thinking on thinking · S7E12

Balancing energy, expectations and perfectionism with Ambika Singh, Founder and CEO Armoire

August 13, 202553 min businessdesignbehavior

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In this special Singh siblings edition of thinking on thinking, Kahran gets deep with his sister and founder of Armoire about how she navigates expectations, keeps up her motivation, manages her brand all while driving a business with high values.

notable moments

Stepping into your own skin helps all of us be who we want to be. How we suit up is an important part of that.

People who buy from small businesses are pretty educated about the fact that it's a small business. The founder's authenticity outperforms celebrities on social media.

Read full transcript

Well, my name is Amika. I am your bigger sister. Actually, I've been on the earth the entire time you have been here. So that's an accomplishment for me. In case my older son was asking me the other day, he was like, where was Nene when I got here?

And I was like, well, he wasn't here. And he was like, well, who was my brother? It was like mind blowing to him that he had existed in a time without his brother. Even though he remembers before his brother, or not really. I think it's like kind of, but it's like the in his mind,

like they are one in the same. And obviously, as we both know, Neum didn't know that he was a different person than Kason for many years. Well, he's only a year and a half, so we can't say many years. Okay, well, for 50% of his life,

he only recognized it on April 20th. I marked the date because I couldn't believe that he recognized he was a separate person. So that's who I am. I'm your bigger sister. Also mind blowing to the boys is the fact that I am older than you

because they think that you are bigger than me, which is the signal of who is older. So Shankar is the oldest, but Shankar actually is the oldest. Yeah, clearly. Right.

Shankar is the oldest. So that's weird. But yeah, in their mind, you're definitely older than me. And I run this company that I love called Armoire. We rent clothes and we watch our members transform into these fun dressed up gals.

And the reason I think it's so important is because getting sort of stepping into your own skin, I think helps all of us be who we want to be. And Armoire, which is part of the reason I picked Armoire as a name, is an important part of how we suit up. And it's funny because both me and you took an extra couple minutes to suit up before this.

And I'm loving your earrings and loving mine. So, you know, even on something like this, we're like, obviously, we know each other very well and we're on Zoom. It still felt important to kind of like suit up and do it the way we want to do it. And so I'm thrilled that we get to be that part of our customers' lives.

You know, I do the best of anyone in our social media, even the celebrities that we have. Interesting. Why do you think that is? Why do you think it is that the founders do so much better? Like, you would think that celebrities would do better.

I do think that the people who buy from small businesses a lot of times are pretty educated about the fact that it's a small business. And this is actually like something that we have a good amount of data on. We look at it in this kind of like interesting way. This might have been your suggestion when you and Shui came in many moons ago.

We look at things in how, like, what are the demographics of the cohort when they arrive? What are the demographics at three months and what are the demographics at six months? So it sort of gives you like a survival profile. An interesting one about this. We bucket like sustainability, women owned and founder stuff into a bucket called values-oriented customers.

And they are the smallest when they arrive. And by the time that six months comes around, they are the second or third biggest. I can't remember what exactly. Out of how many? Meaning like we stack ranked the reason codes for why they came.

Yeah. But like how many reason codes are there? And they're six. I see. So like, okay.

So it goes up like four spaces at least. Yeah. And so like in the beginning, it's like variety price, which is terrible. And those people don't hang around. Variety hangs around brands.

Do not do as well. So I'm looking for high price brands, which is kind of another version of cost. Basically, if they're coming here to get clothes that they can't afford. Yeah. That's not really what we're selling.

Like we are selling a variety in the wardrobe. Also, this what I think is important and apparently what the customers think is important is like, this is a great place to put your dollars. Like we are proud of the fact that they are, we have incredibly tenured employees. We have a warehouse that is almost entirely run by women or people who identify as women,

which is really rare in the industry. It's obviously got a really strong sustainability component. So I think that people are more educated about small businesses than like the average bear. That's not always true, right? Like Universal Standard, we were just talking about before we started recording.

There's the founder is almost invisible, right? I feel like nobody really knows her. But their values are, yeah, I don't think it has to be for us. We bucket me into like the values based content because I think I do a good job of speaking for the brand. Because you know what the reason is.

Yeah, yeah, yeah. Interesting. Hmm. Yeah, I don't know if I have that many interesting thoughts about that. I think it is true, you know, I do think that there are, if you're willing to like shop at a small business,

there's some value that you're associating with that. And maybe it can be, yeah, that they're associated with like what you feel like is like good, right? Like people like me do these kinds of things. There may be also kind of, I think other associations, right? Maybe a higher sense of quality or a higher sense of repairability.

But again, it comes back to values, you know, it does at the end of the day. It's like these are values I care about that are different than just straight up cost. Right. Interesting. Right.

And I mean, generalizations, but in most cases, the small business is not going to be the most price efficient option for the consumer. So it's also probably a survival bias in terms of like you got to be selling something that people want to buy. And if it's not price, what is it? Yeah, yeah, that's interesting. There was somewhere that used to call it.

Oh my gosh, this is I'm really going to date myself. But I remember there was like this is maybe 15 years ago that people would talk about how you would to pay like a queer premium if you wanted to go places because like like the gay oriented apps and things were more expensive. And then we were talking about at the time that there had been this kind of switch where now there was more competition for this notion of like there was like a queer dollar that we are people were after. And so it started to switch where instead of you having to pay this premium, it was like almost like people were courting the courting the audience. But it's interesting.

I remember now. Yeah, I was talking about it in India because in India, people are very used to the notion of saying, of course, there would be a premium. It was in the context of Mr. BNB. It's all come back to me. So there's a service called Mr. BNB and it's like Airbnb, but the prices are uniformly higher.

