From Survival Mode to Structured Planning: Building a Quarterly Review Road Map
I’ve been at my new job for about six months. As anyone who’s ever started anything new, it was a process of intense learning and adjustment. Thanks mostly to when I started, during cold and flu season, everyone in my family (and on the management team I lead) has been sick more than I can count. It was pure survival mode for most of the winter, with little time for creativity or writing and even less time for keeping organized and doing any personal review.
Oh, sweet relief, spring is here, despite the random snowstorm that dumped four inches as I write this, and with that comes another quarter. Life is happening at a slightly more manageable pace, and it’s time for me to recommit to being more organized and having time and space for reflection and planning.
My experience with quarterly reviews has been mixed. I’ve either tried to do too much and failed because it was too heavy a lift, or I’ve gone super casual, written a few things down, and basically forgotten all about it until the next quarter rolled around. With this in mind, I’ve created a new quarterly review process. This new simple is built to keep me on track with three different elements. Because of my love for journaling, I’ve decided on Day One as the primary tool for this workflow.
The Process
The first step is to complete the review. I’ve broken it into three entries, and they include:
A journal entry looking back: Pure reflection on how the quarter went, what I learned, how I felt, where I was successful and where I wasn’t, and the relationships that had an impact.
A journal entry looking forward: Part hopes and dreams, part reflection on what I learned, what happened, and how it applies to what I want to do.
A journal entry roadmap: I am, by trade, an operations person, so this is where the planning happens. What actions will I take to get where I want to be? Each area I’ve written about gets a headline, and after some thoughtful planning, I write actionable steps to help me get there.
Then, there’s a deadline:
The three journal entries that comprise the quarterly review must be done by the seventh day of the first month after the quarter hits. Another thing I’ve been reminded of being back in my day job is that periods, particularly in finance, don’t “close” right away. There’s accounting to be done, numbers to run, and things need to catch up. The seven days give the quarter and me time to breathe. This deadline will also usually catch a weekend, when I have more time to do this successfully.
Finally, there’s an ongoing weekly call to action to review my progress:
To accomplish this, I have a once-a-week reminder and calendar event to review the quarterly road map. At the bottom of this journal entry, I’ve added an area to leave comments or feedback on how I’m doing. This will empower me when it’s time to do my next quarterly review with insights into the process, what worked and didn’t, and how I did overall. In addition to having this on my personal calendar with a reminder, I also have it on my work calendar as a blocked 30-minute time at lunch. I’m setting myself up to honor my commitments, which are often the ones we are most likely to ignore when things get challenging.
I did this new review for the first time over the last week and like the process. It took me less than two hours, and my check-in took me about fifteen minutes when I did it. I operate well with structure like deadlines and check-ins, and this feels like a good way to approach something I’ve struggled with keeping up with by forcing myself to be accountable to the calendar and to myself because, at the end of the quarter, I’ll see which weeks I was able to complete my call to action review and which weeks I couldn’t.
I’m building this quarterly review process because I’m tired of figuring things out by reading the tea leaves. I think a system like this will help me succeed in planning my next steps, permit me the time, space, and data to review what happened in the previous period and help me make better decisions about where to go from here. It also suites my schedule and desire to do a journaling based review. I’m planning an update next quarter and will share with you how it goes.
Day One Improves iOS Navigation — And I Love It
It’s been a busy month at Day One. In addition to launching a Windows version, which I wrote about yesterday, they’ve also been working to improve the iOS and iPad apps.
From the announcement:
“Our latest update for iOS brings a major redesign to Day One’s navigation, making it easier to manage journals and revisit past memories.
With a refreshed layout, this update introduces a more intuitive way to access your journals and key features. Whether you’re organizing entries across multiple journals or revisiting past moments, the new navigation ensures everything is right at your fingertips.”
I found the previous navigational elements clunky, and once Journal from Apple rolled out, features like On This Day needed some love. This redesign has improved all of that, and it looks great.
“As part of this update, we’ve introduced two new tabs—Journals and More—to simplify navigation. The Journals tab keeps all your journals in one place for easy access, while the More tab organizes key features like On This Day, Daily Prompt, and Streaks in one convenient hub.”
The term hub perfectly describes what the More tab feels like. I know that if I want anything other than direct access to one of my journals, it’s over there in a visually appealing and easy-to-navigate space.
They’ve made some small cosmetic improvements to the Journal tab that I really appreciate, like adding a small colored notebook icon next to each of my journals and the ability to reorder how the journals appear in the menu bar. That second feature may have always been available, but with the previous design, I felt no desire to explore the menu. It was mostly functional, but not especially appealing.
I haven’t played with the new iPad version yet, although it also looks promising. I’m heading out this weekend to get a new iPad to replace my now six-year-old iPad Air 3. I’ll share my thoughts on the iPadOS updates soon These navigation and layout changes are a positive step in Day One’s evolution, and I’m glad to see them iterate on the good work they’ve put into their app over the years.
