Tara Mac Aulay on Happiness and Work, Self-Experimentation, and Prioritization

by lynettebye27 min read4th Apr 2020No comments

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This piece is cross-posted on my blog here.

How closely do happiness and productivity overlap? Does being happy make you more productive, or does being productive make you happier? Or maybe both? 

I’m pretty convinced that there’s a positive correlation between the two, despite productivity’s familiar grit-and-bear-it reputation. However, I remain uncertain how tightly the two are correlated and which way the causal arrows point. 

My guest today seems to have this all figured out, at least for herself. Today I’m joined by Tara Mac Aulay, the CEO of Lantern Ventures. Tara was previously CEO of the Center for Effective Altruism. 

Tara’s run dozens, if not hundreds, of experiments in her life. Everything from working many highly planned hours, to not planning her work at all, to testing how much social time leaves her energized, to gamifying admin work. Through running these experiments - and comparing the results with her prior predictions - Tara’s found ways to make productivity feel fun. 

She found that she can work two, four, or even six more hours per day when it’s fun than when it’s not. Because of this extra time, blocking in time to do whatever feels intrinsically motivating turns out to be much more productive than devoting 100% of her day to her top priority. 

Similarly, finding ways to turn boring or ughy tasks into fun or exciting challenges works better than any deliberate attempt to be more productive. And taking the time to discover the best ways for her to rest and rejuvenate pay off in sustainability at work. 

“I guess approaching the whole thing with lightness and fun is what works for me. And I don't do any of these things because I have to, or because I'm trying to get results out of them, or because I'm expecting it will lead to, you know, me being a better, more productive person. I'm just like, “This is a fun experience I can have and a fun game.” And that makes it intrinsically motivating to do all this stuff.” 

You can read the full transcript below for more, including:

  • Tons of ideas for personal experiments
  • Her prioritization systems, including a template
  • Her experiments planning the entire day and not planning anything 
  • Her thoughts on imposter syndrome
  • Why she mimicked people’s behavior for a day 
  • Why she emphasizes predicting what you expect before an experiment and checking how it went afterwards 
  • Why she went to a random meetup everyday for two months 

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Full Interview

Note: This transcript was edited for clarity and length.

Lynette: I'm trying to compile some interviews with people who manage to get a lot done, to figure out how you approach some of the meta productivity things that I work with a lot. Compiling resources and sanity checks on a lot of the stuff that I would cover in productivity coaching. Some of these questions come from the interview that you did with 80,000 hours. At one point in there, you were mentioning things like walking around with a stopwatch to time things.

Lynette: I'm curious what other kinds of specific things you do when you're trying to optimize and decide how to improve the course you're taking to obtain a goal? 

Tara: I guess a thing I do a lot is make explicit predictions about how long a task is going to take me, and I do a really rough expected value estimate a lot of the time as well. To be honest I don't collate these in any kind of ordered fashion, I often just write them down on a scrap piece of paper next to me, but at least I find going through that process very helpful. And after the fact I always review how long it actually took compared to what I thought, and how valuable that thing actually was compared to what I thought before, which I think has allowed me to become pretty well calibrated on which things are worth doing, which things are not, and how long it's actually worth spending on something.

Lynette: I'm curious if you could give me an example showing how you went about making this estimate? How were you compiling how long you thought it would take, and how valuable you expected it to be?

Tara: For large things, I have a Google Docs template that I use which has a series of questions on it that are really basic but helpful prompts. For anything that I think is going to take more than about eight hours, I normally do that. It's really quick, it takes like five to ten minutes. And it just asks explicit questions, like what input the task requires in terms of a time. I give it a rating between one and five, for how kind of draining I'll find the task, or how ughy I'll find the task. I also write down things like whether I need focused or uninterrupted time to do it, or whether it's something that I can do in bits and pieces whenever I have time, because getting focused, uninterrupted time is quite hard. So the total cost of the project is much higher if it has a lot of that. 

Tara: And then, if it's not very straightforward, sometimes I put those things in a spreadsheet and I'll say, "Okay, well, every one hour of focus time is equivalent to three hours of not-focused time." And then I'll try and come up with an estimate, using some of those adjustments. A lot of the time, the main benefit I get from this is not actually having a better estimate, but that a lot of the time I get excited about something or I have an idea. And I'm like, "Oh, this project would be really cool." And then I spend 10 minutes specking it out more, and I'm like, "Actually, it's completely not worth it." So I think 80% of the things I use this chart on I completely abandon, and decide not to do.