Now I was just like, why would you pay for this? Like what is the purpose here? And I guess it is what you're saying, right? Saying you're supporting your values, you're supporting this community. And of course they're saying we're offering maybe a subset of the overall potential accommodations because we think that these are going to be more appealing to our audience.

Yeah. Yeah, I mean, a thing I don't think that our market does a great job on yet is that I don't think that we do a great job of differentiating for the customer. Why we are reflective of their values. So like there are things that the customer can infer by looking at me and seeing that I'm a woman of color and so they can infer that this is like values aligned. But I actually think like as a both as a responsible business kind of, well, I don't know if it's so much responsible.

It's more like, how do I make sure that you, the consumer knows all the things that I'm doing on my side to actually support that purchase? And so for example, like I just told you that our warehouse is staffed by women or people who identify as women primarily. There's like nowhere you can find that on our website. So unless you've been hanging around with me, I don't know that you know that. Or like, you know, it costs us money, but we are every single garment that comes out of our warehouse in an end of life scenario goes somewhere responsible.

And that costs us money. Like if we were throwing it into the trash, it would be cheaper for us. Yeah. But again, like you have to have been hanging out with one of us to know that. So I think we've got work to do in consumers right now have been very generous to assume that we are running this business differently because it's a team of women and women of color.

But like there actually are tactical things that we're doing that I'm proud of that I think we should do a better job of telling the story of. Huh. And you feel that that's a needed thing, right? Because I would almost argue that I think that there's this movement in the world now where it's like, well, if you're you understand the person, right? And you're like, well, I understand who you are.

And if you're going to be recommending this to me, are you're going to be involved with this? I'm going to assume a certain degree of quality. Yeah. I mean, I think that's what my consumers are. They're giving me the benefit of the doubt. It seems like just by sort of taking me at face value, like you're saying, like they trust me, they assume that I will do the right thing.

So maybe that's like me dating myself and thinking like I need to substantiate all of these things. We also do want that. I mean, because that just means the entire brand is kind of carrying on you in a lot of ways. And like there's an argument whether or not that's sustainable, but also I imagine that's like not fun. Is it or is it fun?

Well, I guess I should say me more generally because like these operational decisions that I'm talking about are far beyond me. The fact that we have the team makeup, for example, is like run way far away from me, but we're not necessarily getting credit for that. Yeah, but you're setting a tone that's leading to that. So I still would say that I think there's a really strong association between the Armour Brand and like your personal brand. So like it's, you know, like nothing that Armour Brand does feels like it's not in alignment with your personal brand.

That's a good point. And maybe that is like part of what I think a value would be of being more kind of detail oriented about what the company's values are. And not just values, but like what do we do behind those values? Because maybe it would help create some distance between my personal brand and the company's brand. Because it's annoying.

I don't find it annoying, but I do worry about how scalable it is. It's scalable from the perspective of like it is, it's time consuming to be. Did you see what I posted on Instagram yesterday? No. This is like going around it.

It's like a meme. It's Jennifer Hudson standing in front of a microphone and the captain says something like, wait, all I wanted to do was start a small business. Now I have to be the content creator too. And she's like, what am I doing here?

What am I supposed to do? I do feel like that very often because I don't know how to be a content creator. So I'm learning and I actually, I enjoy it. So it's not that I feel that it's annoying, but I feel that there is a, I do it at the expense of doing other things. So like that is where I feel like there might be some non scalability with my personal time and how big we want the brand to be.

And then I think there's, there's a lack of scalability in like our more is so much bigger than me. It is now, you know, so many humans on the employee side, so many thousands of humans on the member side. And there really is a place for everyone in the brand. But yeah, I'm not going to be the be all end all for all the people. Interesting.

You said like multiple things I'm curious about. So you're not so much saying that like it's, it's troublesome having a brand that's really associated with you. It's more that you're saying that you feel it's reaching a point where it's been limbed. Yeah, exactly that. And that's probably, I can probably say that from this place of privilege because I haven't had knock on all the woods.

Like something really catastrophic happen where I want to separate myself from the brand. I'm sure a lot of founders have had their organization make decisions eventually that they don't like or that are not reflective of their values. I haven't had that. I hope I never do. But that's where I feel like it might for the founder become like.

Hmm. Because you no longer have control, but it's still associated with you. Right. Like let's say I retire and in 20 years they're doing something that I just like don't believe in. That's a problem.

Yeah. Yeah. Also, is it like exhausting that like you're embodying it all the time? I imagine it's like a lot of work. Well, maybe to your point, like right now it does feel so like, I guess synonymous with me that I almost think of that.

I almost think of that question more as like, does it feel exhausting to be yourself all the time? Kind of, but I sort of like myself so I'm okay. You know, like I think she's doing pretty great or more. She's trying her best. She generally makes people happy.

She brings a smile to people's face. She gives them a confidence kick. Like she's pretty good. I like her. But like it's still at the end of the day, like you have one pool of energy, you know, like there's something that helps me realize a little bit where it's like, you know,

now that I'm just like trying to create so much more on a regular basis, it's very hard to do these other types of like creative projects we used to do from time to time. I try to write poetry all the time, you know? Well, I do think that's probably a big difference though. It's like I kind of only do one thing. No, that's not true.

I mean, you also, what are you saying? First of all, running a company is not only one thing. And then you also like have children and you like have a very like active life in Seattle, you know, it's like you engage with your friends. You engage with the community. Like you're very up to date in what things are happening.

Like that would all three of those could be separate lives. They have, with the exception of my children, they have a connective tissue. Like it's not, you wouldn't be the first one to observe that a lot of my friends work at our more or have worked at our more or will work at our more in some capacity. Yeah. Or at least they rent from our more.

