I’ll start with Circling itself, for those who are not familiar. Note: if you plan to try any of these, be careful and make sure everyone involved knows what rules will be used (in advance) before they agree to participate. For all of these, I’d suggest stating a time limit up front and using a timer to end it at that time (of course, when the timer goes off, the group can decide to do it again if they want).

(1) Circling: a group conversation where the topic of the conversation is limited to what’s happening right now, during the experience itself. As Duncan Sabien explains it: “‘Circling’ is a special kind of conversation, in which the topic of the conversation is the subjective experience of the conversation, as it’s happening., i.e., the thing you are all talking about is what it is like for each of you to be present in the conversation as it unfolds. What you’re noticing, what you’re feeling, the impressions and stories you have of the other people, the shifts in your own physical and emotional state. You take the flurry of second-to-second thoughts, feelings, and reactions that would normally shape and inform what you would say next, and instead just talk about them directly, e.g., “Oh, huh—while I was listening to what you just said, I noticed I felt an impulse to [whatever].”

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(2) Hot Seat Circling: like circling, but the focus of the conversation and attention is one pre-determined person who sits in the middle. (This is a known variant of Circling, not something I came up with.)

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And here are my brainstormed ideas for alternatives:

(3) Clear-ing: everyone sits quietly and clears their mind. Each person tries to notice the very first thought that pops into their mind, and then says it aloud to the group. Then the group resets and does it again (I suggest doing this only for a short amount of time – say, 5 minutes).

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(4) Past-ing: the focus of the conversation must be on the past only. For instance, “Hearing you say that, I’m reminded of a time when…”

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(5) Future-ing: the focus of the conversation must be on the future only. For instance, [in response to what someone else said] “That reminds me that I hope to one day…”

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(6) Echo-ing: the focus of the conversation must be the last thing that was said. You start by repeating (or summarizing what the other person said), and then you react to it (and the next person repeats what you said and reacts to it, and so on).

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(7) Feelings: the only topic of the conversation is the feelings or emotions of attendees. It can be their current feelings, past feelings, or feelings in response to feelings, etc.

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(8) Role-ing: each person in the circle has only one thing they are allowed to do. Every 5 minutes, the roles rotate so that participants get to play different roles:

Role 1: You can only express how you feel or what emotions you’re having.

Role 2: You can only express your cognitive/analytical thoughts about what’s happening right now.

Role 3: You can only ask questions (but people must still stay within their role to try to answer).

Role 4: The only thing you can do is guess what you think others are thinking or feeling.

Role 5: The only thing you can do is ask others to elaborate on what they said.

Role 6: You’re doing normal circling (i.e., you can only talk about what’s happening here and now, but you can talk about any aspect of it that you want).

With smaller or larger groups, you can decide which roles you want and how many of each. You can also have a visual marker in front of each person to indicate what role they are in.

An alternative to Role-ing would be that everyone is in the same role at the same time (e.g., everyone starts in Role 1), and every 5 minutes, everyone switches to the next role.

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(9) Weird-ing: you can only talk about things that normally would not be said, or that normally would be unusual, odd, awkward, or inappropriate to talk about.

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(10) Limit-ing: it starts as a normal conversation. Every 5 minutes, someone suggests a new type of thing you’re not allowed to talk about or a new constraint on conversation (e.g., “you can’t talk about the future” or “everything you say must be at least slightly vulnerable”), then there is a vote. If accepted by a unanimous vote, it gets added to the list of rules (if not, someone else proposes a rule, going around the circle until a rule is accepted by a unanimous vote). If no rule is accepted, then continue for 5 more minutes with no new rule additions. Each time a new rule is added, it gets written on a piece of paper or whiteboard that everyone can see, so it’s clear what all the rules are. Each voting round starts with the person after the one who proposed the last accepted rule.

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(11) Squaring (Sam Rosen’s alternative): “Squaring is also an authentic relating game, but it’s less focused on the here and now. It’s about focusing on and discussing true dynamics that exist between people through time. Some examples of squaring would be:

• Hey, I am surprised we aren’t closer friends. Do you know what’s going on there?

• I notice you plausibly deny flirting with my girlfriend. And it’s not a big deal, and I still love you, but I’d like it if you did it slightly less.

• In our past conversations, I’ve felt you weren’t that curious about what I had to say. Am I imagining this, or am I actually boring you?

• I think you are really insightful, and I don’t think you get enough credit for that, so here’s me giving you credit.

In squaring, you should try to give people your best model of yourself. You should focus on the information you think would be useful to the person you are talking to.”

This piece was first written on August 2, 2025, and first appeared on my website on September 29, 2025.

Here it is if anyone wants to try it.

The set-up:

1) Assemble a group – we did it with 6 people, which I think is a good number for this. I recommend giving them a sense of what they are going to be getting themselves into before they agree to participate just to make sure the group is on board with the activities. It likely could still work well with 3 to 8 people.

It could also be done with more people divided into groups that compete with the other groups, with each group trying to be the first to achieve the goal. For instance, you could have 18 people divided into three teams of 6 people, with each group competing to be the first team to get the targeted number of points. Alternatively, you could have a fixed amount of time, and whichever group gets the most points in that amount of time wins.

2) Each participant will be working with their group (all members of that group are on the same team) to complete a series of challenges (here’s an example of a challenge sheet). There are a lot of challenges to choose from, and each challenge earns points for your team (based on the challenge’s difficulty).

3) Make sure everyone gets their own copy of the challenge sheet. I recommend printing copies of the sheet out (digital copies could work, but I don’t recommend using digital copies). If you’re using paper copies, be sure to give each person in the group a pen or pencil.

