Jem Hilton

Up the Stack

With Jem Hilton

Jem Hilton is a former philosophy instructor, turned software developer, and offers a story all the way up the stack. From coding bootcamp, through years in the Chicago startup world, to the Pacific Northwest, Jem's made deliberate choices throughout his career, and is now managing a team of engineers at Leafly, the largest cannabis website in the world.

On the show, we detail tactics and strategies for forwarding a career. From landing a job in tech, through negotiating an offer letter, to managing up, this episode is packed with takeaways.

Time Jumps

You don't need people who are math-magicians. You need people who know how to put together the building blocks.

Episode Transcript

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Kevin Lesht: Welcome to the Day as a Dev podcast. I am your host, Kevin Lesht, and my guest on this episode is Jem Hilton. So excited for this one because Jem offers a story all the way up the stack. He's made deliberate choices throughout his career of the first of which a hard pivot away from his position as a philosophy instructor and into a bootcamp to restart as a software engineer. From there, he's moved with purpose, and is now managing a team at Leafly, the largest cannabis website in the world. We talk about all of it on the show and focus on the tactics and strategies for forwarding a career. Now, my conversation with Jem Hilton.

Kevin Lesht: Seattle, Washington for this one, Jem Hilton is my guest. It's 68 degrees, slightly overcast outside, but that's not stopping us. We've got the sound, the bay, Elliott Bay would you call it, in the distance. We're in Pioneer Square. Jem. Welcome to the show.

Jem Hilton: Thank you. Great to be here.

Kevin Lesht: Yes. So much to talk about. And Jem, this might be the first episode where we travel linearly through a career because your entrance into the tech industry is very interesting. You didn't begin your professional life as a software engineer. And I thought we could start by having you set up your background and just framing for us what prompted a move towards career in tech.

Jem Hilton: Yeah. I was not interested in software engineering in my initial college days. I studied philosophy and anthropology. I wanted to be a professor. We live in an interesting time where becoming a professor isn't really a viable career option any longer. And I also was living in an interesting time and place Chicago in the late aughts, early teens. The rise of startup culture in Chicago. And my wife at the time got a job at a startup in a tech incubator, 1871. And she mentioned to me that there was a bootcamp called the Starter League that was just starting up and they were taking students. And if I was interested in a career change, which I had been talking about for a little while, that the Starter League seemed like it might be an interesting option. So I explored it. It looked like something totally different from your standard, regular college education path. Yeah, I just went for it. And I haven't really looked back since. It was really a turning point in my life. And it was an accident of time in place where my wife and I were in Chicago.

Kevin Lesht: Yeah. Bootcamps are just so interesting to me. We've got at Home Chef where I'm currently employed, plenty of bootcamp graduates. And I always feel as someone who's self-taught that I missed out. I see what they bring to their jobs just the mentality that the bootcamp seem to instill. And then others who maybe got a formal degree. So I'm super curious about bootcamps in general. With Starter League, I would be curious, do you feel that you were set up well for the real world with the exposure? I think Starter League, how many weeks was it? It was maybe-

Jem Hilton: 12 weeks.

Kevin Lesht: 12 weeks. So with the 12 weeks you got out of Starter League, maybe you could give us a rundown of in 12 weeks, what does that curriculum look like? And maybe even down to a given day, what does a day, humor me here, play into the show, Day as a Dev. What does a day in the life of a bootcamper look like? And if you could scale that up to the real world that you entered into, did it prepare you well?

Jem Hilton: Yeah, it's interesting thinking back at Starter League, which was really one of the very first boot camps, and it really was a pioneer of the bootcamp as a mechanism for entering into a software engineering career. It really didn't prepare me for the day to day and sharing. And I don't know at the time, I don't think that that was the intention. It was more of a mechanism to give you the tools to launch your own startup, to give you the tools to create an MVP of a website and pitch investors.

Jem Hilton: So the daily focus was to give you the minimum skills to build a website. And being Chicago at the time, Ruby on Rails was king. That was the easiest entry point to creating a nontrivial web app.

Jem Hilton: So, Starter League really focused on not foundational computer science skills, but getting a website up that is the embodiment of a particular start up business that you're trying to start. And then being able to present that in a way where you could acquire funding, I think was the main focus of that.

