Anyway, I’m not trying to get deep into AI tools today (or ever, probably, in this forum). My broader thoughts have been on technology in general. It feels that in 2026, getting deep is increasingly challenging. AI or not, it’s easier than ever to get a fast answer to questions that would have once led to meandering, nuanced, deep consideration and debate. I find myself fighting this tide by intentionally finding ways to bring back behaviours that are often deemed “old fashioned.”

Here’s a few of the things I’ve done recently and why I’ve found them valuable:

Hand-written cards.

Whether for weddings or thank yous or other occasions, I always try to buy a nice card and write at least ~7 sentences of greeting. It’s so easy to pull up Venmo or PayPal to send someone a gift. While that’s very utilitarian (and I embrace it in tandem with a card), it feels like something is missing in the gifting ritual without a tangible item changing hands. Nostalgically, I always conjure up the image of someone reading an old letter from their better half and holding it up to smell it, imagining the other person writing it.

A home phone.

Like a landline. Remember those? Granted, ours is not a literal landline; it’s a VoIP. But I love it. It brings back the era when a household had a shared communication point with the outside world. It democratizes access to us when we’re at home—call us at this one phone number, and you’ll get someone from the household.

It’s kind of refreshing to have a singular access point as a family, instead of others having to always make a choice on who to contact. I struggle with this whenever we need to set up plans with other couples—it’s annoying to have to create a four person group chat. Why couldn’t every family just have a distribution list style access point? (Landline aside, we also have a joint email and I wish it was easier to use it for more things.)

Pen-and-paper grocery list.

I’ve gone back and forth on this one. Sometimes I think the digital list works better because I can add to it whenever I want, no matter where I am. Other times, I feel that the digital clutter has gotten out of hand and will never be wrangled under control. Paper lists, in contrast, are incredibly satisfying to recycle once I’m done. And it’s also easier than struggling with my phone while shopping. It’s nice to cross things off, be tactile, and also easily share the list. Having the list somewhere where everyone in the household can see it helps tremendously with empowering all of us to contribute and also helps if there’s handoff between us to go pick up items we need.

Hand-written journal.

Every night before bed, I journal. I’ve done this for almost five years now. I’ve recently invested in nice pens to make this experience even more enjoyable. Other than avoiding the harmful effects of blue light on sleep quality, journaling by hand also gives me a chance to slow down. I can type a lot faster than I can write, so being restricted by my writing speed forces my brain to start to unwind.

Are there things that you purposefully do to be more un-tech-ified? I’d love to hear about them!

Leave a comment

I recently helped onboard several people to my extended team and it reminded me of all the different pieces that go into a successful onboarding. Here’s my take on what’s most important, so you can also copy/paste this template the next time you have a new teammate at work.

First: Having lots of time together in the first 30 days makes a meaningful difference.

I try to make myself as available as possible to share as much knowledge as I can. Even if the new hire isn’t my direct report or on my direct team, I always offer to set up recurring time for us to meet. Depending on how closely we work together, I adjust the frequency of our catchups. No matter how good your documentation or onboarding packet (more on these later) is, nothing can beat a live conversation where questions can be triaged in real-time. The benefit of setting up recurring time is that it can always be canceled if needed—canceling is low barrier, whereas adding new meetings can feel awkward or uncomfortable for a new teammate. More often than not, I’ve found that new teammates always find questions that fill the time valuably.

Next: The onboarding packet—aka knowledge shared in written form.

As alluded to above, there’s a critical document: the onboarding packet. This should cover the context and broader history of the organization, as well as squishier things, like the ways of working or other cultural nuances. I like to usually make a singular document that includes links to other resources, as well as some bullet point notes on:

• Who’s relevant (i.e. important 1:1s to set up)

  • This should include people on the team as well as people on adjacent teams, i.e. cross-functional partners

  • They may not be people who are immediately expected to work with this new person, but folks with whom they’re likely to cross paths down the road or otherwise find helpful

• Companywide, higher level strategy documents, board presentations, etc.

• A guide to key forums or meetings at the company/for the team (and don’t forget to add these to their calendar too!)

• Notes on how the team communicates – what goes in email vs Slack vs other places…

  • Along with that, important Slack channels, Google Groups, other tools that are used regularly

• Additional notes on any team norms

• Relevant prior work from the overall team and any other references that provide insight into key priorities for the team

This sort of packet can help the new hire self-orient in the first few days outside of intro meetings and also becomes an important reference for them in the coming weeks.

Third: Project or workstream specific information, paired with an onboarding project.

In the first 30 days, it’s crucial not just to knowledge share but also to let new teammates get their hands dirty. There’s only so much one can learn from listening and reading.

If you are the new hire’s manager, it’s crucial to pick the right onboarding project. Here’s what I typically think through:

• Scope: It should be something that’s narrow enough in scope that the new hire isn’t overwhelmed with processing information from tons of different sources (and potentially overly contradictory). It can’t be a project that’s at risk of having a totally rogue outcome, unless that’s a specific skill this new hire was brought on board for. That said, the project should also be broad and open-ended enough that there’s discovery and net new learning for them to do—i.e. it’s not so obvious what the answer is.

• Timeline: It should be a project where quick progress can be made in 2-4 weeks so that the new hire feels momentum. If the project has significant dependencies on other teams or isn’t sufficiently resourced, then it’s probably not ideal.

• Skills required: Ideally, the project will allow the new hire to dip their toes into various tools that they’ll need to learn. Often this could be some data analysis that they can do independently coupled with light interfacing with other cross-functional partners.

• Precedent: It’s helpful to pick a project where there are precedents, meaning the new hire can reference examples. That can help give them a sense of templates to work off and other norms.

Not every project or workstream they onboard into needs to come with an onboarding project. The onboarding experience could consist of an onboarding project into one workstream alongside a few weeks of context ramp-up on a few other workstreams, where the new hire will later take up responsibilities.

For these materials, whether part of the onboarding packet or not, I like to include:

• Historical documents that led to the current incarnation of the project

• Clarity on who’s involved and each person’s role / responsibilities

• A guide to key forums specific to this project

• A high level overview of the onboarding project (if applicable)

Finally, set up something fun!

Whether it’s a welcome happy hour, sending some welcome swag, or otherwise getting the team together, don’t forget about the human side of onboarding a new teammate. It’s nice to make new teammates feel welcome and special.

Did I forget anything else? Drop a comment about what else you do when onboarding new teammates.

Leave a comment

Clear my browser history

I am an avid user of command + T for a new tab and then typing in keywords and clicking down to find the right webpage out of my browser history. Clearing my browser history feels like a good housekeeping task but I’m so scared of doing it because then I’d be absolutely at a loss for how to find anything. This applies both at work and at home. Should I just do it? Or has technology progressed far enough that having an extensive browser history isn’t really slowing me down?

Tell more people how I actually feel

I take a lot of pride in doing this with my closest friends, but it drops off pretty steeply for people outside of that group. I justify this because being really open, direct and blunt with people can be taxing and requires high trust in order for it to not be misconstrued. Thus, the juice has to be worth the squeeze. However, should I be doing this with more people? Could that actually be freeing? Should I stop nodding along politely in agreement and become a vocal naysayer when I disagree?