4) Make sure to also read the list of rules (below) to everyone in the group and give them a chance to ask questions if they are confused about any of the rules.

5) As a group, set a time limit and a goal and fill those in at the top of the sheet. You’ll all be working together to achieve this goal as a team. We set the goal of 73 points, and we had 3 hours before one of our team members had to leave. In the end, this was perfect as we got 74 points in 2h50m. So I think 73 points in 3 hours is a pretty reasonable (but still pretty challenging) goal. You may want to set a small (silly) group punishment for failing and a small (fun) reward if you all succeed, which is agreed on in advance.

6) Create a shared group chat for participants (e.g., via WhatsApp) and encourage the group to take photos during the event and post them in the shared group at the end (once the event is over).

7) Everyone playing should follow these rules (be sure to read them aloud to the participants and give everyone a chance to ask questions). Also, be sure to explain the goal, e.g., “for the group to get ____ points by ____ O’clock,” or “to be the group with the most points within the next ____ hours,” or whatever you decide. And it’s also best if you print out one copy of these rules for each group (in case they forget any).

The rules:

i) The goal is for your group to get as many points as you can by working together to complete the items on the list. Every time your group completes an item, it should be circled (each item can only be completed once by your group).

ii) You can only get points from each stranger (or group of strangers) once. So if you get someone to interact in a way that gets points from one of the items on the list, that same stranger can’t get you points from any other item (with the exception of the item for someone joining your team, in which case they would then be just a normal team member).

iii) Similarly, you can’t use the same activity to get points twice. For instance, if you could take the same action twice to get points from two items on the sheet, it would only count for one. And, of course, each challenge can only be completed for points a single time.

iv) Always act kindly and respectfully toward strangers and prioritize not making other people uncomfortable.

v) Don’t break the law, and don’t put anyone in your group in physical danger.

vi) Don’t tell people you interact with that you are doing a scavenger hunt (unless the task specifically says to tell them). Telling them you’re doing a scavenger hunt makes it too easy.

vii) You can do the challenge items in any order, and you don’t need to get them all to win (your score will be the sum of the point values for the items that your group completed). When you complete an item, circle the number of points for that item in the “Points for completing” column to indicate you’ve completed it (and earned those points). The more difficult items award more points.

Here’s a link to the challenge sheet we used.

This piece was first written on July 28, 2024, and first appeared on my website on September 26, 2024.

Healthy vs. Unhealthy Emotional Validation 

I would say that the main difference between the healthy validation of emotions and the unhealthy version is that the healthy version is based on genuine compassion, caring, authenticity, honesty, and interest in the other person’s experience, whereas the unhealthy version involves a willingness to sacrifice those things in an attempt to make the other person immediately feel good.

At a more detailed level, I think the healthy way to validate other people’s feelings involves expressing the following ideas (but ONLY when these ideas are true).

Healthy Emotional Validation

1) Care: I care about you.

2) Willingness: I’m totally okay with you feeling this emotion right now in front of me.

3) Acceptance: I don’t think badly of you for feeling what you’re feeling.

4) Interest: I am interested in learning more about what you are feeling and why you are feeling it.

5) Compassion: I have compassion and/or empathy for your suffering and want you not to suffer (unless you want to suffer right now, in which case I want you to suffer only insofar and in the ways that seem appropriate to you, such as the suffering that most people feel is right to feel after the loss of a loved one).

6) Understanding of facts: I understand the facts of what happened in this situation (and if I don’t, I’m going to ask open-ended questions in an effort to understand it).

7) Understanding of feelings: I understand why you’re feeling this way (and if I don’t, I’m going to make an effort to understand it).

8) Legitimization of feelings: I think it is totally reasonable that this combination of your situation, your beliefs about this situation, your thoughts, and your past experiences causes you to feel this way right now (and if I don’t see how the combination of your situation, beliefs, etc., lead to your emotion, I’m going to make an effort to understand it).

While some of this is helpful to say aloud when a friend or loved one is upset, much of it will typically be expressed through body language, attention, attitude, presence, tone of voice, and so on. The main thing is that these ideas get expressed in a way that the other person receives them, whether that expression is verbal or non-verbal, explicit or implicit.

On the other hand, I think that it’s usually unhealthy to attempt to validate emotions when it’s done expressing the following ideas.

Unhealthy Emotional Validation 

1) Disingenuousness: you say things that you don’t really mean or believe, such as supporting their claims about what happened when you don’t believe those claims are true.

2) Emotional reasoning: you support the idea that whatever their emotional response is to the situation is a perfect guide to what actually occurred (e.g., if they feel angry at someone, that implies the other person must have done something objectively harmful, or if they feel they’ve lost someone they had a fight with, that means that person is gone forever).

3) Justification: you support or encourage harmful or self-destructive actions they took or are considering taking as a consequence of their negative feelings (e.g., normalizing them taking revenge on the person they are angry about or justifying why it is okay that they did so).

4) Absolving: you encourage the idea that they made no mistakes or behaved perfectly or that someone else is 100% to blame for the situation (unless, of course, you really believe this to be true). On this point, it is often the case that victims of crimes did nothing at all wrong, but this is much less commonly the case when it comes to, for instance, interpersonal conflict between romantic partners, which usually involves both parties having behaved imperfectly, though not necessarily to the same degree.

To recap, people often want emotional validation from their friends and loved ones when they are feeling upset. People are often confused, though, about what this means exactly. There are both healthy ways and unhealthy ways to do emotional validation. 

The healthy version is not always easy to do, but I think it is what we should aspire to when a friend or loved one wants emotional validation. 

