Mid-Year Reflection and Planning

As we are about to leave June and enter July, we’re hitting the halfway point for 2022. It’s hard to believe we are halfway through 2022. This is particularly true for me with so much change in my life. I’ve now been a full-time MacSparky for six months and I consider this mid-year turn an excellent time to reflect and plan. I’d encourage you to do the same.

There is nothing magical about going from June to July. It’s another day, like any other. However, there is something special about calendar transitions like mid-year and new-year that gets in our heads and makes us all more reflective and more amenable to stepping back, taking stock, and making changes. I prefer planning in quarters, not years or half-years, but the mid-year transition works on me too. I have a system for this sort of thing, and I’d like to share it with you.

Reflect, Then Plan

I want to draw your attention to how I’ve named this: Mid-Year Reflection and Planning. It is all about reflection (which is first) and planning (which is second). So often, you’ll read about these planning sessions that omit reflection. That’s dumb. Attention to your past is how you improve your future. My best plans have always sprung from careful observation of my past. Whether you do this with pen and paper or on a keyboard, I think it is easier to keep reflection and planning as one thing together instead of two separate things.

The Roles Audit

I’ve written extensively about this before. The foundational building blocks of my life are the roles I serve: Husband, Father, Brother, Friend, MacSparky, and Student are a few I’ve identified. If you are curious, I suggest reading this.

Regardless, my mid-year review starts with an examination of my roles. For each, I have a few open-ended questions:

  • How am I doing? (reflection-based question)
  • Where can I get better? (planning-based question)
  • Where am I doing good? (planning-based question)

The questions are simple, but the answers are not. Take as much time as you need to empty your head concerning each one. Examining each role is a critical first step for me. This takes me a few hours.

Consider Challenges

Next, I like to spend time on challenges that I’ve faced and challenges that I expect.

I start by reflecting on the challenges thus far, and I ask a few questions for each:

  • Could I have predicted it?
  • Did I ever lose my cool?
  • How did I handle it?
  • How would I have done it better?

Then I turn my attention to the rest of the year and consider if I expect any challenges heading my way. For each one, I have a list of questions:

  • How likely is it?
  • Can I avoid it?
  • What steps can I take right now to avoid it or make it easier?
  • How can I turn the challenge into an opportunity?
  • What is the worse potential outcome from this challenge?

All these questions probably make sense to you except the last one about the worse potential outcome. I’ve discovered that fear of the unknown is much more painful than knowing a potential challenge or bad outcome. Imagining the worse outcome settles me and (usually) helps me avoid it.

Next Look at Project and Habits

Projects and habits are up next for me. In my mind, projects and habits are on an equal footing. Both are how I move forward.

As to Projects, I begin looking at what I’ve shipped so far in the year. For each, I consider:

  • How did it go?
  • What would I do differently if I had the chance?
  • How were my time estimates?
  • Did anything unexpected happen that I should have seen?
  • Should I do projects like that again or steer clear?

Then I look forward and consider projects for the rest of the year. For each, I consider:

  • What is the deliverable?
  • What are my expectations for the time required?
  • When on the calendar will I do that work? Have I made time for it?
  • Do I need help?
  • What are my expectations for the results of shipping this?
  • Is there anything else in the world I could be doing to better serve the cause?

Habits work the same way.

  • What Habits am I actively working on?
  • How’s it going?
  • Is this still a thing I should be working on?
  • How can I get better at it?
  • What Habits am I unknowingly creating?
  • What should I do about it?

After this, I take an overview of the roles, challenges, projects, and habits with the gut check bandwidth questions:

  • Am I doing too much?
  • What here should I throw overboard?

Hooray! Let’s Start Planning

If you did all of the above, the planning part is easy. Now you know where the role changes are needed, the challenges to be faced down, the projects and habits to nurture. Now go do it.

What actions do you need to take in the next six months to make it happen? Which resources do you need to assemble? What people do you need to reach out to? How do you set yourself up to pull it off? Assemble the troops and make your plans.

Is there a Theme?

My friends Myke Hurley and CGP Grey have themes (and theme journals) to help you simplify the process and make progress on what’s important to you. It’s a great idea that doesn’t land with me. Somewhat related, I do try and observe trends.

For example, looking back at my last six months, it’s clear that the big word for me was “transition”. I made significant changes in my life, and a lot of it was new. I saw transition every day. “Change” and me became close friends.

Looking forward, I expect more transition, but I can also see consolidation becoming a thing as I nail down the workflows to deliver more and better content and (hopefully) complete and move into a new studio space. You could call these themes, but they feel more like trends to me. I’m not choosing them so much as I observe them as they grow out of my decisions concerning my roles, challenges, projects, and habits.

Is All of This Worth the Time

100% Yes! People write to me asking how much time I spend on this stuff and if I wouldn’t be better off spending the time doing “actual” work. In my experience, reflection and planning time is always worth it. You have to experience this for yourself to believe it, but why don’t you take a shot right now? Go through the above questions. Do the work. Make plans. Then see where you are on New Year’s Eve.

