Mid-Year Reflection & Planning Prompts
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The PDF has fillable text blocks, so you can either print it and write in it or download it to type your answers directly into the PDF. I hope you find it as helpful as I have!
I view reflection as a way to practice slow productivity because we’re intentionally taking time to slow down and review our experiences, perhaps learning something new about ourselves and our desires in the process. I’ve written about reflection and shared longer lists of reflection prompts in the past, and today I’m revisiting the two prompts that I’m using for my own mid-year reflection and planning process.
What is Reflection?
The instruction to reflect holds strong across academia, business, and self-development. Yet, regardless of its value, many of us fail to actually follow through on our intentions to reflect.
This may be due in part to the complex double act of reviewing and planning: by definition, the verb “reflect” means both “to bend or fold back” and “to make manifest or apparent.” As it stands, we might simply not know how to do it, why it matters, or we don’t want to waste our thinly-spread-as-it-is time.
In what follows, I break down the “whats” and “whys” of reflection to show the benefits of the practice, describe how to make it work for you, and share with you the reflection practices and questions that are most helpful to me. What better time than halfway through the year to re-see reflection as both an act of “looking back” and a “looking forward”?
The Purpose of Reflection
According to Tracy Kennedy, Lifehack’s Personal Development Expert, reflection offers multiple benefits. As detailed in her article, “How Self-Reflection Gives You a Happier and More Successful Life,” reflection can improve our lives in the following ways:
Improves self-awareness
Provides perspective
Allows you to respond, not react
Facilitates a deeper level of learning
Improves confidence
Challenges your assumptions
In addition to improving our self-knowing and presence, reflection can help us make better decisions when it comes to growth and change. Jennifer Porter, an executive coach, reports in her Harvard Business Review article, “Why You Should Make Time for Self-Reflection (Even If You Hate Doing It)” that:
The most useful reflection involves the conscious consideration and analysis of beliefs and actions for the purpose of learning. Reflection gives the brain an opportunity to pause amidst the chaos, untangle and sort through observations and experiences, consider multiple possible interpretations, and create meaning. This meaning becomes learning, which can then inform future mindsets and actions.
Porter breaks down the purpose of reflection by connecting it to other important ideas and actions: learning, pause, untangle, consider, meaning, and, perhaps most importantly, future. She reports that many of the leaders she coaches actually put off doing reflection, sometimes because they lack an understanding of how to do it or other times because they have not prioritized it. So, let’s learn how to do it, shall we?
A Recipe for Reflection
Although reflection is greatly beneficial for decision-making and planning, it still often ends up on the back burner. I think this is because reflection requires three things: time, energy, and focus.
Time
I recommend that you set aside, and even schedule, time for intentional reflection. The goal is to view reflection as something that serves you, not as one more thing that you’re trying to squeeze in between meetings or forcing yourself to do before bed.
Energy
It’s no surprise that reflection pulls on our mental energy: we are remembering and considering and interpreting. But, I want to note that it may also require emotional energy.
Reflection prompts ask us to think about both the highs and the lows. It is possible for us to get stuck in the quicksand of things we didn’t achieve, heavy feelings like grief, disappointments or embarrassments, or other difficult memories. For that reason, I encourage you to pair questions such as “what didn’t work out well?” with others such as “what went well?” or “what did I feel proud of?”
Here’s a real life example of how this works. When I taught writing to college students, I asked them to reflect after each paper on two things: 1) something they struggled with and improved on, and 2) something that they continue to struggle with. I did this because I wanted my students to know that I did not expect them to become expert writers and researchers in one semester. In fact, I explicitly encouraged them to see the acts of learning and practicing as a continual process.
Focus
You can reflect in multiple ways, including handwriting, typing, and/or sharing out loud with someone else. There’s no right or wrong way to “do” reflection, and while I like the slow rumination of handwriting, typing out my answers allows me to capture more ideas quickly. I’ve done all three, but admit that my favorite reflection process is sharing out loud with someone else.
Less Optimization, More Curiosity
I’m going to share some reflection prompts with you, but I want to chat about optimization first.
You might do the reflection prompts in this post (or the workbook) and then set aside time to develop project plans or update your calendar. You might decide you want to start a new habit or stop an old one. You might have an epiphany and make a big change to the last six months of the year.
Or, you might explore these reflection prompts as a way to get to know yourself better, without any plans to shift the ways you move throughout your days. Any of these options is great because it’s up to you to decide your own purpose for looking back and looking forward.
I usually tie reflection with planning. When we make plans for our projects and set new goals, we may approach our practice with a little too much eagerness. In other words, we could fall for the trap of The Planning Fallacy (underestimating how long a task will truly take us to complete) or we might put way too much on our plate in an effort to ride the wave of excitement and opportunity we feel after a good reflection session.