Lynette: For the time estimates, do you do anything particular there or is it just benchmarking based on how past projects went?

Tara: It's a lot of that. For more complex things, I use Guesstimate a lot.

Lynette: And what do you do in Guesstimate?

Tara: Well, it's nice because you can put in ranges for things, so I can look at how long similar things took, and I can put, you know, five to twenty hours on this part or whatever. And then I use the sensitivity analysis in that, which shows which are the most uncertain parts of the plan. And so then sometimes I spend a bit of time trying to investigate, or learn more about how long it will actually take to do the things where I have the most uncertainty. 

Lynette: Great. And what kinds of things would you do to reduce that uncertainty?

Tara: Sometimes it's just spending five minutes googling the thing, or asking someone else who's done something like that. A lot of the time it really is just start doing it for a couple of minutes and then you have a much better idea.

Lynette: Cool. And how would you decide who else to ask when you're not sure?

Tara: Yeah, I would just usually think of people who've done something similar beforehand. Like when I was at CEA doing ops things, I would ask Malo at MIRI a lot of the time when I was considering something that I thought he had done before or had considered doing himself, or other people in similar roles.

Lynette: How much of your work is deliberately planned exactly what you're going to do in advance versus opportunistic response to what's coming up?

Tara: At CEA, I would explicitly break up my day. And so I would always allocate about four hours of the day to pretty focused things where I was trying to work on my most important priorities, and some days that time would be swapped out for meetings. And then I would always make sure that I have about an hour every day to just do reactive stuff, and then two hours every day to focus on whatever thing I felt was a high priority but that I felt kind of intrinsically motivated to do at that point in time. So I'd give myself a lot of freedom and flexibility.

Lynette: And what caused you to choose this way of breaking up your priorities or your time?

Tara: I think I realized there's kind of a constraint on my energy level or something, rather than the amount of time that I can spend working. So I think that about four hours of focused work on whatever is the most important thing is about as much as I can do, and if I try to make myself do more than that, I'm just not very productive in the additional hours.

Lynette: Got it. And how would you tell, what signs did you see that your output was decreasing?

Tara: I would get easily distracted by other things. I would be trying to do the task and then find myself checking my email or checking the time on my phone or something. Or, if someone came by my desk, I would be way more likely to chat to them for 15 minutes before getting back to my task.

Lynette: Got it. And when you're choosing your top priorities, do you do anything other than the process above to identify, "Here's my top priority for these four hours"?

Tara: For every week, I would pick what I intended to accomplish that week. So then every day, it was a smaller choice, like "Which of these top things or how much of these top things am I going to do?" And then I'd just chain that up. And then every quarter, I would pick the highest priority goals.

Lynette: And what was your process for picking these goals at these different levels?

Tara: I would usually spend at least four to six hours doing it. I would come up with a giant list; I would write every single thing that I could think of doing on a post-it note, and stick them all on the wall. And then I would group them together by some kind of category that made sense in my head. It wouldn't always be similar types of tasks—sometimes it would be things that would take a similar amount of time or resources. And I don't know exactly how I would then distill that down into the things that I thought were most important to get done in the next quarter. Sometimes there are just things that are external constraints, like we have to run EA Global, so it would be some stuff related to that. Like we'd have to do fundraising.

Lynette: Yeah. So for things with clear external constraints, are there things that you would do to eliminate some of those, like, “I'm just going to take these off the plate for sure right now”?

Tara: Oh, definitely.

Lynette: What kinds of steps would those be?

Tara: I guess, for me doing this visual thing where I write down all the things that I would want to do in the next three months. Shocks my brain a bit to realize that it's definitely not feasible to do all of those things. And then I start grabbing the things on a post-it and putting them into a timeline. So I write down this one would take one week—and then it just becomes clear that—it gets filled up before you could possibly imagine. So then I have to start pulling some things out. So I guess, if there are things that I can defer and not do, and I don't think the cost of doing that is very large, then I would take them off. And obviously I’d think about things I could get other people to do instead of doing them myself. 

Tara: I usually try to be pretty skeptical about new ideas; anything that I've thought of in the last week or two before I do this process, I put in its own special category, because I know I'm going to be more excited about those and inclined to want to put them into the list.

