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How to Have a Productive Conversation

Daniel · Dec 9, 2023 ·

Introduction

I find it baffling how difficult it can be to have a productive conversation with another person. It’s one of the most basic and recurring activities in life, but often involves so much friction and misunderstanding.

And yet, in recent years, I’ve noticed marked improvements in my own life when it comes to dialogue, largely thanks to a nurturing relationship and the practice of Nonviolent Communication (NVC).

In this piece, I’m trying to distill some of the learnings that have been most useful to me. My approach will be fairly abstract and conceptual as opposed to practical and step-by-step, focusing on the underlying principles and thought processes that can be applied across various situations and challenges. Maybe I’ll come back and add more concrete examples at a later point.

My aim is to present a framework that fosters more productive conversations, where both parties can efficiently and effectively meet their goals and needs related to the relationship itself (like connection and trust) and beyond (such as enjoyment and safety).

Framework Overview

Here’s an overview of the framework to enhance orientation and integration before delving into details:

  1. Three Levels of Conversation:
    • Content (Substance): What is being discussed.
    • Process (Structure): How the conversation is conducted.
    • Attitude (Worldview): Fundamental assumptions that drive communication.
  2. Four Buckets (Content Management):
    • Observations: Factual, objective elements.
    • Feelings: Emotional responses and signals.
    • Needs: Underlying motivations and interests.
    • Requests: Actionable steps or desires.
  3. Three Activities (Process Management):
    • Self-Connection (Break): Understanding and acknowledging your own perspective.
    • Expression: Clearly and vulnerably sharing your own perspective.
    • Listening: Attentively and empathetically understanding the other’s perspective.
  4. Two Attitudes:
    • Confrontational: Characterized by blame and judgment.
    • Compassionate: Characterized by empathy and humility.

Detailed Framework

1. Three Levels of Conversation

This framework separates a conversation into content, process, and attitude. Content pertains to the topics discussed — the “what.” Process refers to the dynamics and structure of the conversation — the “how.” Attitude reflects your frame of mind or worldview and influences your behaviors in the conversation.

2. Content Level: Four Buckets

At this level, the aim is to understand the situation and guide your actions accordingly. Differentiating various aspects of your current experience is key:

  • Observations are factual, objective aspects of the situation observable to all parties — things that a camera would be able to capture. An example would be that it’s raining outside or that you just had a sip of coffee.
    • ≠ Thoughts: Observations aren’t interpretations, evaluations, or judgments, which are an additional layer of meaning on top of the observation. To continue the above examples, thinking that it’s unfortunate that it’s raining outside or judging that the coffee is too strong aren’t observations anymore. These thoughts are signals about what the observations mean to you in this moment.
    • → Separate factual occurrences from personal interpretations.
  • Feelings represent the body’s responses, signaling whether needs are met or unmet. To make sense of your experience at this level, it’s helpful to develop an emotional vocabulary (see Feelings List) and increase the granularity with which you can identify your feelings. Otherwise, you’re “experientially blind” — your sensory input is just meaningless noise.
    • ≠ Thoughts: Some things we’d intuitively categorize as feelings are thoughts instead. For example, if you say “I feel manipulated,” what’s actually happening is that you have a judgment that the other person is manipulating you. This is already a more complex mental construction, not a feeling.
    • → Distinguish genuine feelings from thoughts or judgments disguised as feelings.
  • Needs are core motivations and interests, i.e., what’s important and meaningful to you. Humans are complex evolved creatures that need a wide range of things to survive and thrive (see Needs List). Needs are abstract and shared between people. They tend to foster empathy and compassion.
    • ≠ Strategies: A strategy is a particular way to meet a need. For any given need, there are many different strategies to meet it. Strategies tend to be personal and idiosyncratic. They can be divisive and threatening.
    • → Focus on the abstract, universal “why” (needs) rather than the concrete, personal “how” (strategies).
  • Requests are actionable steps tied to fulfilling needs. In the context of a conversation, they are ways that the other person can help you meet your needs. To inspire compassion and cooperation in the other person, it helps to share the underlying the need behind the request, make it concrete rather than vague, doable, and positive rather than negative (what you’d like them to do rather what you don’t want them to do).
    • ≠ Demands: A demand is a “request” to another person where you aren’t open to hear a “no” in return. This creates friction in the relationship.
    • → Propose need-connected, concrete, doable, positive language requests while being open to negotiation or refusal.

