Doing a Personal Retreat

I’ve been intrigued by the concept of a personal retreat ever since I heard Mike Schmitz talk about it on Free Agents a while back. He described how he goes off on a “retreat” every three months to review, think, and plan. While I was interested, the discussion on the podcast was kind of barebones. When he announced that he put together a video course I jumped on board pretty quickly. Unfortunately, it came along at a very busy time for me, with the holidays and some travel for work, so I didn’t get a chance to actually do the course until late January.

After watching the videos, I was very eager to put this into practice and wanted to get started right away. While I wanted to take advantage of this burst of enthusiasm one obstacle was finding a location on short notice.¹ Mike emphasizes not doing the retreat at home or another familiar (and distraction-laden) environment. He also maintains that to give the retreat the attention it deserves, you really need about eight hours, especially the first time you go through the process.

Doing it in the great outdoors was appealing in concept, but probably not in practice in January. I had all sorts of ideas for fun and interesting locations (traveling to a distant city, doing it on a long-distance train trip, etc.) but most were too expensive or required too much lead time. I looked into renting an office or conference room for a day, but that whole process seems unreasonably difficult.² In the end, inspired in part by CGP Grey, I just got a local hotel room for a couple of nights.³

Preparing for the Retreat

To get ready for the retreat I watched the course videos a second time and took copious notes. If I had one suggestion for Mike, it would be to beef up the workbook to include more of the prompts and advice from the videos.⁴ There’s a lot of good stuff that didn’t make it into the workbook.

I also listened to an episode of The Productivity Show where Mike talked about his personal retreat practice. This predates the personal retreat course, so some aspects aren’t really as developed, but I still found it useful.

After dinner the night before the retreat I packed up a change of clothes, pens, pencils, and notebooks, along with the course workbook (both printed and in PDF on my iPad). I also assembled some food and drinks so I wouldn’t be distracted by needing to find a restaurant for lunch.⁵

One of the first things I did after checking in was put my iPad into Airplane Mode and my iPhone into Do Not Disturb (with a strong vow not to open it up and look at it until after I was done with the retreat). Since part of the point of making this, a “retreat” was to avoid distractions, I figured that it would be good to start detaching from my usual diet of digital interactions the night before. Cut off from my usual digital feed, I made an early night of it.

The Retreat

The next morning I hit the hotel fitness center and their complimentary breakfast before settling down in my room for the retreat.

Mike based the personal retreat idea off of some of the concepts presented in the book The 12 Week Year. I’d read the book, and I liked the concept, but I found it hard to implement. The core of it seemed like a good idea, but it had some extraneous stuff around it. The Personal Retreat course is a lot more focused.⁶

Based on what he said on the Productivity Podcast and Free Agents, Mike started doing quarterly personal retreats because he’d had trouble implementing his 12 Week Year goals. It’s intended to provide time to look back at the past three months and ahead to the next three. However, it goes quite a bit beyond just quarterly planning, encouraging you to take a look at your values and long term aspirations and so your plans for the next three months are taking you where you want to go in life.

Core Values

The retreat starts out with the big picture: defining your core values. Mike has some excellent questions to get you thinking about these. I answered all of them, then went back through trying to pick out the common threads by tallying up how often certain things got mentioned and making a mind map of how related ideas clustered together.

I’m usually more of a digital guy, but I made a last minute call to do this on paper in a Field Notes Steno Book, rather than on my iPad.⁷ Instead, I used the iPad to display my notes (including all of Mike’s prompts and questions). I did this using iA Writer’s focus mode. It highlights one line by graying out everything else, so it helped keep my attention on the particular prompt I was working on.

I ended up listing my core values as short sentences starting with “I am…”. Mike recommends 4-7 core values. I picked 5, but I did cheat a bit by making some of them compound (two related values, like “I am a writer and teacher”).

Between each exercise, I spent a few minutes walking around the hotel to clear my head.⁸

Where are you right now?

The next exercise focused on the question, “Where are you right now?” It involves an inventory of your commitments and responsibilities and assessing your satisfaction in different areas of your life. I’ll be honest, I didn’t find that this provided quite as much insight as some of the other exercises, though that may just be a product of what my particular commitments are and where my life is right now.

Designing the life you want to live

In contrast, the exercise on designing the life you want to live really grabbed me. Mike has created some great prompts to get you thinking in detail about what you’d like different aspects of your life to be in the future. I almost had too much fun writing about a day in my life five years from now. I probably crammed way more stuff in there than could realistically be done in a day (maybe next time it needs to be a week in the life of my future self).

Retrospective - Accomplishments

From the future, we turn to the past; the next exercise involves looking back over the past three months and listing your accomplishments. I was a bit skeptical when Mike said to allocate 1-2 hours for this, but it did take me over an hour and I filled two and a half pages of the Steno Pad with accomplishments. Not all of these are earth-shattering by any means, but they’re all things that moved the ball forward in one or more areas of my life (making a presentation for work, writing a blog post, etc.).