Tara: And if there are things that I deferred and pulled off the list twice before, and I haven't put them in, then I kind of need to decide if they should be forgotten forever, or if I have to do them this time.

Lynette: Okay. And what kinds of things did make that cut, of switching from "Okay, let's do it now"?

Tara: After I'd already deferred it a couple of times? 

Lynette: Yeah.

Tara: I guess some CEA stuff, like switching over a pledge calculation from this old system that was breaking all the time to the new one. There are a lot of things like that.

Lynette: I'm guessing that this is something that’s kind of a boring task, but you just decide it’s valuable enough to do. Does that feel right?

Tara: Yeah, or a lot of the time it's not particularly urgent, but it is necessary eventually. And for a lot of CEA things, they are things where I think other people are bearing some kind of ongoing cost until we do it.

Lynette: What's the threshold there for “necessary eventually” and “actually, I can just skip this”?

Tara: Rather than a threshold, I have more of a process for going through that. I try to explicitly model out what bad things will happen if I skip the thing. And I use Guesstimate a lot for that as well; I estimate how many people would be mad and would stop donating to CEA or coming to EA Global or, you know, would be less likely to continue being a part of the EA community or any number of things like that. The main metric I used at CEA for thinking about those things was equivalent dollars of donations to high impact charities. And I just used that all the time because it was a nice thing that I could use to attempt to convert every single slightly intangible thing into this one metric, so I could compare between different tasks.

Lynette: Okay. Awesome. And for the stuff that you were doing in those hours of the day when you would do something that's high priority that you feel intrinsically motivated on, how would you choose those tasks?

Tara: I think I give myself freedom in that time to just latch on to whatever feels exciting. I always keep a list next to my desk of ideas. And whenever something pops into my head, like "Oh, I should do that" I write it down, so that I don't get distracted and do it right at that moment. So the first thing I do is go back to that list and see if there's anything there that still feels exciting and motivating. And if there's nothing on that list then I'll go to my quarterly goals and see if there's anything on that list that feels exciting. And sometimes if none of the things on either of those lists feels exciting, then I would just go for a walk, or go home, or read a book, or do something else. 

Lynette: Okay. How can you consistently protect this time for this? I know that a lot of people feel like their core activities just take up every second that they have. And they don't have time for this kind of exploratory, self-rejuvenating thinking time, etc. 

Tara: I put it on my calendar.

Lynette: And that was enough?

Tara: Well yeah, and I put the focus time on my calendar as well. And I guess, sometimes I would have to leave the office to do it, so that people couldn't be asking me questions or distracting me or, you know, set my status on Slack so no one can contact me.

Lynette: So you protected these two hours.

Tara: Yeah, I have to protect those hours from other people wanting my time at that point. But I would never have to protect it from myself, because I always found it motivating to do those kinds of things.

Lynette: Got it. And for your focused hours, do you have to do similar things to protect those from other people?

Tara: Yes and no, I've tried lots of different things at different points in time for this. I think that when I had more of an IC [individual contributor] role at CEA I definitely had to do that. I would, you know, wear huge headphones so people would be less likely to come talk to me and lots of things like that. I have a very strong startle reflex, so once I get absorbed into a task people can be standing right next to me calling my name and I won't even notice. And then when they do eventually get my attention I usually jump out of my seat, and I think that scared people enough that they stopped doing it after a while.

Tara: But yeah, I guess I often find doing that kind of focused work, or at least starting it, difficult because it's usually not the most exciting, fun task. It's just the thing that I have to do, and whenever there's something that I feel like I have to do it sounds less fun.

Tara: So I tracked my mood and energy levels over a long period of time to try and figure out which times of day I could do that type of work more at. And for me, it's often very late at night or very early in the morning; definitely not between 1PM and 8PM. So that's when I scheduled that, and that worked well for me.

Lynette: Okay. And how do you get yourself started? This feeling aversive—how do you flip that switch and beat getting into it?

Tara: I think honestly, the main thing that has worked for me is that I plan my day the night before, or I usually do it either right before I go to sleep or before I finish work on any given day. And then it's like I've already made the decision. So then the next day I just wake up and get ready, and then I start doing the thing that’s the plan. But if I haven't made a plan the night before that usually goes awry, and I will start my day by checking email and responding to urgent things that have come up, rather than by doing the thing I’m meant to be doing.

