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?

Why I’m No Longer Practicing Law

The title says it all, but first a little background…

Project Blue Sky

In January 2021 I started a new project and gave it an exciting name: Project Blue Sky. Specifically, I started the year tired of what I call “running downhill.” Do you remember when we were kids, and we’d start running downhill? It was exhilarating but also terrifying. It just took one slight stumble to end up flat on your face.

Simultaneously running MacSparky and the law practice has felt like running downhill too often, and I’ve been doing it now for 15 years. The idea behind Project Blue Sky was to find a way to create more balance between these two careers so I could have more margin. I felt like a fraud going on the Focused podcast and telling people how important it is to get focused while struggling to hold it together myself. I was fortunate to have two things that I enjoyed and could earn a living at. At the same time, I wasn’t getting the most out of either of them because of the existence of both of them. This is not a new problem to me.

I hadn’t gone over the precipice, but I could feel it approaching. The warning signs were there. I broke a few promises to law clients and MacSparky partners. I kept getting delayed on essential projects because something from “the other side” intervened. Most importantly, I felt I had no time to step back and breathe.

So for the past year, Project Blue Sky has been part of my life. It’s led to me hiring some additional people and making some changes for the better. It’s led to me saying “no” to some big client projects and interesting MacSparky projects—all in the hopes that I would be running downhill less and have more blue sky.

Make no mistake. This has been a serious effort on my behalf. I see Project Blue Sky nearly every time I open Obsidian and OmniFocus. Sometimes, however, it felt like trying to stop a blazing inferno with a squirt gun. I had some limited success with these steps, but as I got to the fourth quarter of 2021, it was evident that I was still running downhill a lot, and Project Blue Sky was going to take longer.

The Creator’s Guild

There’s another influence that I haven’t mentioned before. A few years ago, I started having a weekly meeting with a group of friends that make things for the Internet. We call ourselves “The Creator’s Guild,” and we spend an hour together every week, critiquing and propping one another up as we all try to make our way in this world of online teaching.

My running downhill problem came up during one of our meetings after the DEVONthink Field Guide was released. Specifically, I was lamenting that the Field Guides are the most important thing I make, and I was only going to release one in 2021, despite my Project Blue Sky efforts. So my friends challenged me to come back the following week with a solid plan to make more time to make the things I love.

I remember ending that call and thinking to myself how I already had the answer. I decided I’d scale the law practice down by 25%. I looked at it as another dent in Project Blue Sky and a way to report progress to my friends. But I promised more than an answer to my friends. I also promised I’d go through the process of thinking it through. If I’m being entirely honest, I just wanted to go through the motions so I could assure my friends that I’d done so. I felt I’d already reached a safe conclusion. Twenty-five percent less legal work felt like one more fair compromise.

Showing My Work

So I blocked aside some time and sat down to show my work.

A few months ago, I wrote about a good book, “Ikigai”. one of my takeaways from that was that some very old, very happy people in Japan all had one thing in common, a sense of purpose, their Ikigai. The book explained how their actual purpose evolved during their lifetimes for many of these folks, yet they still did each have a strong sense of purpose. So I started with a simple question.

“What is my purpose? What am I here to do?”

Simple question, right? Simple, but also not easy to answer. Rather than get lost in the big question, I moved on to consider the law practice and MacSparky.

My father was actually against me becoming a lawyer. He thought it would compromise me morally. But at the time, I was pretty sharp, pretty good at debate, and I wanted to do it. Looking back, I think I was also hung up on the trappings of being a lawyer. Before me and my sisters came along, no one in the prior generations of my family went to college. I grew up very much blue-collar.

Once I got into the career, however, I found I was pretty good at it, and I was able to practice on my terms and do some good. What I like most about being a lawyer, after seven years of training and 28 years in practice, is helping people with their problems.

Considering my law practice, I also realized that being a lawyer had become a comfortable part of my identity. Perhaps too comfortable. My recent post about being and doing did not arise from a vacuum. Moreover, being a lawyer for me is safe. I’ve got an excellent group of clients that take my advice and pay their bills. I could easily practice law for the rest of my life with little risk of not being able to make a living. Being a lawyer also comes with costs, including worry of making a mistake, getting paid, and the remarkably dreadful people you must sometimes confront.