Day One Launches for Windows
Last week, Day One founder Paul Mayne announced that my favorite journaling app is now available on Windows.
Based on the launch video, it looks like a solid and well-designed experience with all of the features you’d expect from the app. They’re giving free access to this version, so it won’t count against any device limits. This is a smart way to get people to try it.
I may download it on my work laptop and kick the tires without logging into my personal account. This is one of those times when having a demo Day One account would be very helpful.
The 2024 Gift Guide
'm pleased to share the second annual gift guide here on 24 Letters. While this one is shorter than last year's, it still reflects items I use regularly or hope Santa will put under the tree for me this year.
Books
The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living by Ryan Holiday and Stephen Hanselman
This book feels timeless. It features a daily quote from one of the ancient Stoic philosophers and a modern reflection from Ryan that compliments the selection. I read it daily and recommend it often.
Kitchen Confidential: Adventures in the Culinary Underbelly by Anthony Bourdain
This book transformed Tony Bourdain from an unknown NYC chef with a passion for prose to an international culinary, literary and television star. I reread Kitchen Confidential this year for the first time since its release, and it holds up. I miss Tony, and appreciate his vast body of work whenever I can.
Slow Productivity: The Lost Art of Accomplishment Without Burnout by Cal Newport
The three big ideas in Cal Newport's latest book are simple: Do fewer things, work more naturally, and be obsessed with quality. These ideas are simple but not exactly easy to execute. With Slow Productivity, Newport offers a roadmap for slowing down, avoiding the overhead tax, and balancing intense focus with periods of rest.
I like the noise-cancellation features of my AirPods Pro 2, but I don't always like how snug they feel inside my ears unless I’m doing someting in a crowded area where I needed additional support in staying focused.
These AirPods seem like a happy medium, as they still sit in the ear and offer some noise cancellation with a more comfortable fit.
Somehow, my household managed to use Amazon Fire TV Sticks for our streaming for years, despite my fandom for all things Apple. Over the last year or two, motivated by aging hardware and the sudden and annoying appearance of ads that auto-played on startup, I switched us over to Apple TV devices, and we've been much happier since.
I enjoy the tight remote integration with my iPhone, the ease of connecting with the Apple devices we all own, and the pleasant and easy-to-use interface.
I've been streaming Apple TV+ since it launched and have watched many shows on the network. It's small but has released some shows that continue to be my favorites. Ted Lasso, Slow Horses, Bad Monkey, Severance, The Morning Show, Trying, and many more have made this streaming channel one that I thoroughly enjoy.
I use Day One all the time. It's been my regular digital journaling tool since 2017, and I've used it off and on since 2012. I like the ease of creating multiple journals, the cross-platform approach, the solid backup scheme, and the ability to easily add photos and metadata to any post. Day One is free to use, with subscription options to unlock more features.
I hope this little gift guide helps with some ideas for friends and family, or provides you with a few suggestions to give to that sweet aunt who always gets you socks. Send her here, maybe I can help! Happy holidays!
Note: Some of these items include an affiliate link, meaning your purchase may help support this site. I've only included things in this list I actually use, like, recommend, or hope Santa brings me. As was the case last year, there are no big screen 4K TVs or air fryers here (although my wife and I are tempted by both!).
The Day One Podcast Returns
Despite being an active daily user of Day One, I was unaware they had a podcast. It’s been on hiatus since 2021, and that’s likely part of why I hadn’t heard about it.
The show has recently launched a new season with a new episode featuring Paul Mayne, the creator of Day One. It’s worth listening to if you’re curious about some of their choices with the app, the additional resources they’ve gotten since joining Automattic, where AI fits into the roadmap, and other details on what motivates the developers to keep going.
600 Days of Gratitude Journaling
Yesterday, Day One let me know that I had written my 600th consecutive entry in my daily gratitude journal. I'm proud of this achievement and hope it inspires some of you to start your journaling practice.
Like many apps, Day One likes to celebrate streaks to stay motivated and keep going on a goal. Streaks have a place in helping us build the version of ourselves we most want to be, although I have mixed feelings about them.
I'm sending more thoughts on the pros and cons of streaks to newsletter subscribers next week. You can subscribe below, and I'll send you my quick guide Seven Thought-Provoking Prompts for Your Journaling Practice, when you confirm your email.
If you haven't checked in on the newsletter lately, you’ll note that I’m refocusing it on journaling and working towards sending something to subscribers every two weeks. I'll have more on that soon.
Day One Introduces Shared Journals
From the Day One Blog:
“Today we’re excited to introduce Shared Journals in Day One, a new way for you to safely share life’s moments with friends and family, while upholding the privacy and security you trust.”
As a long-time user, I’m excited that Day One has added this to their app, thus continuing to set themselves apart in the digital journaling space. One of the best aspects of this service is while the creator of the shared journal needs a premium membership, anyone with a free membership can join.
Shared Journals are end-to-end encrypted, and adding or removing members is easy. Members can also comment on posts, which mimics what can be the best (and absolute worst) part of social media.