Just stop replying to texts for a day

I feel a lot of guilt if I’m not responsive, and I also take pride in the service levels I uphold as a fellow texter. However, maybe this is not serving anyone well. I have heard repeatedly that some people find really responsive texters overwhelming because it sucks them into the vortex of rapidfire back and forth… So maybe I’ll just defect to the nonresponsive side and you’ll have to reach me by pigeon.

Admit that my superpower is delegating

I think it’s really weird to speak openly and proudly about one’s own superpowers, but maybe I should get over that. I recently realized that most people are reticent to say anything when others ask them, “What can I do to help?” whereas I’m usually the first to blurt out a list. I don’t know if it’s because I have a long to-do list in my head at all times that I can just recite, or if it’s because I’ve grown to really trust people around me to help. But I have found that I can map outstanding to-do items to people and their skills really quickly, and I’m surprisingly comfortable vocalizing this. Is it time to lean in and not feel guilty about delegating or being good at it?

Sit in peace with not having plans

It feels weird to live so open-endedly and not know what things might look like in a year or even a few months down the road. I feel inclined to book flights and hotels and to plan trips and to envision what my life will be like. But sometimes I think there’s beauty in not doing too much of this and leaving room for spontaneity.

Accept small messes

I used to be way more perfectionist than I am today, but I’m still pretty particular about small messes. For example, it really bothers me that I have a bunch of random files on my desktop and I will periodically take the time to clean them out. What’s stopping me from either accepting them as they are or just sweeping them all into a folder that’s hidden? I don’t think I believe that organizing them is necessarily making my life better, but somehow I still spend my time on it. I wonder how much time I could save by accepting small messes.

Dramatic as it sounds, I know I’m not the only one who’s found myself in this place of despair. As I stepped back to examine what I was doing, I realized that many of these tasks didn’t come with natural, obvious deadlines. As a result, I’d revisit the same task over and over again, often in five or ten minute increments (depending on attention span du jour), and I wouldn’t make any progress. I’d neither finish the task nor formulate a deeper opinion on how I wanted to proceed. Instead, I’d be stuck in this holding pattern—I thought I was making incremental progress when really, I was just zig zagging.

Examples:

• I needed to buy flights for an upcoming trip. Nothing was stopping me from doing this other than a notion of “maybe it’ll get cheaper” or “maybe I can find a good deal with points.” I had dates, I knew which flights I wanted, etc. I’d endlessly refresh the points search engine and Google Flights, and I’d leave this task incomplete on my list for weeks.

• I needed to purchase decorations for an upcoming party. I’d browse inspiration on countless websites, making my way from Pinterest to Instagram to Temu and back to Pinterest. I knew I needed to pick a theme and make a decision on budget, but instead, I was scrolling through option after option, not getting any crisper on my criteria.

• I needed to choose a restaurant for dinner with friends. I scrolled from listicle to listicle, and onto Google Maps. I looked at all my starred restaurants. I starred more restaurants. I wasn’t getting any closer to actually deciding—the options were either to send a short list to the group or just make a reservation. I’d leave this incomplete and then go back to googling restaurants again the next day, often redoing the same steps.

In many cases, I think I was falling victim to Parkinson’s Law, which states that “Work expands so as to fill the time available for its completion.”

There are some other handy ways to conceptualize this:

Once I realized this, I started to make some changes. I was most frustrated that I was randomizing myself with piecemeal progress (or “progress”) on a lot of tasks.

To stop wasting time, I started to set aside explicit time to do specific tasks. I realized that when they were on an infinitely long to do list, it was likely that they would not get done in an efficient way. Also, as a chronic over-planner, doing this gave me the mental safety of knowing that a future task was accounted for, and there would be time to tackle it, enabling me to not start on the task at an inappropriately early time.

Now when I triage my to do list, I break it down:

• Recurring tasks get scheduled time each week in a small block. I don’t give myself too long to dilly dally and I aim to get things done quickly in that window.

• One off tasks get scheduled time based on when they need to be done. I like to give myself some buffer so if I don’t feel like doing those tasks that day, I can move the block to another day. But this way, things get done in time without as much urgency or stress. I try to allot a few hours of time for one off tasks so I can get into the flow (and also this way, I can make an activity out of it—e.g. I can go to a cafe and camp out with my laptop to tackle one clear goal)

• Certain tasks that might be optimized for two or more parts are broken down accordingly. I usually like to put big purchases in this category because it gives me time to reflect between making an initial selection and the final purchase.

I will say outside of setting up this structure, the hardest part of this model is not thinking about these tasks outside of these blocks. Sometimes, inspiration hits and I do some of the work in advance because I just can’t help myself—especially if it’s something I’m really excited about. In those scenarios, I triple check with my gut to make sure that it’s fun and I’m not just torturing myself. Once I’ve made some progress, I shorten the block of remaining time to account for the time I’ve already spent on the given task.

In general, this not only made me more efficient but also reduced my stress and frustration at myself for being inefficient. It’s gotten me out of a doom loop more than once, and I try to constantly remember that gaseous tasks cannot be treated like linear tasks, such as washing the dishes or brushing my teeth. (That said, there’s an important adjacency here, which is that successful timeboxing also entails not yak shaving.)

All in all, this is probably a classic overthink and overoptimize on my part—but hopefully helpful, perhaps for a work context if not personal.

When I worked in consulting, it was very natural to become close friends with others in my start class, particularly since we mostly worked on separate case teams. We were all new college grads who’d moved to a new place and were figuring out how to “adult” together. It didn’t feel that much like being friends with coworkers because we were off on our various projects during the week and often barely caught glimpses of each other in the office. That said, over time, I also became friends with a number of people who’d been on the same case team as me. In those situations, there was a lot more interaction on a regular basis.

When I started working in startup-land, I also became close friends with coworkers. Then, I was working shoulder-to-shoulder alongside these people day in and day out, and also being friends with them in our outside-of-work hours. This felt more akin to becoming friends with my teammates on the same case, except that it was permanent, meaning our overlapping project wasn’t coming to an end after x months had passed. Pretty soon, the pros and cons of this type of friendship revealed themselves.

Since working at a larger company, I’ve pontificated a lot on the tradeoffs of such friendships. When I first started, I had fairly high conviction that I wanted to hold new boundaries and not become friends with coworkers. However, over the past year, I’ve met some great people and gotten closer to them. Naturally, I’ve started to build some degree of friendship that extends beyond work. As my conviction has wavered, I’ve perhaps been reminded of the benefits of friends at work.

On the one hand, it’s way more fun. I can be snarky and exchange true feelings and thoughts rather than always having a veil of seriousness. Whether friends or not, I try to generally be myself at work, but being friends means I can be a bit more unfiltered. This makes work feel less abrupt in the broader context of my life, because it allows me to transition back and forth rather than requiring me to shed one skin and don another. I also believe that being closer to people and understanding them better allows us all to be more effective at our jobs. Sometimes it makes me better at anticipating their needs and supporting them better or empowers me to provide more candid feedback that helps them grow and develop, just to name a few ways.

On the other hand, I think back to some of the downsides that I’ve experienced:

1. It makes it harder to have good work-life balance. There is no compartmentalization or clear divide. A post-work text conversation can devolve from non-work topics to work topics really quickly, if both parties aren’t drawing certain lines.

2. Moreover, it can make simple work obligations or disagreements feel magnified and way more personal. A debate suddenly feels more like a personal attack. Something where there wasn’t a need to bring in ego suddenly feels all about ego, or feelings are suddenly hurt when a decision is made with the wellbeing of the business in mind. What if you disagree at work? Can you continue on perfectly normally outside of work?