Being a lawyer is not easy work, and you do carry the weight of your clients’ problems constantly. Even after practicing for 28 years, I still wake up in the middle of the night thinking, “how am I going to get client X out of that sticky problem?” The pandemic only put an exclamation point on that. I spent so many hours fighting for clients through the pandemic.

Where I became a lawyer with years of training and intentionality, I became MacSparky by mistake. I felt like I had something to share, so I started sharing it. There was no long game or master plan. Things came to me one step at a time. A few articles became a podcast appearance. A few podcast appearances became speaking gigs. It took me six months to commit to Katie before we started producing the Mac Power Users. The growth of my MacSparky business has all been a series of fortuitous and delightful accidents.

So with no planning, I find myself in this place where I get to help people and make a living at it at the same time. When I stop to think about what my life would be like if I hadn’t stumbled into becoming MacSparky, I shudder.

Concerning money, the law is the sure thing, and MacSparky is more of a bet. Continuing to make a living as MacSparky requires me to continue to make outstanding products that people want. Walt Disney once said, “We don’t make movies to make money. We make money to make more movies.” When it comes to the stuff I release as MacSparky, that’s me in a nutshell.

What stands out to me most when I consider my life as MacSparky is how much more I have left to do. I have so many ideas and so much more that I’d like to explore and share. I’ve been talking for the last year about contextual computing. I think this can change people’s lives, but I never seem to be able to get enough time to put enough attention on it. I’ve got other ideas that I would like to share and teach.

This sense of unfinished business stood out for me as I considered my two careers and started thinking about how I would report back to my friends in the Creator’s Guild about what I would do.

At one point, I asked myself if I got hit by a bus and was lying on the side of the street, where would I want more time: as MacSparky or as a lawyer? The answer was clear and immediate. I have so much that I want to still do as MacSparky. I’m good at being a lawyer, but I don’t feel like I have anything left to prove.

That led me back to the question I wrote when I first started this process, “What is my purpose in life?”

The answer to that question is different for everyone. But it is clear to me that my purpose in life right now is to produce MacSparky content. Helping people find a way to use technology to their advantage and, in turn, help them with their purpose (their Ikigai) makes me jump out of bed in the morning. There was a time in my life I would have answered that question differently, but when I’m honest with myself, these days, I am here to do MacSparky work.

It was liberating admitting that to myself. I knew it at some level, but I hadn’t done the work of really figuring it out. With this in mind, I went back to my options.

New Options

For example, what if instead of getting rid of 25% of my clients, I got rid of 50%? What if I cut the law practice in half? What could I do as MacSparky then? The interesting thing about pulling these questions apart is the answers they return that are surprising at the moment but utterly predictable in hindsight.

Being a lawyer has certain costs associated with it. It’s expensive. You have to pay license fees, education fees, rent, insurance, and other expenses to run a practice. It also requires a lot of time. Whether you represent one client or five hundred clients, you need to keep up with changes in the law and be on top of the ever-changing legal climate. You also need to be available whenever a problem arises. Finally, it comes with an emotional cost. I don’t wake up worried about Field Guides. I do wake up worried about clients.

Once I’d thought about going from a 25% to a 50% reduction, it was only a matter of time before I asked myself what it’d be like if I reduced the law practice by 100%? What if I hung up my fancy leather briefcase and gave everything to MacSparky?

The Surprise Ending

You probably saw this coming, but I assure you I did not. Just for a moment, put yourself in my shoes. I spent 35 years in pursuit of and the practice of law. If you had asked me when I sat down to begin this exercise (that I considered a formality at the start) if I ever contemplated ending my law practice, my answer would have been an immediate, “No!”. I’d never really permitted myself even to consider something so crazy. Nonetheless, in very little time, I found myself seriously contemplating and ultimately deciding that the proper path for me was not to get better at riding two horses but instead to ride just one.

Why am I here? I am here to make MacSparky content.

As I write these words, I am no longer a lawyer. I am just … well … a MacSparky.

I’ve spent the last few months shutting down my legal practice. I’ve made arrangements for my clients to get to other lawyers that can take care of them. I’ve spoken personally to all of my clients to explain why I can no longer be their lawyer. I’ve spent a lot of time on this transition, but I wanted to end this phase of my life in the right way.

