The Power of Weekly Reflections

Kevin Lee
Personal Development
Last Updated: 
November 28, 2020

Most operators run at full speed and rarely get to look over their shoulders to process, let alone document, what they’ve learned. But without the intermediate steps of synthesis, it’s difficult to know whether you’ve truly grown over a period of time.

Over the past year of running a new food company, I’ve made hundreds of decisions with corresponding successes and failures. 

In the first few months, I ambitiously maintained a Notion page called “Daily Learnings,” where I logged key learning moments. 

I’ll be the first to admit that I’ve never been able to stay consistent with a journal. As expected, my day-to-day responsibilities grew and that page fell to the bottom of my priorities list. I’d be lucky if I updated it once a month.

I tried another method. Instead of creating another daily task during a busy workweek, I blocked off 1 hour every Saturday morning to run through a list of weekly reflection questions that cover professional and personal topics.

This is the questions template I use every week: Weekly Reflections Template. Feel free to use these questions as a baseline for your own template.

Note: Some people prefer doing these types of weekly reflections on Sunday nights. Even after heavy Friday drinking nights with friends, I’m a masochist who strangely wakes up between 6-7AM on Saturday mornings to do this. Experiment with different time blocks until you find one that gets you most into the flow. 

I wish I could reach through this computer screen, shake you by the shoulders, and tell you how much your life will change from doing these weekly reflections. 

But I can’t. All I can do is tell you that the results of this consistent practice have been nothing short of miraculous.

Personally, I’m filled with regret for waiting decades to do something so valuable for my personal growth. All I had to do was set aside just one hour per week.

Overdramatic… but it’s how I really feel.

In my first product manager job, all PMs were required to send out weekly e-mail updates to all PM owners and executives. The distillation of the week’s learnings, ownership of failures, and celebration of wins created a culture of collaboration through shared learnings, accountability, and self-reflection. 

In hindsight, I should have realized that adopting this in my personal life would be equally beneficial.

What You Will Learn

We often give better advice to our friends than we practice in our own lives. Weekly reflections transport you to a 10,000 ft. view, where you can give yourself the advice you’d give to someone else.

As you build upon this tapestry of reflection every week, you start to see recurring threads that you wouldn’t have noticed before.

Every time you write the same thing more than once, you’re forced to take a deeper look into why it keeps coming up.

Below are a few of my favorite questions that have yielded the biggest areas of improvements in my life:

  • What 20% of actions drove 80% of results?
  • What $10,000 / hour work did I do this week?
  • What was the least valuable thing I did this week?
  • What are things I learned about me?
  • What habit do I want to continue doing?

What I Have Learned

In the spirit of learning in public, I’ve decided to compile a list of key learnings from my weekly reflections that have quantifiably improved my performance.

I’ve been inspired by the interview format in The Observer Effect and have compiled these in a similar fashion. 

Most of these are business-related and are hopefully relevant for any creator. 

On Writing

  • Get better at writing briefs. Briefs can be used for a variety of purposes like outlining new projects or proposing new ideas. Written briefs force clarity of thought and prevent miscommunication. Future team members can read briefs, gain context, and understand why decisions were made.  Below the title of each brief, write a 1 sentence summary covering the goal of the brief. If you can’t write a summary sentence, ask yourself if this brief is necessary.

On Meetings

  • Most meetings are unnecessary. You can achieve the same, or a better outcome by working asynchronously on a Google Doc and leaving written feedback.
  • If a meeting is necessary, set up scaffolding. To run an efficient meeting, create a Notion page or Google Doc with a clear agenda and written desired outcome. This will focus the conversation and reduce the meeting duration.
  • Apply constraints to brainstorming sessions. I'm a non-linear thinker and riffing with others helps me generate new conclusions I wouldn't come to alone. However, it's important to set an expectation with others when the purpose of a meeting is to brainstorm. This ensures that no one else feels like the time is wasted if there is no final decision. Apply constraints by timeboxing live brainstorming sessions. In these sessions, avoid the temptation to bring in personal opinions and treat all ideas as good ideas. After the meeting, agree to rank these ideas asynchronously by leaving written feedback.

