I’m preparing for 2018 (yes, I know it’s barely November)

For folks who are in or work at schools, calendar year 2017 is basically over.*

So what?

Well, for me, it means its time to start planning for 2018. I know (because people tell me often) that I’m far from the norm in my ability to plan ahead but, the more I think about it, the more I want to make planning like this more normal. All we really have is our time and to not be mindful about how we spend our moments from year to year seems really... not good.

For the past few years, I’ve been doing an annual reflection retreat to help me reflect on the year and get strategic about how to make the upcoming better than the previous one.

To prep for 2018 I’ll be reviewing my most recent retreat, making adjustments to that plan, and then trying to find dates for the next retreat in January 2018. Here’s a (pretty detailed) rundown of what I did last year, what I learned from it, and what I’ll do this year.


Reflecting on 2016

Last year’s annual reflection retreat spanned 1–3 January 2017 and went down like so:

Review my calendar, week by week

“How we spend our days is, of course, how we spend our lives.”
— Annie Dillard, The Writing Life

Blurred out screenshot of my digital calendar.

Part of the reason I’m so meticulous with my digital calendar is that it helps me keep track of how I’m using my time. That practice has value day-to-day, week-to-week, and month-to-month for sure. But where it really pays off in my personal system is during my annual retreat. That payoff, in turn, encourages me to keep even better track the next year.

Given that I have such detail in my digital calendar, last year I took an entire morning to go week by week and make a bulleted list of what I did with my time. I don’t write down everything, but here’s one week from the first year I did this to give you a sense of what it is. I did it in a simple text editor in order to not get distracted with formatting:

## week 7 (feb 9-15)

- dinner with clara vu and caroline howe
- attend presencing forum with otto scharmer, dayna cunningham, phil thompson, etc.
- chatted with robert hacker about 100k business plan pitch
- had interview with the food project about crew leader position over summer
- filed 2013 taxes

Review and/or revise my values

Last year I went through the Holistic Visioning process at Infinite Growth. Part of the output from that work (which I think many people should do) is a values statement that helps me make all sorts of decisions. The first year I did this reflection retreat, I was following this guide from Holstee and the second page indirectly asked me to state what was important to me (I think those things were justice, love, rest, friendships, and travel… but I don’t really remember and can’t find the notebook I kept them in).

In both cases, I took a few hours to reflect on how these values felt for the year: did they work (i.e. did holding them in my focus help me make good decisions? did those decisions result in bringing more of the world I envision into existence)? what values felt missing? were there any values in this list that ended up not being that important?

Review my spending

Because I’m a huge nerd, I keep meticulous track of my spending (like most things in my life). I currently use Simple because they’re super convenient (though I’m trying to switch because they sold out to a big bank recently and I’m not about that life… despite the fact that I haven’t switched yet T_T) and because they provide great access to my spending and income data. It used to be even better, but I’m done fighting with them about that now…

Screenshot of my monthly restaurant spending to date for 2017. Graph shows two lines, one for income and the other for spent. The income line is for people paying me back usually.

During this part of the retreat, I take time to dig in the details of my transactions. I make sure that most things are categorized properly and my numbers add up (it’s not worth it to fix everything — I just need to make sure my totals make sense).

And then I just take some time to look the data. Where did I spend the most? the least? What was surprising about my spending? Where does it feel like I overspent? What did I not spend enough on? How my actual income and spending compare to my projections?

Socialize and then sleep

A dear friend was visiting from London during my retreat days and when I was done with each day, we would hang. It was excellent. Having social time to look forward to gave me good motivation to finish my retreat reflecting each day. It was also nice to have someone to share insights with after my focused time was over.

And getting good sleep felt crucial. I slept more than my average by going to be earlier than normal and waking up without an alarm.

Screenshot of the first night of sleep during my annual reflection retreat from Sleep Cycle app.

Reconfigure my calendar

After the reflection, I transitioned to looking forward. Triangulating between my values, how I spent my time, what I accomplished (which sort of surfaces from how I spent my time), and what I want to change that felt off, I start thinking about how to structure my time for the next year. To do a full explanation of how all these pieces fit together would take wayyy too many words but here’s just one example.