Jem Hilton: So it wasn't really of the same vein as the bigger bootcamps that came out of there, like General Assembly and Dev Bootcamp. So in terms of my ability to function as a software engineer, it really didn't provide me with those skills. I had to learn those on the job later.

Kevin Lesht: That is interesting. That is not the answer I was expecting at all. So my exposure mostly to boot camps yes are it's unfortunate that it has now closed down. But Dev Bootcamp graduated quite a few colleagues that I currently work with, and was not expecting that answer because their take on the experience they got out of boot camps was quite the opposite. And that it sounded like it was more so focused on yes, those foundational paradigms that do set you up for practical application. So maybe with you, we pivot into your first job. You graduate from the bootcamp. And then I'm curious when you go after that first job, was there help from Starter League? Or what did your process look like for landing that first gig? And maybe you could even give us some insight too into what your resume, what your portfolio looked like at the time. A lot of our listeners out there, students, career changers. I know even myself going after my first internship, it was anxiety inducing. Granted, you had a career, albeit in a different industry behind you. But for me, going after my first internship, right? I really had my education block on there, and then had to stretch to figure out what I could present, even try to land that first job.

Kevin Lesht: So yes. For you, what'd your process look like trying to get your first role? And if you could give us too just some insight into what your resume looked like at the time of applying to those first jobs.

Jem Hilton: So at the time, I was an adjunct instructor of philosophy at Northeastern Illinois University. I had just gotten my master's degree a couple of years prior to entering the bootcamp. I focused on formal logic and ethics, so I had a pretty solid background in informal logic, which is the foundation of computer science anyway. So I felt very confident in my ability to learn on the job, because the skills were pretty closely related.

Jem Hilton: Aside from that, I knew that I didn't want to pursue a career in philosophy, in higher education. I didn't want to get my PhD. There's a lot that's involved in getting your PhD, and a lot of it isn't conducive to living in one place or having job security, or a secure lifestyle. And we can get into all of the problems in higher education. I was ready to make a change.

Jem Hilton: I'd actually started taking some computer science classes. One of the few perks of being an adjunct instructor at a university is you get free classes. So I started taking some computer science classes because I wanted to at the time segue into either some sort of IT profession, I didn't know what.

Jem Hilton: So when my wife, who is working at a startup in 1871 in Chicago, suggested I take classes at Starter League, I wasn't fully informed of startup life and just the world of tech I guess as a profession. But as I started taking classes in Starter League, which was three days a week, about four hours each day. I realized that I wasn't going to get the foundational skills there, but I was in a place in which there was a very vibrant startup tech community and culture, and that I just needed to just be in it, and absorb it, and start making connections and networking. And that was really a source of my first job and segue out of Starter League. It wasn't putting together a resume as much as it was just directly networking, talking to people, being in the community. That was the biggest reason why I was able to immediately jump into a career into tech rather than struggle to get my first job.

Jem Hilton: It involved me going to happy hours. I know this is all very like kind of cliche and it's hard to say. Well, I got my first job at a happy hour with some tech bros, but that's sort of what happened. And I call them tech bros in a friendly way, not in a pejorative way.

Jem Hilton: There were a couple guys that had their startup at 1871, and we just had a good conversation. I told them where I was at, what I was doing, my background, they liked that I had a philosophy degree. They valued education beyond just what can you do for me. But they saw the capacity. And I think that's an important thing is if you can sell your capacity to learn, especially for your first job. That will go a long way. And I ended up getting an apprenticeship with them. They didn't have an apprenticeship program. It was just two guys with a startup. And they were like, "We just won a competition. We just got an infusion of capital. We can afford to take you on." And they were like, "We'll teach you how to program basically." So it was like a self made apprenticeship that I just negotiated with them at a happy hour.

Kevin Lesht: I love that story. I think it demonstrates that yeah, the two things you hit on there, which really jumped out are a proactiveness. Maybe three things. Okay? A proactiveness, a work ethic, and the community. It seemed like the marriage of those three things are what formed the ad hoc position that was this apprenticeship that that was your first role. So I don't have a insight into other industries, but the community really is a special thing in tech. I think back, the story that triggered too is there's this quote out there, I forget who it's attributed to, we'll have to drop it in the show notes. But it's that luck is really the intersection of preparation and opportunity. And what really drove that home for me is I was at a CodePen Chicago meetup. And candidate was looking for a job and was using the meetup to network. Just as you mentioned you did, going to happy hours and things like that. This candidate put together a bunch ... CodePen for those aren't familiar, it's a platform where users can really upload a front end demonstrations, little demos, experiments, concepts. Although CodePen has really now expanded. We can go a whole show on CodePen to hosting projects and everything else.