Mid-Year Planning and reflection with MacSparky (MacSparky Labs)

Can you believe that we are halfway through 2022? With the move into the second half of the year, I’ll be doing some reflection and planning this week. I will share the process with the Early Access members, and I will do a Zoom call this Wednesday at 16:00 Pacific with anyone doing the same to talk about the process and implementation of mid-year reflections and planning. I’d love to see you there…

This is a post for MacSparky Labs Level 3 (Early Access) Members only. Care to join? Or perhaps do you need to sign in?

Time Tracking Categories

Stephen and I dug deep into time tracking in this week’s episode of the Mac Power Users. Throughout the show, I kept referencing my saved timers. I thought this would be a good place to share them in detail with a bit of explanation.

As I explained in the episode, the idea of saved timers is to give you a way to make sure you are consistently tracking and get more reliable data. In the Timing App, they are projects. In the Timery App, they are saved timers. One of the tricks of doing time tracking is getting data that’s specific enough to help you out and flexible enough to adjust with your active projects.

I explain in the episode how I use different time tracking apps, so you’ll have to listen to that if you want a further explanation, but having the same group of projects or saved timers makes the process easy.

So my main projects are as follows:

Project: Family and Friends

Subprojects: Family, Friends, Ahsoka (the dog)

Project: Personal

Subprojects: Altruism, Comms, Cooking, Down Time, Eating, Errands, Fiction, Finance, Gaming, Household, Media, Music, News, Shopping, Woodworking
This serves as a catch-all for all of my personal tasks, whether reading a book or pulling weeds.

Project: Health

Subprojects: Exercise, Gardening, Hiking, Meditation, Medical, Nap
This is another one that has evolved. Originally it was for exercise and bicycling, but now it’s where I keep anything health-related.

Project: Focus

Subprojects: Incremental Planning, sparkyOS, Planning, Journaling, Time Tracking
I do a variety of tasks to hold things together. They’re both related to my work and my personal life. They drifted between various categories for a long time, but I created a separate project called “Focus” a couple of years ago. These tasks include reading books, journaling, planning, and general work on sparkyOS. “Planning” is what I do day to day. “Incremental Planning” is what I do weekly/monthly/quarterly.


So Many Subprojects: Admin, Blog, Comms, Customer Support, Field Guides (with sub-sub categories for each title), MacSparky Labs, Newsletter, Planning (MacSparky planning only), Podcasts (with sub-sub categories for each show), Research, Screencast Contract Work, Social Media, Speaking, Sponsor Work, The Creator’s Guild, Webinars, Writing, YouTube, Studio Build-Out.

This is another one that has expanded over the years. Anything I do related to being MacSparky goes into this category. And again, because I like data, I don’t mind having quite a few entries under this heading.

Project: DLR Field Guide

No Subprojects
My wife and I have been having a little bit of fun making some videos at Disneyland. This one probably belongs under the personal category. It is a personal project with not any big plans for the future. But ultimately, I decided to give it its own project to keep it separate from other personal time.

Project: Unintentional

No Subprojects

Sometimes, you find yourself drifting off into the unknown when you track time without any real plan. Maybe I spend an hour on Amazon or in front of YouTube or sorting out screws in my hardware drawer. These are voids of time that I follow without any real plan. Whenever I catch myself doing that, I log in as unintentional time. I find the reporting of this to be helpful. When I see unintentional time trending up, it’s a warning sign that I need to look at what’s going on.

I have several friends that, upon learning how much time I track, think I’m crazy. They usually don’t say it to my face, but I can see it in their eyes. The significant benefit for me is getting feedback on where I’m actually spending time. It lets me identify time traps where I’m spending more time than I thought and points out areas of my life that may lend themselves to things like automation and delegation. The trick for me is not to worry too much about the minutes and think more about the hours.

There’s a lot more time tracking, and we covered it in depth in this week’s episode of the Mac Power Users. We’ve also covered it in the past on the Automators and even the Focused podcast if you’d like to learn more.

Note to Self: I Still Can’t Multitask

Just yesterday I was working on something and received a call from an old friend. I forgot to turn on my Focus Mode so the call came through. At that point, I had two good options and one bad one. I could have politely asked to reschedule the call or stepped away from my computer and just talked to my friend. I also could have decided to multitask. I chose poorly. I said to myself, “Self, you can totally talk to this friend and continue this work. You got this.” So off I went for a while, multitasking.

Then I hung up and thought about the advice I gave my friend, that wasn’t as good as it could have been … because I was multitasking. Then today I discovered that the work I was doing at the same time had some errors in it … because I was multitasking.

I think the next time I catch myself multitasking, I’m going to slap myself.

