Welcome to this talk. It's called Diving into the Deep End. We'll get into what exactly that means in a moment. We'll start by just sharing kind of high level what the agenda is.So start by introducing myself as well as the topic and then we'll jump into how to actually set yourself up for success when you do dive into the deep end. Um Talk a little bit about the sort of different factors that I think about when I approach this topic and then look at how do I find these opportunities as well as should I do this? Cool. So start, who am I? So I'm the head of engineering at Sensible Weather. Um Sure, not all of you. Probably most of you have never heard of sensible. That's because we're a pretty small start up. So we actually just raised our series. I it's very exciting. Um But we are a climate technology start up and we work to ensure that your beach vacation, your uh fun jungle adventure, your trip to the water park, your trip to Disneyland, whatever it might be, anything that might involve the weather, we ensure that we will have Well, we won't sure you have good weather, but we'll ensure that at least that your experience is protected against bad weather.

So it's really taking that idea and saying like, hey, I have this trip that's planned and I hope to have a wonderful time and I know that weather is a part of that and normally when we sort of approach that we always get close to the day, we start looking at the forecast. Uh And there's not, there's not really much you can do. You just accept that that's just part of being a human, in human existence. Uh But since we're kind of taking that and we're like, hey, actually, what if you didn't have to just accept that? What if we could actually pay you out when there was bad weather, cold? Um Oh, sorry. All right. Also you share her pronouns always good to go through that. Um What else? So, one thing to know is I am a lover of nuance. Uh So I'm bringing this up for this talk because I want you to take everything I'm saying with a grain of salt. This is my experience. You, I did like this much research this. So a lot of this is kind of like my own thoughts, my own take on things. Um So I hope that you'll use this as maybe a framework or something that's helpful. Um But as a chance to like reflect and not necessarily something to follow to the t so personally, that's my caveat. I think before almost anything you experience in life, but just want to put that out there. I am also an enthusiast of outdoor activities.

I love hiking, climbing, swimming picnics. You're here taking a picnic. Uh Also a huge baker. So lots of things. And I'm also someone who has doped in the deep end, uh sometimes successfully and other times plus successfully. Cool. All right. So what do I mean by diving into the deep end? All learning involves risk like period. So be that learning in school, be that learning a new project? Really just everything you're doing, it always involves some sort of risk, but there is different levels of risk. So what I'm talking about when I say diving into the deep end, I mean, not that like finding a piece of work that you really place your strengths and it's something that's already within your wheelhouse. I mean, tackling something new, something where that risk is slightly higher.

Um And when I say risk also, by the way, I mean, like risk for kind of like personal growth, not talking, even though I do rock climbing, not talking about that kind of risk. Um Yeah, some examples are, you know, maybe leading your first project or joining a start up as an early engineer um or even switching teams. So one thing to note about what I mean, when I say diving in the deep end is people's definition of risk. And their own definition of diving into the deep end might mean something else. My deep end might look like the shallow end to you. And that's totally fine. It's all like a tool to help you think about your own career and your own progress. All right. So when have I over the deep end? So I started out at box.com. Um when I was there, I was working on this admin console. Uh And I wanted to switch teams. I said I wanted to go deeper into the infrastructure stack. So I switched and joined the internal infrastructure monitoring team. Uh I will say this was a medium success. This was kind of my first foray into taking a stuff like that. And I learned a ton, got some really great mentorship, but I definitely could have learned more. I think this is my first uh kind of attempt at this. And my first time realizing that actually the active diving in the deep end is itself a skill. And you do need to kind of like commit to that idea. So that was a good learning for me.

So then I left box, I joined a seven person start up called light stuff. Uh This was great. I really went in head first was just like, cool, I'm here. Now I'm gonna learn everything I can really committed. Uh but also had good mentors around me and it went wonderfully. So chance for success. OK. Bullet lights up, decided. Cool. I've written a bunch of application there code. Now, I'm really set up an infrastructure. I'm gonna set up cock up. This was one of those examples where it didn't go so well. Uh And this is why I think that it's good to have a framework when you do this. So we'll get into that. Uh Then COVID hit. So I think that might resonate with some folks. Uh And then moving to a farm, this probably won't resonate with many folk. I live in this tool shed. I went through a minor existential crisis. Um Which side note if you ever do that, I personally really found uh this article from we, but why about picking a career would be really helpful. So would kind of quick PS A but then I had the amazing opportunity to go and become the first engineering manager at sensible. Uh You might notice prior to this, I had not been a manager.