Kevin Lesht: This candidate specifically put together a demo that he was leveraging to demonstrate just his ability, his passion for front end development to try to land a gig. And after, this was a show and tell meetup after the showing wrapped up, everyone was catching up. We had a conversation, and then this candidate ended up I think landing a job off of a member that was also at the meetup. So you think about going back to luck being that intersection of preparation and opportunity, this person prepared in advance a very in depth demonstration of his skillset. And then happened to parallel that with being in an atmosphere of the tech community, and being able to just demonstrate to others around that he was looking for a job and trying to just best leverage that situation, to network with individuals and to try to land a gig. And I think that's sometimes what it takes. You have to have that proactiveness to go out there and to try to really get these things for yourself.

Jem Hilton: Yeah, I think that that was really, I had a single minded focus. I think that was really the key. I knew that my Starter League education wasn't going to be sufficient. It was the thing that got my foot in the door into the community, and it allowed me access to pitch myself to the community. And I think that was the important thing is finding that entry point so that you can start pitching yourself. Especially when you come from a nontraditional background, right? You have to show capacity, desire, and a very laser-focused intention, to know what the next step is. Realistically, not unrealistically, right? I knew what I was lacking. It was more of a formal or maybe not even formal, but on the job training, you know? And that's where I thought to myself, well I need to not just get a job, but I need to learn more. I knew where I was lacking. I knew where my skills were just missing. I needed an apprenticeship. I didn't need a junior engineer job. I don't think I would have done well. Or it would've been more of a struggle if I had gone directly into just a 40 hour a week junior engineering position, I would have struggled a lot more on the job.

Jem Hilton: As an apprentice, there is this built in idea that you're learning. So there's more of an employer incentive to not just give you stuff to do for them to produce value,, but that they also have an intention to teach you or train you more so.

Jem Hilton: That was my sort of focus. I was like, "I need an apprenticeship. How am I going to get it?" I found some people who were willing to do it, and it was very fortuitous. It was a lot of right place in the right time. I don't want to say that it was all, I mean there was a lot of luck, right? I mean, there was a ton of luck. It was just exactly the right place, right time. We were some dudes too, there wasn't a lot of cultural friction. There was a lot that went into it that was also being a white male in that particular community. Being able to easily connect with other white males, which I don't want to discount, especially when you're a person who doesn't immediately have that same peer group typically. For me, it was easier in some ways because of that background that I had.

Kevin Lesht: Yeah. I think I appreciate it. I think it's a very candid and real thing that exists out there. As far as the apprenticeship program itself goes, that I think is so great because I want to say that for a lot of entry level applicants, it's something they should maybe be looking for. A prove it and earn it kind of relationship I have seen personally play out only in favor of those that are invested, that are genuine about trying to enter the industry, and almost treated as an internship. You might not be getting college credit because you have graduated at this point, but you're positioning yourself.

Kevin Lesht: What's very real about the tech industry is the salaries are generous. And it might take some apprentice, some internship kind of investment for yourself to land there. But if you are passionate about the field, if you want to be here, sometimes that might be what it, what it takes to land there.

Jem Hilton: Yeah. I mean in some ways I think that an approach I've always taken or at least a way that I see the industry is it's much more of a new trade than it is more of a professional industry. In some ways, I feel like today's everyday software engineer is more like an electrician or like a plumber, right? That this idea of the apprenticeship model and the learning of the craft. It's much less, we're doing hard computer science, which there is some of that in our every day.

Jem Hilton: But it's much more we are learning a craft or trade, and following that model that's already been kind of proven out in the trades. Is something that I think going forward for the software engineering industry and just tech industry in general. I see that trend going where experience, what have you done, what can you build is more important than formal education. And also general virtuoso skillset, right? You don't need people who are mathemagicians. You need people who know how to put together the building blocks of libraries, that sort of thing. And I think that that's something that is a very valuable skill. It's like, well what have you built? What kind of work ethic do you have? You don't have to be a genius, you just have to show that you have done things, that you have the capacity to do things. You can work hard, and that you know how to just build. Right?