One of my primary values is love (a very specific type of love, that is). Being able to give and receive love is necessary for me. So it’s important for me to make explicit time to give and receive love. Some folks I give and receive to and from are my bio family and my woes/chosen family. Therefore, it’s important that I carve out time to see my bio-family as well as spend time (regularly) checking in with my woes. I’ve learned that for most of my woes, scheduling bi-weekly hangout sessions hits the spot. The time scale is infrequent enough to have meaningful stuff to catch up on but not so rare that we need many hours to do that catching up. The end result was (# of woes x 2 nights/month for catch up = total number of nights needed per month to make sure I was giving and receiving love from folks I love and who love me).

Soap. Lather. Rinse. Repeat (per value).

Create a budget projection

Holding my values and how I want to spend my time, I think about how my money situation needs to be to make that happen. For the time being, much of this is out of my hands, but some of it I do have control over. For example, one year, I realized I was spending about $200/month on alcohol. That felt like too much. So I looked at my values and realized that I could combine my time spent with close friends with my need to cut my alcohol spending. Buying a six-pack or bottle of wine is effectively the same price as buying a single cocktail out (at least in Boston). I decided to start doing a lot more of that and a lot less going out. Maybe that was obvious, but having a clear sense of my values helped me make that budget decision and in a way that felt good, not just restrictive.

Organize my digital files

Ok. Being honest, I didn’t get nearly as far on this as I wanted to, but I did get started.

First, I cleaned off my laptop desktop. I’m a notorious desktop file saver. I know that that’s bad practice, but I can’t help it. It’s SO convenient! Anyway, I tried to go through as many files as possible, delete ones I didn’t need anymore (i.e. screenshots), relocate files I wanted to keep (receipts, etc.), and I left everything else there. 🤷🏾

Then I went into my Google Drive and started to… wait, who am I kidding? I took one look and was like… nope!

Gif of Tracey Morgan vigorously shaking his head and saying “nope” with increasing vehemence.

But this year, I’m committed to follow this guide to sorting out my files. *fingers crossed I actually commit this time*

Launch projects

Side projects are huge for me. Whether it’s big picture project scheming with Ross, local project scheming with Maureen or Camilo, 3-hour project night, or personal project night, spending time working on projects is incredibly important to me. Projects are a way I learn new skills, flex old ones, and, when they’re collaborative, get to work with friends (old and new).

This past year I set aside an entire day setting up infrastructure for projects that I wanted to launch this year. I kept a running list over the year of projects I wanted to start, but didn’t have time or energy to get going. When looking at my calendar, I also realized that there were some projects that started but puttered along or didn’t get the attention they deserved. I added those, too.

I want to underscore one part of this though: what I used this day for wasn’t launching all the projects. This time was to put in place the systems I’d need in order to launch the projects later during the year. I think I had a list of eight projects and there just wasn’t enough time to launch them all. But using this day to build the structures I’d need for them later (but probably wouldn’t take the time for once the year got busy) felt like the critical point of this day.


OK! Enough about last year. What’s the plan for this year?

Plan for reflecting on 2017

Lessons learned from last year

Last year I did my retreat at the beginning of a week and did a brief reflection on it at the end of the week. Some lessons from that reflection that I’m going to attempt to learn from and embed this time around are:

The actual plan

Here’s to trying!


* This week (week of Oct 30th)is shortened for some folks because of Veteran’s Day holiday on Friday. Next week is a full week which is followed by the Day of Mourning/Wanton Slaughter Remembrance week (staff, faculty and students tend to take at least Wednesday thru Friday off). Then there are three full weeks (which will mostly be full of finals and calendar year closeout work) before the last two weeks of December during which very little substantive work happens. Even if you’re technically working, some many people are in and out that not much moves forward usually.

So even though there are technically 8–9 calendar weeks left, we’re really working with much less. And if you start to take people’s level of focus and energy into consideration, we’re probably working with even less…


Other reflection resources:

Note: There are a few people who have mentioned interest in wanting to do something like this for themselves. Because of that, I’m going to plan in-person gathering for folks to join me on at least part of this upcoming year’s annual retreat. I may also make the framework available online so anyone, in person or not, can participate. If you’re in the Boston area (or not) and want to stay in the loop on that, please let me know at lawrence.barriner.ii+annualretreat@gmail.com.

Also, I’m feeling torn about when to hold this year’s retreat: Jan 2–5, 3–6, 4–8… Hm!

Lawrence Barriner, II

Written by

narrative, communications, facilitation, futurism | lawrencebarrinerii.com

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