It’s often helpful to walk through the above categories from top to bottom. Here’s an example:

  1. Observation: “I’ve noticed that the last three project deadlines were missed.”
  2. Feelings: “I’m feeling concerned about this pattern.”
  3. Needs: “It’s important for me to ensure our team meets its goals and maintains a good reputation for reliability.” (Note that this barely scratches the surface of the speaker’s needs. In some situations, you might want to look for further underlying needs.)
  4. Requests: “Could we discuss how we might address this issue? I would appreciate it if you could share your challenges so we can find a solution together. Would you be open to setting a meeting to discuss this further?”

3. Process Level: Three Activities

The goal at the process level is to monitor and control where the focus of the conversation lies at any given moment in a way that allows the conversation to go deeper and move forward.

From your perspective, you can either focus on yourself — either inwardly by introspecting and gaining clarity about your situation, or outwardly by expressing towards the other person — or you can focus on the other person by listening to them. This leads to the following three activities that you can choose from at any moment in the conversation:

  • Self-Connection (Break): Engage in introspection to gain clarity on your purpose and state in the conversation. The more granular your self-understanding, the better equipped you are to navigate the conversation.
    • You can do this by mentally separating your experience into the Four Buckets that we discussed earlier. What observations do you have? What feelings do you notice? What needs are alive? What might you want to request or suggest?
    • If you’re experiencing strong emotions, it might be best to pause the conversation and give yourself some space to recover before re-engaging in dialogue. Express your desire to take a break by sharing that it’s a way for you to care for the relationship. Agree in advance when you’ll pick up the conversation again to reduce uncertainty and avoid further escalation.
  • Expression: Share your reality authentically and vulnerably to help the other person understand your perspective.
    • Again, you can do this by sharing from the Four Buckets above. Help them understand what’s at the heart of the matter for you and how you’ve come to your current place.
    • In addition to providing clarity and structure, sharing from the Four Buckets also provides a guardrail that helps you stay in your reality and prevents you from stepping into theirs, e.g., by assuming you know what’s true or false, right or wrong about and for them.
    • Try to really reveal what’s going on for you. If you don’t, you keep yourself out of the relationship.
  • Listening: Attentively and empathically follow the other person and try to understand what’s going on for them while suspending assumptions or judgments.
    • Start from a place of ignorance and wonder. Assume that you don’t yet know what’s going on for the other person. Let them help you understand. Put your own stuff aside and make it fully about them.
    • Move towards compassion. Imagine what it’s like to experience the situation from their perspective. Find out what’s at the heart of the matter for them in a way that touches you and goes beyond a mere “intellectual” understanding.
    • Relax. You don’t have to do anything. Just be emotionally and mentally present with them.
    • Periodically communicate your understanding of what they’re sharing and let them correct you. You can make guesses using the Four Buckets for guidance. This creates safety and invites further sharing.

To summarize, at any given moment in the conversation, you’re facing a choice between self-connection, expression, and listening. Your partner faces the same choice. In a productive conversation, both people are aware of their choices and coordinate them in a way that lets the conversation flow. I have two suggestions for that:

  1. Don’t express at the same time. Both people expressing at the same time creates a mess. It’s easy to get lost and triggered. The conversation speeds up, and suddenly you find yourself in a place that’s difficult to get out of. Instead, hold firm that only one person expresses at each point. Separate your stuff from theirs. Additionally, separate your stuff into the Four Buckets. Then take turns expressing and listening.
  2. Keep the focus on a single person for longer. To a first approximation, the quality of a conversation depends on how long one person manages to listen to the other. Try to increase the time interval during which you focus on a single person, and then deliberately shift the focus to the other person. Avoid “ping pong” conversations where the focus shifts back and forth within seconds. As a support, set a timer and let one person express until their time runs out, then switch roles.