Lynette: Cool. I'm curious if you think that there's a big benefit—perhaps in this creative time, perhaps in other times—to doing work that's more exploratory without clearly knowing what it's going to lead to?

Tara: Yeah, definitely. I think some of the most valuable things that I've done have come through that. So I care about protecting that a lot.

Lynette: From your best guess, do you think that these are rough approximations that would generalize to other people; like four hours of priority work, a couple hours of exploratory valuable work, and then meetings and whatever else needs to fit in the cracks?

Tara: Somewhat, but maybe the absolute hours or proportion of times between them might need to vary. I think it's very different also, if you're in an IC role or a management role just doing a very different job. This probably works better if you're in an IC role than in a management role.

Lynette: What factors influence these breakdowns, that you would expect to not generalize to other people? It sounds like your energy level is one of them.

Tara: Yeah, I have a similar pattern every day. And I think a lot of other people have some days where they just get up and they're going to be really productive, and they'll get half their work for the entire week done in that one day. And I think for someone who has a spikey pattern of productivity, this kind of planning wouldn't work very well.

Lynette: Did you always have this steady state? Where you set up a routine and it works better for you that way?

Tara: Ah no. This is the result of a lot of experimentation with different ways of organizing my day.

Lynette: What kinds of experiments did you run that were most useful for you?

Tara: I tried for a long time to just try and increase the amount of time per day I could spend on my most important goals and I cut out that time where I just get to do whatever is fun. Before I had that, I think I was just generally less happy in my work, like unmotivated and unproductive. Giving myself permission to do that was really powerful and important. And convincing myself and other people that that time is valuable was really useful. I also found it useful to switch from—I used to always plan my day at the start of the day—and switching to doing it the night before was really, really good.

Lynette: Yeah, that's a pattern I've seen too.  

Tara: I experimented with going to the other extreme as well, like not planning any of my time and completely directing it based on what felt motivating at the time. And that was less bad than I expected. I thought that I would spend almost no time on the important but non-urgent priorities. Sometimes those would still end up being the exciting thing to do. But still, when I did that, I would find I would get stuck on a project and not really know how to proceed, and then just kind of leave it for an extremely long time.

Lynette: I'm curious if you have any idea of how much worse this was, like how much less you got done with the completely no planning compared to the mix, maybe even compared to completely planning?

Tara: I think when I tried to completely plan everything, I was at least 50% less productive overall. I could just work fewer hours per day; like when I do that I can't do worklike activities for more than eight hours. And when I let myself do what I want, I can work for like 10, 12, 14 hours in a day because it's fun. But I think the main benefit is actually in how much progress I make on the things that I'm meant to be doing, or that are kind of important.

Lynette: Do you have a sense of how that might differ?

Tara: I think, a couple of years ago, I realized I spent about three-and-a-half hours per day doing reactive things or things that just didn't really matter, like replying to emails and messages, or just kind of not being fully engaged in any one task and half doing one and half doing another. So cutting out that was huge.

Lynette: How did you do that?

Tara: Partially, habit and setting the correct expectations, like letting all of my staff know that I'm not going to check email until 1PM. That didn't work alone though; I had to give people alternative ways to contact me if they were bottlenecked or roadblocked, and to make sure that people knew that they could reliably reach me and talk to me if something did actually need my input.

Lynette: What other experiments did you run, that were really useful?

Tara: I think a lot of time-tracking stuff was helpful, but only for a very short period of time. I can get myself to do it for three, four days with a lot of detail, and I can't stick to it for more than that. So I just do that maybe every six to twelve months and get an update. And usually when I do that I try varying a whole bunch of things: like how much caffeine I have, how much sleep I have, I just track everything about my life. I track my mood 10 times a day, I track my productivity level about 10 times a day, and record all of it, and then spend a bunch of time analyzing the data to try and see if there are other things I could tweak.

Lynette: And if you're doing that for just three or four days varying all of this stuff, are you able to get enough data that you can make guesses about what's making a difference?

Tara: Well, it's not going to be significant, but I think sometimes I can still pick out patterns and then reflect on whether the data feels true.

Tara: I've tried a lot of different things about changing my sleep hours in particular, and trying to experiment to find out when I'm most awake—when is the best time of day for me to go to sleep and wake up? Including like, waking up at 3AM or 5AM or at 3PM, the whole spectrum.

Lynette: Got it. I'm curious, what other things did you measure? There's sleep...