Kevin Lesht: Yes. I think that, I love that analogy. I think the craftsmen parallel to that of a software engineer, a technician, a web developer, any of these kinds of things is so true in that. And I think what also plays off of that is why you see such a strong emphasis on the mentor to apprentice apprenti, apprentice?

Jem Hilton: Apprentice.

Kevin Lesht: Apprentice a relationship in our industry. Because yeah, as you mentioned, a lot of it is trade that is learned on the job. You can only grab so much. And it's going to set you up well if you have learning outside of practical application. But you can only take yourself to such a point before you actually have to build out a feature and see how the actual tech stack relates to these concepts that you've learned about. The rubber hits the road, do you know how to build this tool within the specific context of your ecosystem infrastructure, business problems, constraints, right? You're not going to learn that in a classroom or a boot camp at all. It's just not going to happen.

Kevin Lesht: So maybe to play off of that, you're at your first job. And now short-circuiting our way to the end of it. Because for everyone whether it is sooner or later, a job is going to end. And maybe you have to just dig into that for a second. I think closing out a job, it's a totally natural and valid thing. Looking at when to maybe move on, everyone's going to have different motivations. Even for me personally, I think it's primarily about learning. Some companies are going to offer a long vertical that carries good career progression. And I've been fortunate to experience that. But for others, you might find yourself plateauing. And especially in tech, I think it's so important for developers to ensure really for their own safety that that they are still learning.

Kevin Lesht: And learning doesn't have to just be focused on technical application. It could be people, it can be product management skills. There are all sorts of laterals, of valuable attributes to work on that will keep an individual competitive.

Kevin Lesht: So my short question that follows this long setup, because something I appreciated, full disclosure Jem and I, we had the opportunity of working together. What I really always admired about you is you seem to very in tune about just career progression, self advancement. And I'm curious, two angles here. The first being that while someone is employed, how can they best leverage their organization to forward themselves? And then the second end goal that we'll set up as well, would love to dig into both sides of this at whatever hits your first. As maybe you figure out that you're reaching the end of the line, how do you even recognize that, and learn to really start looking for a new job? How do you know when it's time to look for a new one? But maybe if we could first dig into while employed, what can an individual be doing to make sure that they're setting themselves up for success?

Jem Hilton: Yeah, I think that that's an important question. That's much more of just how do you be the owner of your own career question, right? You need to first take ownership that you are in charge of your own development. It's not going to be provided to you by any company, even if they claim to be very proactive about professional development. You need to be the owner of your own career.

Jem Hilton: And the first step is to get a good rapport with your manager, the person who you directly report to. And I think that you need to have a very candid, open relationship with them that involves managing up, setting expectations that you have of them, and then asking them continuously for feedback on your own performance, and goals that you have for yourself. A good manager should help you set goals for yourself in your own professional development. If they're not a good manager, they're probably not going to talk about those. It's still on you to set those goals for yourself, make them visible and public to your manager. Let them acknowledge that those are your goals, and ask them if they are able to help you achieve those goals.

Kevin Lesht: And would that be, so you mentioned a second ago managing up. That would be an example-

Jem Hilton: Yeah, that's exactly what it means to manage up. Set your goals and expectations for what they should do as a manager. And if they can't meet those goals, that leads to the next question that you have, which is how do you know when it's time to move on? Because sometimes you might be in an organization where the organization itself might be somewhere where you want to be, but because of the way that most companies are set up, you're in some sort of hierarchical system, right? You have a manager that you report to, and they have a lot of power or authority over your career progression. In fact, maybe too much sometimes. Right? And in those cases, that's typically when you might know this person has not acknowledged that these are my goals. Or they have acknowledged them, but have not given me any real feedback that they're going to help me achieve those goals.

Jem Hilton: Now in practice, and I haven't been anywhere where I've ever had a manager who's been completely obstinate or has not responded to managing up. So I think that as a new or in progress, or really at any time in your career engineer, these are just good tactics. I think step one, know what your goals are. Step two, communicate those goals to your manager and ask them if they can help you achieve those goals, and whether or not those goals are achievable within your organization. And then keep up with those goals and get feedback from your manager asking them if you are working toward these goals, say you want to be a senior engineer. You're three, four years and you're like, "I want to take the next step to becoming a senior engineer. What do I need to do? These are the kinds of things I want to do. What else do I need to do, and how can we track that progress toward that goal? Is that something achievable within this organization that I'm in?"