To do the healthy version, aim to imbue your responses to their emotions with genuine compassion, caring, authenticity, honesty, and interest in their experiences. And avoid sacrificing those things just to make the other person feel good.

This piece was first written on October 1, 2023, and first appeared on this site on October 11, 2023.

That peak reflects the total sum of your achievements according to your intrinsic values. This may include, for instance, your happiness, the happiness of your loved ones, your positive impact on the world, living virtuously, achieving your deeply meaningful goals, and so on.

Unfortunately, the mountains you face are foggy as hell. Plus, they have dense forests, huge boulders, and brambles covering them. Your mountains are untamed, uncharted.

• The fog means that you can only see clearly for a short distance, and the further you look, the harder it is to tell what’s out there.
• The dense forests mean that to go a considerable distance in most directions, you’ll have to whack your way through with substantial effort.
• The huge boulders will sometimes make a path impassible that had looked promising from around the bend.
• The brambles mean that certain paths will cause considerable pain if you take them. Even more inconveniently, beautiful grasses and flowers sometimes conceal the brambles.

These are your personal mountains, unique in all the world. Your mountains are determined by a combination of:

(1) Your intrinsic values. It is your values that determine the height of each landing and peak, including the height of wherever you’re standing right now.
(2) The structure of the real world, which makes some paths easier to traverse than others. The locations of the forests, boulders, and brambles are metaphors for this structure.
(3) Your current life situation. This is represented by your current latitude and longitude on the mountain range, as well as your physical and mental health, resources, and skills.

Looking out from a distance, you can see the dim outlines of many high-up peaks far away that look promising, but they are in different directions from each other. That means you’ll have to make tough choices about what direction to go, even at the beginning of your journey.

This journey will take your entire life. If you’re like most people, it will be long and hard but also too short. It will be wondrous, terrifying, joyful, and sad.

Rather than trying to travel a great distance in order to climb to great heights, it is easier to find the first comfortable spot, set up a hammock and tent, and make camp there forever. Who can blame you for making that choice (except, perhaps, yourself)?

If you decide to take the journey, you’ll need to use your tool belt, which (if you’re lucky) comes equipped with five (metaphorical) tools.

To have the greatest chance of reaching the highest peaks, you’ll want to train yourself to be a master of each tool.

Here are the tools to master.

Tool 1: The walking stick, which is what you use to move forward along the path you’ve chosen.

By far, the most common tool you’ll use is the walking stick. For every choice of path, you’re going to have to spend a lot of time walking.

Maybe you’ll give up and turn back at the first encounter with a snake, tiger, or tornado. Or maybe you’ll use the walking stick to keep going.

You’re using the walking stick when you create a to-do list and tick items off of it. You’re using it when you push through fear to do something valuable.

Mostly, climbing a mountain involves using your walking stick, but if you only use that, you’re doomed.

Tool 2: The telescope, which allows you to peer at the shape of the mountain, collecting data and facts about the world that you can use to select your path.

The questions that guide your use of the telescope are ones like:

• What questions could I ask that would help me choose my path?
• What do I need to know about the mountains that I don’t yet know?
• What important question am I confused about?
• Where is my lack of knowledge showing?

The scope, like each of your tools, takes many forms. In a start-up, it may look like talking to customers, running surveys, examining other products, or scrutinizing the structure of your own product, keeping a keen eye out for flaws. In your career, it may look like researching career paths, talking to others who have tried different routes, quickly trying things out, and soliciting feedback on your work from your colleagues.

What you’re looking for with the telescope are indications of which nearby paths lead quickest up the mountain, as well as hints for other (potentially faraway) parts of the mountain range that may have yet higher peaks (even if you have to go a ways back down the mountain to get there).

Being good at using the scope means being observant, impartial, curious, methodical, open to criticism, and empirical. And it means being able and willing to cope with reality.

Tool 3: The notepad, which you use to formulate your theories about how the world works, as well as to devise plans.

This tool will most dramatically increase how effectively you use the telescope because there are far too many potential things to point the scope at. Your theories on the notepad, therefore, guide your use of the scope. At the same time, the scope provides data to go into your theories in the notebook.

Some of your theories will be explicit, penned in detail with full awareness, but most will be implicit, born out of the things you’ve seen, etched in your subconscious with a shadowy ink.

In your personal life, your notebook contains your understanding of yourself, your partner, your parents, your friends, and human nature. It contains your understanding of your mountains (as well as other people’s mountains) and your beliefs about where the brambles, boulders, and high peaks lie.

To use the notebook is to sit and reflect, to make predictions, to spell out your thoughts, to reduce ambiguity through precision, to derive new knowledge from other things you already know, to come to new conclusions.

Being good at using the notebook means being thoughtful, philosophical, reflective, logical, cautious, precise, and rational.

Tool 4: The jump rope, which you use to practice and improve your skills.

Sometimes, this will take the form of physical training – maybe you don’t yet have the bushwhacking skills to knock away the brambles. Oftentimes, the training and practice will be mental rather than physical. Maybe you don’t know enough about how to use the scope, or your facility with the notepad is not where it needs to be.

Early on in your journey, you’ll need to use the metaphorical jump rope a lot so that you can build the skills you’ll need for the journey. Over time, you’ll need it less often, but there will always be new skills that are useful to train as you climb higher.

The jump rope is informed by the scope and the notebook. Sometimes the scope will tell you about the sort of paths you’ll soon need to face, and the jump rope will help you prepare for them. Other times, you’ll turn the lens of the scope on yourself to see your weaknesses. You can then use the jump rope to work on these, to reshape yourself.

You’re using the jump rope when you’re reading to learn, taking a course to understand something important, practicing how to do something, asking someone to teach you, breaking a difficult skill into smaller pieces, or asking a question when you’re confused.