3. Does it break some sort of code of professionalism? I generally believe that I can still be professional and good at my job even if I’m sometimes silly or more of myself than just my buttoned up work self. But in moments of insecurity, I worry that being my unfiltered, raw self can lead others around me to doubt my abilities.

At the end of the day, I still don’t have good answers here.

It could be that the compromise is to embrace work friendships so long as there are healthy boundaries.

I actually set a new year’s goal of making one more friend at work this year because I felt that the friendships I’d developed so far have been meaningful and rewarding. I wonder if perhaps it is also easier for me now to be friends with my coworkers, as most people are not a part of my direct team. I don’t work super closely together with one set of people—in fact, it’s quite distributed. It’s entirely possible that the distance helps make it more fun and less risky to be friends.

Alas, I’d be curious to hear thoughts on this in the comments!

Leave a comment

For those of you who know me personally or have seen some of my prior thoughts (like this), this might be a bit surprising. However, The Household (as I like to refer to the collective decision making body) has decided to take a mindset of simplifying in 2026. As such, we’re streamlining the credit cards we keep.

As much as it pained me to cancel some of my cards—I may or may not have likened it to chopping off a limb in a moment of particular sadness—I’m pleased to report that it has made me feel more zen when I buy things. Picking which card to use has become a much faster, simpler process. The decision criteria are very clear, and I no longer have to make mini-optimization choices on the fly. (In particular, I now have one card that yields 2x per dollar spent no matter the category, rather than multiple that I have to choose between.)

[If you laughed at this, please feel free to go ahead and ❤️ this post to get it to more readers!]

As I made this observation, I started to ponder what else I can simplify in my life. My wardrobe has gradually evolved towards a capsule wardrobe (though slightly more generous in variety). Getting dressed has become a much simpler process, although sometimes I feel a little plain.

When I go to the gym, I have a trainer who tells me what to do, so I don’t have to make extra decisions about what to focus on. I’ve noticed that when I go to work out by myself, I am often overwhelmed by the options and resort to the same set of 5-6 exercises as well. (Probably not the best for my overall strength training though, so I’m glad for my trainer.)

I am a big fan of variety in my food, but I’ve started to meal plan for the week with a formula into which the meals slot. There’s usually a big batch meal on Sunday or Monday that will cover at least a few lunches into the week. Midweek, there’s usually another big batch cook to get us through until the weekend. The formula itself is quite repetitive though I try to mix up what we eat within the slots.

Anyway…this wouldn’t be a complete newsletter without a meta reflection. The question that I keep going back to is:

What’s the point of life?

Is it one big optimization/simplification equation to be solved? Does doing that too much remove the beauty in the day to day?

And once again, I think the answer is somewhere in the realm of tradeoffs. It all depends on whether I am excited to spend time and energy on a given task. If the investment is worth a differentiated outcome, then it should probably remain in the “do (more) manually for the beauty and fun of it” category. I guess in large part, this is another manifestation of saying no to drive happiness.

Curious for thoughts from you all on finding this balance—pile in with comments!

Leave a comment

In most of these scenarios, they’ve reached a point where they have a niche and own some specific part of the product/business. Usually, there’s generally a sentiment of accidentally ending up quite useful at work and suddenly finding oneself on the receiving end of many different asks.

On the one hand, it’s kind of a nice feeling to know that you’re important. On the other hand, it’s likely to be pretty damaging to your productivity and work satisfaction, as well as the sustainability of the job. It’s definitely not a long-term solution to just say yes to every request that comes in, no matter how big or small. (It’s time to squash the people-pleasing tendency!) Additionally, if you say yes to everything, you feed the vicious cycle of enabling others to rely on you for things that may or may not rightfully be within your scope. And, I haven’t even turned to the argument of accounting for how expensive it is on your time and productivity to constantly be randomized.

Through many discussions and pontifications about this with friends, I’ve built out a brief framework for what I’d do if I were in this situation.

In general, the “override” criteria are as follows, meaning if some of these are met, you should probably say yes.

• Does it build goodwill with partners with whom you want to deepen your relationship or build your social capital? (i.e. ask them for favours later on)

• Does it earn you visibility with leadership that’s beneficial for your brand? (i.e. is the ask coming from someone really, really senior or otherwise very important in your reporting chain?)

• Does it deepen your subject matter expertise in a way that complements your primary focus work?

• Does it interest you or tickle a curiosity you want to explore further?

• Can it be done without sacrificing your primary focus work?

If any of the following issues come up, then it’s likely a yellow flag and you should think deeply before saying yes.

• Is it something fleeting or will people ask for this again?

  • If it feels fleeting, then the likely answer here is that you should wait to see if this request comes back up again. Usually fleeting requests are not worthy of randomizing your time and distracting you from your core work.

  • If it seems likely that people will ask for this again, understand why and if that’s a sign this is pretty important.

• Do I know where this is going to be used?

  • If not, probe deeper. Understand if it’s a random musing someone had and not a truly serious research question or request. If it’s a deeper business question that has large ramifications, should it be part of some more formally scoped work?

• Is it being asked for with a timeline/deadline?

  • If not, that might be a sign that there’s no clear path for applying the output anywhere. It might just be curiosity, which may make it less worthwhile.

  • However, if for other reasons, you think you want to say yes, establish a timeline that’s reasonable for you. Consider your formally assigned/scoped work and generally do not prioritize the ad hoc request in a way that jeopardizes your “normal” work, unless it’s something truly urgent.

And if you do say yes, here’s what to do:

• Keep your manager up to date on this request and make sure they are also bought in.

• Set realistic timelines and manage expectations, and state to other stakeholders clearly that this is something “above and beyond” your usual scope.

• Share your findings in forums where appropriate—you don’t have to only share this back to whoever asked for it. You can pass it on to other teams or individuals who might find it interesting or relevant to their work as well.

• Keep a record of the ad hoc asks you’ve handled and reflect those in your self-reflection at performance review time to show the breadth of your work and contributions.

Thank you for being on this newsletter journey with me, for inspiring me to keep writing, and for seeding different topic ideas every so often. Here’s to a great 2026!

I’m a big fan of rituals, and accordingly, the end of the year is always a time of certain patterns. I reflect on the year that’s ending, I write about it, I share it with friends, and then I set goals for the year ahead. In recent years, this has expanded in other ways—with one group of friends, we make bingo cards for ourselves with experiences we want to have in the upcoming year. With another friend, we each picked two habits we wanted to cultivate throughout the year and began to track them quantitatively.

I like my end of year ritual, not just because it’s cathartic and calming, but also because it captures a good snapshot in time. It allows me to look back across one, two, three or more years and see the trends in what’s changed versus what’s surprisingly static. Over the years, I’ve learned a lot about myself and the core values that keep coming up, year on year, no matter how much or little I prioritize them.

In looking back at 2025, I realized that my goals and priorities were quite similar to 2024. I wanted to focus on:

• Simplicity in my life

• Fitness

• Stretching more

• Stability—with a routine, eating well, keeping up with friends

• Leaning on my community and asking for help

I graded myself on these, yielding 2 ❔ (didn’t really get to put to the test), 1 🟡 ( partway met) and 2 🟢 (successful). Given the success rate, I kept my goals for 2026 fairly similar, with the same themes.