On Time Management

  • Organize your calendar around your energy levels. I have the most creative energy in the mornings from 7AM-Noon and I try to block that time off for deep work. I’ve also found that I’m the most productive on Mondays, Tuesdays, and Thursdays. Barring a few recurring team meetings, I try to batch all external calls to Wednesdays and Fridays to prevent context switching. There are many ways to discover your optimal time blocks. For the dedicated, try this hardcore calendar experiment from Taylor Pearson. Alternatively, you can block off different time blocks for deep work every week and see when you feel best.

On Task Management

  • Iterate to find an optimal task management system. If you cannot identify, prioritize, and complete your most important tasks, the company will suffer. I’ve iterated through many task management systems to find one that fits my current working style. A Notion dashboard that combines the The One Thing + Eisenhower Matrix works (for now). This is my task management dashboard.

On Communication

  • Think twice before sending a message. The more you use Slack @ mentions, the more you devalue their impact & urgency. Reserve them for important moments. Before sending a Slack message, ask “Is this message necessary?” “Can I solve this myself?” “Is this worth disturbing someone else’s deep work?” “Can I batch this message with other requests later on?”
  • Write daily standups to keep everyone on the same page. Keep a #daily-standup channel on Slack. Set a daily time for everyone to submit written bullet points on what they accomplished yesterday, what they aim to accomplish today, and what is blocking them.
  • Send a monthly investor update. Send a monthly investor update to summarize learnings, accomplishments, and mistakes. Some founders choose to decrease the frequency of these updates (i.e. once per quarter) once they grow much larger. If you don’t have investors, send a monthly update to trusted friends and family. Investor updates hold you accountable for continued progress, communicate your business clearly to external parties, and help you identify areas of the business to improve.

On Remote Team Culture

  • Recreate watercooler moments. We’ve been fully remote since the pandemic started. I won’t lie - nothing will replace the bonds formed from an in-person culture, but there are ways to meet halfway. Here are a few suggestions: before diving into each 1:1, ask the other person about their weekend, or their upcoming travel plans (CEO coach, Bill Campbell, is notorious for this). Create a #random channel for “watercooler banter” that people can check on their own time.

On Mental Health

  • Step away from first person into third person. Recognize when you are feeling emotional, and do your best to name these emotions for what they are. Shift from “I’m anxious,” to “I’m feeling anxiety.” This reframing helps to regulate your emotions so you can make clearer, and more logical decisions.
  • Managing stress. You will experience stress as a founder. Unfortunately, there’s no getting around that. Recognizing and managing that stress for a quicker recovery into a positive mental state will be key for your mental health. My co-founder once spent a month training to become a monk. A lot of silence and meditation is involved. One takeaway he got: "95% of things don't matter in the present and aren't important to stress about." Recognize when something is in your control vs. when it is not.
  • Remove sabotaging voices. No matter what you achieve, you may never feel good enough. Label the sabotaging voices you tell yourself, “We’re not growing fast enough. Our product isn’t the best. Our competition is beating us.” Express gratitude for yourself every single day. “I’m grateful to be where I am. I’m grateful that I’m learning this much. I’m grateful to be serving my users.” Tell yourself that each major milestone is like a checkpoint in a game. No matter what happens, you can reach that checkpoint again.

On Personal Development

  • Invest in executive coaching. The limit of any company is the capacity of its team. Investing to improve the capacity of your emotions and well-being increases your ability to perform and deliver better results. Whether you’re part of a 5 person company, or a 50,000 person company, you want to do the same thing: invest to make yourself and your team more capable. More on this here.

On Creativity

  • Apply constraints. Unbounded problems create paralysis from analysis. Creativity spawns from constraints. If you have trouble coming up with a creative solution, test adding a layer of constraints.
  • Take walks. If you are hitting a wall, get up and take a walk. The best ideas come when you step away from everything.

As I continue with my weekly reflections practice, I’m excited to see how many of these learnings will change or stay evergreen.

If you decide to start this practice and document your learnings in a similar fashion, please DM me a link on Twitter so I can learn from you!

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