If your walking speed is slow, or you find another weakness that is slowing you down, use the jump rope to get that skill up to par. But just as importantly, use the jump rope to hone what you’re already good at, to sharpen it into an exceptional skill.

Tool 5: The whistle, which is how you get the help you need from others.

Most things that are worth doing can’t be done alone, and those that travel without a whistle put themselves in great peril. Sometimes you’ll need the help of others to clear a path, to show you how to use the other tools effectively, or to help you understand why you’re stuck. No matter where you’re headed on the mountains, there are those that have gone that way before who have advice to share.

Using the whistle may mean requesting assistance or a favor, but it can also mean asking advice, asking a simple question, or getting support when you’re mentally exhausted.

Being good at using the whistle means investing time in your relationships, developing deep connections, being a good friend when others use their whistles, meeting new people when you perceive gaps, and being bold enough to call for support when you could use it.

Never travel without a whistle when you don’t have to.

So how, then, do you get to the top of your mountains? Well, you will never get to the very top – the mountains stretch forever. But you can climb high. To maximize your chances, use:

(1) The walking stick (to keep moving forward without giving up).
(2) The telescope (to investigate the mountains carefully and with minimal bias so that you can understand where the brambles and boulders are).
(3) The notepad (to reflect carefully on your beliefs and formulate your plans).
(4) The jump rope (to improve your weaknesses and enhance your strengths).
(5) The whistle (to get help and support).

Good luck – may your climb be a joyous one!

This piece was first written on May 19, 2023, and first appeared on this site on September 22, 2023.

I’ve noticed that it’s quite common for people to struggle to know what they should do to support friends or family members going through a mental health challenge, and it’s also quite common to say counterproductive things in such situations.

With the aim of helping you better help those people in your life who are struggling, here’s a list of five things that are usually a *bad* idea to say to someone who is dealing with a mental health challenge, along with seven things it usually is a *good* idea to do in such cases.

Part 1: things that are usually a *bad* idea to say to someone who is going through a mental health challenge

1. “Just think positively.”

For most mental health challenges, the problem is not a lack of positive thinking, and even if it were, being told to “think positively” would not enable them to actually be able to do so. This advice also trivializes people’s problems and so can come across as quite annoying or condescending.

2. “Focus on everything you have to be grateful for. Other people don’t even have enough food to eat!”

While it may be true that their life objectively has a lot of good things in it, their mental health challenge is not going to go away just by observing that. Gratitude can be a very useful mindset, but it is not a solution to mental health challenges, and being told to be grateful for what you have can lead to feelings of guilt (e.g., “I’m such a screw-up that I can’t even be happy when I have all these good things!”)

3. “You have to choose to be happy.”

It’s extremely rare that people choose to have a mental health challenge, and very few people, if any, know how to take the ongoing action of “choosing” to be happy. This framing of “choice” can also come across as though you are blaming the person for their mental health challenge, which is likely to be counterproductive.

4. “Today is the first day of your new life!”

This assumes that they can suddenly break out of their old patterns by reframing their life as starting anew, but this is a very unrealistic assumption. 

5. You should read “The Secret”/”The Power Of Positive Thinking” (or similar books)

These are in a genre of books that tell you that your problems are the result of not thinking the right way and that if you just start to think differently (e.g., imagine yourself succeeding and believe it with certainty), you will suddenly start to have the life you want. These techniques usually do not work for people with mental health challenges and can leave the reader feeling blamed for how they feel.

Part 2: things that usually *ARE* helpful to do with someone who is struggling with their mental health:

1. Ask open-ended questions about how they’re feeling and what they’re experiencing, without pushing them to reveal more than they’re comfortable with. Listen carefully. Try to really understand what they are going through.

2. Learn about the condition. Reading a book or two about the condition they are struggling with, or talking to an expert about it, can help you better understand what the other person is dealing with and can improve your ability to support them in helpful ways. Keep in mind, however, that their manifestation of the condition may differ from the typical manifestation, so be careful about jumping to conclusions about what they must be experiencing.

3. Empathize with them and show compassion. Don’t blame them for what they’re experiencing. And don’t use their struggles as an excuse to spend a lot of time talking about your own struggles. Though if you have been through similar challenges, they may appreciate knowing that.

4. Encourage them (with gentleness and compassion) to seek professional help (e.g., an excellent psychologist or psychiatrist). If they’re struggling to get started, ask permission to assist, and if they agree, reduce the effort for them (for instance, by trying to track down an excellent professional and provide them with the contact info). Thankfully, most people will improve when they are given evidence-based treatment that is carried out by a competent mental health professional (though it may take a few tries and failures to find a treatment that works well).

If they aren’t willing to see a therapist, you can ask if they would be up for reading a book that is specifically designed to help people who have mental health challenges. If they agree, you can research what the best book is on the topic and buy it for them.

For instance, many people have benefited from the David Burns books Feeling Good (for depression) and When Panic Attacks (for intense fears, such as social anxiety and phobias). Chronic worriers may benefit from The Worry Cure by Robert Leahy. For people who are mean to themselves (e.g., engaging in negative self-talk), the book Self-Compassion (by Kristin Neff) may be useful. For people who have very intense emotions or who have Borderline Personality Disorder, The Dialectical Behavior Therapy Skills Workbook by Matthew McKay may be useful.

If the person expresses openness to it, you may also want to encourage them to engage in other healthy behaviors that may be beneficial (such as eating healthy food, walking outside daily, and getting regular exercise at the gym). It’s ideal if you can make these behaviors easier for them, such as by offering to go to the gym with them three times per week or by buying them a healthy meal delivery plan as a gift (with their permission, of course).