I also want to share some of my other meta thoughts from reflecting:

• Reflecting alone is just as valuable as reflecting in a group; the former probably leads to more clarity while the latter drives accountability. I like having a balance of both in my rituals and I really appreciate having friends who reflect with me or share their reflections.

• For most working adults, it’s valuable to divide up some percentage of the reflection to focus on life outside of work and then life at work. The percentage varies a lot based on the person and can be telling. I actually reflect primarily on the role of my work in my life more broadly as part of this ritual; I feel that I reflect plenty on my work as part of my performance review process already.

• As much as it feels silly to do it, referencing frameworks like SMART goals can be quite helpful in setting goals. The other thing I’ve learned from work that I always apply is setting goals where the drivers are within my control. If the drivers required to accomplish the goals are not in my hands, it’s likely a challenging goal to take on.

• It’s okay to set some “easy wins” within a set of goals, so long as they balance out with a few “reach” goals.

• Sometimes the highlights reel from the year features splashy moments that sound cool but didn’t actually feel as meaningful as the small, quiet moments. Having a mix of both matters—and moreover, finding the right proportion of the two.

For those of you who also reflect at the end of the year (or on birthdays perhaps?), I’d love to hear more about your rituals!

Leave a comment

The key concept of ‘Rest in motion’ is:

• “Many people seem to think the ‘good’ state of being, the ‘ground’ state, is a relaxed state, a state with lots of rest and very little action. Because they think the ground state is the relaxed state, they act like maintaining any other state requires effort, requires suffering.”

• “This is a failure mode that I used to fall into pretty regularly. I would model my work as a finite stream of tasks that needed doing [...] with the rest state being the state where all tasks were completed, and so every new task would push me further from that precious rest state and wear me down.”

• “[In reality, it] is impossible [to] finish all the work before you. [...] Instead of struggling to reach the end of the stream, simply focus on moving along it.”

I was a little perplexed at this point about what “moving along it” meant—it sounded a bit passive, and that made me nervous. I do agree strongly on the idea that the stream of tasks never ends. This is a particular sentiment that I’ve overwhelmingly felt in the past month, especially with a flurry of (self-imposed) end of year wrap up tasks.

Next, the author discusses how:

• “Advertisements and media often push the narrative that the purpose of all our toil is to win a chance at relaxation.”

• “I call bullshit. For almost everybody, inaction is boring. That’s why we pick up books, go exploring, and take up hobbies.”

• “The actual reward state is not one where you’re lazing around doing nothing. It’s one where you’re keeping busy, where you’re doing things that stimulate you, and where you’re resting only a fraction of the time. The preferred ground state is not one where you have no activity to partake in, it’s one where you’re managing the streams of activity precisely, and moving through them at the right pace: not too fast, but also not too slow.”

• “Rest (and personal health, and personal time) are part of the goal [...] Taking care of yourself is very important in order to do all the other things you want to do.”

• “Rest isn’t a reward for good behavior! It’s not something you get to do when all the work is finished! That’s finite task thinking. Rather, rest and health are just two of the unending streams that you move through.”

This is where I started to feel a mix of reactions. On the one hand, I am a strong proponent of pacing yourself—of “managing the streams of activity precisely, and moving through them at the right pace: not too fast, but also not too slow.” The callout about rest (along with personal health and time) resonate deeply. The idea of carving out space and time for them, just as you would carve out time for everything else aligns with my personal philosophy.

On the other hand, I have a deep appreciation for doing nothing—inaction is delightful and it brings me so much joy. As I reflected on my moments of inaction, I realized an important nuance in how I define it. To me, inaction isn’t necessarily doing nothing; instead, it’s going into a block of time with the intention of doing nothing. I am open to whatever happens. The freedom and open-endedness is incredibly intoxicating. While it is important to manage your life such that you find the right pace for the different “streams” that exist, it is just as important to leave time for emptiness. The negative space matters incredibly for giving your brain and soul space to thrive.

To close out, the author writes:

• “Many people I meet seem to think that they need to take damage whenever they’re working, and then only heal it when they rest. [...] They seem to think they “should” be able to be at home doing nothing, and so when they’re not, they’re taking damage. They think that the ground state is a resting state, a state of inaction, and so whenever they’re acting, this is a deviation from the default, and it requires effort to maintain.”

• “The default state, the effortless state, is the one where you’re moving along many streams. It is up to you to make sure that you’re prioritizing the right streams.”

• “The ground state, the state to aspire to, the healthy state, the state that occurs naturally when you aren’t forcing yourself to do anything, is the state where you’re getting done what you want done as fast as is sustainable, and no faster.”

It’s not quite written in so many words, but the way I interpret this is that the best state to exist in is one where you:

1. Prioritize and focus on the “streams” that are rewarding or fulfilling to you in some way, somehow.

2. Find a way to navigate each stream at the right pace in a way that isn’t disproportionally taxing on you.

With this in mind, I leave you with some food for thought—perhaps you spent the holidays in a state of inaction like me (contented, open-endedly), or perhaps you do feel that you don’t need inaction.

Drop your thoughts in the comments!

Leave a comment

That said, here’s my two cents and what I do to try to avoid burnout. I hope some of it is helpful!

[Importantly, I’m thinking about this in the context of work, though arguably some of this can apply in other domains of life as well.]

Here’s how it all starts:

When I take on a task at work, I gauge my attitude towards it. The range is roughly from excitement to dread. When a task starts to slide towards dread, I ask why I feel that way. Is it because it’s hard? I’m bad at it? I don’t enjoy it because it’s tedious? Or is there something deeper, or is it simply situational?

A concrete example of this is the “updating trackers” sort of task. (In a Strategy & Operations role, there are many trackers to be updated. Sometimes I make them and have to chase people for updates and sometimes I have to update other people’s trackers.)

I pretty regularly have to do this type of work. If I’m not time-crunched or feeling overwhelmed, this sort of task falls into fairly neutral territory. However, the moment it’s sitting on a to do list that’s way longer than the time I have to work, the task plops straight into The Dread End. In contrast, some tasks never make it out of The Dread End, no matter the context. And other tasks yet, no matter how busy I get, remain in The Excitement End.

But also:

I think about the broader set of tasks I do at work—how many of them fall into The Dread End? It’s a bit of a chicken-and-egg problem in that when there are too many things to do, more of them start to pile up at The Dread End. But in general, if things are fairly well-paced, do I have a balanced plate of work? Are there some bitter green vegetables (“dread tasks”) to balance out the delicious carbs and the deep fried meat on the plate (“excitement tasks”)?

As soon as I feel the balance slipping, I start to watch out for burnout.

There’s obviously a lot more nuance to it than simply “how do I feel about the tasks I’m doing?” but this sort of framework has generally helped me pick up on the warning signs before it’s too late. Most burnout scenarios I’ve been in have consisted of either:

• Too many unfulfilling, unrewarding tasks that take up too much of my time (all “dread tasks”)

• Not enough time to tackle the tasks at hand, and having to neglect or do a poor job on the “excitement tasks”

Notably, even though burnout is often correlated to intense work, the two do not have to share a causal relationship.

I’ve seen time and time again, countless friends work incredibly intensely without burnout. I’ve also seen people who get burnout without working intensely. Over time, I’ve distilled it down to a few things to get right:

1. Enough of their time (subjectively defined by each person!) is spent on work that excites them – this could be because the work itself is interesting, they believe the work is meaningful/purposeful towards a greater cause, or something else altogether.