4. Attitude Level: Confrontational vs. Compassionate

I’ve enjoyed using small numbers to categorize big things in this note, so let’s take it one step further and distinguish between two underlying attitudes in conversation — frames of mind or worldviews — which are often silently driving the conversation:

  • Confrontational: Communication based on this attitude is driven by criticism, judgment, or demands, and it leads to defensive or aggressive responses. This attitude isn’t “wrong,” but it tends to hinder mutual understanding and connection. There are a few underlying assumptions worth highlighting (taken from the book Difficult Conversations):
    • The truth assumption is the sense that you know (or can know) what’s true or false, right or wrong. It is deeply rooted in how our culture uses language.
    • The intention invention is the sense that you know (or can know) the other person’s intentions behind their actions. Furthermore, you tend to assume bad intentions if the other person’s action has a negative impact on you.
    • The blame frame is the tendency to look for someone to blame when you’re in a difficult or unpleasant situation — i.e., someone or something has to be “wrong.”
  • Compassionate: In contrast, this attitude fosters mutual understanding and connection. It is grounded in a recognition of our shared humanity and the need to co-exist in an empathic and respectful manner. There are a few underlying differences compared to the confrontational attitude:
    • Humility: This attitude is based on a recognition of the limits of our understanding, in particular, our ability to know with certainty what’s good and bad, right and wrong. It leads to an embrace and exploration of both people’s experience and stories.
    • Separate intent from impact: This attitude recognizes that we don’t have access to other people’s intentions; they’re invisible to us. Therefor, describe the impact on you in terms of feelings and needs and hold the question mark about their intentions.
    • Map the contribution system. Figure out how both people contributed to the current situation in a joint and interactive way instead of assigning blame.

Moving from a confrontational to a compassionate attitude involves a paradigm shift. It’s not merely a small modification, but a complete overhaul of the assumptions and practices that were previously accepted as the norm.

I’ve found that this aspect is the most beneficial for improving conversations, but also the most challenging to change. I don’t expect that I’ll be able to fully shift the needle from confrontational to compassionate in my own life. And yet, even small steps in this direction are immensely valuable — and they’re certainly attainable through consistent practice and effort.

Acknowledgments

  • This piece draws primarily from Nonviolent Communication, particularly Marshall Rosenberg’s book, Yoram Mosenzon’s courses, and countless conversations (and accidents) with my partner. I’ve tried to present the key ideas in a way that resonates with me, so I’ve chosen slightly different terminology in some places.
  • Additionally, a series of books such as Difficult Conversations, Crucial Conversations, and Getting to Yes have been helpful to me.
  • There’s much more to learn about each of the elements in this piece, so I’d encourage you to check out some of the resources I’ve linked.

Reflection

Daniel · Dec 18, 2020 ·

One thing I’ve changed in 2020 has been to shift (even) more time towards structured reflection. The volatile and sometimes chaotic environment this year provided a helpful nudge for what would have been worthwhile without it already. In this post, I’ll elaborate on the benefits of reflection as I currently see them and suggest ways to implement it in practice.

Most readers will have an intuitive sense of what I mean by “reflection”, but to be safe: By reflection, I mean taking a break from what you’d otherwise be doing to examine what’s currently happening.

Motivation

Let’s start with why you’d want to reflect in the first place. Based on my own experience at work, as well as observing people who I regard as highly successful in their career, and studying materials on learning and deliberate practice in the context of my coach training, my current understanding is that reflection is mainly useful in the following ways:

  1. Learning and development: Reflection helps you extract maximum learning from experience accumulated in the past, which can improve performance significantly more than spending the same amount of time to accumulate additional experience. By articulating and codifying your past experience, you cultivate a deeper level of insight into the causal relationship between actions and outcomes. Reflection also nudges you to explore issues from multiple perspectives rather than just going with your first intuition.
  2. Prioritisation and alignment: Reflection helps you clarify what matters to you, notice where you’re at right now relative to what matters, and see what you need to do to close the gap. It’s a way of thinking about what you do strategically, leading to an increased alignment between your values and actions. Without reflection, on the other hand, you tend to drift and get distracted by the good opportunities while missing out on the great ones.
  3. Motivation and self-efficacy: Finally, reflection can help you look at your situation with fresh eyes — an antidote to boredom and stagnation. It can help you see richness and possibilities in a way that rejuvenates you and builds momentum towards your goals. Further, reflecting on past experience with a specific task tends to reduce your uncertainty about your ability to perform that task competently in the future, leading to increased self-efficacy and future performance.