5. Avoid advice until they are ready to hear it. In an attempt to be helpful, people are often much too quick to give advice, which can be very frustrating to the receiver (especially when the advice-giver doesn’t really understand the circumstances well). The time to give advice is after you have done a lot of listening and when the other person has indicated that they would like your advice. If you aren’t sure if they want advice, you may want to ask something like, “Would it be helpful if I gave you some suggestions now for how to do X, or would that not be useful at the moment?” Of course, once they are ready for advice, you should absolutely give it. When you do give advice, try to make it clear when you are confident in what you’re saying versus when you aren’t as sure (and they may want to consult someone else, such as a mental health professional).

6. Do nice things for them that you know (based on past experience with the person) they’re likely to appreciate – whether it’s spending more time together, sending a random compliment, reminding them you love them, giving an extra hug, planning a fun activity for the two of you (that they feel well enough to enjoy), or offering to help them clean their apartment. What matters, of course, is what they would actually appreciate in their current state, not what you would appreciate if you were them, and not what they would appreciate if they weren’t in their current condition.

7. Make your help sustainable. Remember that it is not your job to “fix” this person’s mental health, nor will you be able to do so. Mostly, you can only help someone when they WANT to be helped and only in ways they are WILLING to be helped. It’s also important that you take care of yourself in the process. This person may have a mental health challenge for a long time, so (other than in cases of acute crises where extra action is needed), it’s not a good idea to extend yourself in a way that will not be sustainable. Don’t jeopardize your relationship with this person by taking on more than you can realistically handle, which could lead you to experience burnout or resentment. Just because someone is experiencing a mental health challenge does not mean you should let them violate your boundaries. If the person is acting in a way that is harmful to you, it’s important that you clearly assert your boundaries to prevent yourself from being harmed (while you continue to help in whatever ways you can, without giving up on those boundaries).

Conclusion

Everyone is different, so it’s always possible someone would benefit from items in the “bad” list above or dislike items in the “good” list. But I believe that following these guidelines will, more often than not, make you more effective at helping the people you love.

In summary, as a friend/family member, your job is to provide love, empathy, and the level of support that you can sustainably manage. Avoid giving shallow suggestions such as to “think positively.” Instead:

• ask open-ended questions

• learn about their condition

• empathize with their experience

• encourage the person to get high-quality professional help

• avoid giving advice (until they want it)

• do nice things

• make your help sustainable

This piece was first written on January 8, 2023, and first appeared on this site on May 28, 2023.

If you’re like me and really dislike small talk, you may find these ideas useful.

(1) If you end up talking about their work, ask what they (i) most like about it and (ii) find most challenging about it.

(2) If they end up asking about your work, try to explain what you do in a way you’ve never experimented with before.

Example: if you’re a programmer, maybe you’ll say your job is to convert ambiguous human goals to instructions that are so precise a computer can follow them.

(3) Pay close attention to the other person’s vibe and make a positive (and genuine) observation about their personality or manner. For instance, if they have a really pleasant-sounding voice, tell them that. If they give off a lot of confidence, compliment them on it.

(4) Assume the other person is worth knowing. Give them the benefit of the doubt. Now your job in the conversation is to explore what’s interesting about this person.

(5) When the conversation lulls, say, “This is random, but I’ve been thinking a lot about something lately, and I’m curious what your take on it would be.” Then ask a question you’ve been pondering (e.g., “How do you decide how much time to spend making new friends?”)

(6) Assign yourself the goal of figuring out what they would enjoy talking about (but without directly asking – since “what would you like to talk about?” puts uncomfortable pressure on them). Ask questions about their thoughts and interests to discover the right topic.

(7) If there’s something interesting in the environment, remark on it and ask what their reaction to it is or open the door for them to comment on it too.

Example: “I just noticed that house has a different style of architecture from the others. Do you like its style better or worse?”

(8) Ask the person what sort of things they are interested in. This can be a slightly awkward question, but I think it’s often worth it. In my experience, it tends to have a good payoff in that it helps you jump to talking about something the other person cares about. Sometimes people will talk about work (when they enjoy it), but other times, they will bring up an idea they are interested in or a hobby they are passionate about, etc. From there, I find it’s typically much faster to get to mutually interesting conversations than if we started with small talk.

The thing about small talk is that it’s designed to be low-risk.

Deviating from small talk increases the chance that a conversation ends up being awkward.

And, of course, it’s possible the other person just doesn’t want to engage with you on a deeper level than small talk. It’s important to stay attuned to how the other person is feeling and not push them beyond the level of engagement that they feel comfortable with.

But when done skillfully, strategies like these often make the conversation much more interesting for everyone involved.

This was first written on December 3, 2022, and first appeared on this site on June 4, 2023.

One way to cut through the noise is to look at the commonalities between the advice that many different highly successful people give (i.e., take the “intersection”), letting the noise and contradictions drop away. If many of them provide the same advice, we can be at least somewhat more confident that it generalizes. Having said that, we should nevertheless remain mindful of selection effects (affecting who we hear advice from), including survivorship bias.

With that in mind, here’s my attempt to “intersect” the repeated advice I’ve read or heard from many different highly successful people who come from a wide range of fields and life circumstances. I expand on each piece of advice by listing common themes I’ve heard around that advice (that I also largely agree with), and then I give a relevant quote.

Ten Repeated Pieces of Advice From Highly Successful People

1. You won’t automatically be happy when you reach your goals.

Achieving goals breeds new ones.