I'm going to try setting up a shared journal with my wife where we can document memorable moments with each other and our family that we want to share. This may be the opportunity I've been waiting for to get her interested in exploring a regular journaling habit, too.
Apple Launches Journal for iPhone
With the release of iOS 17.2 earlier this week, Apple launched Journal. I spent some time with the new app last night, and my initial thoughts are positive. I will share more after I’ve had a chance to kick the tires.
Today, Day One, my journaling tool of choice, announced support for Journaling Suggestions. This is a keystone feature for Apple’s Journal, so it makes sense that Day One would add it as well.
Today we’re excited to announce a new way to deepen your journaling practice: Journaling Suggestions. Journaling Suggestions in Day One provide personalized journaling recommendations inspired by your photos, locations, activities, and more, bringing a whole new level of introspection and discovery to your daily reflections.
Everything I’ve read from the folks at Day One about Apple’s entry into this space has been totally classy. Last summer, I shared Day One’s founder Paul Mayne’s thoughts on Journal when it was announced.
Rather than seeing this as competition, we embrace Apple’s entry into digital journaling as a testament to its growing importance. This evolution is not just beneficial for Day One but also for our valued users.
I believe that journaling can improve people’s lives, and having an app included on a phone that’s in about a billion and a half pockets worldwide means more people will start a practice. That’s a really good thing.
Analog vs. Digital: Results From My Journaling Format Poll
I recently conducted a poll on Threads and asked folks about their preferred journaling format. I offered three options: print, digital, and hybrid.
Print was the winner with 47%. Unsurprisingly, given the results, the comments largely favored pen and paper. One user shared that writing by hand helped them remember what they had written, and another said it was about the art and connection with the tangible nature of paper.
Another respondent shared the challenges she faces when attempting to write in a new journal and said she preferred the ease of editing digital journals for that reason.
I wrote a post entitled Your Story Matters: Overcoming the Perfect Journal Fallacy for those facing a similar struggle around getting started in a paper journal. It's a common challenge, and given how popular analog journaling is, I wanted to share something encouraging.
For my journaling practice, I fall into both groups. I use Day One for most of my regular journaling practice. I use a Subtle Notebook, and a Field Notes Memo Book for my analog needs.
Whatever tool you're using, remember this: the most important aspect of journaling is doing it in whatever format most likely to help you succeed.
Paul Mayne, Creator of Day One, on Apple’s Journal App
Day One Creator Paul Mayne shared his thoughts on Journal, Apple’s new iOS app coming later this year.
From the Day One blog:
Rather than seeing this as competition, we embrace Apple’s entry into digital journaling as a testament to its growing importance. This evolution is not just beneficial for Day One, but also for our valued users.
I’m thankful that Day One and other apps will be able to access the Suggestions API. I remain curious what exactly that will look like, but it’s always fun to see how app developers take these API’s and run with them in ways that best suit their users.
You can read Paul's whole post and what I wrote about Journal earlier this week. Apple releasing this app will get more people into journaling, and that's a win. Most people I've encountered who journal are better for it, and those who don't could find so much value in starting a practice.
David Sparks on Journaling as a Maker, a Manager, and a Consumer
Last week I wrote a piece for the Finding Focus series about the benefits of waking up early and quoted podcast host and MacSparky Labs founder David Sparks' idea that, as creators, we should make before we manage.
David wrote more on this idea a few years ago and shared his thoughts about how being a maker, a manager, and a consumer impacts the purpose of his journaling process. He writes about the evolution of his journaling:
My purpose in journaling is tracking how I'm spending my time in these roles. I don't view any of them as inherently good or bad. The magic is in the balance. While making is most important to me, both managing and consuming enable making. I want to spend more time making than consuming. I need to spend time managing, but not go down the management/productivity rabbit hole so far that I don't make anything.
So with this in mind, I've been focusing my journaling lately not so much on what I had for lunch, but what I make, manage, and consume. Using tags, I can then see it on a daily, weekly, and even monthly basis. If I look at my week and realize I spent most of my time sharpening pencils and sorting tasks (manager) and not enough time producing content (maker), I know I need to make changes. You can get similar information by tracking your time, but I think there is something more concrete looking at a list of things you've made, managed, and consumed over a period of time.
David suggests using Day One and assigning a tag to each role as an effective way to aid in planning and review. More good advice from someone who, to quote another often used Sparks phrase, pays for his shoes as a self-employed creator.
A journaling practice is a powerful way to see where and what you've been doing. Of course, your journal cannot predict the future, but you can certainly use it to forecast where you might end up.
I’ll be doing more writing about journaling here and in the monthly newsletter. The April issue focused on the topic and offered some ideas on how to get started or stick with your own practice. You can subscribe here if you’re interested. Just be sure to check your email (and spam folder) for the opt-in confirmation that’ll get sent. If you're interested in the April issue, let me know and I’ll get it to you.