2. When things get stressful, they anchor themselves in calm; this could be by having sustainable outside-of-work hobbies/activities/routines, but can also be the ability to take a step back and see things holistically with perspective. But overall, they maintain a low level of stress.

3. They never reach a point of overwhelm. Some of this is again tied to being calm, but it’s also about being self-aware and knowing when to take a step back. That could be making changes about your role and what you work on, taking a sabbatical, changing jobs altogether, or working through some internal reframing of what work should be.

tl;dr

• Staying ahead of burnout is the best way to avoid it

• Reflect on the tasks you do at work and plot them on a scale of Dread to Excitement

• When too many things fall in The Dread End, investigate why you dread them

• Pinpoint the broader balance of work you do to understand if there’s a healthy balance between The Dread and Excitement Ends

• Check out my three observations above on how some of my friends avoid burnout

This week, I reflected on what I’m most grateful for. I’ll keep it short and sweet so it’s easily digestible in a post-feasting haze.

1. I am (shockingly) grateful for the unexpected

Often, when things don’t go to plan in my life, they end up working out quite well in a way I could not have predicted or planned. I feel this frequently—especially with missed opportunities, whether it’s jobs I could have taken, events I could have gone to, trips I could have gone on, or other things I “missed out on.” A top of mind example is that earlier this year, I was devastated when my manager decided to switch jobs. Since then, the structure of my team has morphed quite a few times. Ultimately, I’ve been exposed to way more insight, learning, and new experiences than I could have imagined. I’ve also gotten the chance to work with great new teammates. It’s made my day-to-day fascinating and my work very rewarding.

2. I am grateful for community

The more I pontificate on the state of adult friendship, the more I realize that there are very few one-size-fits-all friendships—I tend to have different friends to whom I go for different topics or matters. Through different chapters of life, as I go through new experiences and new questions pop up in my mind, I’ve been particularly grateful for the ability to find these random little pockets of community, often in unexpected places. Lately, I’ve noticed that a lot of these communities form through friends of friends and often exist online, meaning that location is no longer a barrier to feeling connected.

3. I am grateful to be challenged

I have recently felt that I am surrounded by many critical thinkers and people who go beyond the surface when assessing a problem or making a decision. Sometimes it’s exhausting because I wish I just had access to easy answers to things. However, I recognize how important it is to challenge and to be challenged—particularly in the world we live in where things that can be created so quickly and mindlessly, especially given the prevalence of AI tools, and downstream/often relatedly, fake news and social media exaggerations. I err on the side of moving overly quickly and I can be gullible (ask those closest to me, they’ll back this up!) and so I am grateful for a roster of minds around me that balance out my instincts.

I have a pretty extensive list of recurring 1:1s at work. Most of them are monthly—in fact, only 2-3 of them are weekly and those are with close teammates. I believe that I have slightly more 1:1s than the average engineer or product manager might, largely due to my role being extremely cross-functional. Not only do I work with my manager across an org of several hundred people (so I cover a broad range of topics and work with a lot of people), I also work a lot with people outside of our org.

I’ve had to figure out the right cadence of 1:1s over time as I’ve adjusted into this role. For most folks, once a month is the right frequency to check in where there’s new information for us to share with each other, we stay at a high level and broader vantage point, and the goal is clearly not to get into the weeds. If we do collaborate more closely on something, we usually end up with dedicated time on a more frequent basis to get into execution.

When I first started in this role, these 1:1s helped me build a sense of community, find kindred souls and people to whom I could ask my dumb questions when I’d exhausted my manager with them. Now, over a year in, I’m realizing these 1:1s play quite a few other roles.

First:

They often help me better understand the work I’m tackling, even if someone isn’t directly involved in the topic in question. I gather extra context and perspective. I gain a deeper understanding of my own work or the areas where I am uncertain as I describe what I’m working on to different people through the repetition. I identify blindspots or new areas that I need to seek clarification on from my manager or other stakeholders.

Second:

Sometimes, these 1:1s help me identify new areas I should be involved in. I learn about an initiative where they need some support from an S&O person. I learn about an initiative that’s closely tied to another one I’m already working on. Or, I directly get asked to help with something. This helps me grow in my role as I start to play a more active role in determining where I focus.

Third:

They help me stay more connected across the company. I learn about areas that are not that adjacent to mine. I find new topics of interest. I gain insight into who’s an expert on which topics and I learn about the quirks of various teams or leaders. I generally become a more educated citizen within the context of the company.

So, what should you takeaway about 1:1s?

• They’re not just for you and your manager. You should find people who work adjacent to or alongside your team and start with a first 1:1 to introduce yourselves, get to know each other, and understand more about each other’s roles. If it feels helpful, suggest a recurring 1:1.

• Even if you’re not in a cross-functional role, 1:1s can help you develop professionally and gain more context and perspective. No matter your role or title, that makes you better at driving towards good output and results.

• Go in with some questions for the discussion. Especially if you initiate. Good questions to start with include:

  • What do you do in your role?

  • What is your team most worried about or focused on right now?

  • What is tough for your team?

  • How might my team be able to help your team?

  • What are some interesting initiatives you’ve seen around the company lately?

  • What do you enjoy doing the most in your role?

(Also important sidebar: on principle I try not to look at LinkedIn, nor do I endorse perusing LinkedIn. There’s definitely good stuff but then there’s also a lot of bad stuff that just drains your soul. Proceed with caution.)

The more I thought about it, the more I realized that conviction is what drives happiness in a lot of situations. When you have conviction that you made the right decision, even if the outcome is not as expected, the confidence in that decision mitigates a lot of regret / unhappiness. When you lack the conviction, you question the decision and torment yourself with what ifs ad nauseam.

Before I get into thoughts on how to build this conviction, a quick paragraph for my recurring soapbox:

Most of the examples mentioned in the LinkedIn post were around making choices on how to spend one’s time. Are you open to a speaking engagement? What about some extra customer meetings? One of the comments on the post emphasized the importance of considering one’s time as money. I think that’s generally true, though I would also propose that one’s energy is just as valuable a resource. With time but without energy, a lot of things are not possible—it’s extremely hard to do a good job even if you have an hour set aside to complete a task if you’re absolutely drained. And likewise in the other direction: if you have no time but plenty of brain cycles, it’s also going to be a challenge to create any meaningful output.

And with that out of the way, some suggestions on building conviction:

• Have clear priorities. Whether this is within the context of your job, your career more broadly, your family, or something else, know what matters the most. It’s easiest if you have one north star within each domain. You might have one primary and one secondary focus. Be able to verbalize what the north star is. Update this quarterly or a few times a year.

  • For example, my biggest priority at work is learning from my peers and my manager. I wanted to work at a large company to understand how leaders operate and get stuff done (and also to understand how large companies generally function). If given an opportunity to work on a new project that sounds slightly tedious or uninteresting, I immediately default to asking myself, is there something I can learn from this work? If yes, then it’s much easier to justify saying yes in spite of the downsides. If no, then I spend more time considering the opportunity costs (including, of course, the political cost of saying no)

• Be very wary of type 2 fun. REI helpfully defines it as “miserable while it’s happening, but fun in retrospect” while type 1 fun is “enjoyable while it’s happening.” Everyone has limited tolerance for type 2 fun. It’s too easy to say yes to something just because “it’s good for me.” Candidly, if I have a type 2 fun commitment in one domain of my life at any point in time, I basically say no to all other type 2 fun requests otherwise. Unsurprisingly, the maximum limit is universal across all domains of life.