Like I do, I think the connective tissue is pretty strong in my social life. And most of the stuff I do for my community basis now has a good amount of connective tissue too. And it might just be in my own lens, but like where I have moved, I recently joined the Seattle Chamber Board. I'm on the United Way Board. Like those things feel very important to me, even in a heightened way, because my company is here.

This city is, it's important to me that it looks the way I want it to look for my children and for my company. But I still wouldn't say that that's not a different job. Like that is still a different thing. It's still a different thing, but it feels connected to me. No, arguing about whether or not it feels connected.

I'm just saying that it, like if we're saying that there, it's one thing you're doing, I'm objecting to that contention, that it's one thing that you're doing. Because you, like when I was running with the Annex, like, like when I had to run different functions, it's a very different job. Or when you even have to just like embody the brand, like when I had dad there and dad was really able to be the face of the brand and really just like out there, like just living it all the time. It takes some of the burden off of you.

And so I just feel like those things are work. And so that's why I'm curious, unless you're saying it doesn't really feel like work, which is totally possible. Like some things are work that don't feel like work. Yeah, I think that's a good point. I think most of the time it doesn't feel like work.

I'm trying to think of like when it feels like taxing. And the things that feel taxing, frankly, are not sort of like brand related. Like the things that feel taxing are like the things we don't have control over, like shipping or COVID or like those are the things where if I think about when I feel really exhausted, it's like I don't have any control over these things that are happening to me. But the brand, I feel, I think it generally, like, I can't think of a time where it's like embodying the brand felt exhausting to me. Interesting.

And like shipping, even though that's not, that's just like a fixed thing. Like that feels more exciting. No, but like shipping will always be a cost. It's never going to be not a cost center. And it may vary by, you know, I don't know, maybe even 100%.

Right. Like maybe it can double sometimes or almost cut in half of where it was. So, but like, you know, at the other day, it's still like a somewhat fixed cost, but that will feel more like there's only limit. I'm saying there's limited investment you can put into that where this you could argue that brand or children or your company or unlimited investment, all of those, you know. Like all of those, there's no, you could keep putting more energy into them, but it doesn't feel that way.

I'm not trying to make it seem scary. I'm just curious. Yeah, no, I mean, I think the children example is a really good example because like I have found a lot of similar feelings in both places. And like, I think because children are so sacred, it's probably like easier for myself to like see the parallels. Because like, yeah, I think that's a good parallel where it's like it kind of, of course, like having children is exhausting.

We just spent a couple days of them in a confined space. It's exhausting, but I'm never like, I wish that I had to invest less of myself in them. It just feels like, I guess, the things I think about are like, how do I make this easier, but not sort of like, how do I do it less? It's almost like, how do I do it more but better? Interesting.

Do you sometimes have moments where you're like, oh, I could do this better, but I'm too tired to do it better? That doesn't really happen. I mean, I think I have had those like questions, but like one, I think going on maternity leave both times taught me like pretty quickly that I am not a good full-time parent. So like, if I'm questioning with myself like, okay, could I be a better parent if I spent more time with them? Because certainly like, yeah, I asked myself that.

I remember that I am not a good full-time parent. Hmm. Okay, let me give you a very different example. So I just finished turning in my folio for my summer writing program, right? So I had to turn it in by the first. Congratulations.

Thank you. And I was rereading it because the person who I was submitting it to let me know, she still hadn't received it a couple of days ago. I was like, what? I turned it in last week. So then I realized it had been some form that I submitted online and she hadn't received the form.

Fine, I emailed it to her. So after I emailed it to her, I went and looked at my set messages and I was just skimming it. And I realized that there was this point where I had changed one of the essays, what are like the second essay, the author it was about. And at some point I had forgotten that I had done this and I had one of the wrong authors, right? So instead of being Erica Hunt, I referenced this woman named like something Carla Harriman or something.

And then I was like, I'm going to find them Lee and this like, you know, sixth paragraph of the of this essay, I'm like, you know, whatever the 10th page. It just randomly mentions this other author, right? It says Harriman instead of saying hunt. I was like, damn it, right? Like if I had had it, like if I'd finished it a little bit earlier, I would have like proof read it one more time and I would have seen that I had done this, you know, but I just like didn't have the time or rather I think at the point when I was turning in, I did not have the energy to reread it, right?

I was just like, I am done with this thing. Like this is. Yeah. I'm just asking where it's like, I feel like sometimes it's like, you get the thing done because you have to get it done. But when you look at your like, oh, if I had had more energy to bring to this at this point, there's a higher level of caliber that was accessible to me, but it wasn't accessible to me, not because I didn't know it, but because I didn't have the capacity for it.

Did those moments happen? Definitely. I mean, and I guess that is a good point. And like, interesting that it was like, I separated myself from that like so easily. I mean, that happens to me all the time, like seven times a day.

Almost every meeting I get on, I'm like, man, if I had had 10 minutes to prep for this, I would be doing a better job than I am right now. Yeah. But somehow I don't know, maybe it's I'm a narcissist, but I like don't when I walk it backwards. I'm not like, oh man, like if I just if I just had spent more time on my job, I would do a better job because maybe part of it is like, I also don't think I can spend any more time on my job. Yeah, that's also possible.

Right. Like there is you have a capacity of how much you can work on something. Yeah. But then is it so then how are you making the time for additional things you're getting more efficient at the things you're doing? That's how you add more.