Kevin Lesht: I like that setting right there, which is that is this achievable within my organization? Because I think the reality of the real world is that there are constraints. Everyone has a boss. Every product has certain directives that they need to drive forward. So yeah, unfortunate as it may seem, sometimes you may hit up against those walls. And then to your point, it's just about having the awareness for recognizing them, and then knowing that maybe both sides of this relationship have gotten as much as they can out of it, and that it's time to move forward.

Jem Hilton: Yeah. I think that's kind of how you can move on to the next phase, which is I'm going to start looking for an organization that can help me achieve these goals. So for me personally, going from place to place, I've worked at four places I think before I finally landed at my job at Leafly. Each one of them, I advanced in the way that I had hoped up until a point. And when I realized I was going to have to sit for a year or two longer or there was a leadership change, after I felt like I was advancing.

Jem Hilton: Here's a good example. I got a job at Centro in 2016-ish. I'm trying to think now. It's been a long time. And that was my second engineering role. Full engineering role, not an apprenticeship. Within six months, I was made a team lead. Probably prematurely in terms of my technical skillset, but I had done a good job of the soft skills of being a team lead, and working with product, and understanding how to ship a product, even if I wasn't building it. Awesomely, right? My code wasn't the greatest, but I wrote good tests, and it shipped on time.

Kevin Lesht: Always test your work.

Jem Hilton: Exactly. So if you don't write great code, write good tests. And it's okay. Right? So the person, the director who had put me into that team lead role got let go and we had new leadership. And that new leadership didn't think that I should be in that team lead role.

Jem Hilton: So that was an indication to me that this wasn't the place that I needed to stay at. Right? So a lot of times people that again, that are in positions above you who are your advocates or helping you progress in your career. Even if they know you're not quite ready for the role but they believe in you and believe in the capacity that you show, if they're still there, that's how you know that this is the place you can grow in, right? You have people that are going to bat for you, and they're there to help you, and they're going to put you in positions to succeed even if you yourself are not super confident in it, having people believe in you. But when those people are no longer there and you don't feel like you've got people going to bat for you, that is typically a good indicator that it's time to move on. And thankfully, we've all chosen a profession where we have a lot of options, which is not the case for a lot of different jobs.

Kevin Lesht: That's right. Yeah. So to give you maybe what plays into a couple things there. To give you an example from outside the tech industry that hits on I think what in an essence you described, which is having an awareness for just the dynamics that are your workplace. It could be a position that you love the organization, you love the team, but you just don't see growth ahead. And I think that it's a really hard decision to make, but sometimes one that you do have to you know understand is going to be for the benefit of your longer term career.

Kevin Lesht: The example that I wanted to pull in was a friend of mine was working for a professional sports organization. This was his dream job. He grinded out a finance position prior to this where he was putting in 100 hour weeks just to set up his resume so that he could land this dream job, that was at this professional sports organization.

Kevin Lesht: He got there, and it was very quickly that he realized it was a small, close knit team. And the two managers that were directly ahead of him, they also loved the job, and they weren't going anywhere anytime soon. So he did not see a track ahead and he sort of had to come to the realization that, this is a very ambitious person. If he wanted to forward himself, he was going to ... and he loved, he loved this team. The team that was the sports team, and also that was his immediate colleagues and peers around himself. But if he wanted to forward himself, he had to move on. And it was, I think of such a difficult decision for him. And something that is just really hard I think to make in general.

Jem Hilton: Yeah. No, definitely. Every place I've worked at has had, I've been very lucky. I think partially, it's a gut feeling you have when you're interviewing, knowing that you're going to go into an organization that has a relatively good culture and life work balance, etc., good people. But, I have a mercenary streak inside of me and I think that's something that everybody should cultivate a little bit.

Kevin Lesht: How about this for a segue? The moving out part. When we did work together at Home Chef, you were in office, but then you moved out and you went remote for awhile. And what I would love to set up for our listeners would be just even how that looked. I think that it's sometimes difficult to raise those kinds of, I don't know what you would call them, I guess workplace requests up to your manager. And I'm wondering if you could stage for us when you were looking to move out of the office and to a full time remote position, what did that conversation look like? How did you just first broach it to begin with?