• Hold quality as a personal value. I mean, take it or leave it. But one of my personal values is quality—or rather, the notion that I’d rather do the things where I can commit 100% than give more things half my attention.

  • Examples: If I had to choose between spending more time with my friends where we all scroll our phones and don’t really feel interested in engaging with each other or seeing them less often but being 100% engaged the majority of the time, it’s a fairly easy choice for me. Likewise, if I were asked to join an extracurricular where I’d only be able to make half the sessions in a given semester, I’d feel poorly about not making the most of it and also holding back the others in the group.

So, tactically, how can this help you say no?

1. Redirect: As suggested by Dave, if there’s someone else who’d be a good fit for the ask, propose reaching out to them to see if they are interested

2. Prioritize: You can tell the asker that you’re really focused on certain areas and offer to help in the future if there are asks that align with your priorities. Share what those priorities are. “Thanks for thinking of me, but I’m really focused on building my skills in X this year rather than Y. If there’s anything that comes up in X area, I’d love to be involved.”

3. Quality: You and the asker both want a good quality outcome. “This sounds really cool, but I don’t think I’d be able to do a great job on this given what’s on my plate at the moment. I want to make sure your event is a huge success and I wouldn’t want to be the weak link in the chain.”

Having been in this situation a few months ago, I jotted down some notes on what I did to make this transition easier.

First off: Logistics

• Understand the timeline and work backwards to make a plan from today through the last day you have with your manager

• Make sure this covers: (1) handover of any content that you’re taking over from them, (2) professional development wrap-up, and (3) final reviews

• On #2, importantly, this should include getting final feedback (informally), documenting what your own goals are, and where possible, asking your manager to share this information with your future manager. You should also cover any promotion timelines and to-dos

• On #3, this refers primarily to admin logistics — even though this is on your manager, you should check with them to make sure that any reviews they need to submit for you or any other forms/paperwork are completed

Second: Finding other support

Oftentimes, when a manager is leaving, their backfill isn’t figured out yet. This means you’ll likely have an interim period where you report to a skip or maybe someone else. These arrangements tend to be a little awkward and can result in reporting to someone who doesn’t fully understand your scope. If this is you:

• Find a few other stakeholders or colleagues who can support you in the interim. They could be peers, mentors who are more senior in their careers, or even colleagues in completely unrelated teams

• Some ways they can support you may include:

  • Being a sounding board when you’re faced with a tough problem to crack

  • Providing career guidance and mentorship on key decisions

  • Serving as an outlet for venting in moments of frustration

• Having someone at your manager’s tenure can be particularly helpful as they can answer “manager”-y questions as they come up, especially if your interim manager is stretched thin

Third: Candid conversations to have

Fairly self-explanatory, but having a manager who’s on the way out is a gem just waiting to be discovered. Ideally, you can set aside some dedicated time and outside of the office to have a longer, deeper conversation. Here are some conversation starters I recommend:

• What are your unfiltered recommendations for me as I approach my role and career here?

• What are things to watch out for?

• What are your reasons for leaving?

• What are you most excited for in your next role?

• What will you miss the most about this workplace?

• What was your experience recruiting for your next role?

• How do you think about your career over the next decade?

• Do you have any other wisdom/advice for life?

In closing:

This is pretty much the checklist I followed a few months ago. It served me extremely well and set me up to handle the world without my awesome manager. Readers, anything else you’d add to the list?

Leave a comment

I spent a lot of July and August preemptively mourning the end of my twenties, and by the time September actually rolled around, I was pretty accustomed to the idea of bidding farewell to my twenties and started to see the bright side of turning thirty.

This year, to mark such a big birthday, I opted for multiple weekends of celebrations. (I figured that as time goes on, it only becomes more and more socially unacceptable to be such a diva about one’s birthday, so I wanted to go all out while I had a good excuse.)

As I reflected on the celebrations, the theme became evident to me: quality time with my favourite people.

I had a weekend with friends who flew in from out of town, where the focus was on having fun, relaxing together, and letting them get to know each other better. I wanted to feel all the warm fuzzies, rather than any thrills or specific experiences. I have a similar weekend planned with local friends to do dinner and karaoke.

The weekend of my actual birthday was spent with my parents. We didn’t do anything particularly crazy like fancy meals or extravagant outings; instead, we ate a bunch of homecooked meals and celebrated with a cake at home. Old me would have keeled over at the thought of being at home, wearing comfy pants, and eating a mishmash of home cooked food and takeout on my birthday.

But this year, it all felt right. The best presents I got (other than a Labubu, lol) were gifts of time.

There was the gift of people spending time with me (and traveling to do so). Then, there were also gifts like handmade quizzes/games for the group to do together, a special playlist, an incredibly fancy (and made from scratch) meal, and so on. When my parents asked me what I wanted, I racked my brain and could not think of anything. (I ended up asking for couch cushions. For the ergonomics.)

And for all of this, I feel so much gratitude.

I am grateful for friends who put in the time to spend with me. I am grateful that my needs are met such that I can luxuriate in solely wanting time. I am grateful that I have the physical wellbeing to enjoy this time. Relatedly, when I was asked at (one of) my birthday dinner(s) to deliver a speech, I chose to use that time in the spotlight for my soapbox du jour:

You only get one body in this lifetime and you ought to take care of it.

It’s pretty self explanatory. On the actual day of my thirtieth birthday, I got out of bed, ate some food, and went to the gym. I didn’t really want to, and I went light that day, but I knew it was important above all else that I went in order to keep my 3 workouts / week commitment to myself.

Anyway, I’ll wrap up with a few other lessons I’ve learned:

1. A lot of the small things I used to care a lot about are pretty silly. Cherishing what we have in limited supply is what matters the most—and that’s likely time and wellbeing in tandem.

2. The importance of chosen family. I’m extremely grateful that I love my non-chosen family. But also, my life would be incomplete without the chosen family—i.e. my closest friends—that I’ve surrounded myself with. They represent so much to me and make up a lot of the fullness of the life I live. I’m grateful to have so much love around me, and to be a part of so many other people’s lives as well.

3. If you poll your close coworkers on how old they think you’re turning, that tends to be a dead giveaway that it’s a milestone birthday. So it makes the guessing game kind of lame.

4. This is the time to watch teenage drama shows. I just finished XO, Kitty and it reminded me of the naïveté of teenagehood and high school. Such a big part of that was seeing how big life can be when you love big and fall hard. And I love that. It’s something we could probably do more as adults.

A few weeks ago, we had a sleepover with my second cousins who are in middle school / just starting high school. It’s always such a breath of fresh air and so fascinating to see what their lives are like. From watching my cousins, I was reminded of the importance of:

• Being silly

• Snuggling up to one another

• Asking why and why not

• Assuming simplicity when approaching challenges

As I heard about their summer vacations and back-to-school plans, I was also inspired to ponder:

• What extracurriculars would I do if money were no object?

• What would I be excited for, if I were headed back to school?

• What would I do with an entire summer vacation ahead of me?

It’s easy to think that as adults, we know so much and we are so wise. But it is truly humbling to see a day in the life of a fourteen year old. To be curious for the sake of curiosity, and to find joy in simple things without overthinking, and so on…

what would wednesday do?