Important and Urgent

I’ve been thinking a lot lately about my work. One of the advantages of journaling is that it gives you a way to check in with yourself and find out what’s on your mind. Sometimes that feedback isn’t all positive. A few months ago, I went back and read several journal entries. What surprised me most was the sense of urgency that seemed to permeate nearly all of my recent journal entries.

Somehow, I’d drifted into a mindset where every day felt like a race for my life, and my journal entries reflected that. The Eisenhower Matrix explains that we can put most things in a two-axis grid.

Eisenhow Matarix.jpg

If you ever go down the rabbit hole of productivity literature, this is one of the first things you’ll stumble across. The critical point here is that the Important/Unimportant axis is entirely separate from the Urgent/Not Urgent axis. Indeed, one of the big lessons of the Eisenhower Matrix is that doing important work that is not urgent is one of the best places you can spend your time.

Eisenhow Line.jpg

I knew and understood this, but looking back at journal entries, it became clear that I’d turned the Eisenhower Matrix into the Eisenhower line in my head.

I got in the habit of thinking of all critical work as urgent and all unimportant work as not urgent. This mindset led to all sorts of bad habits on my part:

  1. I was looking at all my important work as urgent. That’s silly. Most of my important work is not urgent at all. Nevertheless, I’d been adding a level of anxiety for no good reason.

  2. With the increased anxiety, I felt more stress than I should. That made me think I should back off so much “urgent” work. Think about that for a moment. I told myself to do less critical work because of this urgency/important trap I’d laid for myself. I was tying myself in knots over that because I’d forgot to separate urgency from importance.

  3. I had some small personal items fall through the cracks. They were not essential tasks, but they had some urgency. My linkage of priority with urgency worked in the opposite direction, too, at my own peril.

The truth is that there is no relationship between importance and urgency. Those are two attributes entirely separate from one another. So I’ve taken steps to disabuse myself. Specifically, I’ve added to my journal prompts the question, “Where have I created false urgency?” Forcing myself to answer that question daily has helped, and things are more in balance again. I’ve turned the line back into a matrix.

So often, we get hung up on little things like this that wreak all sorts of havoc. The difficulty isn’t usually course-correcting once you find the problem; the difficulty is noticing and identifying the problem in the first place.

Useful Complexity

I’ve been thinking about the many emails I have received about my recent posts about my status board. I wrote about this on Monday, but that only spurred another round of email from folks that can be summarized as a concern for useless complexity.

In summary, I already have systems to manage projects and tasks, but recently I’ve been using a personal status board to give me an overview of what’s on my plate and its current status. This is all data already in my existing systems but not as accessible to my visually-biased brain as a big diagram.

All of these folks writing to me are not coming from a place of criticism so much as legitimate curiosity. Why would I add one more thing to managing projects rather than spending that time doing projects? From my perspective, this status board was born out of frustration (and underlying anxiety) that, despite my systems, I didn’t have a way of quickly seeing everything and where it stands. I have many oars in the water, and the various threads of my life are very different. I added the complexity of the board to address this problem. The status board is, for me, what I would call ”useful complexity”.

I understand the drive for simplicity. A simple solution is, nearly always, superior to a complex one. But at the same time, a simple solution can also only get you so far.

While in law school, I had one job: stay in the top 20% and keep my scholarship. I thought about it every day. I didn’t have a job. No wife. No kids. Really no commitments except testing in the top 20%. To make things even more interesting, in law school (at least my law school), there was only one test at the end of the semester. Particularly at the beginning, I had no idea if I was any good or bad at being a law student. None of us did.

So with a single goal every day, my system was pretty simple. I wrote three things down on my napkin each morning. I stuck it in my pocket. I didn’t go to bed until they were done. Trust me, I came to appreciate the benefits of simplicity during those years.

Now my life is much more complex. I have clients that rely on me, customers that buy things from me, partners and team members that depend on me, and a family that needs me. Complexity in obligations begets complexity in management.

Ultimately, that led me down the road of creating one more bit of complexity in how I manage my projects. It was not some desire to fiddle, but a genuine need for another tool to make sure I don’t blow it.

Whether something like a status board makes sense depends entirely on where you exist on that spectrum between 1991 and 2021 Sparky. I think the real lesson I’ve taken from all this feedback is not to be afraid to add useful complexity, provided it is actually useful. So long as the bang is bigger than the buck, you‘re okay. I probably spend less than 30 minutes a week managing the status board, and in exchange, I no longer feel that where-the-hell-is-everything anxiety.

Maybe one day, things will slow down for me, and I will be able to turn the complexity knob down with some of these tool. But for now, they are making me better, not worse. My lesson is not to be biased toward simplicity or complexity but instead to be intentional about where I draw those lines for myself.

Where are you drawing those lines? Are you always looking for the most complex solution? Are you worshipping at the church of simplicity only to fail at your commitments? These are both slippery slopes and only something you can manage if you pay attention.