Tara: Yeah, sleep, caffeine, food: what I ate, everything that I ate, how many times I ate, whether I ate a snack. How much water I drank. I measured how often I go to the bathroom. That was actually very interesting; it worked out best for me if I drink enough water so that I need to go to the bathroom at least once an hour. Because then I just get up from my chair and think about things and come back to my desk, and I re-focus on what's the most important thing I should be doing right now. How much exercise I got. A big thing with social time: if I don't get enough social time - quality time, one-on-one with people that I care about - then I'm just way less able to focus and less productive. That was a much stronger effect than I had predicted.

Lynette: Approximately how much social time is enough?

Tara: Like about 14 hours per week.

Lynette: Okay. What other things did you find that have particular insights?

Tara: Don't know exactly how to describe this, but I don't react well to feeling like there's something that I have to do or I’m expected to do, or having restrictions on my time. I think a lot of people use tools or apps to block various websites or make it slow to load their email or Slack or anything distracting. All of those things backfire for me, and then they just make me really miserable. So I think developing some kind of compassion for myself, and recognizing that I'm inclined to, I don't know, do unproductive things, there's probably a reason for that. Maybe I should actually rethink my current approach to the task, or reconsider how important it is, or just take a break, or go chat to a friend or something, you know? I guess I kind of use that as a signal that something is not right about my current situation.

Lynette: When you were in a place where you were doing a lot less than you wanted, was feeling compassion and trying some of these other things enough to help you do what you thought you should be doing?

Tara: I think that's just always a good trigger to stop and reassess. And sometimes when I find myself in that place, then I just need to take a step back and reevaluate everything, and I do mean everything. Like, “Who am I spending time with? Should I be changing jobs? Should I be changing my romantic relationship? Am I spending enough time with my family? What's going on with my finances? Is my health okay?” I just go through all of those categories. I have a list of all of those categories on my phone, and I just try and ask myself, “Am I feeling okay about my friendships, am I feeling okay about my whatever…” And then I try and figure out where something is wrong. 

Tara: And I think I get a lot of benefit out of, I don't know, knowing the bad things explicitly. It's like, as soon as I have a list—I always make a long list of all of the things that are causing me stress or discomfort in some way, or that I'm not happy about in my life overall—and when I put them all down on a piece of paper, I'm like, "Oh, great. That's all of the things. Like, only one page full of things isn’t bad."

Lynette: Okay. And if you don't mind sharing, what are some of the things from this list that have like, “Okay, this is something that I needed to change in order to release this bottleneck,” and make you feel happier again with your work?

Tara: Often, it was the people that I was spending time with. And that was sometimes very hard. Even a couple of months ago, I did this reflection and realized that there was a friend who I value and love, but then every time I spent time with her, I felt kind of drained and didn't feel good about myself. And then that affected everything else that I wanted to do. And so then I just wrote down a list—I decided I still wanted to have that friend in my life—but I wrote down a list of boundaries I could set in place so that I can make that relationship more positive for me, and that helped. 

Lynette: Have there been times where this feeling just kind of went away on its own without you discovering the cause?

Tara: Yes, like sometimes I'll be at work and just not be making any progress on anything, and just a little bit out of it. And I'll just go home and read a book and get a good night's sleep. And then the next day, everything's fine again. Allowing myself to do that is usually enough.

Lynette: Has there been times when some sort of work was a bad fit for you, in a way you weren't able to resolve? And if so, how did you find what was a better fit?

Tara: Yeah. I've had a lot of jobs where there were things about that job that I just really hated. And honestly, a lot of the time then I just realized that, quit my job the next day, and then, you know, figured out what to do next. Sometimes I have realized that something is not going very well and then I've moved houses or moved country or something—just changed my entire situation and kind of started from scratch. And it's easier, when I haven't been able to figure out what the thing is, to just change everything.

Lynette: So I frequently run into people who are in some bucket like this, where they feel they should be doing something, but they feel unmotivated. And it does sound like pushing themselves less and giving themselves time to do things they enjoy may be an important part here. But what advice would you have for them if they do do that, and it doesn't get better? Other than maybe change your job and move countries.

Tara: I think, change more things.... I think if you take time to rest and you come back, and it doesn't feel better then probably the ways that you've chosen to rest aren't in fact the most restorative things you could be doing. And so I would suggest trying a lot of different things: a lot of different types of social activities, or physical activities, or intellectually engaging activities. 