I'm trying to do. Yeah. I mean, like I think that's a mantra for all of us that are more right now, which is like we're trying to do fewer better things, which we borrowed that fantastic tagline from a brand that we admire. Do you know Kuyana? I'm not sure if I do.

You should look them up. Also in your with your other retail forays, I think they have a really strong brand. That's very interesting. But yes, their brand tagline is fewer better things and they make really high quality items and they want you to keep them. But like obviously I translate that into the productivity space.

Not well. I mean, I think I'm an evolving quantity, but it's like, yeah, if I could do things in a less less like haphazard way. I know that they would be better. The challenge is always like that. And the reason that I know that this is like a personality thing is because I do it in my social life too, where it's like, if we only had one thing to do that day, we wouldn't be running late to everything.

And I wouldn't have like forgotten the gift and the this and the that. But it's like, I want to go to both things. Interesting. I wonder if this would be resonant for you. But something that Divya and I have talked about is that sometimes I will have trouble remembering to post our podcast.

Like last week, I completely forgot to post our podcast. I was whatever in Seattle, you know, I had to turn in my homework, all this stuff. And so I posted like six, five, three days late, four days late, whatever. And usually what will happen is I'll get very upset with myself, right? So by the time that like she and I have talked about it, I've already been like grumpy that I did this for like, you know, two or three hours or something or even more.

And then her point to me was like, in the process of being grumpy, you've almost like you've given you, you've, you've incurred the suffering that you feel you should have incurred. And so then you don't feel a need to change the system because you've, you've taken that kind of like that, that negativeness, right? And instead of like applying it to saying, okay, you know, something systemically was broken here, maybe there's a difference. Like maybe we need to look at this. It's that you, you've paid the pennants, right?

You've done the effect of your rosary. Exactly. So I'm curious if that notion feels resonant to you. It's just a creature. So, so interesting because I, on a parallel conversation that we were having, I was reading this thing about time out with children and it had like a similar argument that like, you don't actually want to send the kids to time out.

So Neum, who's not yet too, has been saying out loud, I'll do time out. Like after he does something terrible. And I'm like, wait, this is obviously already backfired because his point is like, well, I can punch my brother in the face anytime. I just have to stand in that dark room over there. Like this is great.

Thanks for figuring this out for me. So I think that's like really interesting because like, yeah, we do have this like internal reward punishment system where we think that like, as long as we have accepted the punishment, we've like done our part. Yeah. Because when you were saying that you feel like you'll start meetings and you'll feel like, oh, I wish I'd been better prepared. That's why that's what made me think of that.

Yeah. I like that. I think I should totally think about that. Now I really think I should double down on the no time out thing. Like you need to teach them that like, no, the problem has already, and exactly to what Divya is saying, like you can fix it next time.

Yeah. You don't have to be punished. Yeah. I go time out. I go time out.

No. He's very sweet. I mean, he's only two. He's not even two. Yeah.

But that is like so powerful because that means like it's in there already. So I'm sure that's what we're doing to ourselves. Yeah. Interesting. But you don't feel like you're willing to kind of have that for your meetings.

Well, maybe it's because I've been punishing myself and so I haven't like thought about the fact that like I can do better. Well, not just better. Well, it's not just better. I think part of it is also this notion of saying that I'm not, I'm going to reflect that I'm going to to understand that there's a systemic issue here and it's not a personal failing. But sometimes the scary thing is you don't want to confront what the systemic issue is.

Like I'm like she and I have also talked about this and sometimes I don't want to confront the fact that I've over scheduled myself. Right. So if you don't confront it, but but generally what ends up happening is you actually lost time in feeling stressed about the fact that you've over scheduled yourself versus if you could just do the items you'd be fine. Yeah, I have thought about that too. Like the amount of time that I spend optimizing my schedule so that I can over schedule myself is like probably equal to the amount of time spent in the fun thing.

Okay, so should we make a commitment to doing one thing better? What does better mean? Not feeling like one meeting a week you're unprepared for. Interesting. I don't know.

If that feels like an attainable goal, what makes it feel not like I mean, you said, you know what to do, you would need to read for 10 minutes beforehand. Right. Okay, here's an example. Our board meetings are getting better. But like one of the things that we we did not kind of like come up with for ourselves, but our board members demanded that we start sending the pre read out a week before the meeting.

Yeah. And it's been like somewhat life changing in terms of like how prepared I am for the meeting because I've literally had a week to think about the deck. Since then I still think like I could get better and like even this last one I was like, man, I wish I was better prepared, but it's not as much of a disaster. I do think like also the external forcing function is really helpful for me. Wait, so you're saying that made you not feel unprepared for your board meetings whereas you used to feel unprepared.

I'm saying it hasn't solved the whole problem because I still do feel unprepared, but I feel less unprepared. Interesting. Is this a feeling of like, hmm, like when I was leaving Seattle and then my flight was delayed, I was actually talking to chat GPT about this. So I was like, oh, I could go home and like hang out with mom and dad. And it was like, yeah, but you were just home for four days.

Like you could also finish your homework. And I was like, hmm. And so I'm wondering like, is it one of those things where you it's more that you're feel that there's a feeling of it's not a question of time investment is what I'm getting at. Like there's there's a there's a there's a threshold to be reached and it's not quite it's the threshold could be reached with more time investment, but it may or may not be reached with more time investment. It may just be this kind of like feeling of being unprepared or late or over scheduled that you just kind of like will always be in.