What you want to get from reflection might look different from the above, so I’d encourage you to clarify that before you start since the right reflection practice might look very different depending on what you’re optimising for.

Implementation

Having a sense of what we’re trying to get from reflection, we can now consider what to do in practice. Again, I’d expect that the ideal solution will look very different depending on your preferences and environment, so take some time to consider what might work for you.

On a fundamental level, establishing a reflection practice is about deciding when and where to direct your attention. The first part is about time: When and for how long do you want to pause and reflect? The second part is about content: What do you want to do during that time?

To determine when and for how long to reflect, consider if there are any specific times when reflection would be most useful, given what you’re trying to get from it — for instance, making a deliberate decision at the start of the day about what you’ll work on that day. Also, consider whether there are any natural time intervals in your life that you can use as an anchor — for instance, the start or end of the workday.

Before you can decide for how long you want to reflect, you probably need to get a better sense of how you’ll use that time. Here, think about where you’d have to direct your attention to accomplish your desired outcome, and what guidance and prompts would help you with that. The four directions for reflection by David B. Peterson, former Senior Director of Executive Coaching and Leadership at Google, help illustrate the point about directing your attention:

  1. Look inward: What is most important to you? What are your goals, and what are you doing to achieve them?
  2. Look outward: What matters most to others? What expectations do they hold that you need to address in order to be successful at your endeavours? How do they perceive you?
  3. Look back: What have you been trying to learn and what new things have you tried? What has worked well and what hasn’t worked? What have you learned?
  4. Look ahead: What will you do differently? What do you need to keep learning? Where are your opportunities to try new things?

Based on the above steps, you can come up with a reflection schedule — see the next section for an example. For many people, starting small and building their way forward towards their ideal schedule instead of making one large shift will have a higher chance of success. Pick one new reflection point and build it into your existing systems in a way that ensures you’ll actually do it. Schedule a time in the future when you’ll evaluate how the new routine is going and decide whether and how to adjust it.

Sample reflection schedule

Below is a collection of individual reflection points that together make up a reflection schedule. It’s ordered chronologically and in increasing order of time investment. The idea is inspired by David B. Peterson who’s been mentioned above already. You could expand the schedule and add quarterly, annual, and even less frequent reflection points using the same principles.

Momentarily (10 seconds)

Whenever you snap out of “autopilot” and become present again:

  • Zoom out: What’s important now?
  • Zoom in: What’s the next step?
  • Alternatively: Who do you want to be, right now?

Hourly (1-3 minutes)

This is roughly the level of an individual task. Here, you could ask yourself at the start:

  • Desired outcome: What are you trying to achieve?
  • Benefits: Why does it matter?
  • Obstacles: What might make this difficult?
  • Plan: What are the individual steps?

Daily (5-10 minutes)

At the start of the day:

  • What are the three most important tasks for the day?
  • When are you going to work on them?
  • What else matters today?

At the end of the day:

  • What went well today?
  • What didn’t go well today?
  • What do you want to do differently tomorrow/moving forward?

Weekly (10-30 minutes)

Look back over the previous week:

  • What progress did you make? How satisfied are you with that?
  • What did you learn?
  • Meta: What other useful questions could you ask yourself at this point?

Look forward over the week ahead:

  • What’s important in the week ahead? How can you meet your monthly goals?
  • What are the 4-6 most important tasks you want to accomplish this week?
  • What are your key learning opportunities?

