The Perils of Streaks

A few days ago, I broke a long streak in Readwise. Frankly, it was a relief. A popular feature in applications these days is streaks. Apps keep track of how many days in a row you use it, and, like a monkey, you get invested in that integer. Before you know it, you’ve got this long streak and feel you must keep it going. But generally, streaks are beside the point. They become an artificial source of stress for no reason.

Many apps these days feature some streaks system to try and make sure you touch the app every day. This isn’t just true for creepy social media apps. Plenty of productivity apps are in on the action, too.

This “don’t break the streak” mentality is table stakes for most habit apps. These streaks can quickly become a weight around your neck. You get more invested in continuing the streak than the actual benefit of the visit. In the case of Readwise, I found myself tempted on busy days to click through the daily quotes without really meditating on them because I didn’t have much time, but I didn’t want to break my streak. Why not in that case take the day off and not worry about an artificial streak? Generally, when I’m working on a habit or trying to maintain a daily practice, I am much more concerned about missing two days in a row than I am about keeping up a streak.

It is for this reason that I turn off streaks whenever possible. Instead, I have a repeating task in OmniFocus with gentle suggestions like “consider reviewing Readwise”. Don’t become a slave to your streaks. Don’t be a monkey.

The Morning Routine Journal Template

A few months ago, I did a webinar about how I journal. Since then, several folks have asked for copies of some of my templates. The first one I want to share is my Morning Routine template. I look at, and fill in, this one nearly every day.

My Morning Routine Template

  1. Daily Priority
  2. Morning Gratitude
  3. Daily Meditation
  4. What’s on My Mind
  5. How will my actions today show my character?
  6. Morning Checklist
    – AM Meds
    – Meditation
    – Journal
    – Blog Post Up
    – Weigh In
    – Brush/Floss

Daily Priority

I’m a big fan of the idea of a daily priority so the first thing I write down is the one thing I want to get done during the day … my daily priority. You’ll be tempted on occasion to write down two things here, but don’t do that. It’s “priority”, not “priorities.” Forcing myself to pick just one thing is a great way to inspire some focus. I usually pick the one thing the night before, but if I didn’t do it the night before, this prompt forces me to do it first thing. Very rarely do I fail to get the one thing done. I think it is this process of writing it down is where the commitment becomes real for me.

Morning Gratitude

Getting caught in a negative loop any more is so easy. I try to avoid that trap with gratitude. I find taking a few minutes to think about something I’m grateful for every day really helps me start the day right. For bonus points, try to never repeat a gratitude entry. Find something new each day. You’ll surprise yourself.

Daily Meditation

Every day I find something inspiring to mull over. For everyone this is different. I have friends that will use a bible verse. For me, the daily meditation usually arises from my morning review in Readwise, my spaced repetition system.

I don’t just block and copy, though. Instead, I’ll take a passage and try to summarize it in my own words. I’ll also go back and read it throughout the day. I try to get it to stick for me. I also will journal on it for a few sentences (or paragraphs) on why it is important to me.

What’s on My Mind

This is the actual journaling part of this template. If I’ve got a problem or concern or something I’m particularly happy about or something special planned for the day, I’ll take this time to brain dump it onto the page. This is the section I’m most likely to dictate in this particular template.

I find the process of emptying my brain into the journal gives me a way to examine my thoughts from a different angle. It also helps me let go of anything I’m obsessing on so I can get focused back on the daily priority.

If you wake up with worries or concerns, use this journal entry to work through them. Then when you set down the pen (or keyboard), they have much less of a hold on you.

Some days this section is just a few sentences. Other days it is a lot more.

How will my actions today show my character?

This is in my morning template for a few reasons. First, it’s a reminder that my character will come out in all of my actions. It is too easy to forget that. Second, it gives me an opportunity to keep myself honest. The older I get, the more I realize that moral ambiguity is bullshit. There is a right and a wrong. The more I can be clear about that in my own head, the more I can make a difference everywhere else.

Morning Checklist

I used to keep a morning checklist in OmniFocus but about a year ago I sent it into my morning routine template. These are a few items that I want to make sure to get done every morning. I don’t keep a database or track streaks with any of this stuff. This list is just a gentle reminder to brush my teeth, take my pills, meditate a bit, and get rolling.

We are all different and this Morning Routine list has evolved (and continues to evolve) for me. I hope it gives you a nice place to get started building your own Morning Routine list.

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.