Thinking of all of these was difficult, but I found a few things that helped. I started by just brainstorming, but when I ran out of steam trying to remember things off the top of my head I looked back over my calendar to see what I’d been doing for the past three months and perused my blog to see what I’d posted there. What really helped was the gratitude journal I’d started keeping after taking Shawn Blanc’s Focus Course. Rather than being a full journal, this just involves writing down one accomplishment and two things I’m grateful for every day. Many of those daily accomplishments are too small for the personal retreat list, but others were large enough to make my quarterly list or prompted me to think of related things that should be listed. One thing I found was that in many cases, the daily accomplishments represented incremental progress on more significant accomplishments that did belong on the quarterly list. I may want to start calling out those bigger things explicitly as I go along, rather than waiting until three months later.⁹

Retrospective - was What you’re going to change

After a break for lunch, I started up on the second half of the retrospective: thinking about what things you’re going to change. Mike has a nice, structured way to do this involving looking at what went well and what could have gone better and what lead to these outcomes. This, in turn, leads to the three critical questions: What should I start doing? What should I stop doing? What should I keep doing?

For me, this process mostly lead to practices, rather than commitments, which I’m not sure is what Mike had in mind (looking back it’s a bit ambiguous). However, it worked for me, and I think the outcome has been very useful in terms of reinforcing good behavior, discouraging things that are hindering me from accomplishing my goals, and brainstorming ways that I can do better.

Setting your goals

The culmination of all of this, the core values, where you are right now, designing the life you want to live, the retrospective, comes in setting your goals for the next quarter. Mike recommends no more than three goals, and if you’re doing this to the first time, limiting it to even fewer, just one or two. I ended up picking two goals, and I kind of cheated a bit since my first goal, “Spend my time more intentionally” is kind of a cross-cutting issue that affects all sorts of areas. My second goal for the next three months is to write more.

Mike talks about how your goals should be connected to your core values and vision. I actually found it worthwhile to write out for each goal which core values it supports and how and which pieces of my 5-year vision it connects to. I also noted how each goal connected to things I said I should keep doing, start doing, and stop doing. For my time goal, this ended up being quite the task, since how I manage my time ends up touching so many other areas that I filled two and a half pages of my notebook writing it all out. The process really reinforced how being more intentional with my time could have a significant, positive impact on my life.

Another thing Mike emphasizes is breaking each goal down into milestones and daily habits to help ensure you actually accomplish it. The goal is the “what,” the milestones and daily habits are the “when” and “how.” Neither of my goals were all that amenable to milestones, so I didn’t set any. They are ripe for daily habits, however.

For spending my time more intentionally, my primary habit is going to be time blocking every day.¹⁰ This is something I’d been doing last year, but I’d kind of fallen off the wagon. After I stopped time blocking it felt like I wasn’t being as productive with my time, which is part of the reason I’d like to start up again.

Essentially, this time blocking practice involves writing out a schedule for each day, saying what I’ll be doing and when. That way I know what I’m supposed to be working on at any given time. It keeps me from having to make a decision of what to work on in the moment and makes it less likely that I’ll fail to decide and end up diddling around on the internet.

Of course, things come up, and there will be times when I have to adjust on the fly.¹¹ That’s why my second habit to help me spend my time more intentionally is to do a post-mortem every day and look at how I actually spent my time compares to how I’d planned to spend my time. Did something unexpected come up? That’s fine; is it something I could account for in the future or is it something truly unexpected? Did something take longer than expected? That’s ok; how can I do better at estimating how long this sort of thing will take? Did I just blow off the schedule? That’s not really ok.

When I’d been doing time blocking last year I just did it for my working hours. This time around I decided that I’ll be applying it to my entire day. That doesn’t mean I’ll be working 24/7 though. One of my regrets about frittering away my time is that when I look back on how I spent my recreational time I spent a lot of it in ways that I don’t really value (primarily frittering it away on the internet) rather than recreational activities that I value more (reading, playing video games, watching good TV shows). I’d like to change that and blocking time for specific types of leisure is a way to do it.

For my goal to write more, my only habit is to write every day. It doesn’t matter what. Could be fiction, non-fiction, a blog post, a novel, anything. Just as long as I’m spending some time every day moving the cursor.¹²

To track my progress towards these goals, I’m going to track how many days I time block for, how many days I do a post mortem, and how many days I write for at least 30 minutes. I’m not going to track how much I write, or how many days I stick to my schedule. The goal for the next three months is simply to do these things consistently.

The other aspect of goal setting Mike talks about is looking at your commitments for the next three months and seeing what might interfere with accomplishing your goals. I wrote out my commitments, using the list I developed back in the second exercise, looking through my calendar, and thinking about what else I had coming up. It’s a long list, but a manageable one. In addition to making sure it wouldn’t interfere with my goals, getting these commitments out of my head and onto one sheet of paper was also valuable in and of itself.