Monthly (15-60 minutes)

Look back over the previous month:

  • What progress did you make? How satisfied are you with that?
  • What went well and why? What can you improve and how?
  • How much are you enjoying your work right now, 1-10? How to make it a 10?

Look forward over the month ahead:

  • What are the three most important objectives for the next three months?
  • What can you do this month to make progress towards them?
  • What else matters this month?

If you’d like to explore these ideas further, here are a few resources you might find useful:

  • Making Experience Count: The Role of Reflection in Individual Learning – Giada Di Stefano et al.
  • Step back: Bringing the Art of Reflection into Your Busy Life – Joseph L. Badaracco
  • How to Regain the Lost Art of Reflection – Harvard Business Review
  • Why You Should Make Time for Self-Reflection – Harvard Business Review
  • On Reflection – Neel Nanda

Self-care

Daniel · Oct 23, 2020 ·

Self-care is challenging yet essential for almost anything you care about. In this post, I’m going to address why I think that’s true, and offer a few strategies that you can implement to manage yourself more deliberately.

If you’d prefer a more animated version of this post, you can find a recording of my talk on self-care at the Effective Altruism Student Summit 2020 at the bottom of this page.

Why it matters

By “self-care”, I mean paying attention to and supporting your physical and mental well-being. It’s a broad category, including things like the state of your mind, emotions, relationships, and resources.

Your physical and mental well-being matters both intrinsically and instrumentally. It matters intrinsically because your well-being is valuable in its own right. Whatever you can do to increase your well-being is a good thing. I emphasise this point because it often gets left out of the discussion around self-care, which typically centres around how self-care can make you more productive at work.

Besides, your physical and mental well-being matters instrumentally, as it’s arguably one of the critical ingredients to almost anything you may want to achieve in life. For instance, if you want to maximise your lifetime impact, you’ll find that hard to do while struggling with your own health. Instead, you’ll likely burn out and quit before you’ve reached the positions where you can have the biggest impact. This way, you’ll help others less overall and suffer yourself at the same time — a lose/lose situation.

One way to look at the instrumental value of self-care is through the frame of the cycle of sacrifice and renewal. It’s a simple model that has two parts: “Sacrifice” is any activity that burns through your reserves in the pursuit of your goals, and “renewal” is any activity that replenishes your reserves and builds capacity for the next sacrifice cycle. You need both parts for maximum effectiveness and productivity. How much you get out of each sacrifice cycle depends on how well you manage the renewal part.

This model shows that you can’t afford not to take care of yourself, and whatever you can do to renew yourself is itself productive work. Athletes understand this and plan their periods of stress and recovery accordingly. A few years ago, I started viewing myself as a “corporate athlete” because it raised the bar and evoked the right attitude and behaviour for me. A label that actually made me smarter.

Why it’s hard

Many factors push against good self-care, especially among altruistic and ambitious people. I’ll name a few factors to make a case for why it’s hard to look after oneself and to motivate the next section.

  1. Limited self-awareness: It’s hard to notice how you’re feeling and whether your needs are met — it requires the capacity for introspection and space where you can slow down and turn off external noise and distractions.
  2. Delayed consequences: Self-care habits compound over time, which means that the most significant outcomes lag behind. The lack of immediate results makes it hard to start and maintain good self-care habits and notice and stop bad ones.
  3. Achievement drive: Your internal ambition and drive can make you somewhat mindlessly focused on getting things done in the moment and cause you to lose perspective on how you manage yourself over time.
  4. Demandingness and social comparison: It’s somewhat common for people who discover effective altruism to feel like they now have to spend every waking hour toward helping others, continually feeling like they’re not doing enough. Social comparison with “the most impactful people” in the community can reinforce this dynamic and put altruists under a lot of pressure.
  5. Lack of supportive social cues: Many social environments don’t inspire and reward good self-care habits, but instead reinforce a sacrifice mindset. Moreover, what others are doing to take care of themselves is often invisible to you, leading to a false impression that “others don’t need it.”
  6. Biased view of future time slack: In general, people expect that they’ll have more idle time in the future than they do in the present, leading them to make more sacrifices now with the promise of investing more into recovery later. And when tomorrow comes, they repeat the same mistake.