Tara: I did this a lot when I was in my early 20s. I picked a random event from meetup.com every day for about two months, and I just had to go to whichever thing came up. And then I would write down beforehand whether I thought I would enjoy it and feel drained or refreshed from that activity. And then I would compare afterwards what I actually felt and, I don’t know, that was really informative and good for me.

Tara: But I personally like novelty. So it's doing something that is pretty low cost for me and exciting and fun. And maybe that's probably not true for most people.

Lynette: Yeah, you seem pretty good at being able to track your experience of things and assess whether you're actually enjoying this or not accurately. Is that a skill you developed?

Tara: I would say yes and no. I think part of why I do the ‘predict it before and then compare results’ thing is just so that I can generate more insight into that.

Tara: But, I think that I have a pretty good experiential memory. So it's like I can recall all of the previous times I've done something similar to that activity, and then reflect on how I felt afterwards before, and draw some conclusions from that. And I find that really helpful.

Lynette: Cool. And what are the ways that you personally find you’re best rejuvenated and rested?

Tara: Being near water and swimming, but not in a swimming pool, it has to be natural water. Being in nature. Reading a book, especially reading a book in a park or by a lake or something like that. Spending quality time with close friends or family just having a conversation for an hour with no particular goals, I find really rejuvenating. And eating a really nice meal; one where I can kind of savor all of the different tastes and textures. 

Lynette: So what are some of the other things that you found that are really important for balance? For example, exercise?

Tara: I think exercise only helps me if I do exercise that I am kind of intrinsically motivated to do or that I enjoy. So I found that going to lift weights with friends is surprisingly good, because I get to have a good chat with them for an hour, and it's not strenuous enough that you can't have a conversation. But if I was to go on a bike ride with friends or something else where you can't talk, it's not as nice. And my main exercise is probably just walking and dancing. I go out dancing a lot on my own, to go and see music artists that I enjoy, and I just dance like a crazy person until I'm really tired and then I go home, and that's amazing.

Lynette: Awesome. Going back to the 80,000 hours podcast, at one point in it you mentioned that at first you thought CEA had made a mistake in hiring you. This kind of imposter syndrome ‘worried I’m not good enough’ type of thing seems to be pretty common. I'm curious how you get information that what you're doing is good, while still being not overly confident and open to feedback and that sort of thing?

Tara: The main thing I love about my job right now is that I get instant feedback in that every day I know how much money I made, or how much money I lost. And I know how good I was doing at my job every hour of that day. It's amazing. And I've never had anything like that before. 

Tara: But yeah, I don't know, every other kind of situation I've been in—I'm not sure I would change it because I think the imposter syndrome thing drives me to constantly want to do better, and learn more, and keep improving—it feels kind of shitty, but it's kind of good.

Lynette: Okay. How did you create feedback loops for yourself?

Tara: I just always set my own goals for myself. And I have really high standards for myself. I would never expect anyone else to live up to the things that I'm trying to, that would just be mean. But I guess that's part of why I like the planning thing, because then it gives me that metric. It's like, "Okay, well, if I get all of these things done that week, that was a good week, like I did enough or I’ve been good at my job this week." And that's easier because you can get more metrics, right? Like your staff gives you feedback, or you're doing a good job if your staff are performing well. It's easier to reflect on whether my staff are doing well than it is on whether I’m doing well. So I can be like, "Oh, well, everyone has been doing amazing that must mean I'm doing a good job."

Lynette: And did you have to go through a calibration phase when you started predicting how long tasks would take where you were just totally off for a while, or with new tasks?

Tara: Definitely, but I think I was always pretty good at predicting how long things would happen in the less than half an hour range and the two to four hours range. I was extremely bad at predicting—if I thought something would take like forty-five minutes, that was really not true, it could take anywhere from fifteen minutes to three hours. And then if I thought something would take a long time—I was pretty bad with that too. 

Tara: But I think the main reason that I was bad at that is that I was imagining that I could spend eight hours every day making progress on that goal. And that's just not realistic. I still have to read emails and do other stuff. So I would always say, “Oh, that would take three days.” And that means it would take, yeah, not that.

Lynette: And was just making these predictions and reviewing them enough to cure that fallacy?

Tara: Well, making them helped. But also breaking the time down helped, and even trying to put it into my calendar, like “I'll do this part of the task on this day, and that part on that day,” that helped.

