The Benefits of Going on an Overnight Retreat: A Guide to Planning and Taking a Productive Retreat

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The word “retreat” is not a positive word for everyone. I can evoke memories of religious retreats they were required to attend, some kind of hippy-dippy, new-age spiritual experience, or boring corporate retreats where you were forced to do a lot of group exercises but nothing changed as a result.

But there’s also a more neutral meaning of “retreat.” A retreat can be a dedicated period of time when you go somewhere out of the ordinary to work on something important. That’s the sense of retreat to which I’m referring in this post.

In his PDF Guide and Video, David Sparks (aka MacSparky) describes a method that helps people to define their life roles, write a “best version of themselves” for each role, and probe each role with a series of questions.

He urges those who want to do this work to take the process seriously and “go somewhere else” on a minimum one-night retreat.

Why take a retreat to work on a special project? Why not just block out a few hours at home or in your office?

1. The Benefits of Overnight Retreats

Sometimes to go deep, you must first go big.

Cal Newport, Deep Work

Here are some great reasons to go somewhere else:

1. Cal Newport, in his book Deep Work, points out that when we do special work at a location besides where we normally work it heightens our sense of commitment to the work. “By “going big” in making special arrangements, it emphasizes its priority and “helps unlock the needed mental resources.”

2. Getting away from our normal surroundings helps us to focus and concentrate. As MacSparky points out in his guide, you need to get away from your normal workspace because “The problem with staying in your usual workspace is that is the same place that you usually work. It will be super tempting to spend your retreat time doing the same things you do every other day.”

3. It’s important to get away from people you know to avoid distractions. If you stay at home or go to your office, you will be in contact with people you know and you will be distracted.

2. Where Can You Go for an Overnight Retreat?

Here are some of the locations you might consider for a retreat:

• A location within reasonable (or close) driving distance. I’d suggest that you stay somewhere within easy driving distance so you don’t use a lot of your retreat time traveling.

• A location with some basic cooking facilities. At a minimum, you’ll want a refrigerator, a microwave, maybe a toaster and a coffee maker. That way you won’t have to leave your room for all your meals.

• A resort or hotel. Look for a room that has a comfortable chair and desk so you can stay in your room and work. You can also use the breakfast area in your hotel after breakfast hours.

• A spiritual retreat center. Many retreat centers allow visitors to use their facilities for an “unguided retreat,” meaning you can do your own thing and not be a part of a formal program.

• An Air BnB rental. You can rent a room, a cabin, or a home. Often the expense is much less than a hotel or resort.

• A friends 2nd home or vacation cabin.

3. How Long Should Your Retreat Last?

• How long your retreat lasts depends on what you’re trying to accomplish. Some projects can take a day, others 3 days or longer.

When I went on my first Life Roles retreat, I followed MacSparky’s advice and planned two nights (one full day, and two half-days). I needed every bit of that time to accomplish my initial roles identification and review.

Now, when I do my quarterly life roles inventory and planning process, I find that two half days and one overnight is sufficient.

• Even if you have a progression of steps planned, it’s not necessarily going to be a linear process. As you get deeper into your retreat, you’ll likely think of things you didn’t think of earlier and do a lot of bouncing around between aspects of your project. That takes more time than you think.

• For most involved projects, plan for at least an overnight. Give yourself time to reflect and go back to sections you thought you had completed.

4. Go on the Retreat By Yourself

As tempting as it may be to share the retreat space with a spouse or friend, don’t bring anyone with you.

On one two-night retreat I took my wife with me to the local resort I was staying at. I enjoyed her being there, but it was a constant source of distraction. Even though we only met for meals and were together for the evening, it kept me from totally focusing on my work.

Now, I go by myself for the period of time I estimate I’ll need for my retreat. If she’d like to come also, we plan another night or two after my work is complete and she joins me at the close of my retreat. I then have time to focus on her instead of trying to split my focus between her and my work.

5. Have a Retreat Plan

• What is your goal, and what are you trying to accomplish? Decide on an outcome, or goal, you are wanting to reach by taking the retreat.

• What are the necessary steps to achieve your goal? Figure out what specific actions you’ll need to take to reach your goal, and in what order.

• Prepare a process outline or checklist showing what youll be doing at each step. Build a roadmap of what you will be doing during the retreat. Refer to it as you work through your retreat so you don’t lose track of where you are or don’t go down irrelevant rabbit holes.

• Decide how you will keep a record of your work. Digital or analog?

I decided to use a digital recording medium because I knew that writing everything down would soon become an unwieldy mess. 

When I did my first roles retreat, I used MindNode to build a large mind map that included each role I identified, my “best version of myself” for each role, and a series of probing questions and my answers. In addition, I also included an “action steps” section with checkboxes for items I needed to take action on after the retreat.

Now when I take my quarterly roles inventory and planning retreat, I use a Quarterly Reflection & Planning Template that I fill out in Craft

6. Try an Overnight Retreat

Planning and taking an overnight retreat is a hassle, but it’s worth it. The investment you make in finding a suitable location, planning your retreat activities, planning your trip and meals, and the time you invest in the process will repay itself abundantly with focus and commitment.

If you can’t do an overnight retreat, I suggest you at least go to another location than where you normally work. This could be a coffee shop where no one knows you, or a library.

If you must stay at home, take steps to eliminate or minimize distractions. Inform other people in your home what you’re doing, close the door, hire a babysitter if you have small children at home, and block off time on your calendar to focus.