Jem Hilton: So I was very strategic about even taking the job at Home Chef. I had actually had two competing offers, one at another company that was actually a slightly better offer. But, their requirement was that they would never be, at least in the near to medium term, a remote friendly company. And when I was speaking with Home Chef, I had talked to them about the possibility that I at some point want to move, and if they were open to having a remote engineer. And they said they did not have a current remote policy, but they would be open to it on a case by case basis if I demonstrated being responsible and adding value to the company.

Jem Hilton: So I set it up from the very beginning, and I think that's an important thing when you're interviewing at places is to get them to not necessarily 100% agree, but at least be open to it, and then you can kind of just bet on yourself. And that's what I did. I just bet on myself. I knew that I would add value to the company. I knew my work ethic and what I could bring to them. I also knew that I was not getting everything I wanted in terms of a title and salary. So I knew that this would be part of the total negotiation package that at least I would be getting a flexibility. So that set up the conversation that I ended up having about nine months later.

Kevin Lesht: I think that's an important thing to consider there in that if the offer letter you don't immediately receive meets what you are looking for, there are other things that you might be able to incorporate. Vacation days, remote work, whatever it might be. The important thing there I think is as you mentioned, seeding that early. You talk about in the initial conversations even setting this up, so that just the groundwork is laid for that eventual, set yourself up for that option if you eventually do want to pursue it.

Jem Hilton: Yeah, I think that that was the key was just being very strategic from the very beginning. That's something that's very difficult in general. You just have to have very clear goals. So this is something that is not specific to a software engineering career, but maybe just in life in general. What are your goals, what do you want? And if you can bring a very clear focus to any sort of job negotiation that's built off of your goals and ask the right questions that will let you know whether or not the goals you have personally are going to be achievable within this organization. Whether they're professional, whether they're lifestyle, then that should be part of your process by which you determine where you want to go work, what kinds of companies you're going to want to pursue work that might involve in your friend's case, a lot of upfront work to even get considered for that position, right? So absolutely, clear goal setting is really the elephant in the room here, right?

Kevin Lesht: I think sometimes too, it's just so difficult. Because especially as a person entering the field, you might just get so caught up on receiving that offer letter, that you don't take a step back and really reflect on what your goals are, what your position in the market is to go after these things. And it's such a valuable thing.

Kevin Lesht: But thank you Jem. That is so helpful because I think there a lot of hesitation around just even talking about these kinds of things. So offering up real patterns for people to follow out there is really what this show is about. So I am very excited that we've been able to dig in. And I as an extension of remote work, the other thing I'd love to dig into is I love a good work from home day just like anyone else. Anything from being able to run laundry in between tasks, or just be in a more relaxed environment. It's an awesome perk. But on the other side, I always do wonder about what that set up would look like in more of a longer term fashion. I do think about if I would miss the social aspect that is the office. Going in, seeing friends, colleagues, just being in an atmosphere with your peers. So I wonder in your remote experience, were there any unexpected negative consequences that you ran into that you didn't necessarily project?

Jem Hilton: Yeah. So I have a particularly difficult situation in that I have two very tiny kids. And my wife was working freelance at the time that we went remote, so all four of us were home at the same time. So that was a little bit of a difficult-

Kevin Lesht: Just a few distractions out there.

Jem Hilton: Just a little bit. So that may not be the case for most people. So in terms of the actual remote work itself, really for me as somebody who doesn't need as much in office culture. Because I'm older, I have family, kids. It wasn't really a huge deal other than needing to just have some sort of time out. Yeah, time out. So I would go to coffee shops, coworking spaces as well. I think those were just strategies for me to feel like I was out and about and not totally isolated.

Jem Hilton: In terms of being a remote engineer, we can go into detail about the skills and habits of a good remote engineer in a separate topic if we want to. But just in terms of how I made that transition, I felt great about it. I really enjoyed the ability to focus on just the work and not all the distractions. I felt like I was pretty productive. Although I did start looking for another job pretty quickly. So I feel like I didn't really get to do remote for a very long period of time, and you probably want to talk to somebody who's been doing remote a lot longer.

Jem Hilton: I do know from the position of a hiring manager now and having conversations in our company about remote engineering, what we look for. And that's typically somebody who has a track record of remote work. So I wouldn't recommend it for a junior engineer to begin with. And transitioning to remote is something I would probably only recommend for somebody who's been doing it for four or five years or more.