Lynette: Is that something you still do now when you're planning?

Tara: Not most of the time. I do still do that when I'm going to do something that is less familiar or new, or something I haven't done in a long time. Or like, not my day to day work.

Lynette: Cool. So another question; I'm curious about the balance between something like paying your dues and building up your skill in an industry, versus trying to solve things immediately. It seems that you took more of a path of going and trying to solve things immediately. I'm curious how well you think this can replicate, and how much context someone needs before they're more likely to do good than harm?

Tara: I think in hindsight, I would have had a better experience with this approach, had I had a better understanding of organizational politics, and perhaps better skills at, I don't know, persuasion and stuff like that. When I first started doing it I ruffled a lot of feathers and I made a lot of enemies, because I was just, “This is a better way of doing things, and I'm going to do it and I don't care if you don't like it.” So I think it's not something I would recommend to everyone. 

Tara: I think you have to be reasonably socially savvy to take this approach and have it go well. And I think you also need to be good at something like big picture thinking: being able to correctly model all the people in an organization and what their goals are, what things they have to report to their boss, and what the organization overall cares about, and which things actually matter and which things don't.

Tara: But you don't get that context unless you start explicitly trying to model it out or think about it. You're not just going to pick it up by observing an organization passively for a year or two.

Lynette: So the the idea here might be something like, work there for a while, but be actively trying to model it, trying to figure things out and looking for room for improvement, but kind of putting in some time before pushing for those things so that you have a better model of the organization or the cause?

Tara: Yeah. But I would say even more explicit than that—being extremely curious; asking every person you come across what things they're working on and why, and what their main priorities are, what things their boss cares about? And I've at lots of time drawn this all out on a chart. Again, I like post-it notes on the wall with all of the people and all of their goals, and who they report to, and what their KPIs are. So that I can try and figure out where there are bottlenecks or problems.

Lynette: How much stuff do you write out; how much of your thinking is externalised in writing?

Tara: Very little. But I think that this is the kind of thing that I just enjoy thinking about. So I spend all my time commuting to and from work thinking through these things in my head. And a lot of my free time talking through it with my friends as well, and getting their feedback and their ideas. I tend to find writing kind of crude and messy. Because really what I want is a picture of this entire web that's changing all the time and really complex, and it’s not a good way to represent that.

Lynette: And what particular things do you do to get insights into all the people? Obviously asking them questions, but are there other ways of approaching this or ways of thinking about it, kinds of resources that you found useful in building those models for yourself?

Tara: I think early in my career, I did a lot of experimentation, especially with mimicry. I would try to find which employee I thought was my boss's favorite employee in the organization and I would just try to behave like them for the day and see if that made my boss be happier with me or something. And then from doing that I would get a clearer picture of what it was that they appreciated about that person's approach to their work or their way of solving problems. And I did a ton of experimentation with this, even with people in really different industries—like any time I met a person and observed them working in a way that was different than mine—even if they were a barista at a cafe, I watched the way that they moved around, or something. Like “What if I tried doing my job like that, with a very fluid motion?” I just pulled in lots of things from all different sides, and it just feels like a game honestly. It’s very fun to play around with different things like that. It makes boring parts of the job much more interesting. 

Lynette: Right, okay. I'm curious if there's other things that you did to gain the skills? Like a lot of this seems to be about, experimentation observing, playing around with things. Is there anything you did to build that skill set?

Tara: I guess just doing it makes you better at it right? I fucked up a whole bunch of times, but I think I explicitly tried to put myself in situations where experimentation was low cost. When I wanted to do social experimentation I would usually go to a different part of town that I didn't normally hang out in and interact with strangers. And just find ways to make the side effects of the thing I try less terrible.

Lynette: Sounds good. How do you generate what kinds of experiments to run? Are there any internal meta processes there?

Tara: Honestly, I really just follow what I'm curious about. I’m curious about other people's ways of doing things. So a lot of it just comes from watching someone else and trying to pull in the good things about their approach. I did read a ton of books about productivity and business and whatever, when I was younger and pulled some things from each of them. I spent about a year where I would read a book about, I don't know, stuff like a lot of pop psych books like "Deep Work", or that kind of thing. I would be like “I'm going to do everything that this book suggests for a week very extremely.” And then lots of parts of it wouldn't work and some parts of it would, so I'd keep a good part and throw away the bad ones.