Incidentally, we also starting watching Wednesday at the insistence of my cousins. It’s surprisingly not as creepy as I thought. I caught a line early in season 1 that was Enid saying, “What would Wednesday do?” I dug around on the internet and realized that’s already been turned into a book. The AI summary for the book is as follows:

"What Would Wednesday Do?" is a popular question, often referencing the character Wednesday Addams from The Addams Family. It's a phrase that encourages embracing one's individuality, even if it's unconventional or dark, and making choices that are true to oneself, regardless of societal expectations. It's about stepping into your "villain era" and thriving by being authentic.

So, take this as a reminder to be yourself and defy expectations. You don’t have to fit into a mold.

making mountains of molehills

Finally, I’ve been thinking a lot about how to properly celebrate life and milestones. It’s easy to end up in autopilot and look back on a few months or even a year and find it to be one long blur. Since graduating from college, I’ve always liked to bookend my life with special occasions, celebrations, or trips.

Sometimes, I feel like I’m a bit of a drama queen and I make mountains out of molehills (but with positive molehills, like birthdays). For example, the celebrations for my 30th birthday that I have planned span a few weekends. Is it ridiculous to celebrate a birthday for an entire month? Probably. But also, I’ve optimized my plans around the things that matter the most: quality time, good conversation, new experiences, and relaxation with my friends. It can be hard to make time for these things when life gets busy, and sometimes making mountains out of molehills is what it takes to remind us to stop and smell the flowers.

In the second half of the book, here’s what stood out to me, along with some reflections:

There’s a lot of debate about whether your coworkers can really be your friends. I suppose it depends on your definition of friend. I don’t expect my colleagues to know me like my closest life-long friends, but I also don’t think that means they’re not my friends. I like them. I care about them. I know at least some things about their lives. I’d help them if they needed me. I want to spend time with them. And I do spend time with them—quite a lot sometimes. That’s friendship enough for me!

I have spent a lot of time grappling with this question. In every single place I’ve worked, I’ve ended up making friends. Often, they become friends not just at work but also outside of work. When I was working at a startup, I became really close friends with a few of my coworkers. After leaving, I wondered if that was too much friendship for work and thought I’d give it a different approach at my next job.

I knew that it would be impossible for me to work alongside people that I didn’t at least know something about. Just as Bree writes, I also do want to enjoy spending time with them. Thus far in my current role, I have indeed made friends that fit the definition above. The contrast between my first few weeks (when everyone was a relative stranger) and now really brings this into light: It makes a significant difference in how I feel about my day to day. I’m a lot more motivated and excited to go to work when I know the people with whom I work.

So although you can follow all kinds of advice about how to pick a career or job (e.g., pick the work you love, pick the job you’re most skilled at, pick a job with growth opportunities, pick the highest-paying job), my advice is this: figure out who you like hanging around, and then go work with them.

Because you should like the people you spend your days with.

Now, while solid advice, I’m also unsure how actionable it is. Everyone I’ve met in an interview has seemed pretty nice… Instead, I’ve always been a strong proponent of researching the culture of a given workplace before joining. However, this sort of research can be quite nebulous—it’s largely based on other people’s anecdotes. At the end of the day, it’s highly subjective.

The one thing that I’ve found to be somewhat more reliable is asking friends and friends of friends about their experiences. I trust that if someone I respect and enjoy collaborating with has gone to a given workplace and enjoys it, then I’m likelier to also enjoy the culture there.

If the work you have people doing is inherently fun and the team genuinely enjoys spending time with each other, you don’t have to mandate shit.

When I worked in startup land, we grappled with this debate a lot. We understood the fundamental tenet but there were many not-so-fun tasks that had to be done in order to grow the business. We instead approached the problem by trying to make sure each person had a portion of their time that was spent on fun tasks to balance out the other stuff. We were able to make it fun-ish at least some of the time, and I’d like to believe that helped positively shape the team experience.

On this topic though—something that Bree didn’t cover in this chapter is the side effects of having a very close team. For us, as the team grew closer and started to care deeply for one another, it introduced a host of different challenges. For one, it made a lot of debates and arguments deeply personal. It also made it harder for leadership to make tough decisions because everyone felt like they should have an equally-weighted say in the decision, even when that did not make sense.

I’ve noticed the absence of this dynamic now that I work in a much larger company. It’s not to say that people aren’t kind and friendly with one another, but rather that the level of closeness isn’t uniformly deep across the company. As a result, when contentious decisions are made or specific individuals have a bone to pick about how something works, the frustrations are aired and sometimes addressed… But not in a way that creates disruption for the entire team, as was the case at the startup. It’s an interesting contrast and maybe a lot of it stems from the size/stage of the company. For those who’ve experienced both types of workplaces, I’m curious if you’ve also seen similar trends. (Drop me a note in the comments!)

Leave a comment

If you know you will occasionally have to eat into your people’s non-business hours, then you’d better give some business hours back.

This piece of advice resonated deeply. The best managers I’ve had thus far in my career have always done this. I’ve always tried to pass this on when managing teams as well. That said, I also know there are many otherwise-great managers who struggle to do this despite their best intentions. And they might just be the majority of managers you’ll encounter out there. I believe that in order to thrive at work, you need to draw this boundary for yourself at appropriate moments. If no one else is setting the boundary for you, you should take it upon yourself to do so!

The best strategy is to always believe your people are good. Good and misunderstood maybe. Good and in the wrong role. Good and overwhelmed. Good and feeling insecure. Good and lost. Good and without the right skills. It just takes an honest, loving conversation to figure out which it is. Once you know, you can do one of two things:

1. Repair the rift

2. Fire them, with love

Sometimes you might help them find a better fit in a role elsewhere in the organization. Other times, it’s just not going to work, and that’s okay. […] But if you know in your bones it’s just not going to work, then gather the most generous severance you can and cut the person loose to find a role that’s better for them. You owe it to that person, and to the rest of the team who has likely been picking up that person’s slack.

As I wrote last week, sometimes I read passages that are just incredibly eloquent at capturing sentiments I’ve had before. I don’t have anything to add here—simply wanted to highlight it.

Outside of the ER, most urgency is made up—by us. We decide to do quarterly business reviews, to set internal deadlines, and to promise 24-hour turnarounds on who knows what. Sure, sometimes these things are helpful forcing functions, but more often we make ourselves crazy with them, and the amount of actually brilliant work we do suffers because of it.

This concept was quite similar to the one two quotes above, about drawing boundaries for yourself. Again, it resonated deeply. Draw these boundaries for yourself—define what is or isn’t reasonable. And as a responsible employee, carve out time for deep, brilliant, thoughtful work alongside the day-to-day craziness of keeping a business running.

“In hard times, urging people to stay positive doesn’t boost their resilience. It denies their reality.” […] Dr. Becky Kennedy shares the phrase “two things are true” to describe how you can validate the feelings of those around you, while not denying the simple facts of the situation. That can sound like this:

“We can be proud of what we accomplished this week and never want to repeat that intensity ever again.”

I really liked the two quotes shared here as they encapsulated a lot of my past frustrations with leaders and myself when in a leadership role. This feels like a good rule of thumb to keep handy for tough situations, and it’s as much a reminder for myself as a PSA for everyone else here.