It’s okay, and sometimes even a nice relief, to reflect purely out of curiosity instead of decision-making or planning. I hope that you find these prompts fruitful, playful, and interesting, and should you decide to shift from reflection to planning, I encourage you to do so with mindfulness and compassion for your capacity. In other words, don’t forget to plan for rest and play!
Prompt 1: Start, Stop, Continue
This is one of my go-to reflection prompts because it’s short but also offers clear instructions for shifts you may want to make. When you reflect on what you want to start, stop, or continue, it may help to select themes for your own life to explore the prompts, like work, creativity, or mental health. Or, you may want to apply it to your life in general as a way to identify your highest priorities for starting new things, continuing to support yourself, or setting new boundaries.
Here’s a short version.
What new practice or approach do you want to start—and why?
What do you want to stop doing, participating in, thinking, or choosing—and why?
What activity, mindset, project, or approach do you want to continue doing or pursuing—and why?
Here’s the longer version.
What Do I Want to Start?
What am I craving?
What am I curious about?
How do I want to spend my personal resources (time, energy, focus, spoons)?
What are three new things I want to try over the next six months?
What Do I Want to Stop?
What actions, beliefs, and/or behaviors are no longer serving me?
Is there anything I’m doing just because I feel like I “should”?
Are there any boundaries I need to set or reaffirm?
How can I bring grace and softness to ending something? (This is important if you feel apprehension or nervousness around stopping a behavior.)
What Do I Want to Continue?
What is bringing me joy and nourishing me?
What are my favorite parts of my day, week, or month?
What matters the most to me right now?
What will be my three biggest focuses for the next six months?
Prompt 2: Choose a Theme Word
I love working with theme words because they provide structure and limitations while allowing me to re-see things through a different lens. If I’m struggling to make a decision, I can use my theme word as a guide to choose an option that lines up with my intentions. If I’m feeling stuck or confused, I can get creative and see how my theme word allows me to reimagine a path forward.
If you already chose a theme word for 2023, mid-year is a great time to check in with how it’s going and to reaffirm your commitment to your word’s intention. Or, you might choose to select another word that feels like a better fit right now.
I chose Wild & Precious for my theme this year, but I found that I prefer to choose a different theme word for each of my seasons. I get a tarot reading once a year on my birthday and learn which card will be guiding me through each season. My card for Summer 2023 is Emergence, which means I’ll use the act of emerging as my lens. I like to apply my theme word’s lens to my whole life for a period of time, but you might choose separate themes for your work, relationships, etc.
Checking In On Your Word
If you did choose a theme word for the year in January, here are some questions you might want to reflect on now that 6 months have passed:
Why did I choose my theme?
What did my theme mean to me when I first chose it?
What does my theme mean to me now?
What has my approach to my theme been?
You Can Choose a New Word Anytime
If you would like to choose a new theme word, these prompts may be helpful for you.
You don’t need to commit to a word for the rest of the year. You can apply a theme to your month, week, day, or to a particular project. When you are facing something new, ask yourself:
How do I want to feel during this process?
What strengths am I bringing with me?
What do I want to learn or develop through this process?
What excites me most about this process?
What will an ideal (“good enough”) outcome look like?
What will help me to feel grounded and calm if I run into bumps in the road?
Once you’ve reflected on these questions, review your answers and identify a theme, word, or metaphor that will motivate you to meet your personal goals. You might put this word on a sticky note to hang above your desk or set it as your phone background for a consistent reminder.
Thanks for joining me for a mid-year reflection. I’m wishing you a peaceful and fruitful rest of your year.
Curiosities
This section of my letters is for things that made me say “hmmm” or “wow!” recently.
It’s nacho season in the Henry household. Kris and I made pico de gallo and added beans for a little protein and I’ve been melting cheese on corn chips in the oven before slathering it with salsa. YUM.
I read a handful of other Substacks and today I want to shout out two of my favorites, Naive Weekly and Queer Computer. Naive Weekly is a collection of experimental websites that are sometimes interesting and sometimes downright beautiful. Queer Computer is a witty analysis of contemporary things happening in the digital world. In a recent Queer Computer post, author Joel Humphries answered a Q&A from a person who wondered about hacking the account of an ex, describing in detail how frighteningly easy it is to dupe AI into setting up a hack (Joel didn’t actually follow through on it, but proved a point by taking us through the first few steps). As far as technology goes, I’d rate myself as “I know how to build my own websites but not how to code,” so it’s fun for me to learn quirky behind-the-scenes details from people who understand tech but also have excellent, humorous tastes.
For Your Consideration
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Order my book, Tend to It: A Holistic Guide to Intentional Productivity
Listen to my podcast interviews
xo,
Dr. Kate