A terrible situation creates misery, but a good situation doesn’t imply you’ll be happy. Happiness takes inner work, and it benefits a lot from gratitude for whatever it is you already have. The good life is a journey, not a destination.

Quote: “Happiness cannot be traveled to, owned, earned, worn, or consumed. Happiness is the spiritual experience of living every minute with love, grace, and gratitude.” – Denis Waitley

2. High levels of accomplishment almost always require hard work over a long time. “Overnight successes” are rare and are often misidentified. If you look closely, usually, the person was practicing for 5-20 years before they were an “overnight success.”

Always be looking for how you can do your work better, and focus on improving in those areas. Compounding improvement over a long period is how people become great at things.

Quote: “I’m a great believer in luck, and I find the harder I work, the more I have of it.” – Thomas Jefferson

3. Life is unpredictable. When young, people usually don’t know what they’re going to “do with their life.” That’s fine!

Life takes crazy, unexpected twists and turns. Plans are great, but you should expect to modify them. Be adaptable and on the lookout for great, unexpected opportunities.

Quote: “Sometimes, when you go looking for what you want, you run right into what you need.” – Wally Lamb

4. Don’t let fear stop you. Attempting hard things will bring stress, fear, and anxiety. 

If you avoid what you fear (more than is warranted by the level of danger), your potential will be curtailed. Learn to push through your fears to do stressful things that are valuable.

Quote: “Life shrinks or expands in proportion to one’s courage.” – Anaïs Nin

5. Choose who you spend time with wisely. Be thoughtful about who you are friends with, whether you spend enough quality time with your loved ones, etc.

Spending time with the wrong people will waste time or even sap potential. Make enough time for the people that matter most to you.

Quote: “You Are The Average Of The Five People You Spend The Most Time With” – Jim Rohn

6. Learn to say no. People will ask you many things from you. If you always say “yes,” it will drain energy & focus.

Say “yes” to your loved ones and to requests that are aligned with your deepest values. For others, consider if you realistically have the bandwidth to handle the request without taking away from your most important priorities. If not, give an authentic “no.”

When you’re starting out, it makes sense to say “yes” to more things. The more successful you become, the better you have to get at saying “no” – otherwise, your life will be dictated by other people’s demands.

Make choices based on your own values rather than based on what pleases or impresses others. Be your authentic self.

Quote: “Half of the troubles of this life can be traced to saying yes too quickly and not saying no soon enough.” – Josh Billings

7. Take care of your body. Exercise regularly, reduce sugar intake, eat healthy foods that make you feel good, make enough time for sleep, and avoid excessive alcohol/drugs.

Good health has ripple effects and will help you achieve your goals. Your body impacts your mind.

Quote: “The groundwork for all happiness is good health.” – Leigh Hunt

8. Take care of your mind. Meditate regularly (or find another practice that refreshes and resets you). Sleep enough. Seek treatment for mental health challenges.

Get out of relationships where people mistreat you. Have compassion for yourself, and treat yourself with kindness.

Know your limits, and keep stress within those limits. Take some time just to relax and have fun with no obligations. Take vacations.

Quote: “If your compassion does not include yourself, it is incomplete.” -Jack Kornfield

9. Expect to fail many times. That’s normal and expected. 

The key is to learn from every failure, pick yourself back up, and keep going. If you’re not willing to fail many times, you aren’t prepared to do hard things.

Quote: “I have not failed. I’ve just found 10,000 ways that won’t work.” – Thomas Edison

10. Leverage habits. Figure out what daily pattern works for you. 

Maybe it’s an hour of writing at 6 am, strong tea in the morning, a carefree walk in nature at noon, or jumping jacks in the early afternoon. Experiment to find what works well for you, and stick to it.

Quote: “First, forget inspiration. Habit is more dependable. Habit will sustain you whether you’re inspired or not.” – Octavia Butler

This piece was first written on January 26, 2021, and first appeared on this site on October 14, 2022.

The Setup

Person X and person Y are friends (or lovers or close work colleagues or whatever). Person X and Person Y happen to both feel the same way about each other (i.e., equal amounts of interest, affection, lust, respect, etc.)
Person X’s ideal is to make plans with person Y every two weeks, whereas person Y (who has a lower amount of free time, or less need for social interaction, or a project they are prioritizing, or whatever) wants to see person X every three weeks. Hence, they differ in their preferred time interval between hangouts.

So what happens? Approximately every two weeks, person X asks person Y to spend time together, which means that person X ends up doing essentially 100% of the invites (since three weeks rarely elapse without Y receiving an invitation from X, so Y almost never asks X to spend time together).†

In other words, Y wants to see X at only a moderately different rate than X wants to see Y (e.g., every three weeks instead of every two weeks) but ends up doing 0% of the invitations.

Person X then assumes that their relationship is imbalanced, and person Y must not feel the same way about the relationship that they do (but happens to be wrong). This can lead to awkwardness and relationship problems.

So how should X handle a situation where X ends up doing all of the inviting without Y reciprocating (but with Y agreeing to see X whenever X does send an invite)? We’ll assume in each of these cases that the people actually do spend time together when an invite is made (i.e., it is not a case of one person purposely ignoring another).

Some would suggest that, if both people simply ask each other their preferences, that can work best for the right types of people. Especially if both are on board with such explicitness of conversations about relationships, know the other person is on board too, and are confident that negative ramifications such as damaging awkwardness won’t result from that explicitness. In most cultures, the explicitness of the form “I’d prefer to see you every three weeks, how often do you want to see me?” is not the norm but certainly is normal in some subcultures.