Tara: Again, really opportunistically—like, some person mentioned reading some book that worked for them and I’d say, "Okay I'm going to do that.”

Lynette: I'm curious, were you always this curious? Like, “Let's dive in and try everything”?

Tara: I guess to some extent, yes. My mom describes when I was a child, that I would run around and touch everything, and want to talk to every different kind of person and ask them a lot of questions until they were really sick of answering questions.

Lynette: Yeah, at a meta level I'm curious how much of all of the things you're picking up, do you think people can explicitly try? Like, the purpose of me doing these productivity interviews is trying to get these details from other people about what they're doing. So I can try and see what can replicates, and what I can scale with the people I work with. 

Tara: I think that a lot of the more explicit things I tried, I think that other people can also try. Anyone could do the go to a random meetup thing, or read a book and try doing exactly what it says for a week. Or try like, copying another person's way of interacting and see how that goes. But yeah, I guess people who find a lot of social situations stressful or difficult might find that not very easy. Or not very fun.

Lynette: Are there any meta ways of how you would go about setting up these experiments that you think would increase how much other people get out of trying similar things?

Tara: I think being able to debrief on the experience with another person is really helpful, especially when they can just talk to you and say like, “What did you notice and what things felt uncomfortable and what things felt good?” Because I think for me, I've learned a lot from trying to do that kind of verbal debrief, and I think some other people will find doing a written debrief more useful than I do. I guess, trying to focus on noticing one specific thing at a time would be good, like, only try to copy a particular person's body language, or one aspect of their body language. 

Lynette: Okay. What about things like making predictions in advance and tracking them? For a couple of these things you mentioned that. Is that something to do with most of your experiments?

Tara: Yeah, but I think that that's something that's so deeply ingrained for me that I just do it automatically. And really, as a game—every time I go to any place and I'm like, "Oh, it will probably take 23 minutes to get there, and I will arrive at this time." And then I'm happy if I'm correct; if it took 23 minutes. 

Tara: Yeah, I find tracking the predictions explicitly is onerous. I think a lot of people expect that they can't get valuable information unless they write it down so that they don't remember it incorrectly or change their mind. But for me, I prefer just saying it in my head, like, "I predict this is going to happen" and making a very specific prediction means that you can't do that. And yet you can still generate these results.

Lynette: Yeah, I think for a lot of people, they just forget that they made the prediction afterwards.

Tara: Yeah, maybe that's right. I guess I just have a habit of reflecting. Like, every time I finish something I'll just reflect on how it went, or how long it took. And I just think that's a good habit.

Lynette: What kinds of questions do you ask yourself?

Tara: Just “How I feel now that it's finished? Do I think that I did a good job? Is there anything I think I could have done better? Is there anything in particular that I did that was good?” It's pretty general stuff.

Lynette: Okay. Awesome. So anything else that you want to cover or throw out there?

Tara: I guess approaching the whole thing with lightness and fun is what works for me. And I don't do any of these things because I have to, or because I'm trying to get results out of them, or because I'm expecting it will lead to, you know, me being a better, more productive person. I'm just like, “This is a fun experience I can have and a fun game.” And that makes it intrinsically motivating to do all this stuff. 

Lynette: Yeah. What percent of the things you do feel that way? Feel intrinsically motivating?

Tara: Like 80 or 90%. I've worked very hard to get it to that stage. I used to feel like I got to only spend five or ten percent of my time doing things that I want to do.

Lynette: What changed to enable this much greater capacity?

Tara: Well, I find ways to make everything a game, or set myself some kind of challenge. And that makes it more fun even if it's a boring task. Like if I'm categorizing receipts or doing my taxes, I'm like, “I bet I can do this in an hour.” And then I'm racing through to try and do it in an hour. Or like, “I did 100 of these receipts in the last hour, let's see if I can do 90 this hour.” Yeah, it just makes everything much more fun.

Lynette: I'm curious. It sounds like previously, there was a time when a lot less of what you were doing was motivating. Is that that you've gotten further in your career to a point where you're happier with things or did you change your approach to things?

Tara: I think a lot of it is just changing my approach. It's doing things like that, finding a way to make the thing feel more enjoyable. Which could just include, you know, doing my taxes with a friend, so that it's more fun and less bad. I just found a lot of ways to make things that used to feel kind of ughy feel good to me now, and feel exciting to me.

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