible, that’s okay. Do what you can with the time you have.

The sweet spot for me is between 3-5 days. On my most recent trip, I left on a Monday and came back on a Friday and it was perfect. 

I am an incessant planner, usually planning my trips months (if not years) in advance. However, with the benefit of personal retreats being that they should serve who you are at that time in life, I have found that planning my retreat between 2-4 weeks away is the best time. It is close enough that I can target specific issues I’m facing, while still giving me enough lead time to prepare properly.

Step 2: Figure out your Big Ideas

This is perhaps the most important part of the planning process. There’s a big difference between planning a vacation and a personal retreat, and it’s called your Big Ideas. In essence, you are answering the question, why are you going? What is the point? What issues are you trying to solve, and what do you hope to get out of this experience? 

Answering these questions can feel overwhelming (they are big questions for big ideas, after all!). Here are mine as a jumping-off point.

  • With a big life transition on the horizon, my main goal for this retreat was to re-establish my core values
  • A problem I’ve been facing in my life is too much distraction and overwhelm produced by my phone; I needed to do a digital detox
  • A growing issue I noticed in tandem with the two points above is that I had a lot of “big idea” (small caps) thoughts in my head that I didn’t have the time or space to write about in my everyday life
  • A smaller goal was that I was way behind on my reading list and I wanted to catch up
  • I wanted to finally complete the Virginia Triple Crown, a set of three iconic hikes that were challenging and rewarding

I ended up failing with this last point, but we’ll discuss that more below. 

So those were my five main points: thinking, reading, writing, hiking, and staying off my phone. With these guiding principles in place, I was ready to begin my personal retreat.

Step 3: Plan your Supporting Events

This may vary drastically from person to person, but a crucial step for success for me was to not just plan time away, but to plan things during my time away that supported my Big Ideas. If your goal is to write your business plan or get your finances in order, print the necessary forms that will guide you through and then schedule it as an “event” in your calendar during a block of time. If one of your goals is to connect with yourself and relax and do nothing, book a massage or facial. A common theme in personal retreats is “creative play”, which I would highly recommend adding as a “supporting event.” There are some great ideas in this post and this post.

Here were my supporting events:

  • A life-coaching session with my Airbnb host (who was a certified life coach) to establish my core values and define my “why”
    • This was helpful because she sent documents ahead of time, and then we had a very meaningful discussion that gleaned remarkable insight on defining who I am, and who I am not
  • A Book Party: I devoted one whole day to nothing but re-reading The Third Door, one of the most inspirational books I’d ever read. Scheduling this as an event made sure I completed it
  • Hike Tinker Cliffs, the final hike in the Virginia Triple Crown that I still needed to complete

I scheduled three supporting events during my 5-day retreat, but only ended up completing two of them. On the second-to-last day, we were hit with a nasty storm that prohibited me from completing the iconic hike. Instead, I did a more local hike that I didn’t mind doing in the rain, and would be more safe completing. 

Step 4: Embrace Spontaneity and document it

After you do all that planning, it’s time to throw caution to the wind and let the chips fall where they may. I know it may seem counterintuitive to make all these plans just to let them go, but I find that this is the best way to actually get what I need out of a retreat.

It is important to note that I didn’t overschedule myself during this retreat. With 5 days, I only scheduled three things. This left enough space for me to shift plans or allow spontaneous adventures to find me (and they did; one of the days I rented a bike and hit 10 miles of trails, and went to a beach at the base of a mountain in the afternoon). 

Instead of letting things just happen to me, never to be heard of again, I decided to carefully record what I did each day so that at the end of the week, I could reflect on what I wanted more of or less of next time (more on reflections below). The first day, I made a “projected schedule” and an “actual schedule” to see how my planning differed from reality. After being delighted by how the day unfolded, I decided to not plan the following days, and it worked well for me.

Step 5: Reflect

This step is nearly as crucial as deciding on your Big Ideas in the preparation phase. At the end of your retreat, schedule some time to step back and decide how it went. Here are some questions to ask yourself:

  • Did I make any progress on my Big Ideas?
  • What revealed itself to me that I wasn’t even looking for?
  • Was this time away worth it:
  • What did I experience during this retreat that I want to take back with me? What do I want to implement in my everyday life?

Keep these answers somewhere where you can access them during the next stretch of time before your next personal retreat. If you make a habit of taking regular offsites, then use this information to build into the next. Perhaps add the questio,n “What would I do next time to make this trip even better?” You can define “better” however you wish – productive, relaxing, efficient, informative, or something else.

Final Thoughts

Embarking on a personal retreat can be a transformative experience, providing the much-needed space to address life’s big questions and reset our mental and emotional compass. As I reflect on my own retreat, I am reminded of the profound impact that intentional solitude and purposeful planning can have on our lives. 

By thoughtfully selecting a location, defining the duration, identifying Big Ideas, planning supporting events, and embracing spontaneity, we create an environment ripe for personal growth and clarity.

Reflecting on this experience, I realize the importance of not just planning but also documenting and learning from each retreat. These insights help in shaping future retreats, ensuring they continue to meet our evolving needs. Whether it’s a few days in a secluded Airbnb or just a few hours at a local park, the essence of a personal retreat lies in the intentional pause it offers—a chance to step back, breathe, and realign with our true selves.

If you find yourself at a crossroads or simply in need of a mental reset, I highly recommend giving yourself the gift of a personal retreat. It’s an investment in your well-being that pays dividends in clarity, peace, and direction, ultimately empowering you to navigate life with greater ease and confidence.

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