Well, no, or maybe it's something entirely different. Like maybe it's a feeling of like feeling ungrounded, you know, and it's like, oh, you know, you're still like your thoughts are in the previous meeting and you haven't had a sense. Like what you really need is maybe like, like 30 seconds to like quickly skim what happened in the last time you saw these people so that you feel like you have the context of like maybe it's something different is kind of what I'm getting at. That's not like, I don't know, this is not going to be my best metaphor. But like, you know, let's say you're like digging a pit and and

you start to realize like the dirt starts to become very muddy at some point, right? So then as you're continuing to dig the sides are starting to slide in. Now you could keep digging, but you're not going to be able to go any further because like the tool you're using is no longer correct because the substance you're trying to dig is no longer as firm as there need to be for you to be able to use a shovel. So I'm wondering if it's something like that where it's like, you've reached a point where you're not able to go any further. Yeah, that just being prepared and more prepared is not going to be the thing like you need to do something else.

Like in my case, for example, like what I wish I had done with the board meeting now we're sending out the pre read, but I wish I would have practiced because like once I did it once I was like, man, like I would have managed the time differently. I would have spent like different. Yeah, more than that. I would have spent different amounts of time in different places. But now you have four of them or whatever, right?

Because you're doing them individually. So you got to do that. I did get to do that and it got better. That's amazing. Yeah, it did get better.

Interesting, but you don't look at it like that. We're doing that again. Yeah, you're right. I didn't look at that because overall that was such an overwhelming experience. I mean, I'm not sure if I could do that.

I mean, I'm not sure if I could do that. I mean, I'm not sure if I could do that. You're right. I didn't look at that because overall that was such an overwhelming experience that I think we've canceled that as a good idea.

Huh. But here's an example of like you actually did get to do it four times. You saw the material, you got to go through the material and then you, right? So did you feel more prepared by the last one? That is a great point.

I felt way more prepared by the last one. I really felt like I knew what I was doing. Interesting. And I had made adjustments along the way too. Yeah.

How do you think about efficiency? Like what's the first thought that comes to mind when you hear efficient or like, how do I think about my own life efficiency or what? Well, kind of like, I was just thinking about like, you know, yes, it's great that you felt prepared by the fourth time,

but at that point you probably had invested five amount of time that you normally would spend in preparing for it. If you count the number of like, if you count them all as practice, the ones that you did up to the last one, right? So I'm just curious about that.

Like sure you can get to this point where it felt like you made, I mean, didn't actually say you achieved the level of preparedness you wanted, but let's assume that for the moment. And so I'm just curious now that like, now that you've found your, your, your grail or your North Star, how would you, how do you think about like,

is that, was that an acceptable amount of time investment to get to that goal? Or then do you start to look and say, how do I make that path more efficient? Or is that not how you kind of think about efficiency at all? Be honest, I think I think very little about efficiency. Which maybe make it easier like this, like other tasks that maybe you do regularly,

like see like, oh, this used to take me this amount of time, you know, two years ago, seven years ago when I started our bar, but now I'm able to kind of do this. I think I should think about this more. Like I'm thinking of when Laura Butler worked here, absolutely love Laura and Mr.

She like tried to mentor me into some of these things or she would be like, okay, like, I mean, time boxing, I think is like a great strategy where it's like, you can time box things like, according to what you think it's worth to you or worth to the business. But I think that I tend to resist that kind of like structure. And I end up sort of like having like a kind of somewhat emotional response to like how much effort I should put into it.

Actually, you pointed this out to me at the ripe age of I think like 37 or something. So it's a little bit that this was a new thing. But like I didn't realize that I was a perfectionist until you said that to me. Remember, I was like so shocked when you said that. I didn't consider myself a perfectionist because I think of like these things that like in my mind a perfectionist like time box as well and like starts ahead of time and like builds in all of the like edit cycles and all that kind of stuff.

Like that was my image of a perfectionist. But what I think it actually is is like, or at least in my case, like what it is is that I have trained myself into knowing that I'm willing to kind of like sort of kill myself in the last mile. And I'm willing to take that last mile and turn it into 10 if it needs to be. And it's some imaginary calculation that has something to do with probably like some amount of outcome oriented, but it's like my perception of outcome. Huh. I mean, that can't always be true.

Like there's some point where it's going to be like, you know, it's not worth chasing an optimization in this scenario. I'm bad at that. Like you see me even in my personal life chase absurd optimization. Yeah, there's some point where it's like, you know, now the die is cast, you know, I'm trying to think if I could give you not a strength of mind. It is not a strength of mind to cast the die and walk away.

Like I think I'm very lucky to be surrounded by people who help me do that. Like if you think about the people who are really close to me on a daily basis, like, you know, both of my closest operators are very much those people like Shafali and Kristen cast the die and walk away really well. And that's not to say that. Okay, here I thought of an example for you. So, you know, we were talking before we started about pulling this clothing rack behind you into the frame, right?

And now as I look at this clothing rack, which I didn't really do before, but like, you know, all of the clothing's on the left are, I guess you're right. Are basically the same, right? They're like a golden rod. Maybe I don't know what that is, a curtain. It can't be a curtain, but right.

So like it's quite arguable that is maybe not the best thing for the like to give a sense of the clothes that our more has. But you didn't think about changing the clothes on the rack. You were just like, I'm going to pull the rack in. So at some point you were like, this is not, it was not a reasonable optimization to try and chase that. I think that's a good point.

So I did notice that, but I was also like under pressure or perceived pressure to like start. So I'm making some kind of like weird calculation. I was looking at the time I was like, okay, it's 209. We were supposed to start at two. I want to make this look better.

But it's like, if I had been really a rule follower, I would have never tried to pull the rack in in the first place because like, you know, came from across the room. I ran into the TV. Like I kind of knew that it was like not super simple, but I also was looking at the screen and being like, that looks ugly. So it might be that my desire to not put other people out like helps keep my keep me on track. Interesting.