Finally, I wanted to close the newsletter with two quotes that sum up so much of what the book conveyed to me. Firstly:

The trouble with work is that it can be greedy. Sometimes you may work too much because that’s what the job requires. Other times it might be because you find it fun and even addicting. But either way, there’s a cost, and it can’t be avoided.

When you overwork, you underlive.

And secondly:

Purpose is a tool, and just like any tool, it can be used for good or for evil. Unfortunately, it can be hard to tell if purpose is helping you find meaning, or if it’s stabbing you in your sleep. The truth is I don’t have a good litmus test to help you tell good purpose from stabby purpose. I, myself, just listen to my bones.

And have been using it in as many conversations as possible, so it felt only fitting to write about it in this week’s newsletter as well.

YAK SHAVING
/ ˈjæk ˈʃeɪvɪŋ / Noun

Programming lingo for the seemingly endless series of small tasks that have to be completed before the next step in a project can move forward.

To bring this to life, here’s a non-technical example (source):

You want to bake an apple pie, so you head to the kitchen.

In the hallway, you notice some paint chipping on the wall.

So you walk to the hardware store for some paint.

On the way, you pass a bakery and stop in for a cupcake.

While eating the cupcake, you feel a pain in your mouth. It’s that cavity that you’ve been putting off.

You pick up your phone to call the dentist to make an appointment, but you see a notification from your friend Cher, who’s having a party.

You don’t want to show up empty-handed, so you stop for a bottle of wine.

(For the nerdier readers, find more examples in this Reddit thread.)

So, when is yak shaving okay?

If the downstream activities that I suddenly “must” do are things that I’d otherwise avoid (that I probably should do), then I usually set myself free to do some yak shaving. For example, at work, the yak shaving might entail fixing a broken SQL query or a slightly broken spreadsheet. It’s likely hobbling along and getting 75% of the job done, or I’ve developed a silly workaround. But it’s probably not in a good state for the long run and ideally, I should patch up the holes.

If the downstream activities that comprise the yak shaving are not along the lines of infrastructure investments or strengthening the foundation, I will generally take into account whether I enjoy these activities, if there’s something I’ll learn (a new skill or a new tool), and if it will truly make the end result of the original task better.

And what does this even have to do with automating manual processes?

Automating manual processes is probably the single most common instance where I find myself highly likely to fall into the yak shaving trap. Whether at work or at home, I often catch the thought: ‘I seem to spend a lot of time doing this repetitive, manual task. Should I automate it or somehow improve the manual process?’

This thought process has become increasingly prevalent with the advent of AI tools. I hear, “This is a great use case for LLMs, let’s try using those!” (I’m also guilty of saying this.) However, the reality is that countless hours are spent on trying out the supposed flow and addressing the bugs and making tweaks. And then, once some sort of minimally viable output is achieved, hours are then spent on QAing the output to make sure it’s actually accurate and usable.

There’s an xkcd comic that captures a lot of the opportunity cost / tradeoff math that we should probably be doing more often:

What are my key takeaways?

• Shave yaks if it’s accretive to you / your team (e.g. you learn something, you invest in truly needed infrastructure improvements, etc.)

• Before you pursue automation or improvement of a manual process, calculate the time you will save and the breakeven vs the time required

• Also, it’s just fun to say “yak shaving” out loud

Without further ado, here are the six things I’ve learned:

🩴 People wear sandals to work!

This probably sounds super silly to anyone who’s never worked in a formal workplace, but coming from consulting—where jeans were only allowed on Fridays—seeing open‑toed shoes at work still takes me by surprise. More broadly, the dress code is very flexible. I’ve seen the full range from very casual to very dressed up. It’s kind of cool that people get to pick and choose and it definitely feels more like a form of expression than in consulting, where conforming tends to be the norm. That said, it is definitely a double edged sword. It’s nice to be able to dress more casually, but I do also spend more time thinking deliberately about how to dress because that could shape how others perceive me.

🔃 For the most part, flexibility is real

I really appreciate that people can make work fit around the rest of their lives. Stepping out for daycare pickup/dropoff or a doctor’s appointment is never a big deal. And when I go into the office, I’ve noticed that the flexibility also shines through where many people have nontraditional arrival and departure times. I love this for myself because it means I can avoid peak commuter hours when I go in. I can also split my day up to work from home partially and go into the office when I have in-person meetings.

🗓️ Calendars are mostly transparent to everyone

Last time, I talked about generally migrating to Google Workspace. In my opinion, the most interesting consequence of being on Google Workspace is that their default calendar setup is for all events to be visible to all members. Others can see what's actually happening on your schedule. This makes it easier to actually maintain flexibility because people can see, understand, and schedule around your holds/blocks. (In contrast, Microsoft Office defaults calendars to busy/free, so you can’t see meeting details. I think that plays a pretty significant role in shaping workplace culture in subtle but significant ways.)

Of course, calendar transparency also leads to the occasional calendar‑stalking rabbit hole, so it’s a bit of a double‑edged sword. It’s definitely shocking at first to have this level of transparency across a large organization and can make one feel a little naked/exposed. But once adjusted, I’d say this is a productivity multiplier.

📬 Learning to triage between Slack and email

Back in startup land, we basically only used email for external communications with customers, partners, etc. Internally, it was all Slack, all the time. In big tech, the lines are a bit blurrier. Most internal conversations still happen on Slack, but there are also things like shipped emails, onsite logistics, and company‑wide announcements that live in Gmail. You end up having to check multiple places, and over time, build an instinct for what goes where.

In the setup at my company, there are also a plethora of email distribution lists set up through Google Groups that one can opt into. Many of them are open to whoever wants to join, and so there’s a treasure trove of email subscriptions you can basically opt into. Likewise, on Slack, there are countless Slack channels that you can join. Back at Bain, there was relatively little in terms of the information sharing infrastructure, given that most cases are relatively confidential. For the most part, we only had such shared resources for “extracurriculars.”

👨‍👦‍👦 Finding the org chart is only step one

Every company handles org charts differently. Sometimes they’re integrated into the HR system; sometimes they live on an internal tool. Coming from a 20‑person startup to an 8,000‑person company, I had to get way better at not just finding but understanding the org chart. My friend who’ve worked at other big companies speak similarly about the importance of being able to navigate the org chart and make sense of it.

When I first started, I had to spend a while learning the names of key leaders and figuring out their respective scopes of ownership before I could follow rapid‑fire conversations. Even today, I frequently reference the org chart to better understand where different teams sit. Org charts are super helpful to reference when starting cross‑functional projects. They help me understand incentives, goals, and making sure that I have the right folks in the loop.

🔍 Document diving is a crucial skill

At Bain, we had a tidy folder for each case team, and we rarely needed to go outside of that. Client files came in via a third‑party file transfer service and generally got merged into the same folder. In startup land, we were building the team from scratch so everything lived in the same shared drive that I set up.

However, in big tech, where I’ve parachuted into a massive company? Document diving has become a whole skill of its own. I’ve had to spend time learning where to go for which type of document—whether it’s likeliest on Google Drive and searchable, not searchable (and therefore requires tracking down the right person), in our dev team’s wiki, in a Sales document repository, etc. For each platform, there are different search features and some work better than others. It definitely took a while to figure it out, but getting good at hunting down files and data has been a huge part of being able to move quickly.

That’s a wrap. If you’ve made a similar leap, I’d love to hear what caught you off guard in the comments:

Leave a comment