Chapter 1: Introduction to Personal Retrospectives

Greetings, esteemed reader! Allow me to dive deep into a topic that has significantly shaped my life over the last decade. I’m continually refining this process, and I’m eager to learn about your own methods if you’d like to share!

In the mid-2000s, I entered the tech scene in San Francisco, where I immersed myself in agile methodologies. It was here that I discovered the transformative power of the retrospective — a mindful practice conducted regularly to reflect on recent work experiences.

It’s intriguing how countless engineers and analytical minds embraced a process that, at its core, is profoundly creative. I witnessed how effective it was in fostering reflection, celebration, and constructive evaluation within the workplace.

During a retrospective, we typically pose two questions at the conclusion of a work sprint:

🏆 What went well? and 🤔 What can we improve?

I also like to add a third optional question: ⛔️ What should we discontinue? (My take on the "No List.")

Integrating retrospectives into our workflow establishes a consistent routine that’s easy to replicate and essential to our processes. This practice not only enables learning from our experiences but also encourages us to appreciate our successes. It offers a supportive environment for providing feedback, celebrating achievements, learning from setbacks, and practicing gratitude. In a world rife with unproductive meetings, I find that retrospectives often become the highlight of everyone’s week.

But the real breakthroughs happen when you apply this process to your daily life.

Over the years, I’ve championed the personal retrospective, which has become a vital component of my life management system. Besides enhancing my overall organization, it plays a crucial role in supporting my mental well-being by alleviating symptoms of anxiety and depression. It serves as a straightforward framework for reflective thinking.

Timing Your Retrospectives

I conduct retrospectives of varying lengths and frequencies: daily (brief, typically three questions), weekly (shorter), and monthly (more extensive). These reviews seamlessly integrate into my annual evaluation process.

I utilize my weekly and monthly retrospectives to generate forward-thinking "Weekly Intentions" and "Monthly Intentions," reflecting the same categories.

Incorporating Retrospectives into Daily Life

This practice can be done individually, with a partner, or even at the dinner table with family. At its most basic, it resembles mindful practices like "Rose, Thorn, Bud," "Peaks and Valleys," "Highlights and Lowlights," or my personal favorite, "😍R Happy and 💩R Crappy," which your child might have learned in preschool.

🌹 Rose: "What went well?" — Recognizing wins, expressing gratitude, noting interesting sensations.

🌵 Thorn: "What should we stop doing?" — Reflecting on stressors or frustrations.

🌱 Bud: "What can we improve?" — Identifying opportunities for growth and reframing thoughts.

The common thread across all these activities is the creation of a non-judgmental space for observation and reflection.

What Questions to Ask During a Review

I usually initiate my weekly reflections with a concise list of my week’s highlights (details below on how I compile this). This might include a short list of accomplishments and notes, structured as follows:

• Positive experiences from the week
• Meals I enjoyed
• Media consumed (books, shows)
• Distance run or adventures undertaken
• Connections with friends
• Notable achievements and other random metrics

I then explore basic questions (what went well, what didn’t), and if time permits, I delve into a selection of rotating questions for deeper self-inquiry. This practice blends inquiry, journaling, and gratitude. Even spending just ten minutes on this activity regularly can yield significant benefits, though I prefer to take it a few steps further.

In-depth Questions for Personal Retrospectives

👯‍♀️ Who Questions:

• Who did I connect with?
• Who did I unintentionally harm?
• Who do I need to forgive?
• Who contributed to my growth?
• Who nurtured our relationship?

🤔 What Questions:

• What brought me joy this week?
• What habits should I reduce?
• What actions should I engage in more?
• Which personal values did I embody this week?

🧠 Energy and Flow:

• What energized me this week?
• What drained my energy?
• What activities felt most natural?
• Who filled my emotional cup?

Productivity stems from managing energy rather than merely tracking time. I strive to monitor my mental credits and debits.

Lastly, I incorporate a set of open-ended questions for contemplation:

❓ Open Questions:

• What if I…?
• How might I…?
• Who should I…?

In recent years, I’ve gained insights from books like "A More Beautiful Question" and "The Artist’s Way," which have inspired me to ask more meaningful questions during self-reflection.

Tools for Conducting Your Retro

The simplest approach involves using a paper journal and pen (which I often do for my daily retrospectives, currently utilizing Intelligent Change's 5-Minute Journal). For my weekly and monthly reflections, I typically use personalized templates in Evernote, creating a copy each week or month. When I’m feeling particularly artistic, I may engage in a visual representation of my monthly review.