Like if I had been recording this by myself, I probably would have turned it on at like 9pm. Like running around trying to like change my outfit and like do all this stuff. And so like, I do think that having people around me that keep me like moving has been really valuable. I mean, like my partner in life, Schunker is great at not optimizing on the, he makes decisions very quickly. He's really comfortable with his decisions up front.

And as far as I can tell, barely ever goes back to like revisit them. Yeah, I am in the process of redoing our last like 12 hours of our trip in Africa because I was mad about. But it's like, we're going to have spent so long traveling there. And I felt like if we spend the last like, you know, eight to 10 hours, like in transit, it'll be really unpleasant. And so I'm going to spend an extra four or $500 and we're going to have this like really lovely dinner and we're going to go stay at this villa and like it's going to be really lovely.

And was it worth it? Your spouse would have done that. No, Gourav would absolutely not have. Gourav has like, yeah, no, I know this. And I'm like, mainly looking at like, you know, I made it like, I know why I did it.

It was significantly cheaper to fly with two stops, but I am kind of like considering whether or not I can try and figure out a way to like get rid of that stop. But you know, those to me feel like it's a point where I draw the, the num, I draw the line where I'm like, yeah, this is worth. I find some sort of enjoyment out of it. Like I like kind of like sitting with certain things and being able to keep optimizing them or just thinking about like, what if this could happen? But the interesting thing that they just pushed me on.

Sorry. Go ahead. Well, in that scenario, how did you stop your wheels spinning? Like, did you tell yourself? Well, that, that, that gets to what I was, I was going to say, which is this interesting thing that they've been pushed me on a few weeks ago when I was feeling very stressed about finishing all of this work.

It was writing I had to do and she was like, well, can you write out how long it's going to take you? And so I went to write out how long and she was like, and then you'd figure out which ones you're wrong about. And like the one I didn't realize I was so wrong about, but I think I kind of knew was transcribing the poetry I'd written in my notebook. I thought that that would take me like some reasonable amount of time. I think I said 15 minutes to like transcribe six poems.

It took me like 10 minutes of poem because it was like so hard for me to understand what I was talking about. And sometimes I couldn't read my handwriting. So then I had to really understand what the poem was about in order to figure out what the word was. It just, and it took so long, right? And I, but then after that, it's weird because everything is actually, it's been a lot easier for me to do this now in the mornings to be like, oh, what are the things I need to do?

And then how long are they going to take? Mostly because I divide everything into 15 minute blocks. I write things that I think will take 15 minutes. I didn't even realize it, but I realized that that is like the time period that I seem to write things down in. Like there are things that take me about 15 minutes.

It's also because I realized that's about how long I can work on something in a single go by myself. I mean, I think that that's also a good insight because like that's maybe part of what I'm saying about like having other people around me that like keep it moving or having a schedule. Like similarly, I've been promising I would make some content and it's been going on for weeks. And today I had seven minutes and it just like I had another meeting and then I made it in seven minutes. But like otherwise I would have sat here and like thought about what I should do and it didn't look good and blah, blah, blah.

Well, it's just that those are actually discrete items, right? So like thinking about the content would be its own item versus the creating of the content, right? So then you put a time block for your thinking about the content and then you just have to be like, well, okay, so this time I thought it was going to take me 10 minutes to think about the content, but actually it took me 45. So then you know that like you set to fix your estimation. So instead of it becoming a problem of like, oh, I need to be less time, it just becomes a problem of fixing your estimation.

And in the process sometimes some of these things were like, oh, why am I spending so long on this? You know, but like instead of it being a question of like, oh, I'm trying to fix how long I'm spending. It's just a question of getting accurate in how long your estimations are. But like with something like the travel or the content, I think the problem is like what is good? Because like you could decide that optimizing your travel is worthy of taking 20 hours.

Yeah, so I mean, I've had like a 15 minute block for like every day now for the last like four days. And sometimes it's been two 15 minute blocks. I guess what I'm saying is like, but I'm saying like at the end of that it's like, I can see is there stuff that I would need and I haven't been that good about this. But like generally it's been like, is there other stuff I need to do? Usually in that 15 minute block, I've done the things I needed to do with it, right?

I needed to respond to the adventure trip, the people who are planning our trip, right? I needed to send them a message. I needed to look at something. But like a lot of items, it's not what are you going to do? You know, like, yes, you can keep looking at them. There's like, there's diminishing returns, you know, and so you can do like the big chunk of it.

And then oftentimes you come back to it, the big chunk of it may have been, they'll be more accessible. But like if you keep it putting time, you know, now you're digging the water of the mud out with yourself. I mean, a good way maybe to recognize diminishing returns is that that like time block idea that you're saying? Because like maybe it's like in the beginning, you make a lot of progress in the 15 minutes probably. And then like by your 15 minute time block, you're probably not making that much incremental time, like incremental, I don't know, what's the word?

Achievement or growths, achievement, whatever. Yeah. I like that. I've had, I have heard other people, by the way, that 15 minutes, I've heard other people say that that is like, they're also there kind of like time block. So I don't think it's crazy to think that that might be your time block. Yeah, interesting. But even when you really put so much like energy into these things, I feel like I never see you wake up like tired or like have a moment in your day when you get tired. Like that happens to me and I feel like that happens to mom and I feel like that never happens to you or dad.

We're like, this is just a lot so far and I need to have a little break from this before I can do this more. Well, I think I'm an extreme extrovert. And that probably comes all the way back to like your question about like, is it exhausting to be the brand? I think like I probably am like pretty on the spectrum of like the people, being around people gives me energy. But being by myself is very scary for me.