Having now had to explain myself to clients, friends, and family members, I’ve faced a variety of responses. Some are incredibly supportive. Others are worried about me. Some are skeptical of my ability. Even a few are angry at me. Maybe a few years ago I would have cared more about what these people think, but I find that none of it has made a difference in my thinking.

I fully understand I could crash spectacularly (and publicly). I am okay with that. I’m no longer interested in compromise. I would rather pursue MacSparky as my only thing and fail than not attempt at all. Not taking the shot would hurt way more than taking the shot and missing.

So here goes. No longer do I split my time between two careers. For the first time since 1992, I will have complete control of my schedule. No longer will a client emergency force me to set aside the work that has become my calling. I’m all in, and I have big plans.

To begin with, I’m turning up two dials on my MacSparky work: quality and quantity. With me able to give this my sole focus, the content is going to get better, and there will be more of it on this blog, in the podcasts, in the Field Guides, and in everything else I ship as MacSparky. I can’t wait to get started.

If you’d like to support my work, I’m also opening up a membership program, The MacSparky Labs. One thing about my MacSparky work is that I’m constantly trying out new apps and workflows. Much of that never gets published. Historically I couldn’t share it because I have so much confidential client data. My data is no longer full of confidential client matters, so now I can let you behind the curtain a lot more. In other words, I can let you into the MacSparky labs with a bunch of exclusive content and early access to what I’m up to, planning, and experimenting on. You can learn about it at MacSparky.com/join/. Regardless, I appreciate your support.

If I were to break my life into three parts, I’m now at the age where I’m about to begin the third act. I wouldn’t be able to take this journey without you. Thank you!

I’ll be talking more about this big move on today’s episode of the Mac Power Users and tomorrow’s episode of Focused. I also made a video about my big move.

Year-End Reflection Prompts

There is something therapeutic and hopeful about hitting January 1. While I’m not one for new year resolutions, I’m a big fan of year-end reflections. Before the year ends I always try and stop and collect some wisdom from the year prior. For me, this involves some journaling. You can do this with fancy pen and paper or in a text file. The important thing is to get these thoughts out of your head and on a screen or piece of paper so you can examine them closer and from different angles.

Here are my year-end prompts in no particular order:

  • What went right this year?
  • What went wrong this year?
  • Where did I make progress?
  • Where did I fall behind?
  • What should I have done differently?
  • Where did I stand in my own way?
  • What gave me the most energy this year?
  • What took the most energy from me this year?
  • What was my biggest mistake?
  • What was my best move?
  • What brought me the most joy?
  • How did this past year show my character?
  • Summarize this year in a sentence.

You don’t have to answer all of these. (You don’t have to answer most of them.) But spending some time thinking about the ones that resonate with you may help you head into 2022 with just a bit more wisdom.

My Six Month Planning Wallpaper


Sample Planning Wallpaper Mac Main 2019-07.jpg

I talked about planning wallpaper recently on Focused. I’ve been doing this for a few months now and find it a good way for me to keep my big projects rolling. All of these items are already in my calendar. I know these dates in my head. I think about these plans all the time. Nevertheless, the reason I go to the trouble of putting this on my desktop is to give me a nudge when I need it most. As part of my monthly review process, I open the file, delete the past month, move the others around, and add a new month to the end so I’ve got an updated planning wallpaper heading into the new month. I have multiple monitors but just keep this on my iMac, center screen.

The quote at the top is from my friend, Merlin Mann on one of his podcasts. (I have no idea which one.) I first saw it in a wallpaper designed by Chase Reeves (but I can’t find it anymore). Regardless, it still inspires me when I’m feeling the resistance. Merlin does have a knack for words. I used a chisel because I felt that was the tool that best represents the sentiment. If you wanted to modernize it, a jackhammer could also work. Grin


Screen Shot 2019-07-05 at 1.49.19 PM.png

Several folks asked me to share the wallpaper so here is a version of it. I’ve included the OmniGraffle project below. If you spent a little time on it, you could recreate something like it with Preview, but it’d be more work. Rather than make this a full sized desktop wallpaper, this is actually much smaller. I just center it on the screen and then, on my Mac, match the background color of the rest of the desktop to match the background of the text. Enjoy.

Planning Wallpaper OmniGraffle File