So this was not only my first time being a manager, is also a new start up. Also my first time being the only manager. So definitely a chance to dive in the deep end. And so far I think it's going swimmingly. I think one of my engineers is here so she can tell you if it's working or not. Uh I think it is though. All right. So how do you set yourself up for class? But I think the first thing is you really need to embrace uncertainty. You're gonna be entering a world. It's new. There's a lot you're not going to know how to do and it's a skill to become comfortable with that. So, and with that, the idea of taking risks, it's a muscle. It is something you have to practice. So, uh, you know, most work related risks, one thing you know about that is like the risk here, it's kind of a risk to your ego, which once you've accepted that and stared that in the face, it's also going to help you really think about that better because you can say how big of a risk is this really.

And also once you realize it is more of an ego, risk, you can then also practice that. You can say, ok, what's like a tiny way for me to kind of try that risk of my ego. Um So one way that I start really little is like I started by just speaking up more and meetings. I was always that person who I would just like sit there and think all my thoughts and wait till the very end and then go talk one on one with someone like I was just too nervous to really talk about. So that's actually a really good way to practice this risk taking though is like, if you have that idea, say it, see how that goes, see what that feels like. Um Yeah, practice risk. Cool. Uh The other thing I like to say is it's also good because when you are in this unknown, you're also going to be making a lot of decisions and it's good to practice making decisions. So I'm a huge advocate of gathering information uh collaborating. But also even with that, you do need to learn how to make decisions on your own.

So uh yeah, and it's for me the best time to practice that is when there are times where there's actually just zero risk involved and you can practice taking this like this decision with no input from others. My favorite way to practice that is when I go to my favorite bar, uh firm bar. I'm like, OK, I'm not gonna ask anyone else which cocktail I should get, I'm gonna choose on my own which cocktail and deal with the consequences. Uh This might sound really silly but uh honestly, I think it's a very good way to practice making decisions and kind of test out yourself and see, OK, I like made this decision, this risk which I'm ordering cocktails. It's not that risky. Uh And then kind of seeing how it goes, seeing my own emotions, especially if I ordered one where I'm like, oh, this one wasn't so good, like great sit with that feel, feel what that's like. Well, the other thing about tackling uncertainty, it is helpful to have a practice in place. So this is how are you going to approach this? The other piece is to add in that idea of pauses. So I know I just talked about like making decisions. But the other piece is that sometimes you don't have to make that gut reaction decision, you have to answer that question right away. You can actually pause, take a breath. That's also a huge part for me.

And a big part of the framework that I added is when I am in this unknown, I'm tackling something new. It's OK and good to take a moment and reflect, breathe, figure out what you want to do. Uh One of my ways to kind of do that is the classic. That's a great question. Let me get back to you. Another thing that's part of my practice, especially when I'm in this like, oh my God, there's so many things in my head, so much to tackle. Uh is I do a lot of journaling. I write a ton. Um So I kind of intentionally have, even within that, I have my own practice, which is I start free form uh just to get everything on the table. And sometimes I find that, that uncovers things I wouldn't have thought of necessarily. But then from there, I turn that around and turn that into more a very structured bullet um breaking down the problem seeing. OK, what do I know what's in my control? What is my end goal? And then once I have those very clear questions asked, then I can start thinking about how the steps that will take me to finding my own sense of certainty within this vague world. Ok? I'm just gonna check in and see how everyone's doing. Cool, great, looks like everyone's still with me. All right. So the other part that I think will make you successful in diving in the deep end is finding comfort in learning from moments of failure. So we just talked about you're going to be dealing with lots of uncertainty.

That's kind of the before the moment you've made a decision. But now that you are dealing with uncertainty, you've made a decision, you're gonna fail sometimes. That's just how you learn. So I've kind of reframed how I think about failure. And that's by taking this idea of the four stages of competence. So this is honestly a very helpful framework. Uh I've had the wonderful privilege of working with a coach recently, which if you ever ever have the opportunity to do it. Uh And day one, this is something he told me about. And so there's four stages to competence. The first one is unconscious incompetence. That's you don't even know the things that you're not good at yet. The second is conscious incompetence. It's like great. Now, I know that I'm bad at this. The third one is conscious competence. So that means it's, you know what you're doing, you can kind of do it, but it's, it's just hard, like you have to think about it every step of the way. The last one is the unconscious competence. And that's when you've really hit that level where it's like no longer a grind, you can kind of just do it naturally. Um And one thing about this framework is like, there'll still be stages within this. So even if it's uh you know, getting comfortable with working and going, you'll probably go through a few stages of this. So don't feel like you're gonna get to the top and then you're done, it's gonna, it's always gonna keep going.