How to start

Disclaimer: I’m not a medical professional, and I’m not giving medical advice. If you believe that you might have more serious mental or physical health issues, please reach out to a professional. As a threshold, consider whether your mental and physical health is interfering with your capacity to function in daily activities, both professionally and personally. You could reach out to Ewelina Tur who offers psychotherapy for EAs.

I believe that the best self-care strategies depend a lot on the person and their context. However, there are a few high-level strategies that seem robustly positive, which I’m sharing below. I encourage you to take them as a starting point for your reflection and experimentation.

  1. Set boundaries: The people I work with (myself included) are typically “happy workaholics” who love what they do and always have more work to do. They have a bias towards sacrifice over renewal, and they find it hard to strike the right balance in the moment. They need to make decisions about how they manage themselves in advance, by setting and enforcing supportive boundaries. Schedule time in your calendar for renewal every day, and treat it as if it was a work meeting.
  2. Establish self-care routines: Fill the space that you’ve created above with practices that reliably rejuvenate you. Those might look very different from person to person. The important thing is to find something that works for you, start small wherever you’re at right now, and do it consistently. Here are a few strategies that I’ve found helpful:
    • Mindfulness: Create quiet moments in your day to tune in to what’s going on inside you. Regular practice increases your self-awareness, which allows you to make good choices about how you manage yourself. Any method that helps you to become aware and attend to your experience is helpful — it could be meditation, journaling, or an honest conversation with an empathic friend.
    • Exercise: Exercise has a myriad of benefits. The key is to find some form of physical activity that you enjoy and can do regularly. It can be as simple as going for a walk after work or doing a 7-Minute Workout every day.
    • Sleep hygiene: Sleep amplifies or diminishes almost everything else that you do. There are many articles out there on how to get a good night’s sleep, so I’ll only cover a few key points: Try to go to bed and wake up at the same time every day. Do calming activities before bed and after you get up, such as stretching, journaling, or going for a walk. Pay attention to how your actions and environment affect your sleep quality and improve what you do over time.
    • Seeking joy: There’s a risk that your self-care practice turns into yet another obligation, to the point where it feels more like additional sacrifice rather than renewal. To avoid this, deliberately choose to play a different game during your self-care time. Merely do what you enjoy, without aiming for some other outcome. Do whatever makes you feel alive in the present moment. Stop where it starts to feel like work.
  3. Reflect regularly: Reflection allows you to step back and evaluate how you’re currently doing, assess how effective your self-care strategies are, and decide what you might want to do differently moving forward. It allows you to monitor the changes in your life and stay tuned in to potential wake-up calls and notice early when you’re heading down the wrong path.
    • Daily: Set aside one minute at the end of your workday to check in with yourself and deliberately choose how you’re going to use your downtime for renewal.
    • Weekly: Look back and reflect on how you’ve managed yourself during the previous week. Look ahead and anticipate the demands on your resources in the week ahead, and make a plan for how you’ll manage the cycle of sacrifice and renewal.

Reflection

I’d encourage you to take a few minutes right now to reflect on the following:

  1. What are your learnings and takeaways from this post?
  2. Based on those, what do you want to do differently moving forward?
  3. What’s one thing you can start doing today? What exactly will you do?
  4. How can you make sure that happens?

If you take away one thing from this post, let it be this: Identify your most important daily self-care habit and find a way to do it consistently.


This is the recording of my talk on self-care at the Effective Altruism Student Summit 2020.

If you’d like to explore these ideas further, here are a few resources you might find useful:

  • Rest: Why You Get More Done When You Work Less – Alex Pang
  • Desperation Hamster Wheels – Nicole Ross
  • Work-Life Balance Is a Cycle, Not an Achievement – Harvard Business Review
  • The Making of a Corporate Athlete – Harvard Business Review
  • There’s No “Right” Way to Do Self-Care – Harvard Business Review
  • Rest in Motion – Nate Soares
  • Making Self-Care Tactical – First Round Review

Energy Log

Daniel · Jun 6, 2020 ·

Being able to show up energized and motivated every day is necessary to achieve big goals and enjoy the process. This post presents a tool to benchmark your current energy levels as the basis for improvement.