Always Ask Strategy

The default strategy would be for person X to just persist in making the invitations every two weeks. One drawback is that person X might feel bad about always being the one to make invitations. Another drawback is that person Y might feel frustrated because they end up having to stall regularly on those invites to get their desired rate of spending time together, or else agree to see X on X’s preferred schedule rather than their own. Yet another drawback is that person X might be misreading the signs: maybe person Y just feels bad about saying no and so agrees to see X despite not wanting to? Person X knows that person Y is not reciprocating the invitations by sending invites back to X but doesn’t know the reason Y isn’t reciprocating.

Tit-For-Tat Strategy

Another strategy would be for person X to never make two invitations in a row. That means that person X would make the first invite (after two weeks), and then person Y would make the next invite (after three weeks) and then person X the next and so on. This isn’t a terrible solution since they would see each other every 2.5 weeks, which is a nice compromise. However, it does have a very major drawback, which is that if person Y forgets to make an invite back, then they’ll be stuck not seeing each other. In other words, it’s leaves room for mistakes, and could inadvertently destroy a great relationship. Hence far from ideal! This could be expanded to a “Tit-For-Two-Tats” strategy, where X makes two invites in a row but not more than two. But this actually is not really more robust in this scenario than Tit-For-Tat, since after two invites from X (which will definitely happen in this scenario), if Y then forgets to make the next one, no more invitations will occur.

Exponential Strategy

A third strategy would be for person X to double their invite time interval each time their last invite does not get an invite in return, and then reset back to their original invite time as soon as they get an invite back. (It doesn’t have to be double, of course, it could be X multiplying the invite time by any constant C>1.)

To see what I mean in more detail, consider the situation where X still prefers to see Y every two weeks, but now Y prefers to see X every ten weeks. First, person X makes an invite after two weeks, and they see each other at that time. Then since Y doesn’t reciprocate, X multiplies their time by two and so makes an invite after four weeks. Since Y again doesn’t reciprocate, X multiplies their time by two again and makes an invite after eight weeks. Since person Y’s desired time to see each other is ten weeks, then Y will end up making the next invite (since X wouldn’t make their next invite for 16 weeks). Now since a reciprocation occurs, X resets and so sends the next invite in 2 weeks, then the invite after that in 4 weeks, then eight weeks, etc.

There are some neat things about this strategy. First of all, it’s robust to mistakes since even if person Y accidentally forgets to make a reciprocation, person X will still end up reaching back out with an invite. Second, it does a pretty good job of balancing the desires of both parties by finding an average meeting frequency that is a compromise of both their ideals. The math gets a bit complicated†† but, suffice it to say, for most values of K (person X’s ideal timing between invites), C (the multiplier that X applies to their invite time interval with each unreciprocated invite), and N (person Y’s ideal timing between invites), the average time delay of the two people seeing each other will be fairly close to halfway between X’s and Y’s ideal time delay (to be more precise, it’s usually in the range of 25% of the way from K to N up to about 75% of the way from K to N).

Another neat thing about this strategy is that in the event that X has misjudged this situation, and Y actually doesn’t want to spend time together, Y gets pestered with exponentially decreasing frequency, meaning that the total annoyance Y experiences and the total embarrassment from non-reciprocation that X experiences are both limited.

One final point about the exponential strategy is that it works well if both parties use it even in an environment where forgetting is common (i.e., if 30% of the time people get distracted and so forget to make an invite).

Takeaways

In reality, one would, of course, not do calculations like this formally, and this simple model doesn’t include all relevant factors. But perhaps the Exponential Strategy can give us a decent intuition for how we might handle these sorts of situations in real life. When we want to see someone at regular intervals, and the person does agree to see us when we make invites but doesn’t make invites of their own, increase our invite time interval by some constant factor (say, 2) each time we have a non-reciprocation, but reset back to our most desired invite time interval whenever a reciprocation occurs.

† Note that this math works out even if X has some amount of noise in when they ask Y to spend time together, but as this noise gets large, the math eventually breaks down.

†† The average delay D that occurs between invites when person X is using the Exponential Strategy will be:
D = (N + K * sum_{t=0}^{M-1} C^t ) / (1 + M) where M =Ceiling[Log[N/K]/Log[C]]

Since punishment reduces certain behaviors, it’s important to consider whether we actually want to reduce the behavior we’re punishing. It’s critical that we not punish behaviors that we actually want others to do or that are generally healthy or good for others to be doing.

The micro-punishments we mete out shape the behavior of those around us and can have a substantial impact on other people and our relationships with them long term.

Punishing the important people in your life can be even worse than I’ve made it sound, though, because while it usually punishes some specific behavior (which may or may not be desirable), it almost always also punishes them for being around you, at least to a small extent. In other words, if you punish a lot, you are training people to avoid you.

One important detail regarding reward and punishment is that, typically, what’s most strongly rewarded/punished is what’s happening at the present moment. So, if when your roommate comes into your room to say “hi,” you annoyedly ask them to do chores that they’d forgotten, the primary thing you are punishing is them coming in to say “hi.” You’re only secondarily punishing their failure to do the chores.

Consider these common sources of punishment that may have unintended negative consequences:

1. Aggressively pointing out flaws or logical leaps in other people’s comments. Others may become less likely to make logical leaps around you, but they may also become less inclined to bring up ideas with you in general.

2. Becoming non-responsive each time your partner brings up an important problem in your relationship. Your partner may learn to stop trying to fix the problem.

3. good-naturedly teasing a friend about something embarrassing or personal they just told you. You might be training them not to tell you personal things.

4. Nagging your child when she calls. She might learn to call you less.

5. Giving only critical feedback when a colleague shows you their work. They may eventually stop showing you their work.

6. Giving a disgusted facial reaction when friends express opinions you don’t agree with. Your friends learn not to express opinions around you.