Executing the Plan

The final exercise is to plan your ideal week. One of the biggest obstacles to achieving these kinds of goals is not setting time aside to work on them. The ideal week exercise allows you to plan out when you’ll work on your goals for the next 12 weeks. Of course, not every week is ideal, but this at least provides a starting point.

Obviously, this complements my goal of spending my time more intentionally and the time blocking habit quite nicely, so I kind of went whole hog on this exercise. I abandoned my paper notebook and went digital, breaking out the Numbers app on my iPad and using it to block out an ideal week in 15-minute increments. I set aside time for writing every morning, time for planning out the following day, and time for doing a post-mortem on the day every evening. I also made some other adjustments from how I’m currently spending my time (notably, a lot less time on the internet). Everything got color coded as well. Like I said, I really went whole hog.

As a reward for all this effort, I made myself a nice dinner (baked boneless buffalo wings, one of my favorites) and sat down with a drink and the latest episodes of The Grand Tour.¹³

The Results

I feel like my first personal retreat has been an incredibly useful experience, one that will pay dividends going forward. Of course, where the rubber meets the road is actually going out and implementing these habits and achieving my goals. We’ll see where I stand in three months.

In addition to the quarterly goals and planning, the retreat also helped with some deeper insights. Defining my core values and imagining the life I want to live five years from now are valuable beyond just setting goals for the next three months. Listing out my accomplishments from the last three months was encouraging. For a time in my life that I didn’t feel was very productive I actually accomplished quite a bit.

One thing the retreat helped me realize is that I have a “teacher” itch that isn’t really getting scratched right now. That’s not something I can really remedy in the next three months; rather, it’s something to work on long term (for now I’m going to try to scratch it by writing more).

As I mentioned earlier, I’d read The 12 Week Year and while I liked the concept, some of the other stuff in the book kept it from really grabbing me. Having done the personal retreat (and gotten so much out of it), I feel like I should try rereading the book and see if there are aspects of it resonate more with me now.

One other thing I learned from this retreat was that not looking at the internet when I had my phone out for some other reason was surprisingly hard. It wasn’t even a lack of willpower so much as thoughtlessness on my part. As soon as I was done with what I’d gotten my phone out to do (check my calendar, log some food or exercise, etc.) my thumb just instinctively just went to Safari, Reeder, or Spark. I’m a bit disturbed by just how automatic it was, but it’s a problem outside the scope of this personal retreat.¹⁴

Changes for Next Time

I’m definitely doing this again in three months. While it went really well this time I can already see some tweaks, I want to make. For one, I think that I’ll make taking stock of commitments for this quarter a separate exercise of its own, one that comes before goal setting. That way I can take these commitments into account when setting my goals (or change my commitments to accommodate my goals).

Of course, I’m anticipating that there will be differences just because it will be the second time through the process. This is one thing I wish Mike covered a bit more in the course, though I can see why it’s mostly geared towards first-timers. Next time I’ll already have definitions of the core values and vision of my future life (though its probably worth going through the exercises again to see if there’s anything I want to change). I’ve scanned my notes from the retreat and stashed the notebook where I’ll hopefully be able to find it in three months, so I’ll have all of my material from the first retreat available for reference. Of course, the big change will be assessing how well I did on my goals and the associated habits for this quarter.¹⁵

One thing I’d like to change between now and then to make the retrospective easier is to do a better job tracking my more significant accomplishments as they happen, rather than having to try to remember them months later.

Something that I won’t change is doing the retreat on paper. That worked really well; it helped keep me focused and slowed me down a bit (in a good way). I did realize about 3/4 of the way through that I need to leave more blank space in the notebook as I write so I can go back and add things that I think of later. I guess I’m too used to doing stuff digitally where it’s easy to insert content in the middle of what I’ve already written.

While the hotel room worked out well, I may consider some other options that more advance planning (and warmer weather) might make possible.

Concluding Thoughts

Doing the personal retreat was a really great experience. It’s already paid off with some great insights, and I think it’s going to continue to pay off over the next three months. I’ll definitely be doing it again.

I really want to thank Mike Schmitz for developing the Personal Retreat course. The way he’s structured the retreat works really well, and it includes some great prompts and questions to really help you get at things that can be hard to pin down, like your core values and a vision for your future. I’d definitely recommend the course and the practice of regularly doing a personal retreat.

January 27, 2019

---

Previous post

Review of Build Your OmniFocus Workflow I’ve been using OmniFocus for a long time. In fact, OmniFocus was the very first paid iOS app that I paid bought back in 2008 when the App Store

Next post

Trying iA Writer In the past few years I’d been doing most of my writing in a combination of Bear and Ulysses. Bear for note taking and shorter form stuff; Ulysses