Putting the board decks together is like a nightmare. And so I've learned to like do it in collaboration with people because otherwise I'm bad at it. Yeah. And I get really exhausted and bored and mad and sad. Yeah.

It was a real difficult change when I had to work by myself. It's been a whole thing. Yeah. How does that work for you? I mean, you know, we were discussing it, right? You build all these little like techniques to kind of make things more smaller and more achievable and less require less energy from you basically. Because you're not in some ways I feel like if you're, what should I say?

I've also been in that situation where I feel like I have been able to kind of like just keep going. Like I feel like when I was running with the annex, like we just have days where you just would be working for so long and for so many of them continuously. But I do feel like there was a little bit of like a burnout I got to, you know, where I was just like, I don't know if I want to keep doing this. And I think that that comes from your drawing from, yes, maybe that you're drawing from energy from other people, but you're just kind of like drawing more than you really have right now. Yeah.

And that that kind of being in places where you aren't being able to do that forces you to kind of figure out where your limits are or where the sustainable ones are. Because if you're going to pick up and do it again the next day, it's it's this really big difference. I think I've learned about whether you're you're trying to achieve a goal or you're trying to build a habit. And I think when you're going after goals, it's a lot easier to kind of figure out how to get the energy you need to get there. But when you're trying to say, I'm going to keep doing this, you know, when you're trying to build as a habit, then it has to be from a sustainable place of investment.

Yeah. Yeah, that's interesting. I mean, I like I always think about this with you and with mom that it's like really amazing to me that you appear to be personally motivated without both goals. I think goals are important to me and also the external like pressure from the goals because like, I think I perform well under pressure, which is like a nice way of saying like I procrastinate a lot, but I don't want to fail in front of others. I mean, would I have written 70 pages of poetry in the last month if I didn't have to turn it in?

Probably not. Fair. You know, like, yeah, yeah. And there are people who would write, right? Like there are people who can just sit and they would write it every day.

Because they're like driven by that desire to keep writing. To create to see it in the world. But I don't know my dance teacher, that's not the she actually says it really interestingly where she was like when she was learning to dance, you didn't have to summon all the motivation yourself required because some of it came from your teacher because you were kind of afraid of them. Right. And some of the motivation that you needed to like kind of get through all the really hard days didn't have to be intrinsic.

Like he came from like, and she was talking about how now you know, you can't be afraid of your teacher in the same way. Right. You're never worried they're going to like hit you or yell at you or throw you out of the same thing. But in some ways it means that there's more motivation that the students have to bring, which in some ways is actually harder. So I don't know. I mean, I think, yeah, motivation is an interesting question. Like I think that giving yourself the tools you need can sometimes be helpful.

Like I frame it sometimes as like, you know, in your best moments, you can make decisions for your worst moments. Yeah, because I think it's like that. I think this like thinking about motivation and goal achievement and habits like sort of naturally leads to like the higher level question of like, why? Like, what are we doing and why in life? Yeah. Does it? I mean, I think so.

Like if you if you start to trade off between like, am I creating a habit or am I trying to achieve a goal? Like to me, the natural question then is like, well, what, like what's up here? Well, okay, I think you can take it there. But I could take you a different way, which is like, you know, if I want to look back at this year at the end of the year, I can look at it as saying, oh, you know, hopefully I climbed a mountain, right?

Or maybe I guess two mountains. I forgot about the one in January. But right, I climbed two mountains, or I could look and say, you know, of my of the time that I spent, you know, 20% of my time, I spent outdoors and, you know, exploring things at altitude, you know, and it's like, it's the measuring of saying, is it the outcome of the time spent or the time spent? And I'm saying that you can frame it around the time spent versus the outcome. And I feel like that is what that to me feels like it becomes more of like a sustainable set of motivation.

And even just a more sustainable achieve achieve it, what things do you do after achieving versus kind of the goal oriented, in my opinion, I guess the reason I would connect it to that is because like, I think it points you to like what how like what your philosophy on the Y is. It's like, take an extreme example, like somebody in a really tough situation. They're not thinking about the habits that they're forming. They're thinking about like, I've got near term goals. I got to eat, you know, get out of this like wherever bad place I'm in. And it's like very, yeah, I guess like goal achievement oriented.

And like, as you get away from that, what does your why become? Are you trying to like achieve something to talk about it? Do you want to buy something? Do you want other people to look up to you? Or are you trying to like improve yourself? And that's like what I think about with the habits where you have a vision of how you think you should live your life. Like are your habits supporting how you think you should be living?

Interesting. For while you were talking there, I was thinking for a minute that it sounds like almost like a little bit more of like how that like eastern philosophies will look at life where it's like, you know, even in difficult situations, were you able to find moments of like, like serenity and kind of like peace, right? Like, well, that would be that you're able like that in some ways is achieving, you know? Uh huh.

But then where you ended, I'm not as sure if that was as applicable. Well, yeah, I mean, I guess if in your, in your example, I mean, like religion for people in tough situations, like gives them a guide that is beyond like, do I did I eat today? It's like, okay, did I find the moments of serenity or did I find God or did I behave the way I was supposed to? And that could be separate from whether you achieved the goal of eating. Yeah, pretty sure.

I'm not sure like where I shake out on all of this stuff. So I'm just kind of like talking because like I tried to have like an existential crisis. I think before my 40th birthday and couldn't quite like get anywhere. I'd ask myself for a few months, kind of like regularly like, what is the point of all of this? And like, do I understand what the blocks are that I'm building towards?

Like in that to come, we'll circle, I guess, back to like where we were talking about before about like parenting versus the company. Think about whether my time allocation was correct. Um, but like then to kind of like manage for that, I felt like I needed to understand the why. But to be clear, I didn't get anywhere. Interesting.