Kevin Lesht: I think you raised an interesting perspective there that I hadn't ever considered, which is that you get to maybe a different point in life as you mentioned, and you don't necessarily value those in office things as highly as some other things, like being able to be close to your family or whatever else might come along with anyone's remote situation. But then yeah, to your point, I suppose you do then need to find that separation so that you can can be productive.

Kevin Lesht: Now that's not to say that there aren't distractions. You think about a lot of the offices now trending to an open format where not only is someone's conversation really disrupting that given person, but also those surrounding them. So always no matter your environment, probably just factors to be aware of.

Kevin Lesht: You mentioned there for a quick second, do want to get you back to that family of yours, and we'll have to peg some more remote questions for another future episode. Because what I would like to get into as we get close to wrapping up the show here, is you have very recently at Leafly now transitioned from being an engineer to being a manager. And I'm sure we could even spend an entire episode just on those things alone. But I would love to hit you with just one question, which is that how have your responsibilities changed as you've moved into now a position of management coming all the way up the stack from a bootcamp, to an engineer, to a senior engineer, and now to that of someone who is overseeing engineers?

Jem Hilton: Yeah, it's been a very dramatic transition in one that I knew was going to take place. But when you're actually in it, it's a lot more intense and it's a lot more just frenetic. So as an engineer, you can focus on a problem for many days sometimes, right? You might be working on a feature that might take two weeks. And that's your whole kind of aside from team related backlog grooming or general process stuff. You're kind of just focused on one thing. For a while as an engineering manager. I pretty much only have about 15 to 20 minutes to focus on one thing at any given time in my day before I have to switch to the next thing.

Jem Hilton: So that constant context shifting, whether it's jumping into meetings with product or data team, product managers, one-on-ones with engineers. You're kind of just jumping from one thing to the next. You're not really able to code at all really, very little. So that transition, it's been a little tough that. You feel very unproductive to be honest. And that's something that I know is just a thing that every person who transitions to a managerial role struggles with. You can't knock out a feature or some bit of code that has an immediate impact that you can see it's out in production. Instead, you're just dealing with people issues and process issues.

Kevin Lesht: As I have heard these, it's interesting that you mentioned, yeah, I've heard very similar conversations speaking with others in managerial roles. And I guess as they frame it too, which it seems like what you just said. You might only have a few minutes with a given individual, so you need to know that you are imparting something that is going to have a cascading effect. Leading through delegation. Especially, you have to use the value that is knowing the more macro level business context and then just disseminate that to the individual that as you mentioned, can then spend the week on a feature or whatever it might be, to handle the actual execution of the directive that needs to be handled.

Jem Hilton: Yeah. I think being a, some people call it a force multiplier. Where you yourself are not doing the thing. You're just there to unlock or accelerate the thing, and it has to be 100 things, right? So you have to be on the drop in. One thing that I've had to become a lot more just aware of is how prepared I have to be for every meeting because my time is so much more precious. So a lot of time spent planning, sitting down, task lists, checklists, very small. You're doing 100 small tasks, but they all add up to more work than you can do in a day. Yeah, it's definitely been an interesting transition. I really like it. I can see now, before I as an engineer, I never really saw it, but I can see now how burnout is a real thing. That's something that I know that just engineers are at risk of depending on where they are, engineering managers even more so.

Kevin Lesht: I could imagine. I think the mental fatigue that anyone experiences coming out of just a long running feature. Trying to imagine that as you juggle all of these different laterals happening, these different things going on across the business can be very difficult. Absolutely.

Kevin Lesht: Maybe the theme of this show, which seems to be the long running thread across all of our conversations is that you have to be prepared for any of these things, whether it be an engineering task, a people management task, or a task of just self advancement. And to execute on any of those things to, a proactiveness also has to carry with that. Jem, this has been awesome. I feel like there are just so many takeaways from this episode that people can just start applying today. As we close out the episode, wonder if you have any parting thoughts for our listeners out there.

Jem Hilton: I would just encourage people to take ownership of their own career and really think about what they want out of it. When you have clarity of purpose and what your goals truly are, that's when you can really direct your energy toward that goal. So focus, set goals, execute.

Kevin Lesht: Yes. Jem, thank you for your time.

Kevin Lesht: For show notes and more on this episode, head on up to the site. That's While you're there, check out our release notes. This is a short newsletter that we send out about once a week. It includes updates along with all sorts of other goodies, packaged up for your inbox. Thanks for listening. For the Day as a Dev podcast, I'm Kevin Lesht.