Energy levels are a complex issue where causal links are hard to establish. There are too many variables at play to be highly confident about any particular interaction. However, you can often make meaningful improvements by becoming aware of your patterns and running targeted experiments.

The first step is to collect data on your current energy levels. I suggest using an Energy Log every day for 2-3 weeks to keep track of a few variables that have a good chance of influencing your energy levels. In a second step, you can evaluate the data and look for patterns, and come up with ideas for experiments to increase energy levels.


If you’d like to explore these ideas further, here are a few resources that you might find useful:

  • Manage Your Energy, Not Your Time – Harvard Business Review
  • Energy Audit – Matt Mochary
  • A bunch of reasons why you might have low energy – Alex Lintz

Issue Log

Daniel · Jun 6, 2020 ·

Mistakes are one of our best opportunities to learn and improve. Unfortunately, we’re conditioned to associate mistakes with failure instead of opportunity and to deny or turn away from them. This way, we end up staying the same and likely making the same mistakes over and over again. To start learning from mistakes requires a change in mindset and habit. This post presents a few ideas on the former and a tool for the latter.

Pros are just amateurs who know how to gracefully recover from their mistakes.

Kevin Kelly

The chief trick to making good mistakes is not to hide them—especially not from yourself.

Daniel C. Dennett

Mindset

  • Mistakes are inevitable. No matter how careful you are, you will make mistakes.
  • Mistakes don’t define you. Disassociate your self-worth from the outcome. Don’t identify with the painful thoughts and feelings associated with mistakes. Instead, be kind and understanding toward yourself.
  • Learning is a top priority. Whatever your goal, there’s a good chance that investing in your learning is among the highest-value things you can do. In the long run, the learning benefits from mistakes often outweigh their cost.
  • Invest in mistakes. If you want to get good at something, you need to spend a lot of time being bad at it. View mistakes as an investment, rather than something to avoid.
  • Maximize your curiosity. Mistakes educate you in the same way that successes do. Recognize that there’s something to learn for you here, and develop a desire to find an answer.
  • Pain + reflection = progress. Pain and other unpleasant feelings are a useful signal that there’s something to learn. Take a step back and reflect when you experience pain.
  • It’s an iterative process. You don’t have to get this right in one single step. Taking smaller steps and failing more often is a way to succeed sooner.

Routine

I recommend using an Issue Log (adopted from Ray Dalio) to develop a habit of learning from mistakes and “failing better”. Here’s how the tool works, step by step:

  1. Notice that you’ve made a mistake, or that something in your system isn’t working correctly—this is the cue that triggers the routine below.
  2. Accept and acknowledge the issue. Notice any emotional reaction with self-compassion. Reframe the situation as an opportunity to learn and improve.
  3. Log the issue. Using a new row on the Issue Log, write down what happened. Try to do this immediately while your recollection of events is fresh. Decide which of the following categories best describes the issue:
    1. Random accident: Simple statistical fluctuations that don’t hint at any systematic issues. The best response is to acknowledge the issue and move on.
    2. Enduring weakness: Mistakes that happen predictably over and over again but that you can’t simply eliminate because the source of mistakes is hard to change. The best response is to avoid situations that prompt these mistakes.
    3. Growth opportunity: Mistakes that happen predictably but where you can identify the source and fix the system. This is where you want to direct your attention. Ask yourself what you can learn from this event and what you can do differently next time.
  4. Reflect on the issue and identify learnings, again using the Issue Log. Do this periodically, such as once a week or month.
  5. Improve your systems based on insights from the above procedure.

If you’d like to explore these ideas further, here are a few books that you’ll find useful:

  • Principles – Ray Dalio
  • Designing Your Life – Bill Burnett and Dave Evans
  • Strategies for Learning from Failure – Harvard Business Review
  • Why You Should Practice Failure – Farnam Street
  • The Ruling Out of Possibilities (On Failure) – Ed Batista
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