Tracking Your Activities

When completing tasks, my mind often erases them from working memory. Thus, when I sit down for a retrospective, I start by hunting for clues in various places. I review my phone’s photos, my calendar for meetings, my sent emails, and my text and call logs to recall connections made.

Utilizing Retrospectives for Emotional Regulation

Here’s why I consistently return to my personal review system:

Retrospectives are not merely organizational tools in the conventional productivity sense. They represent a self-compassionate practice that directly benefits my mental health.

This structured thought exercise addresses a variety of needs:

• Acknowledgment of Accomplishments: It helps me recognize the work I’ve completed, counteracting the Zeigarnik Effect (the tendency to remember unfinished tasks better than completed ones). When I finish things, I often forget them, which helps combat the negative thought pattern of "I haven’t done enough." In reality, I’ve accomplished a lot; it’s essential to give yourself credit.
• Regular Gratitude Practice: I prefer to call this "Good Things." Numerous studies highlight the link between gratitude and increased happiness. Even during challenging times, reflecting on positives reliably lifts my mood.
• Emotional Boundaries: Having a dedicated time for reflection allows me to manage my emotions and energy throughout the week. I know I can defer certain processing until my retrospective, where I can address challenging experiences.
• Identifying Behavioral Patterns: It helps me recognize recurring actions or inactions that do not align with my goals (mindless scrolling, for instance).
• Incentive for Positivity: Knowing I’ll review my experiences encourages me to seek out enjoyable activities to anticipate for the upcoming week.

Getting Started with Your System

🔥 Start Simple: Set a timer for five minutes right now and try it. Pose two questions: What went well this week? What could you improve? Keep it brief; just jot down a couple of points. (I’ll wait!) Did you do it? Seriously, pause reading and give it a shot.

Don’t overthink it. The most effective process is one you will actually implement. The simpler you make it for yourself, the better the results will be. After a decade of practice, I’ve allowed myself to expand and adapt the process.

When to Conduct Your Retrospective

I typically do mine on Saturday mornings, sipping coffee in silence before my weekend begins. It usually takes about 30 minutes. Others prefer to do this on Friday afternoons to wrap up the week. I also allocate a few hours at the end of each month for a comprehensive monthly review. Other opportune times for this practice include after completing significant projects, meeting deadlines, or experiencing major life transitions.

Solo or Collaborative Reflections?

Honestly? Teamwork enhances the experience. One of the key factors in maintaining consistency with this practice has been collaborating with others. At work, we conduct team retrospectives, and for my personal reviews, I start solo and then engage in weekly check-ins with my organizational buddy, Rebeqa. I’ve also facilitated this process in mastermind groups and led workshops to help others initiate their reflective practices.

Quick Version for Busy Schedules

⏰ Time Constraints? No problem! Try a lighter version: during dinner, practice "Rose, Thorn, Bud" with your family. Alternatively, initiate a weekly text chain with friends, committing to a shared set of retrospective questions.

Advanced Retrospective Skills

Over the years, I’ve refined my system to enhance its effectiveness and enjoyment. The complexity of retrospectives fluctuates based on my energy levels, commitments, and life changes. While I’ve occasionally dropped the habit, those instances are becoming rare as I’ve clarified my "why" behind the process.

Here are some advanced skills I’ve explored:

💛 Personal Values and Leadership: Developing and refining a set of personal values has helped me focus on what truly matters in my planning and decision-making. During my reviews, I cross-check my actions against my values to gauge alignment.

🧠 Seeking Clarity Amid Uncertainty: During uncertain times when my energy wanes, I often begin with a retrospective. It serves as a simple reminder of my accomplishments, helping to reignite my motivation for activities I love.

✍️ Curating My Lists: A fulfilling life requires intention. To facilitate this, I’ve developed curated lists to help me engage in desired experiences. These include a movie spreadsheet, reading lists, kitchen resolutions, small comforts, joy-sparking activities, cornerstone habits, and more.

👩🏻‍🏫 Teaching the Process: One of the greatest joys I find (and a fantastic way to reinforce learning) is teaching this framework to others. Over time, I’ve honed my process into something I genuinely cherish, and I enjoy helping others create their tailored systems.

👉 Seeking Accountability? Join my next Retro Workshop on January 31st at 6:30 PM Eastern. Register here.

👋 For more insights and a glimpse into my regular systems, follow me @alphaprep on Twitter or here on Medium, and I’ll strive to deliver more valuable content in 2022!

Exploring Retrospectives Further

In this informative video, learn how to create an Agile Retrospective template in Excel, which can enhance your review process and streamline your reflections.

Enhancing Personal Reviews

Discover effective strategies for conducting a personal annual review in Notion, complete with a free template to guide your reflection process.