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.
PKM Toolkit: End Your Day With This Powerful Personal Review Question
After a lengthy absence from daily personal review, I decided to revisit my four-question Day One review template that I put together a few years ago. In the last few editions of The Journaling Guide, my bi-weekly newsletter, I wrote about how the changes in my life, particularly returning to work, influenced my decision to give it another try. It’s been going well, and I’m pleased to take a few minutes at the end of each day to build this habit.
These are the questions in the prompt:
What happened today that went well?
What happened today that could have gone better?
How did I make a positive impact on those around me?
Is there anything unfinished or that needs to be written down for tomorrow?
Of the five questions, the most valuable one for me right now is the last one, where I ask if anything needs to be written down for tomorrow. This simple question unburdens me of something, and there’s always something I didn’t get to or forgot about. It means one less thing swirling in my head and helps me continue to hone my organizational skills.
I’ve written and talked a lot about gratitude journaling, which I have done daily for years. When asked by someone interested in starting their own journaling habit, my go-to advice is to start by writing a sentence or two about something they feel grateful for and repeat it at an interval that works for them. I haven’t dispensed as much advice about the daily review, mostly because I’ve not been a regular practitioner. However, this experience has me again seeing the value of the process, and particularly of including this question in it. It’s an extremely valuable way to move something from a mental burden to a planned task.
If you’re interested in a daily review process, try these questions and commit to a two-week trial. Find yourself a notebook or journal, or start a note or document on your phone or computer. Take five or ten minutes at the end of the day to reflect on how things went.
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.
Basic AF #47: The Journaling Guide with Joe Moyer
I was pleased to return to the Basic AF Show and discuss journaling. This is my second guest spot with my friends Tom and Jeff (the first one here), and once again, they made me feel welcomed and valued. From the episode page:
_ Ever wondered if journaling could make a difference in your life? This week’s guest, Joe Moyer, believes it can. Joe shares his personal journey with journaling and practical advice on how to build a habit—even if you only have five minutes a day. We cover gratitude journaling, the benefits of recording daily thoughts, and how to avoid the “perfect journal” trap. He also provides tips for those who are new to journaling, with simple techniques to get started._
This was a fun conversation, and I hope you’ll listen. I think everyone, particularly young men, needs to hear some of what was said on the show and pay particular attention to the productive struggle, where we talk about being kind to ourselves, working through complicated feelings and emotions, and growing.
The Ugmonk Pen
I’ve never been a fancy pen guy. I always used a Pilot G2 or a Uni-ball 207 for my writing, but lately, I’ve found them to be a little lacking.
I wanted a pen that felt more significant but had a similar gel ink output, so I began casually looking. When I got an email last month from Jeff Sheldon announcing The Ugmonk Pen, made in collaboration with Leuchtturm1917, it was an easy buy for me.
I also picked up the walnut pen tray, which is a thing of functional beauty and is where my Apple Pencil often lives as well.
The pen and tray combo arrived just in time for some heavy use, not for writing or journaling but for a bunch of lengthy insurance-related documents that, due to poor design, needed to be printed out and handwritten. It took hours to do it all, and it was made more pleasurable and easier with the Ugmonk Pen. I’ve since used it for some print journaling and to-do list building, and it’s really delightful to write with.
I believe that the message matters most, and the tools we use, particularly in journaling, should serve that cause. This pen does that for me, and I’m pleased to have finally spent a little bit more money for something of much greater and lasting quality.
This reflection originally appeared in The Journaling Guide. Delivered every two weeks and packed with real-life stories of history's greatest journalers, reflections from my own experiences studying how journaling helps improve our lives, and actionable insights for you, it's like having a close friend guide you on your journaling practice.
Sign up today and I'll send you my valuable quick guide, Seven Thought-Provoking Prompts for Your Journaling Practice, when you confirm your email.
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.
The Journaling Guide on Threads
I’ve been on Threads since it launched. My focus has been on sharing prompts, tools, and tips to help people with something I’m really passionate about, starting and growing a journaling practice. I know some of you like to journal. If that’s you, please give me a follow and say hi!
Don’t worry, I’m not abandoning this site to spend all of my time on social. Threads is (thus far) a positive community that I enjoy. It’s also a place where I can workshop new ideas and connect with readers of this site and other creators.