Um But why am I talking about this? The reason I'm talking about this is that moment when you realize you failed, I actually take that and I say great, I've actually just leveled up from step one to step two. I went from not even knowing that these are things that could go wrong to. Now. I actually know that this is a skill that I don't have yet or that this is a thing that I could get better at. So it's not this moment of like, oh no, I've done horribly instead. It's like, hey, I just leveled up from stage one to stage two. Great. How do I get myself to stage three now? So that's been very helpful. All right. I think another thing for this failure idea is it's helpful to bias towards action. Um And that's because you need feedback to learn. So how do you get feedback? In order to get feedback, you have to actually do something to get feedback on. The other thing is that you need to have someone else to give you that feedback to some degree, you can kind of learn on your own and uh give yourself feedback. But the best feedback is honestly gonna come externally. So if you can do something, do it publicly, show it to someone else, something like that, show it to your mentor, show it to a teammate, whoever it is.

Uh It's best to be able to get that feedback from someone else and then take that feedback and iterate so great. If someone gave you some like that's not the right way. Perfect. Take that, do it again, learn the right like learn the right way. Uh I think another thing and this kind of goes back to that theme of practicing. Um I don't know if you've heard of, I feel like grit has been a very buzzword, Angela Duckworth's book on grit is great. Also everyone to read that. Um So grit is passion and perseverance for long term goals. And part of the reason I want to bring this up is that it's, it's this idea of sticking with something and there's this piece I haven't really talked about yet and I'll get to this later on, but this, it's not just grid at anything. It's not like I'm gonna keep hitting my head against the wall for what, no matter what it is, I'm gonna do it specifically for things that I really care about and things that are this longer term growth. So that's kind of helpful to keep that distant viewpoint. And also each time you do do a little setback. Remember again, you're practicing, you're building up a skill of resilience and this one seems really random, but I listen to a lot of desert island discs. Uh It's OK.

I don't know if you, if you've never heard of it, it's just this great interview podcast where they ask celebrities, what are their top? I think it's like eight disks they would take to a desert island. But the reason I love it for this is it's a lot of people who have made it very successfully in weird niches and they've gotten there through sometimes very weird places. They've maybe like completely failed the academic system but have gone on to be amazing animal advocates or something. And I just feel like it's this exposure to this idea that you can be really successful and do awesome things and have also moments of just like, oh yeah, I was really bad at this thing or like I overcame this thing. Um I just think it's helpful, surround yourself with positive vibes and other people who have gone through uh circles. All right. So should I take the flash? So, going back to the idea of this grit di in the event is for special occasions. Don't do it all the time. But uh you mind, you sign your time, you should be doing that incremental learning.

This is for that moment where you're like, all right, I've hit some sort of point and I want to try really jumping in because part of that piece with like building grit is it's this longer term goal. So if you're always i in the deep end, you're probably never actually like, really learning or leveling up or getting there. So it's this thing that you do infrequently and when you do do it, you go all in. So how do I know when it's time though? When am I at that inflection point? I was reading not 10% research. Uh And Forbes says if you're self sabotaging because you're getting bored, that's a good sign. Uh You've hit a ceiling or you feel like you're wasting your potential. So you're like, I think at this point, I've, there's no more growth for me that I can see. Uh This is really interesting. Your fears don't stand scrutiny. So that's like if you're sitting there, you're always telling your friends or your partner or somebody. And you're like, I'm so afraid of this and they're like, that's not a real fear. That's kind of a moment to say, oh, wait, maybe I should just go do this thing. Uh Your life is in flux. Anyway, what thing you notice is, uh like maybe you're moving. Uh There's some sort of natural break. Personally. I'm a little bit iffy on this one. I think if your life is really in flux, sometimes it's good to have stability in some part of your life. So take that one with a grain of salt.

Uh And then the other piece and this is kind of like they say, like you're being called, maybe there's some like North Star that just draws you like you need to go save animals or the planet, whatever it is. Um For me, that was also like an incredible opportunity presents itself. So if someone kind of walks up to you and says, I have this amazing opportunity, honestly, that itself could be a great time. Uh I think the other piece though is that you have to be in the right headspace. So all that stuff about dealing with uncertainty being OK with failure, you're not in that headspace 100% of the time I've been in headspace in the past where that's just not something I can cope with. So this is that moment where like you have to be in the right headspace and I have one minute left. So I'm gonna fly through this. Uh Great. We're going to answer that cool last piece. How do I find these opportunities? Uh Just look to lead a project, look for cross functional initiatives, switch teams. Basically, there's a ton of different ways to do it. Ok. To end you. Have any questions, please email me questions, thoughts, ideas, questions about sensible.

Do you just want to say hi, whatever it is I am available. Um Do you have a slide of resources? You can't copy those down, so I will keep them. And if you want to email me and ask for slides, I'm happy to send them to you and I think we are at time. So hopefully that was enjoyable or you learn something. All right. Thanks so much.