Where I ended up from a wise sage friend of ours, Mona said, like, try to look at kind of like a rolling 30 days and like, would you be spending your days differently? Which is like closer to what you're saying, I think in terms of like habit forming, like, do you like the way that you are allocating your time? Do you like the habits that you're creating or maintaining? Yeah, not to encourage you to go down this path again. But the way I asked the question was I was like, if I had never done this, what would I have done?

And this means at the time it was, well, I mean, I played this game a lot when I was 27, right? And I had just left 27. Yeah, just left like New York the first time and moved to up to live in Rochester because I left like I'd done my whole career in technology at that point. And I was like, I've never gone into tech and never gone into this type of consulting. What would I have done?

And that was when I arrived at I would have written I would have cooked. And then those were kind of two things I pursued a little bit. I don't know. Yeah, it's like, yeah, I think it is an interesting question to kind of sit with. I feel it's harder sometimes to ask the way you framed it because you don't always know where the block, it's hard to know where the blocks are going to lead until the blocks have built, you know, like who knew it like it's hard to know which way the shapes are going to fit together.

Yeah, yeah. I mean, I think it becomes challenging on the time front when when you don't exactly know how the blocks are going to sit together because like, I mean, trying to make it super simple, right? It's like, okay, if I really cared about what my kids were going to do, and I believe in myself, then I should spend all my time with them and like figure out how to make them the safest, happiest, like all the things. I mean, I don't think I would have had to be like my singular focus if that was my wife, or like by contrast, if that was my, if my company with my why, then I should be trying to like spend all my time there. But like, it seems like I actually have a third why which is myself, where I want myself to have some kind of, I guess, amalgamation of things in my life.

Yeah. But they come at the expense of each other. Interesting. Yeah. And then, Indra, she recorded a podcast on the Knowledge Project that just came out like two weeks ago.

So we were listening to it as we were driving home a couple of days ago. And it was just interesting because she talks about that a little bit. She's like, you know, you can't be CEO PepsiCo and be a great mother. Like, you know, you can be a good mother. You can do the best you can.

She's like, I think that's what I did. But she's like, I'm not going to be like, oh, you know, I was there for every moment. Because she's like, I wasn't, but we figured it out and we managed to be there. And it sounds like she has a great relationship with her kids and like. But it's also just interesting because like, yeah, you know, you don't become CEO of a sports and buy a hundred company because it's just not possible.

And I do think and I don't know. I mean, I haven't looked at her tenure specifically, but it just from the way she sounds like it does sound like she's the kind of person you would like to have running a company like that. You know, so I think it's, yeah, we can't. We can't preclude people from being like what they could be because they like want to achieve something else, you know, because you want to be able to have to be a mother. It means like, we can't say that then they can't be.

That must be the thing you're the best at. Therefore, nothing else you could do. You can commit to in the same way that you made that commitment. But I also think relevant to that conversation is what you were saying earlier about diminishing returns. At least this is what I tell myself at night is that there is also diminishing returns on motherhood.

Like, I think if your objective is to make your kids as happy and resilient and I don't know, you know, whatever as possible, safe. I don't think that me spending 100% of my time with them is actually in service of that goal. Well, yeah, because then how are you modeling for them what you want them to do? Unless what you're modeling for them is that they should have children that spend 100% of their time with them, you know? And like, I'm not the be all end all, right?

It's like, I'm modeling that for them and they're stuck with me all the time, which means like they can't get one on one or one on many external influences. So, like, I do think there's a nuance in that. I know in there, in there and newie has been famous. There's like, she's told some kind of like terrifying stories of like, you know, did she talk about that one with the mother in law? Something about how I think she got a lot of like.

We didn't finish it. So, at least that's one that I've read about just kind of like the expectations of culturally of what a mother in law expected out of her with a small child. And I did. Yeah, I have heard. I think it was in the preview or something. We didn't get to that part because we positive.

But yeah, I know you'd. Yeah. And like, at least what I chose to read into that subtext was like, yeah, but like, who cares if she wasn't the one to do X, Y and Z? Yeah. Yeah, I think that's true. I mean.

And also, did you ask her question? He said she didn't really, she just like felt like you are able to bring this like super women persona to so many different parts of your life. And she was curious about like, how do you like do it? Like, how do you bring the energy to everything? So I kind of did, I feel, I mean.

What I would say is that like one, that's a very nice compliment. But I don't think that it's I bring particular super woman energy. I think it's a combination of the fact that like, I really feed off of other people. So that is helpful in terms of like perception. But like, actually, I think what happens is that people who are very extroverted versus people who are very introverted, you get a get an extra pass in an extroverted person's world.

Because we're like, right now, who knows where we'll go in the in the next chapter in the AI world, or there'd be extrovert will continue to roll. But in an extroverted world, people perceive that you're one way because they only see you in an extroverted context. Oh, so do you feel really tired when you're by yourself? Yeah. Oh, that's what happens to me too.

That's why I always feel extremely tired after it's yes, I like have had four hours of meetings, but it's also that now I'm by myself in this room. And there's no one else here. And I'm like, oh, yeah, like, I mean, Shankar and I talk about this all the time. I work hybrid. And so on the days that I stay home, I end up like a lot of the time feeling like really grouchy, because it's like, I've been with me and my computer the whole day, I had a like an unreasonable list of things that I thought I was going to get done. I got like one thing done, whereas like when I leave my office, I think I'm not altogether sure what I was going to get done, but it was great.

Yeah, I feel happier about the fact that like it was just great. Justine. Have a great day.

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