7. Sounding angry when discussing politics. You may be training people to avoid the subject.

8. Sounding defensive when you’re given constructive criticism that’s intended to help you. You might be teaching the people around you not to try to help you improve.

The flip side of punishment is the reward. What are you rewarding the people in your life for? Are you rewarding them enough when they do behaviors that you appreciate? You are also shaping behavior with each micro-reward you give.

Consider these ways you can reward the people around you to increase positive behaviors:

1. Noticing when friends make interesting or well-reasoned points and giving compliments accordingly. Your friends may become increasingly enthusiastic about discussing ideas with you.

2. Being highly receptive and responsive when your partner brings up a problem in your relationship. They may be more motivated to fix problems that come up rather than letting the problems fester.

3. Listening to your friend with interest, kindness, and understanding when they tell you a personal thing. They might learn to open up to you more often.

4. Responding with great enthusiasm when your child calls. Your child might start calling more often.

5. Pointing out what’s right and well done about the work your colleagues have done. They may increase the rate at which they do these things the right way.

6. Channeling and really experiencing your warm feelings for a person while you’re talking to them. They find themselves wanting to spend more time with you because they feel liked around you.

7. Being excited and engaged when someone brings up a political topic that you really enjoy discussing. People may learn to bring that topic up with you more in the future.

8. Being grateful when you’re given constructive criticism that’s intended to help you. You’ll be teaching people that you want their help to become better.

—

The excellent book “Don’t Shoot the Dog” (http://amzn.to/2fKCup7) by Karen Pryor got me thinking about this topic of interpersonal reward and punishment for the first time (when I read it many years ago). It’s about how Operant Conditioning (basically, the scientific theory of reward and punishment, as typically used in animal training) works and how to apply it in your life.

TIME

– Stay in touch: if one of your closest friends doesn’t live nearby, try to either plan visits or video calls or both; otherwise, a long time can go by without interacting

– Hangout in groups: when strapped for time, try to schedule group events to see more of your friends more often (i.e., when you don’t have enough time to schedule one on one hangouts with everyone); that way, you don’t have too much time elapse before seeing friends

– Hangout alone: hang out one on one with your close friends at least some of the time (don’t get in the habit of only hanging out in groups, as it doesn’t usually facilitate the same depth of connection)

– Plan retreats: plan trips with your friends where you spend a couple of days straight (or more) together

– Create a community: introduce your closest friends to each other on multiple occasions (e.g., by inviting them out together or by hosting dinners or events) so that some of them become friends too, and ideally, so that you all find yourselves hanging out together

– Befriend their partners: take the time to really get to know their long term romantic partners, and make an effort to forge connections with them too

THOUGHTFULNESS

– Share nice thoughts: if you happen to think something nice about your friend at a random moment, text the nice thing to them

– Give compliments: at least occasionally tell your friends what you think is awesome about them (in detail if you can); they’ll likely really appreciate hearing it

– Express caring: at least occasionally tell your closest friends that you really care about them, in whatever way they would be most receptive to hearing it

– Give surprise presents: if you see something small at a store that you think a friend would love, buy it for them and surprise them with it

– Send cool stuff: if you see a cool thing online that you think your friend would love, send it to them

– Remember occasions: remember your friends’ birthdays and other important life events (e.g., put it as an event in your calendar to help you remember) and call them or write them a note when these events occur

– Reschedule quickly: if you have to cancel plans with a friend, then immediately reschedule the plan (rather than leaving them hanging open) and try to let your friend know about the cancelation with as much notice as possible (also: try not to cancel frequently)

– Remember on trips: when you go traveling, send your friends photos during or after

– Apologize: if you are irritable with a friend when he or she didn’t deserve it, or you did something unfair to a friend, admit it immediately and apologize; accepting full responsibility

– Explain how you work: if you have personal quirks or triggers that people who are close to you can benefit from knowing about, tell your close friends so that they can better model you and so that they know how to make you happier

– Forgive one-off mistakes: if a friend makes a mistake that you think they are unlikely to ever make again, just forgive them immediately

– Explain desired behavior: if a friend makes a mistake or does a thing that bothers you, and you think they might end up doing the thing again, tell them how the thing made you feel and how you would prefer they act in future situations like that one, then forgive them

– Avoid excessive negativity: try not to be TOO negative TOO often when the same friend is around, as it can inadvertently be a form of punishment for spending time together, which is not good for either of you

– Explain what you need: don’t assume your friends can read your mind about what you need or want; tell them if you need or want something

SUPPORT

– Reach out when they need it: if you know a friend is going through a hard time, reach out to them periodically (so they know you are there for them) rather than assuming they will reach out to you if they want your help

– Reach out when you need help: contact your friends when you need help with a difficult problem or need emotional support from them, don’t assume they will automatically know when you need their help

– Varied Support: if you are in a period where you’re frequently needing emotional support, try to spread that needed support among multiple friends if you can arrange things so that one doesn’t end up bearing all the weight of it

– Support the way they want: if a friend is telling you about a problem they are having, try to figure out if they desire empathy, validation, optimism, or problem-solving, and give them whichever of these they actually came to you for (rather than what YOU would want to be given in that situation)

– Delay judgment: if your friend does something that you have a judgmental reaction to, try to delay that reaction and take the time to ask questions to understand WHY your friend did that thing (the more you can relate to their reasons, the less judgmental you are likely to be)

– Express concern: gently express concern when your friend tells you about something they are doing that seems like it could be harmful or self-destructive (since encouraging harmful behavior is a harmful form of support, and harsh judgment is usually not helpful and may cause your friend not to tell you about those sorts of things in the future)